Traditional phishing techniques are in decline as a result of the disruption of the Tycoon2FA phishing-as-a-service (PHaaS) platform, Microsoft said in a new report, “Email threat landscape: Q2 2026 trends and insights”.

“Phishing volume linked to the platform fell 92% from pre-disruption averages, including QR code phishing and CAPTCHA-gated phishing both declining from their March highs,” the company wrote in the report.

The takedown reduced activity across multiple phishing categories, forcing attackers to shift to newer delivery methods.

Riding this shift in were a few notable phishing campaigns, including an automated business email compromise (BEC) campaign that reached 42,000 organizations in under three hours, and a multi-stage phishing campaign that used nested email (EML) files, calendar invitations, and a Microsoft authentication redirect to deliver malware.

To counter phishing attacks, Microsoft recommends blocking emails containing known bad URLs/ subject fields, enabling password-less authentication methods, or moving to MFA for accounts that still require passwords.

Tycoon2FA disruption sent attackers exploring

The take-down of Tycoon2FA forced its operators to abandon portions of their infrastructure and rework hosting, domain registrations, and delivery mechanisms.

“After falling 15% in March and another 22% in April, Tycoon2FA-linked phishing volume dropped 74% in May to just 1.5 million messages, then fell another 20% in June to 1.2 million, by far the lowest monthly volumes observed in at least a year,” Microsoft said.

The decline extended to QR Code lures and fake CAPTCHA pages, two phishing techniques in which Tycoon2FA accounted for 12% and 14% of industry activity in June, respectively. This indicated that the platform’s customer base had not been able to migrate to a replacement infrastructure.

But cutting off one head of the hacker hydra only gave rise to new tactics elsewhere.

The adaptation came in the form of using Microsoft Teams as a social engineering channel. Attackers established conversations to build trust before attempting credential theft or delivering malicious payloads. “Teams-based phishing volume climbed steadily throughout Q2, with the average number of detected attacks rising 19% from March to April, holding roughly flat into May (+1%), then increasing another 10% into June,” Microsoft said.

Microsoft also observed a highly automated BEC campaign that reached over 67,000 users using scripted emails, Amazon Simple Email Service (SES), and engagement tracking, alongside a separate phishing campaign targeting 107,000 users that abused Microsoft’s authentication flow and trusted cloud services, including Teams archive recording and ICS calendar invite, to disguise malware delivery behind legitimate infrastructure.

Phishing changes but the defense doesn’t

While QR Code and Captcha-based phishing attacks dropped significantly in the second quarter, business email compromise (BEC) charted jumped 121% between March and April, before dropping down again in May.

QR Code phishing represented 8.3 million attacks in June 2026, down from a peak of 18.7 million in March. Similarly, Captcha-gated phishing fell from 12 million attacks in March to 2.2 million in June.

BEC attacks hit 9 million in March, falling to 3.9 million in June.

But even as these phishing classics lost momentum and newer techniques emerged, Microsoft’s defensive advice remained rooted in the basics. It noted organizations should complement email filtering with phishing-resistant authentication such as passkeys and phishing-resistant MFA to reduce the effectiveness of credential theft campaigns.

The company also recommended strengthening Exchange Online Protection and Microsoft Defender for Office 365 with capabilities such as Safe links and Zero-hour Auto Purge (ZAP), in which malicious emails already delivered to mailboxes are removed before they are read, alongside enforcing password-less authentication methods like Windows Hello, FIDO keys, and Microsoft Authenticator.

Microsoft concluded its report with a list of indicators of compromise (IoCs) from the threats observed in the quarter to support detection efforts.

This article first appeared on CSO.

The European Commission has fined Google a total of €890 million ($1 billion) for its breaches of the Digital Market Act (DMA).

Just over half the fine — €460 million — was because Google illegally gave preference to its own services in Google Search results.

The remainder was because in the Google Play store for Android apps, the company prevented app developers from leading consumers to alternative, often cheaper, purchase channels. Under the DMA, app developers who distribute their apps via Google Play or Apple’s App Store should be able to inform customers of alternative offers.

Now Google must give third-party services featuring in its results the same treatment as its own services, and allow developers of apps in the Play Store to communicate about offers both in and outside the Play Store, or face further fines.

The Commission first raised these issues with Google in March 2025. In April of this year, the Commission laid out plans as to how Google should allow other third-parties to share its searches, suggestions that the tech firm firmly resisted. Earlier this month, the Commission also said  Android should be open to other AI agents and not limited to Google’s own Gemini.

Google is not the only US company to have fallen foul of the DMA. In April 2025, Apple was fined €500 million for breaching the Act and, last month, the Commission fired the first shots at cloud hyperscalers Microsoft and Amazon.

When it comes to building an effective AI stack, context is king and power isn’t everything it’s cracked up to be.

“Smaller, smarter, safer — this is a bet our company has taken in how we deploy AI internally,” said Ricky Thakrar, head of sales and account management at Zoho, provider of a suite of popular cloud-based software solutions for sales, marketing, and finance.

“I’m on the business side, and so decisions made by our CIO and IT folks affect me directly, and my teams’ workflows and processes,” he added.

Speaking to a room of tech leaders at the CIO 100 Leadership Live New York event last week, Thakrar explained that every company wants the speed of AI-generated work wedded to the quality of human work, even though these two are diametrically opposed. No amount of model upgrades or spend will close that gap, so the only way forward is to architect your way out. Thakrar encapsulated this idea in a simple formula:

• Smaller: Stop deploying maximum firepower on every task. Many tasks don’t need it.
• Smarter: The system around the model decides more than the model does.
• Safer: Verify at the point a mistake gets locked in, not just downstream of it.

He noted that organizations that win with AI won’t be those deploying the biggest, most powerful models or the most sophisticated architecture, but the ones that figure out that the model is the easy part and the right architecture is harder. That means understanding the hardest element, and the biggest differentiator, is building a human system that learns and compounds alongside agentic systems.

To get it right, organizations need to prioritize the context layer. The size of frontier models like the GPT series, Claude, and Gemini mostly exist to compensate for missing context, Thakrar explained. Without enough context, models need to be able to reason harder and infer more about what a user actually means because it doesn’t know the user’s account, process, or history. A rich context layer makes it possible for enterprises to run workloads on much smaller, lower-power models.

“The intelligence moves from the model into the architecture around it,” he said.

A steep learning curve

One of Zoho’s earliest AI agents was a churn management agent to help the account management team detect churn in customer subscriptions. So when a subscription became inactive, the agent would collect context from notes, meeting recordings, and Zoho’s data enrichment tool, then create a summary of reasons the account might have churned, and schedule a call.

“What happened was I got this churn agent a couple months later, already embedded in our CRM, and within a week my team no longer trusted that agent,” Thakrar said. “The reason is we forgot to collect one very key point.”

In Zoho’s CRM, when a customer buys a bundle of products, that bundle is represented as a single line item. That means the status of any products the customer may have previously purchased individually changes to inactive as they’re moved to the bundle. That’s not churn, but it was interpreted it that way. Zoho fixed it in the second version of the agent.

Then a new problem arose. Many potential customers first purchase Zoho products as pilots or sandboxes. As those customers move from pilot to live instance, they close down the pilot versions. And again, the CRM would record that as subscriptions going inactive.

“The trust deteriorates again because everyone got excited for version 2,” Thakrar said.

Sometimes, a certain product might not be the best fit for a customer and Thakrar’s team will suggest the customer move to another product. That’s deliberate churn, not a churn risk.

“You may have a similar story like this where the agent sounds so good, it’s going to do something quick and add value, but it’s missing context from the account managers, and there are so many more pieces we’re still building out,” Thakrar said. “It’s been almost a year and the problem I have is my team still doesn’t trust it. They’ll see [a message from the agent] and go out and do all the research anyway to make sure it gave the correct answer.”

The team is more on top of potential churn, though, but the promised productivity gains have yet to materialize because the agent has to earn back lost trust due to a lack of context.

“My goal for this year is having an AI-assisted customer journey from sales to account management where the handoff is clean, the context flows, and every piece of information we gather about a customer is weighed, identified, and coached so the sales team can close more deals,” he said.

Zoho’s early experience with agents has led to the idea that constrained, context-rich, deterministic architectures consistently outperform expensive models bolted onto fragmented systems. It all comes down to three pillars: routing, harness, and specialization.

Routing

Routing is about sending workloads to the proper model for the job, which entails providing enough context to a given task that a small, cheap model can handle it without the need for spare reasoning capacity to fill gaps.

Frontier models are expensive and companies can burn through a year’s budget worth of tokens in months. But most tasks can be handled by much smaller, more constrained models at a fraction of the cost.

“You don’t always have to pay the frontier guys for every task,” he said. “We’ve observed with some clients that we could save them 95% with a 3 billion parameter model.”

Harness

An AI agent harness is the software infrastructure scaffolding around an LLM that differentiates an agent from a chatbot. It’s what enables an agent to act on tasks rather than simply respond to prompts. A model reasons through a problem and decides what to do about it. The harness connects the model to the tools, systems, memory, guardrails, and execution environments required to perform the actions determined by the model. The term is frequently used more or less interchangeably with orchestration layer.

“It’s the process around the model, which matters way more than the model itself,” Thakrar said.

In benchmark tests, a superior harness on a less powerful model produces better results than an inferior harness on a much bigger model.

For the best results, Thakrar said, it’s essential to understand the deterministic and non-deterministic elements of a given workload, and build that into the architecture. Machines can read, organize, and validate, and they excel at deterministic tasks. Humans, on the other hand, are exceptional at non-deterministic tasks like judging, synthesizing, and deciding.

Those non-deterministic tasks in a process are the ideal point for AI agents to incorporate a human in the loop, what Thakrar calls human harness. He pointed to a stakeholder mapping agent Zoho built for sales as an example, which takes the context of an initial meeting and third-party enriched data like a LinkedIn profile, weighs probabilities, and makes an educated guess about the stakeholder map.

“The initial goal was just to eliminate that task completely from the human workflow,” he said. “The stakeholder map is done, it’s in the folder, and you can look at it.”

But the agent would struggle to capture nuance. The meanings of titles in organizations always vary, and the politics and dynamics of any given meeting can be difficult for an AI agent to discern. Rather than keep feeding the agent data to try to make it intelligent enough to make those determinations, it was simpler and more efficient for the agent to create a proposed stakeholder map and hand it over to a human who could make changes and explain why those changes were necessary.

Ultimately, Thakrar said the agent still saved human team members time because the stakeholder map was usually pretty close, and the corrections also helped the model grow smarter by adding richer context.

Specialization

Specialization is transitioning a process from testing on a frontier model to production on a much narrower, smaller model. Once you’ve proven that an agent can do a job well, you want to stop paying master-craftsman rates to keep doing that one job well.

Specialization is all about capturing your subject matter experts’ best judgement and pattern recognition to build an open-weight, open source, trained, and fine-tuned model that can be deployed in your own data center.

“The true enterprise bet is to keep that orchestration layer, which is your IP and knowledge, in house,” Thakrar said. “You don’t want to host that on someone else’s model. The goal of everyone in enterprise should be to run, train, and host their own models.”

Over the past few years, I have learned that basic prompts produce inconsistent, hallucination-prone results that no executive would trust in production. What turned the tide was my move to advanced prompting techniques. These weren’t theoretical experiments; they became a practical foundation for reliable, measurable outcomes. I want to share the techniques that consistently delivered the biggest gains in my projects, complete with real before-and-after examples, copy-paste templates, lessons from failures and guidance on when to evolve beyond prompting to agentic systems.

Why advanced prompting still matters in enterprise settings

Sophisticated prompting remains essential for control, reliability and compliance. If you “ask nicely” and hope for the best, you need deterministic behavior, auditable reasoning and minimal risk of hallucination. Here’s what worked for me.

1. Chain-of-Thought (CoT) and its variants: Unlocking step-by-step reasoning

The problem: Models would jump to conclusions on complex analysis tasks, especially involving data interpretation or multi-step logic.

What I did: I started explicitly instructing the model to “think step by step” and show its reasoning.

Before (basic prompt): “Analyze last quarter’s sales data and recommend three actions.”

After (CoT prompt):

“You’re a senior business analyst. Analyze the following sales data step by step: [data]. First, identify the key trends. Second, calculate the rates and anomalies. Third, link findings to business context. Finally, recommend the three prioritized actions with expected impact. Explain your reasoning at each step.”  

Results: Accuracy and depth improved dramatically.

Variants that worked well: Self-consistency. I ran the same CoT prompt multiple times and took the majority consensus. This reduced variability significantly.

Template you can use:

You are [expert role]. Solve this problem by thinking step by step.

[Task or question]

For each step:

1. State your observation or calculation.

2. Explain the implication.

3. Proceed only when confident.

Final answer in this format: [structured output]

2. Tree-of-Thoughts (ToT): Exploring multiple reasoning paths

For truly complex decisions such as resource allocation or risk assessment, linear CoT isn’t enough. Tree-of-Thoughts lets the model generate and evaluate multiple branches.

Example: I was helping a client evaluate three potential vendor platforms for an AI deployment. A standard prompt gave a superficial comparison. With ToT

Prompt Snippet:

Explore three different reasoning paths for selecting the best vendor platform:

Path 1: Focus on cost and scalability.

Path 2: Focus on security, compliance and integration.

Path 3: Focus on innovation and long-term roadmap.

For each path, evaluate pros/cons against our requirements [list].

Then, compare the paths and recommend the strongest overall option with justification.

Outcome: The model surfaced nuanced trade-offs (e.g., one vendor had superior security, but higher integration cost).

When to use: Strategic planning, troubleshooting or scenarios with high uncertainty and multiple viable approaches.

3. ReAct (Reason+ Act) and prompt chaining: Moving toward agentic behavior

One of the biggest leaps I have noticed comes from combining reasoning with tool use and chaining prompts.

ReAct example: (used in data analytics workflow)

You are an AI analyst with access to tools. For the query below:

1. Reason about what information you need.

2. Choose the appropriate tool or action.

3. Observe the result.

4. Repeat until you can answer confidently.

Query: [user request]

In practice, I chained this with retrieval tools. One automated quarterly compliance reporting; the system reasoned about required data, pulled relevant records, validated them, and generated the reports.

4. Meta-prompting and self-reflection: Letting the model improve itself

Use the model to refine its own prompt. This is a huge time-saver.

You are an expert prompt engineer. Improve the following prompt for clarity, structure and effectiveness with [target model]. Make it more precise while preserving intent.

Original prompt: [paste]

Provide the improved version and explain your changes.

Self-reflection loops (asking the model to critique its own output and revise) are a game-changer for content generation and code-review tasks.

5. Multimodal and structured output techniques

With vision-enabled models, I started combining text with images (e.g., uploading architecture diagrams or dashboards).

Tip from experience: Be extremely specific in describing what the models should focus on.

Best practices I learned the hard way

• Start simple, then layer complexity: Over-engineered prompts from Day One usually backfire.
• Model specific tuning: Some models respond better to XML delimiters; others to explicit reasoning.
• Evaluation and versioning: Treat prompts like code if you track versions and run automated evals.
• Security guardrails: Always include instructions against prompt injections and respect data boundaries.
• When to stop prompting: For repetitive, high-stakes workflows, move to full agents or an orchestration framework.

Final takeaways for technical leaders

Advanced prompt engineering has now become a core competency for anyone responsible for enterprise AI outcomes. Start by picking one technique and apply it rigorously to a real business problem. Document before/ after and you will notice why it’s worth mastering.

The field continues evolving towards more automated and agentic systems, but the ability to precisely direct AI reasoning remains foundational.

This article is published as part of the Foundry Expert Contributor Network.
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Traditional phishing techniques are in decline as a result of the disruption of the Tycoon2FA phishing-as-a-service (PHaaS) platform, Microsoft said in a new report, “Email threat landscape: Q2 2026 trends and insights”.

“Phishing volume linked to the platform fell 92% from pre-disruption averages, including QR code phishing and CAPTCHA-gated phishing both declining from their March highs,” the company wrote in the report.

The takedown reduced activity across multiple phishing categories, forcing attackers to shift to newer delivery methods.

Riding this shift in were a few notable phishing campaigns, including an automated business email compromise (BEC) campaign that reached 42,000 organizations in under three hours, and a multi-stage phishing campaign that used nested email (EML) files, calendar invitations, and a Microsoft authentication redirect to deliver malware.

To counter phishing attacks, Microsoft recommends blocking emails containing known bad URLs/ subject fields, enabling password-less authentication methods, or moving to MFA for accounts that still require passwords.

Tycoon2FA disruption sent attackers exploring

The take-down of Tycoon2FA forced its operators to abandon portions of their infrastructure and rework hosting, domain registrations, and delivery mechanisms.

“After falling 15% in March and another 22% in April, Tycoon2FA-linked phishing volume dropped 74% in May to just 1.5 million messages, then fell another 20% in June to 1.2 million, by far the lowest monthly volumes observed in at least a year,” Microsoft said.

The decline extended to QR Code lures and fake CAPTCHA pages, two phishing techniques in which Tycoon2FA accounted for 12% and 14% of industry activity in June, respectively. This indicated that the platform’s customer base had not been able to migrate to a replacement infrastructure.

But cutting off one head of the hacker hydra only gave rise to new tactics elsewhere.

The adaptation came in the form of using Microsoft Teams as a social engineering channel. Attackers established conversations to build trust before attempting credential theft or delivering malicious payloads. “Teams-based phishing volume climbed steadily throughout Q2, with the average number of detected attacks rising 19% from March to April, holding roughly flat into May (+1%), then increasing another 10% into June,” Microsoft said.

Microsoft also observed a highly automated BEC campaign that reached over 67,000 users using scripted emails, Amazon Simple Email Service (SES), and engagement tracking, alongside a separate phishing campaign targeting 107,000 users that abused Microsoft’s authentication flow and trusted cloud services, including Teams archive recording and ICS calendar invite, to disguise malware delivery behind legitimate infrastructure.

Phishing changes but the defense doesn’t

While QR Code and Captcha-based phishing attacks dropped significantly in the second quarter, business email compromise (BEC) charted jumped 121% between March and April, before dropping down again in May.

QR Code phishing represented 8.3 million attacks in June 2026, down from a peak of 18.7 million in March. Similarly, Captcha-gated phishing fell from 12 million attacks in March to 2.2 million in June.

BEC attacks hit 9 million in March, falling to 3.9 million in June.

But even as these phishing classics lost momentum and newer techniques emerged, Microsoft’s defensive advice remained rooted in the basics. It noted organizations should complement email filtering with phishing-resistant authentication such as passkeys and phishing-resistant MFA to reduce the effectiveness of credential theft campaigns.

The company also recommended strengthening Exchange Online Protection and Microsoft Defender for Office 365 with capabilities such as Safe links and Zero-hour Auto Purge (ZAP), in which malicious emails already delivered to mailboxes are removed before they are read, alongside enforcing password-less authentication methods like Windows Hello, FIDO keys, and Microsoft Authenticator.

Microsoft concluded its report with a list of indicators of compromise (IoCs) from the threats observed in the quarter to support detection efforts.

This article first appeared on CSO.

Traditional phishing techniques are in decline as a result of the disruption of the Tycoon2FA phishing-as-a-service (PHaaS) platform, Microsoft said in a new report, “Email threat landscape: Q2 2026 trends and insights”.

“Phishing volume linked to the platform fell 92% from pre-disruption averages, including QR code phishing and CAPTCHA-gated phishing both declining from their March highs,” the company wrote in the report.

The takedown reduced activity across multiple phishing categories, forcing attackers to shift to newer delivery methods.

Riding this shift in were a few notable phishing campaigns, including an automated business email compromise (BEC) campaign that reached 42,000 organizations in under three hours, and a multi-stage phishing campaign that used nested email (EML) files, calendar invitations, and a Microsoft authentication redirect to deliver malware.

To counter phishing attacks, Microsoft recommends blocking emails containing known bad URLs/ subject fields, enabling password-less authentication methods, or moving to MFA for accounts that still require passwords.

Tycoon2FA disruption sent attackers exploring

The take-down of Tycoon2FA forced its operators to abandon portions of their infrastructure and rework hosting, domain registrations, and delivery mechanisms.

“After falling 15% in March and another 22% in April, Tycoon2FA-linked phishing volume dropped 74% in May to just 1.5 million messages, then fell another 20% in June to 1.2 million, by far the lowest monthly volumes observed in at least a year,” Microsoft said.

The decline extended to QR Code lures and fake CAPTCHA pages, two phishing techniques in which Tycoon2FA accounted for 12% and 14% of industry activity in June, respectively. This indicated that the platform’s customer base had not been able to migrate to a replacement infrastructure.

But cutting off one head of the hacker hydra only gave rise to new tactics elsewhere.

The adaptation came in the form of using Microsoft Teams as a social engineering channel. Attackers established conversations to build trust before attempting credential theft or delivering malicious payloads. “Teams-based phishing volume climbed steadily throughout Q2, with the average number of detected attacks rising 19% from March to April, holding roughly flat into May (+1%), then increasing another 10% into June,” Microsoft said.

Microsoft also observed a highly automated BEC campaign that reached over 67,000 users using scripted emails, Amazon Simple Email Service (SES), and engagement tracking, alongside a separate phishing campaign targeting 107,000 users that abused Microsoft’s authentication flow and trusted cloud services, including Teams archive recording and ICS calendar invite, to disguise malware delivery behind legitimate infrastructure.

Phishing changes but the defense doesn’t

While QR Code and Captcha-based phishing attacks dropped significantly in the second quarter, business email compromise (BEC) charted jumped 121% between March and April, before dropping down again in May.

QR Code phishing represented 8.3 million attacks in June 2026, down from a peak of 18.7 million in March. Similarly, Captcha-gated phishing fell from 12 million attacks in March to 2.2 million in June.

BEC attacks hit 9 million in March, falling to 3.9 million in June.

But even as these phishing classics lost momentum and newer techniques emerged, Microsoft’s defensive advice remained rooted in the basics. It noted organizations should complement email filtering with phishing-resistant authentication such as passkeys and phishing-resistant MFA to reduce the effectiveness of credential theft campaigns.

The company also recommended strengthening Exchange Online Protection and Microsoft Defender for Office 365 with capabilities such as Safe links and Zero-hour Auto Purge (ZAP), in which malicious emails already delivered to mailboxes are removed before they are read, alongside enforcing password-less authentication methods like Windows Hello, FIDO keys, and Microsoft Authenticator.

Microsoft concluded its report with a list of indicators of compromise (IoCs) from the threats observed in the quarter to support detection efforts.

The European Commission has fined Google a total of €890 million ($1 billion) for its breaches of the Digital Market Act (DMA).

Just over half the fine — €460 million — was because Google illegally gave preference to its own services in Google Search results.

The remainder was because in the Google Play store for Android apps, the company prevented app developers from leading consumers to alternative, often cheaper, purchase channels. Under the DMA, app developers who distribute their apps via Google Play or Apple’s App Store should be able to inform customers of alternative offers.

Now Google must give third-party services featuring in its results the same treatment as its own services, and allow developers of apps in the Play Store to communicate about offers both in and outside the Play Store, or face further fines.

The Commission first raised these issues with Google in March 2025. In April of this year, the Commission laid out plans as to how Google should allow other third-parties to share its searches, suggestions that the tech firm firmly resisted. Earlier this month, the Commission also said  Android should be open to other AI agents and not limited to Google’s own Gemini.

Google is not the only US company to have fallen foul of the DMA. In April 2025, Apple was fined €500 million for breaching the Act and, last month, the Commission fired the first shots at cloud hyperscalers Microsoft and Amazon.

Over the past year, I had the same conversation with almost every team starting an AI initiative. Should we build on Semantic Kernel, AutoGen or Foundry?

At first it felt like the most important architectural decision we’d make. Each framework had its own philosophy, each promised to be the foundation for enterprise AI, and picking the wrong one felt like an expensive mistake. I spent a lot of time helping teams weigh the trade-offs.

Looking back, I think we were asking the wrong question. I certainly was.

I watched teams spend months debating SDKs while the decisions that actually decided whether their applications survived production went unexamined. Some built elaborate orchestration layers for workflows that a few deterministic functions would have handled. Others avoided agent frameworks entirely and later found they’d designed themselves into a corner.

Then Microsoft settled it for us. It introduced the unified Agent Framework, quietly moved Semantic Kernel and AutoGen into maintenance mode, and the debate I’d spent months refereeing was suddenly over. Turns out the answer to “which of the three” was “none of the three, here’s a fourth.” The framework hit version 1.0 and general availability in April 2026, stable across .NET and Python.

What surprised me wasn’t the decision. It was how fast a debate that had eaten so much of our attention stopped mattering. Microsoft changed the menu.

It didn’t change the meal.

The framework was never the hard part

Framework selection dominated almost every early conversation I had about enterprise agents. Which SDK do we standardize on? Which orchestration model gives us the most flexibility? Which one is Microsoft actually betting on?

Fair questions. But after a year of watching these projects play out, I’ve slowly come around to a different view. Those weren’t the questions that decided anything.

The first question I ask now is much smaller. Does this thing actually need an agent?

It sounds obvious, and I still get it wrong sometimes. But it’s the mistake I see most. On one project, a team spent weeks designing a multi-agent workflow for a process that ran the same four steps every time: read a document, validate it, call an API, send a notification. The diagrams looked great. The system in production didn’t. A few well-tested functions would have been easier to build, easier to maintain and a lot easier to trust.

Part of this is just that “agent” has become the word everyone reaches for. Sometimes it’s the right call. Sometimes it’s a workflow we already knew how to build, wearing a newer label. An agent earns its complexity when it genuinely has to decide things you can’t predetermine, choosing between tools, adapting to what it finds, working out its own next step. If you already know every step, you have a workflow, and a workflow is usually the better engineering choice. The consolidation didn’t change that. It just made it easier to see.

What building production agents actually taught me

Once I stopped fixating on frameworks, the same three problems kept showing up. None of them had anything to do with the SDK.

Context beats model choice

Early on I spent a lot of time comparing models, the way you’d agonize over a restaurant menu and then order what you always order. Now I spend most of it thinking about context, which is far less fun and far more useful.

I’ve watched good models fail because they were handed too much, not too little. One team I worked with gave the model access to nearly every internal document they had on the theory that more information meant better answers. It went the other way. Responses got slower, less consistent and sometimes skipped right past the thing that actually mattered. When we cut the context down to only what the task needed, the quality jumped almost immediately. I didn’t predict that. It taught me to be suspicious of “just give it everything.”

The best agent systems I’ve worked on weren’t the ones with the biggest context windows. They were the ones careful about what reached the model, and when. That’s not something the framework hands you.

Failure is where the real work is

Most agent demos look great because they’re built around the happy path. Production doesn’t extend that courtesy.

I remember a project where everything held up in testing. Then a downstream API timed out after the agent had already completed several earlier steps. We couldn’t just restart, because part of the business process had already gone through. We ended up spending far more time on recovery logic than we ever spent on prompts. That project changed how I think about this work. The hard part was never getting the model to make a decision. It was making sure the system didn’t fall apart when reality refused to follow the script.

Tool calls fail partway through. APIs return inconsistent data. Models call the same tool over and over because the last answer wasn’t what they wanted. That’s not the exception; that’s a normal Tuesday. Whether you retry, roll back, pause for a human or push on with partial results is a judgment call, and no framework is going to make it for you.

Identity is the real security boundary

This one surprised me most. The moment an agent stops being a chatbot and starts touching real business systems, identity matters more than orchestration.

Every project gets to the same question eventually. Who is this agent actually acting as? The developer’s credentials? A service account? The user who asked? Get it wrong and you’ve built something autonomous running with more access than any single person should have, which is exactly the kind of thing that looks fine until an audit. The Agent Framework, like most modern tooling, makes it easier to wire agents to tools through standards like the Model Context Protocol. That helps. But where human approval belongs, what needs extra authorization, how much rope to give the thing, those are still yours to decide.

The surprises weren’t technical

Here’s what I didn’t see coming. The hardest part of last year wasn’t technical at all. It was organizational. The moment a team heard “agent,” expectations shifted under everyone’s feet. Business stakeholders started expecting full autonomy. Developers assumed the thing could reason its way through anything. People started designing for flexibility before we’d even agreed on what problem we were solving. The word did damage before any code did. I found myself spending as much time resetting expectations as I did discussing architecture.

Build for change, not for today’s winner

I don’t think the teams that struggled last year picked the wrong framework. Semantic Kernel was reasonable. AutoGen was reasonable. Foundry made sense for plenty of cases. I’d have signed off on any of them.

The ones that got hurt put all their eggs in one framework, treating it as the foundation of the whole system instead of as one more dependency. Microsoft provided a migration path. But teams that had tightly coupled their applications to framework-specific abstractions discovered that migrating and rewriting are not the same thing. That wasn’t Microsoft’s doing. It was their own architecture’s. The teams that moved easily had kept their business logic, prompts and orchestration loose enough to evolve independently of any one SDK. For them, the change was a manageable project, not a teardown.

For what it’s worth, nobody I work with is treating this as an emergency. Most are moving the smaller workloads first, watching how they behave and leaving the production-critical systems alone until they actually understand the new abstractions. That’s the right instinct. And I doubt this is the last consolidation we’ll see, the ecosystem is still young, frameworks will keep absorbing each other and over time the differences between them will be operational more than architectural.

I don’t regret the framework debates, honestly. They were reasonable at the time. What changed wasn’t Microsoft’s roadmap.

It was mine. Watching these systems run in production taught me that the framework is the easiest piece to swap out. Recovery logic, context management, security boundaries, the business workflow itself, those stay with you long after today’s SDK gets replaced by tomorrow’s.

So, Microsoft made one decision easier by turning three frameworks into one. Good. Five years from now we’ll be on different tools, and we’ll still be asking the same handful of questions.

Does this actually need an agent? Does it have the right context? Can it recover when something breaks, because something will? Is it acting as the right person?

Those questions outlast every rewrite. That’s where I’ve learned to put my effort.

Frameworks come and go. Good architecture has to survive all of them.

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Over the past few years, I have learned that basic prompts produce inconsistent, hallucination-prone results that no executive would trust in production. What turned the tide was my move to advanced prompting techniques. These weren’t theoretical experiments; they became a practical foundation for reliable, measurable outcomes. I want to share the techniques that consistently delivered the biggest gains in my projects, complete with real before-and-after examples, copy-paste templates, lessons from failures and guidance on when to evolve beyond prompting to agentic systems.

Why advanced prompting still matters in enterprise settings

Sophisticated prompting remains essential for control, reliability and compliance. If you “ask nicely” and hope for the best, you need deterministic behavior, auditable reasoning and minimal risk of hallucination. Here’s what worked for me.

1. Chain-of-Thought (CoT) and its variants: Unlocking step-by-step reasoning

The problem: Models would jump to conclusions on complex analysis tasks, especially involving data interpretation or multi-step logic.

What I did: I started explicitly instructing the model to “think step by step” and show its reasoning.

Before (basic prompt): “Analyze last quarter’s sales data and recommend three actions.”

After (CoT prompt):

“You’re a senior business analyst. Analyze the following sales data step by step: [data]. First, identify the key trends. Second, calculate the rates and anomalies. Third, link findings to business context. Finally, recommend the three prioritized actions with expected impact. Explain your reasoning at each step.”  

Results: Accuracy and depth improved dramatically.

Variants that worked well: Self-consistency. I ran the same CoT prompt multiple times and took the majority consensus. This reduced variability significantly.

Template you can use:

You are [expert role]. Solve this problem by thinking step by step.

[Task or question]

For each step:

1. State your observation or calculation.

2. Explain the implication.

3. Proceed only when confident.

Final answer in this format: [structured output]

2. Tree-of-Thoughts (ToT): Exploring multiple reasoning paths

For truly complex decisions such as resource allocation or risk assessment, linear CoT isn’t enough. Tree-of-Thoughts lets the model generate and evaluate multiple branches.

Example: I was helping a client evaluate three potential vendor platforms for an AI deployment. A standard prompt gave a superficial comparison. With ToT

Prompt Snippet:

Explore three different reasoning paths for selecting the best vendor platform:

Path 1: Focus on cost and scalability.

Path 2: Focus on security, compliance and integration.

Path 3: Focus on innovation and long-term roadmap.

For each path, evaluate pros/cons against our requirements [list].

Then, compare the paths and recommend the strongest overall option with justification.

Outcome: The model surfaced nuanced trade-offs (e.g., one vendor had superior security, but higher integration cost).

When to use: Strategic planning, troubleshooting or scenarios with high uncertainty and multiple viable approaches.

3. ReAct (Reason+ Act) and prompt chaining: Moving toward agentic behavior

One of the biggest leaps I have noticed comes from combining reasoning with tool use and chaining prompts.

ReAct example: (used in data analytics workflow)

You are an AI analyst with access to tools. For the query below:

1. Reason about what information you need.

2. Choose the appropriate tool or action.

3. Observe the result.

4. Repeat until you can answer confidently.

Query: [user request]

In practice, I chained this with retrieval tools. One automated quarterly compliance reporting; the system reasoned about required data, pulled relevant records, validated them, and generated the reports.

4. Meta-prompting and self-reflection: Letting the model improve itself

Use the model to refine its own prompt. This is a huge time-saver.

You are an expert prompt engineer. Improve the following prompt for clarity, structure and effectiveness with [target model]. Make it more precise while preserving intent.

Original prompt: [paste]

Provide the improved version and explain your changes.

Self-reflection loops (asking the model to critique its own output and revise) are a game-changer for content generation and code-review tasks.

5. Multimodal and structured output techniques

With vision-enabled models, I started combining text with images (e.g., uploading architecture diagrams or dashboards).

Tip from experience: Be extremely specific in describing what the models should focus on.

Best practices I learned the hard way

• Start simple, then layer complexity: Over-engineered prompts from Day One usually backfire.
• Model specific tuning: Some models respond better to XML delimiters; others to explicit reasoning.
• Evaluation and versioning: Treat prompts like code if you track versions and run automated evals.
• Security guardrails: Always include instructions against prompt injections and respect data boundaries.
• When to stop prompting: For repetitive, high-stakes workflows, move to full agents or an orchestration framework.

Final takeaways for technical leaders

Advanced prompt engineering has now become a core competency for anyone responsible for enterprise AI outcomes. Start by picking one technique and apply it rigorously to a real business problem. Document before/ after and you will notice why it’s worth mastering.

The field continues evolving towards more automated and agentic systems, but the ability to precisely direct AI reasoning remains foundational.

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When it comes to building an effective AI stack, context is king and power isn’t everything it’s cracked up to be.

“Smaller, smarter, safer — this is a bet our company has taken in how we deploy AI internally,” said Ricky Thakrar, head of sales and account management at Zoho, provider of a suite of popular cloud-based software solutions for sales, marketing, and finance.

“I’m on the business side, and so decisions made by our CIO and IT folks affect me directly, and my teams’ workflows and processes,” he added.

Speaking to a room of tech leaders at the CIO 100 Leadership Live New York event last week, Thakrar explained that every company wants the speed of AI-generated work wedded to the quality of human work, even though these two are diametrically opposed. No amount of model upgrades or spend will close that gap, so the only way forward is to architect your way out. Thakrar encapsulated this idea in a simple formula:

• Smaller: Stop deploying maximum firepower on every task. Many tasks don’t need it.
• Smarter: The system around the model decides more than the model does.
• Safer: Verify at the point a mistake gets locked in, not just downstream of it.

He noted that organizations that win with AI won’t be those deploying the biggest, most powerful models or the most sophisticated architecture, but the ones that figure out that the model is the easy part and the right architecture is harder. That means understanding the hardest element, and the biggest differentiator, is building a human system that learns and compounds alongside agentic systems.

To get it right, organizations need to prioritize the context layer. The size of frontier models like the GPT series, Claude, and Gemini mostly exist to compensate for missing context, Thakrar explained. Without enough context, models need to be able to reason harder and infer more about what a user actually means because it doesn’t know the user’s account, process, or history. A rich context layer makes it possible for enterprises to run workloads on much smaller, lower-power models.

“The intelligence moves from the model into the architecture around it,” he said.

A steep learning curve

One of Zoho’s earliest AI agents was a churn management agent to help the account management team detect churn in customer subscriptions. So when a subscription became inactive, the agent would collect context from notes, meeting recordings, and Zoho’s data enrichment tool, then create a summary of reasons the account might have churned, and schedule a call.

“What happened was I got this churn agent a couple months later, already embedded in our CRM, and within a week my team no longer trusted that agent,” Thakrar said. “The reason is we forgot to collect one very key point.”

In Zoho’s CRM, when a customer buys a bundle of products, that bundle is represented as a single line item. That means the status of any products the customer may have previously purchased individually changes to inactive as they’re moved to the bundle. That’s not churn, but it was interpreted it that way. Zoho fixed it in the second version of the agent.

Then a new problem arose. Many potential customers first purchase Zoho products as pilots or sandboxes. As those customers move from pilot to live instance, they close down the pilot versions. And again, the CRM would record that as subscriptions going inactive.

“The trust deteriorates again because everyone got excited for version 2,” Thakrar said.

Sometimes, a certain product might not be the best fit for a customer and Thakrar’s team will suggest the customer move to another product. That’s deliberate churn, not a churn risk.

“You may have a similar story like this where the agent sounds so good, it’s going to do something quick and add value, but it’s missing context from the account managers, and there are so many more pieces we’re still building out,” Thakrar said. “It’s been almost a year and the problem I have is my team still doesn’t trust it. They’ll see [a message from the agent] and go out and do all the research anyway to make sure it gave the correct answer.”

The team is more on top of potential churn, though, but the promised productivity gains have yet to materialize because the agent has to earn back lost trust due to a lack of context.

“My goal for this year is having an AI-assisted customer journey from sales to account management where the handoff is clean, the context flows, and every piece of information we gather about a customer is weighed, identified, and coached so the sales team can close more deals,” he said.

Zoho’s early experience with agents has led to the idea that constrained, context-rich, deterministic architectures consistently outperform expensive models bolted onto fragmented systems. It all comes down to three pillars: routing, harness, and specialization.

Routing

Routing is about sending workloads to the proper model for the job, which entails providing enough context to a given task that a small, cheap model can handle it without the need for spare reasoning capacity to fill gaps.

Frontier models are expensive and companies can burn through a year’s budget worth of tokens in months. But most tasks can be handled by much smaller, more constrained models at a fraction of the cost.

“You don’t always have to pay the frontier guys for every task,” he said. “We’ve observed with some clients that we could save them 95% with a 3 billion parameter model.”

Harness

An AI agent harness is the software infrastructure scaffolding around an LLM that differentiates an agent from a chatbot. It’s what enables an agent to act on tasks rather than simply respond to prompts. A model reasons through a problem and decides what to do about it. The harness connects the model to the tools, systems, memory, guardrails, and execution environments required to perform the actions determined by the model. The term is frequently used more or less interchangeably with orchestration layer.

“It’s the process around the model, which matters way more than the model itself,” Thakrar said.

In benchmark tests, a superior harness on a less powerful model produces better results than an inferior harness on a much bigger model.

For the best results, Thakrar said, it’s essential to understand the deterministic and non-deterministic elements of a given workload, and build that into the architecture. Machines can read, organize, and validate, and they excel at deterministic tasks. Humans, on the other hand, are exceptional at non-deterministic tasks like judging, synthesizing, and deciding.

Those non-deterministic tasks in a process are the ideal point for AI agents to incorporate a human in the loop, what Thakrar calls human harness. He pointed to a stakeholder mapping agent Zoho built for sales as an example, which takes the context of an initial meeting and third-party enriched data like a LinkedIn profile, weighs probabilities, and makes an educated guess about the stakeholder map.

“The initial goal was just to eliminate that task completely from the human workflow,” he said. “The stakeholder map is done, it’s in the folder, and you can look at it.”

But the agent would struggle to capture nuance. The meanings of titles in organizations always vary, and the politics and dynamics of any given meeting can be difficult for an AI agent to discern. Rather than keep feeding the agent data to try to make it intelligent enough to make those determinations, it was simpler and more efficient for the agent to create a proposed stakeholder map and hand it over to a human who could make changes and explain why those changes were necessary.

Ultimately, Thakrar said the agent still saved human team members time because the stakeholder map was usually pretty close, and the corrections also helped the model grow smarter by adding richer context.

Specialization

Specialization is transitioning a process from testing on a frontier model to production on a much narrower, smaller model. Once you’ve proven that an agent can do a job well, you want to stop paying master-craftsman rates to keep doing that one job well.

Specialization is all about capturing your subject matter experts’ best judgement and pattern recognition to build an open-weight, open source, trained, and fine-tuned model that can be deployed in your own data center.

“The true enterprise bet is to keep that orchestration layer, which is your IP and knowledge, in house,” Thakrar said. “You don’t want to host that on someone else’s model. The goal of everyone in enterprise should be to run, train, and host their own models.”

Some of OpenAI’s most powerful AI models teamed up to escape their sandbox and attack systems at Hugging Face in a cybersecurity evaluation gone wrong, the company has admitted. The models under test were modified to allow them to perform potentially harmful actions that production versions would refuse. The incident highlights how, if AI prompt guardrails fail or, as in this incident, are removed, then enterprises must have robust sandboxing or other technical restrictions in place to protect systems.

In OpenAI’s evaluation, GPT-5.6 Sol and a more capable pre-release model were competing to solve cybersecurity challenges in ExploitGym, a benchmarking tool for cybersecurity capabilities. They concluded that systems at Hugging Face could have the answers, and set out to gain access, OpenAI wrote in a blog post about the attack on Hugging Face.

ExploitGym challenges AI models to turn security vulnerabilities into attack exploits. OpenAI gave its models limited access to the internet through a package-registry proxy to download code to build their attacks. However, the models exploited a zero-day vulnerability in the proxy to obtain unrestricted internet access, then used stolen credentials and other flaws to access Hugging Face systems.

For CIOs and CISOs, the concern extends beyond cybersecurity research. AI agents connected to corporate databases, source code repositories, or payment systems could expose sensitive resources unless access controls and sandboxing continue to work when model-level safeguards fail.

“Prompt guardrails are not security controls,” said Biswajeet Mahapatra, principal analyst at Forrester. “They are behavioral controls that can fail, be bypassed, or be intentionally disabled during testing.”

How containment failed

Despite the relaxed model safeguards, the surrounding infrastructure was supposed to contain the activity. Network access was restricted to an internally hosted third-party service that acted as a proxy and cache for software package registries. Such proxies are typically used in the enterprise to protect against software supply chain attacks coming from the outside.

OpenAI said the models discovered a zero-day vulnerability in the service, exploited it and carried out privilege escalation and lateral movement until they reached a node with open internet access.

Once online, the models inferred that Hugging Face might hold models, datasets or solutions related to ExploitGym. OpenAI said that, in one attack path, the models combined stolen credentials with zero-day vulnerabilities to obtain remote code execution on Hugging Face servers.

In its account of the activity on its infrastructure, Hugging Face said a malicious dataset abused two code-execution paths in its data-processing pipeline. The actor then obtained node-level access, harvested cloud and cluster credentials, and moved into several internal clusters.

OpenAI said the models ultimately obtained ExploitGym test solutions directly from a Hugging Face production database. The models remained focused on solving the benchmark, despite the lengths to which they went to achieve that objective, it said.

Sanchit Vir Gogia, chief analyst at Greyhound Research, said the package-registry proxy should concern enterprise security teams because it was a narrowly permitted exception inside an otherwise restricted environment.

“Every enterprise estate is built from exceptions of exactly that kind,” he said.

In this incident, OpenAI’s models were performing the intended — albeit by unintended means — but enterprises should take care that their own AI systems are kept on target.

Mahapatra said enterprises should treat AI agents as “high-risk non-human identities,” confining each one to an isolated environment where access is limited to the assigned task and credentials expire quickly.

“An acceptable blast radius means a compromised agent can affect only a single workflow, dataset, or application rather than providing a pathway into broader enterprise infrastructure,” Mahapatra said.

And Gogia warned that services allowed to reach package registries, update systems, or other external resources can become escape routes if they are not subjected to the same scrutiny as the agent itself.

Defenses enterprises need

Hugging Face said the intrusion resulted in unauthorized access to a limited number of internal datasets and several credentials used by its services. It found no evidence that public models, datasets or Spaces had been altered and said its published software packages and container images were not compromised.

The company closed the code-execution paths used to gain access and rebuilt the affected nodes. It also revoked exposed credentials and tightened the rules governing workloads admitted to its clusters.

Whether they are keeping their own AIs in or rogue Ais out, Gogia said enterprises should test whether their containment boundaries work, rather than relying on architecture diagrams or stated policies. Such tests should attempt to obtain credentials, cross trust boundaries and reach systems outside the agent’s assigned task.

Mahapatra said enterprises should assume that one containment layer may fail and ensure that an agent’s access cannot provide a route into unrelated applications or broader corporate infrastructure.

OpenAI said it is still investigating the incident with Hugging Face, and is imposing stricter configurations on its research environment while the vulnerabilities are being addressed, even if that means slowing down its research. It is also strengthening containment and monitoring around future evaluations.

Last year Anthropic gave away one of the most successful things it has ever built. And, no, I’m not talking about Claude. I’m referring to MCP, the now ubiquitous Model Context Protocol, which Anthropic donated to the Linux Foundation’s new Agentic AI Foundation⁠. At the time, MCP was pulling nearly 100 million monthly SDK downloads across more than 10,000 active servers⁠, prompting the question as to why any company would give up such a popular piece of technology.

Google did much the same months earlier, handing its Agent2Agent (A2A) protocol to the Linux Foundation⁠ with AWS, Cisco, Microsoft, Salesforce, SAP, and ServiceNow signing on as founding members. OpenAI, not to be outdone, supports remote MCP servers in its Responses API⁠, sits on the MCP steering committee, and contributed AGENTS.md to that same foundation alongside its fiercest rival’s protocol.

It’s like Game of Thrones, except the principal AI powers seek regime change through seeming acts of beneficence rather than violence. For those who have been around for a while, it’s also entirely predictable, following a similar script we’ve seen in the cloud, on-premises servers, and more. Platform companies don’t give away technologies they’ve stopped caring about. They give away technologies they no longer need to own because competitive advantage has shifted to new ground.

What does this mean for AI?

Gravity has shifted before

Google has long been an exceptionally active contributor to open source. As I wrote in 2017, Google wasn’t open sourcing TensorFlow and Kubernetes out of generosity but rather turning these open source assets into on-ramps for Google Cloud. Google was playing catch-up to AWS and Microsoft. As then Google product manager Martin Buhr said, the company hoped to “create a gravity well in the market for container-based apps [so] that a significant percentage of them will end up with us.”

In other words, platform companies routinely commoditize one layer of the stack so they can compete somewhere where they hold a stronger hand.

GitHub may be an even better example. Git is open. Anyone can host a Git repository and, once upon a time, different companies did just that. Yet GitHub became the default place software development happens for millions of developers. Nobody pays for Git, but lots of people pay for GitHub. We’re seeing this same phenomenon play out in AI.

Trading contributions for control

Anthropic and OpenAI have both pretended at being all for humanity’s good, but that’s not a good explanation for why they’re racing to give away things like MCP. The deeper reason is that the model itself has turned out to be a poor place to build a lasting moat, and they’re trying to figure out what’s next. As I pointed out recently, the frontier model leaderboards change almost weekly. As such, enterprises shouldn’t build their AI strategy around the assumption that any one vendor will remain permanently ahead on model quality. Instead, as I suggested, AI may be sexy, but the “dull reality” is connecting those models to enterprise data, workflows, etc.

The AI companies understand this better than anyone. Sure, they’ll continue spending billions training ever more capable models because frontier models attract developers, generate headlines, and open enterprise doors. But they’re also quietly acknowledging that benchmark leadership alone doesn’t create a durable platform.

Developers return to the places where their tools, workflows, teammates, and accumulated work already live. Enterprises double down on the systems where their data, permissions, governance, and business processes are already connected. Every new integration makes that destination a little harder to leave, and every new workflow increases its pull. That’s what MCP, A2A, etc., are all about: increasing gravity around the models.

Every major AI company wants to become the place where AI-assisted work naturally happens, and they’re now amassing armies of forward deployed engineers and trying other means to get legacy infrastructure to tie back to their frontier models. The enterprise incumbents want the same thing, but from the opposite direction. They don’t need to own the frontier; instead they need to connect the frontier to the systems that already safely run the business.

That’s why I’m skeptical whenever someone confidently predicts that AI will sweep away enterprise software. I’ve seen this movie before. Developers absolutely live on the frontier, but enterprises don’t. Enterprises create value by connecting new capabilities to decades of accumulated applications, data, policies, and business processes. The newest model matters, and so does the newest agent framework. But neither creates much business value until it’s connected to customer records, financial systems, supply chains, HR data, and everything else enterprises already depend on.

That’s where incumbents still possess enormous gravitational pull. My employer, Oracle, certainly believes so, just as Microsoft, SAP, Salesforce, and ServiceNow do. (Disclosure: I run developer relations at Oracle, which participates in the Agentic AI Foundation.) Ironically, open protocols strengthen that position rather than weaken it. If every model can speak MCP and every agent can interoperate through common standards, enterprises gain the freedom to adopt whichever frontier technology looks best without rebuilding every integration. The protocol becomes interchangeable.

Open standards don’t stop gravity

None of this diminishes the importance of open standards. MCP succeeded because it solves a genuine problem. Developers shouldn’t have to build a custom connector every time an AI application needs access to a database or other business system. Neutral governance also matters because nobody wants foundational infrastructure controlled by a direct competitor. But we shouldn’t confuse open interfaces with open markets.

An enterprise may find it easy to swap one MCP-compatible model for another while still remaining deeply dependent on the place where its prompts, evaluations, security policies, and employee habits have accumulated. Again, we’ve seen this before. Kubernetes made workloads dramatically more portable without making AWS, Microsoft Azure, and Google Cloud interchangeable. SQL has been standardized for decades, yet databases remain fiercely differentiated businesses. Standards reduce friction, but they rarely eliminate competitive advantage. They simply move it.

In like manner, Anthropic, Google, OpenAI, and others are happily standardizing how models, agents, tools, and enterprise systems communicate because they don’t expect the connection itself to determine the winner. Instead they expect to win by becoming the place where AI-assisted work naturally accumulates. Along the way, we’re going to see copious quantities of code given away, increasing developer productivity for all and outsized financial bonanzas for a few. Game on.

Last year Anthropic gave away one of the most successful things it has ever built. And, no, I’m not talking about Claude. I’m referring to MCP, the now ubiquitous Model Context Protocol, which Anthropic donated to the Linux Foundation’s new Agentic AI Foundation⁠. At the time, MCP was pulling nearly 100 million monthly SDK downloads across more than 10,000 active servers⁠, prompting the question as to why any company would give up such a popular piece of technology.

Google did much the same months earlier, handing its Agent2Agent (A2A) protocol to the Linux Foundation⁠ with AWS, Cisco, Microsoft, Salesforce, SAP, and ServiceNow signing on as founding members. OpenAI, not to be outdone, supports remote MCP servers in its Responses API⁠, sits on the MCP steering committee, and contributed AGENTS.md to that same foundation alongside its fiercest rival’s protocol.

It’s like Game of Thrones, except the principal AI powers seek regime change through seeming acts of beneficence rather than violence. For those who have been around for a while, it’s also entirely predictable, following a similar script we’ve seen in the cloud, on-premises servers, and more. Platform companies don’t give away technologies they’ve stopped caring about. They give away technologies they no longer need to own because competitive advantage has shifted to new ground.

What does this mean for AI?

Gravity has shifted before

Google has long been an exceptionally active contributor to open source. As I wrote in 2017, Google wasn’t open sourcing TensorFlow and Kubernetes out of generosity but rather turning these open source assets into on-ramps for Google Cloud. Google was playing catch-up to AWS and Microsoft. As then Google product manager Martin Buhr said, the company hoped to “create a gravity well in the market for container-based apps [so] that a significant percentage of them will end up with us.”

In other words, platform companies routinely commoditize one layer of the stack so they can compete somewhere they hold a stronger hand.

GitHub may be an even better example. Git is open. Anyone can host a Git repository and, once upon a time, different companies did just that. Yet GitHub became the default place software development happens for millions of developers. Nobody pays for Git, but lots of people pay for GitHub. We’re seeing this same phenomenon play out in AI.

Trading contributions for control

Anthrophic and OpenAI have both pretended at being all for humanity’s good, but that’s not a good explanation for why they’re racing to give away things like MCP. The deeper reason is that the model itself has turned out to be a poor place to build a lasting moat, and they’re trying to figure out what’s next. As I pointed out recently, the frontier model leaderboards change almost weekly. As such, enterprises shouldn’t build their AI strategy around the assumption that any one vendor will remain permanently ahead on model quality. Instead, as I suggested, AI may be sexy, but the “dull reality” is connecting those models to enterprise data, workflows, etc.

The AI companies understand this better than anyone. Sure, they’ll continue spending billions training ever more capable models because frontier models attract developers, generate headlines, and open enterprise doors. But they’re also quietly acknowledging that benchmark leadership alone doesn’t create a durable platform.

Developers return to the places where their tools, workflows, teammates, and accumulated work already live. Enterprises double down on the systems where their data, permissions, governance, and business processes are already connected. Every new integration makes that destination a little harder to leave, and every new workflow increases its pull. That’s what MCP, A2A, etc., are all about: increasing gravity around the models.

Every major AI company wants to become the place where AI-assisted work naturally happens, and they’re now amassing armies of forward deployed engineers and trying other means to get legacy infrastructure to tie back to their frontier models. The enterprise incumbents want the same thing, but from the opposite direction. They don’t need to own the frontier; instead they need to connect the frontier to the systems that already safely run the business.

That’s why I’m skeptical whenever someone confidently predicts that AI will sweep away enterprise software. I’ve seen this movie before. Developers absolutely live on the frontier, but enterprises don’t. Enterprises create value by connecting new capabilities to decades of accumulated applications, data, policies, and business processes. The newest model matters, and so does the newest agent framework. But neither creates much business value until it’s connected to customer records, financial systems, supply chains, HR data, and everything else enterprises already depend on.

That’s where incumbents still possess enormous gravitational pull. My employer, Oracle, certainly believes so, just as Microsoft, SAP, Salesforce, and ServiceNow do. (Disclosure: I run developer relations at Oracle, which participates in the Agentic AI Foundation.) Ironically, open protocols strengthen that position rather than weaken it. If every model can speak MCP and every agent can interoperate through common standards, enterprises gain the freedom to adopt whichever frontier technology looks best without rebuilding every integration. The protocol becomes interchangeable.

Open standards don’t stop gravity

None of this diminishes the importance of open standards. MCP succeeded because it solves a genuine problem. Developers shouldn’t have to build a custom connector every time an AI application needs access to a database or other business system. Neutral governance also matters because nobody wants foundational infrastructure controlled by a direct competitor. But we shouldn’t confuse open interfaces with open markets.

An enterprise may find it easy to swap one MCP-compatible model for another while still remaining deeply dependent on the place where its prompts, evaluations, security policies, and employee habits have accumulated. Again, we’ve seen this before. Kubernetes made workloads dramatically more portable without making AWS, Azure, and Google Cloud interchangeable. SQL has been standardized for decades, yet databases remain fiercely differentiated businesses. Standards reduce friction, but they rarely eliminate competitive advantage. They simply move it.

In like manner, Anthropic, Google, OpenAI, and others are happily standardizing how models, agents, tools, and enterprise systems communicate because they don’t expect the connection itself to determine the winner. Instead they expect to win by becoming the place where AI-assisted work naturally accumulates. Along the way, we’re going to see copious quantities of code given away, increasing developer productivity for all and outsized financial bonanzas for a few. Game on.

See also:

• What Anthropic Glasswing reveals about the future of vulnerability discovery
• Anthropic’s Mythos signals a structural cybersecurity shift
• Beware the ‘son of Mythos,’ security experts warn
• Mythos is a signal, not a siren: What frontier AI should change for CISOs

An automated chatbot working for Anthropic this month shot down a Wiz researcher’s security hole report, saying that it “falls outside of the Claude Code threat model.” That was news to the security researchers at Wiz. 

It also turned out to be news to Anthropic execs, who had a very different view. 

In reality, Anthropic was one of many victims of the hole — including Amazon, Google and Cursor, among others. But what makes the incident so bizarre is that, far from dismissing the threat, Anthropic had detected it before the security researchers and had even patched it before the researchers alerted them. 

As these AI bots are wont to do, the bot didn’t merely reject the request. It confidently explained its rationale, even though its reasoning was wrong. 

“This falls outside our current threat model,” the chatbot said, according to a report by Wiz. “When the user first starts Claude Code in a directory, they must confirm that they trust the directory prior to starting the session. The scenario you describe involves a user explicitly confirming a permission prompt inside of a directory containing a malicious symlink, which falls outside of the Claude Code threat model.”

That researchers said Anthropic management later clarified the situation: “The symlink warning in the Edit/Write permission dialog shipped in v2.1.32 (Feb 5, 2026), nine days before this report was submitted to us. It was added as part of proactive security hardening based on internal review. The decline to comment was an autoreply from our triage system.” 

An autoreply from our triage system? How many other make-believe replies did this system send? And what level of damage is Anthropic exposing itself to? 

This is not just an Anthropic issue. There have been numerous enterprise bot glitches in communications  with customers. Some of my favorites include:

• Bots that chose on their own to cancel customers. (This actually was another Anthropic incident.) In this case, an Anthropic bot cancelled the AI account of a Swiss company that depended on the service. A lawyer got involved and the account was restored within a day — minus 80% of the data. Oops.
• A Cursor bot decided to log customers off when they switched devices, which it shouldn’t have done. The bot then emailed customers and lied that, “The logouts were expected behavior under a new login policy.” A Fortune story detailed how “the news spread rapidly in the developer community, leading to reports of users cancelling their subscriptions, while some complained about the lack of transparency. Cofounder Michael Truell finally posted on Reddit acknowledging the ‘incorrect response from a front-line AI support bot’ and said it was investigating a bug that logged users out. ‘Apologies about the confusion here,’ he wrote.”
• Voters in Scottish elections were tricked by government AI bots that “variously invented fictitious scandals, gave the wrong date for the election, claimed wrongly that voters in Scottish elections needed ID at polling stations and placed candidates in the wrong contests.”
• And let’s not forge the classic story about the Air Canada bot, where “Air Canada was ordered to compensate a customer after its chatbot gave incorrect information about the airline’s bereavement fare policy. The tribunal found that Air Canada was responsible for information provided through its website, including the chatbot.”

Let’s be clear, here: Bots should be limited to relaying only pre-approved scripts. 

Generative AI allows for far greater chatbot sophistication, but that also means the chance of far greater errors. This is untenable in any business function. And when the app is pretending to be a human — and interacting with human customers — it’s even more unacceptable.

For a decade, Kubernetes was the right answer. It organized containers, scaled services horizontally and gave platform teams a shared vocabulary for running software in production. It abstracted away enough of the underlying complexity that engineers could stop thinking about servers and start thinking about services. Most cloud-native infrastructure today is built on top of it, directly or in spirit, and EKS made that model the default for the majority of enterprise teams running workloads on AWS.

The workload that defined that era was the stateless HTTP request, fast in, fast out, disposable. A user action triggers a request, the request hits a service, the service returns a response and the container is done. Kubernetes was optimized for that pattern down to the scheduler internals: Bin-pack containers onto nodes, autoscale on CPU and memory, evict and reschedule when something goes wrong. The whole system is tuned around the assumption that individual units of work are short, stateless and interchangeable.

That assumption no longer holds for the workloads that matter most right now.

The agent workload is structurally different

Agents are long-running, stateful processes. They reason across time, call external tools, spawn subprocesses, write and execute code, and make decisions that depend on what happened five steps earlier in the same task. A single-agent workflow might run for minutes or hours, touching a dozen external systems and generating intermediate outputs that subsequent steps depend on. The compute layer for that kind of work needs to do things the old model was never asked to do. That is the new pattern: Execution infrastructure designed around agent semantics rather than request semantics.

The Kubernetes community itself has acknowledged this mismatch. In March 2026, Kubernetes SIG Apps published an introduction to Agent Sandbox, a new CRD-based abstraction designed specifically for singleton, stateful agent workloads. The framing is direct: The ecosystem is moving from short-lived, isolated tasks to deploying multiple, coordinated AI agents that run continuously, and mapping those workloads to traditional Kubernetes primitives requires an entirely new abstraction. The fact that the Kubernetes maintainers built a dedicated primitive for this, rather than recommending teams compose one from existing resources, is itself the clearest signal that agent execution does not fit the old model.

What agent execution actually requires

Concretely, it requires four things. First, isolated execution environments that provision in milliseconds, not minutes, so each agent task gets its own sandbox for code execution and tool calls without blocking the reasoning loop. The difference between a two-second environment and a two-minute environment is not a performance optimization; it determines whether the architecture is viable at all. Second, durable state management across the full task lifecycle, so an agent can pause, hand off or resume without re-initializing from scratch and burning tokens to reconstruct context it already built. Third, coordination primitives for multi-agent work: The ability to spawn subagents, pass structured outputs between them and track task dependencies across a graph of concurrent processes. Production agent systems are rarely single agents; they are pipelines of specialized agents with handoffs that need to be reliable and inspectable. Fourth, credentials and secrets management that travel with the execution context, so agents can authenticate to external services securely without exposing credentials in the task definition, logs or the environment variables of a shared container.

The mismatch shows up fast in production

Kubernetes and EKS expose the mismatch quickly in practice. Pod eviction terminates an agent mid-task with no clean recovery path. Autoscaling reads CPU utilization as the load signal, but an agent holding a long inference connection looks idle to the scheduler even when it is doing the most consequential work in the pipeline. Provisioning a new environment takes 45 seconds to two minutes on a well-tuned cluster; agent workloads need that in under two seconds or the reasoning loop stalls and the user experience degrades visibly. These are not edge cases or misconfigurations. They are the normal operating conditions for production agent workloads running on infrastructure that was not designed for them.

The utilization data makes the broader cost picture even starker. The 2026 State of Kubernetes Optimization Report from CAST AI, drawn from analysis of over 23,000 production clusters across AWS, Azure and GCP, found average CPU utilization at 8 percent, down from 10 percent the year prior. Memory utilization fell from 23 to 20 percent. CPU overprovisioning jumped from 40 to 69 percent year over year. These numbers reflect clusters running traditional workloads, and the pattern is worsening, not improving, as environments scale. Agent workloads compound this problem further. An agent holding an open inference connection or waiting on a tool call registers as idle to a scheduler that reads CPU and memory as the only meaningful load signals. The infrastructure responds to the wrong metric, overprovisioning capacity for demand it cannot measure, while the actual bottleneck, environment provisioning latency and state continuity, goes unaddressed.

Security is not the same problem it was before

Agent workloads change the threat model at the infrastructure level. A compromised stateless service exposes a narrow surface defined by its API contracts. A compromised agent exposes every system it can reach, every credential it holds and every action it is authorized to take on behalf of the user. Agents generate and execute their own code, make non-deterministic tool-call decisions and accumulate context across long-running sessions. Standard container namespacing does not contain that kind of risk. Kernel-level isolation, default-deny network egress, scoped credentials per session and agent-aware observability are not optional hardening steps. They are baseline requirements for running agents in production.

What teams that ship agents have already figured out

Some of the clearest evidence for this shift comes not from infrastructure vendors but from product engineering teams running agents at scale on their own code. In late 2025, Ramp’s engineering team published a detailed account of building Inspect, their internal background coding agent. Each Inspect session runs in a sandboxed VM with a full-stack development environment and deep integrations across their observability, CI, and deployment tooling. The architecture requirements map almost exactly to the four primitives above. Filesystem snapshots keep sessions starting in seconds rather than minutes. Sessions are isolated and stateful. The agent can run tests, review telemetry, query feature flags and visually verify frontend changes in a real browser. And the whole system supports unlimited concurrency, so engineers can spin up ten parallel sessions exploring different approaches to the same problem without contention.

The results speak for themselves. Within months of launch, roughly 30 percent of all pull requests merged to Ramp’s frontend and backend repositories were written by Inspect. That level of adoption was not mandated. It happened because the execution environment was fast enough, capable enough and well-integrated enough that the agent was strictly better than a local workflow for a meaningful share of tasks. The key insight from the Ramp case is not about the model. It is about the execution layer. As their team put it, session speed should only be limited by model-provider time-to-first-token; everything else, like cloning and installing, needs to be done before the session starts. That is a statement about infrastructure, not intelligence.

The ecosystem is catching up, but defaults are sticky

None of that is a criticism of the tools. Kubernetes solved exactly the problem it was designed for, and it solved it well. The issue is that infrastructure defaults are sticky. Teams inherit them, build on top of them and optimize within their constraints long after the underlying workload has changed. The Kubernetes community’s own response, the Agent Sandbox project under SIG Apps, validates the thesis that a new abstraction is necessary. The new primitives the community is building include warm pools for near-zero cold starts, lifecycle management for suspending and resuming idle agents without losing state, and pluggable kernel isolation for secure execution of untrusted code. These are not incremental improvements to existing resources. They are net-new abstractions that acknowledge the old model does not stretch to fit.

But adoption of purpose-built agent infrastructure remains early. Enterprises building agent pipelines today are largely running a request-oriented orchestration model against an execution-oriented workload, and the mismatch shows up in task failure rates, runaway costs and debugging cycles that have no good tooling because the observability layer was also designed for stateless services.

The structural advantage is available now

The infrastructure to close that gap exists now. The prerequisite is recognizing that agent execution is a first-class compute pattern with its own primitives and its own requirements, not a variant of the stateless service model that defined the last decade. Teams that make that shift early will have a meaningful structural advantage. The ones that do not will spend the next two years wondering why their agent systems are unreliable at a scale that should be tractable.

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Today’s CIOs must master a complex balancing act of maintaining operational excellence while enabling AI experimentation, modernizing legacy environments while accelerating innovation, leading workforce transformation while maintaining culture, and communicating fluently across boards, business units, customers, and technical teams alike.

Few leaders understand this balancing act better than former Verizon CIO Jane Connell. Over her career, Connell has helped some of the world’s largest enterprises modernize operations, reduce complexity, and transform how technology enables business value at scale. As a 2026 CIO Hall of Fame inductee, she is widely respected not only for operational excellence and strategic vision but also for her commitment to mentoring, workforce transformation, and preparing the next generation of leaders for a rapidly changing future.

On a recent episode of the Tech Whisperers podcast, we unpacked Connell’s unconventional leadership story and the playbook that has shaped one of technology’s most impactful leaders. In this exclusive interview after the show, edited for length and clarity, Connell shares more lessons from her Hall of Fame journey and why she believes the future of technology leadership will depend less on org charts and more on curiosity, credibility, and human connection.

Dan Roberts: When you think about preparing the next generation of technology leaders, what capabilities or mindsets do you believe will matter most in this next era?

Jane Connell: One is curiosity, or what I call the “why” factor: What do we need to do and why do we need to do it? It’s having a mindset of unlocking the art of the possible. You must be comfortable with what you know, what you don’t know, and asking the question why, because in this era of AI and where technology is going, it’s not about automating things you know; it’s about what you don’t already know, and what that unlocks. AI creates patterns and opportunities and re-engineers through its own intelligence, so there has to be a lot of instinct involved, and you’re going to have to understand and learn what it’s telling you.

I’m on the board of Rutgers, and one of the conversations we’re in with future leaders in education is that you don’t have those entry-level jobs anymore. They’re going to be AI. But those were building blocks for us. We came up the ranks and did those jobs, and that created the knowledge. [Future leaders are] not going to have that, so how do you create the foundation of knowledge — which is that art of asking why or what — to question if the bots or the patterns are biased or wrong. You’re not going to have the experience to rely on and say, “That’s wrong; I know that’s wrong because I did those. I know how this operates.”

Second is having humility and being comfortable in your skin — that you don’t know everything, but you’re going to learn it. You’re going to involve yourself with people. It’s about workforce structure, not organizational structure. Who do you need to talk to, and what do you have to find out?

I also believe followership is going to be huge, because the way work gets done is not hierarchical. It’s going to be engineered based on the process and AI. You have to create followership of people working together, and they’ve got to want to work with you. This isn’t going be “you work for me, do as I say.” Followership is going to be a key skill for influencing and organically having that kind of impact, versus someone with authority.

With that is the accountability to have high integrity, be credible, and be a person someone would trust. Because all this is going to break down the hierarchy of authority, you have to bring that human side and be a really good leader, which means people want to follow you, they trust you, they want to work with you, and they know you’re going to take them to a better place.

One recurring theme throughout your career has been your ability to bridge deep technology expertise with strong business acumen. Why is that combination becoming even more critical in the age of AI and digital transformation?

You can’t impact anything tech-alone. It all resides on having business acumen and then having the technical ability to know how to use tech to solve the problem, not the other way around.

At the root of all this is every company’s Achilles’ heel: the data. Access to data has been a privilege — those who have it, those who don’t. Now you’re bringing structured and unstructured [data] together for these AI models to work, and that’s a new skill set that requires you to know the business inside and outside.

You also have to stay externally relevant and know where innovation is coming from. And you’re going to need to know how to architect that into the way your company goes to market, which requires you to know the business processes, how it runs, and how it could run.

That’s the role of leaders moving forward, immersing yourself in the problems the business needs to solve. There’s no boundaries there. It’s not what department you report in and what process you own. It’s seamless. That’s the duality people need to command and grow into.

Looking back on a career that spans multiple industries with different operating models, cultures, and regulatory environments, what were some of the most important calculated risks you took in terms of your growth?

There were two pivotal moments in my career that were the biggest risks but probably my biggest gains in growth. One was when I went into a full-time tech role and ran infrastructure. I was a fish out of water, and not the likely successor. Part of the reason I did it goes back to a something we talked about on the podcast: Well, why not me? And I want more. That’s just my tenacity.

It was during the dot-com days of the late 90s, early 2000s. It didn’t matter if you were the CEO or a board director, if you didn’t know tech and you didn’t understand how to wield it, you were never going to be successful. I knew that no matter what job I may want in the future, I had to know tech. So it was a calculated decision: I’m going to jump into tech.

Some very senior supply chain leaders who controlled my career told me, “You’re going to fail, and I’ll have a safety net for you when you come back.” Well, I didn’t fail and I never went back. That pressure was there, but I knew why I was doing it. This wasn’t just a job for ego’s sake. This was, I have to know tech. The future is tech. It’s kind of like AI now.

The other pivotal moment was changing industries. I left Johnson & Johnson at a great time. We had gone through a huge transformation, started our global services organization, and the perfect moment happened for me to retire early there. I didn’t know what I wanted to do. It was the first time I took a break in my career to let the world come to me instead of me planning it. Do I want to open a business? Do I want to consult? Do I want to stay retired? I was fortunate enough that I could, but I got bored.

The financial industry wasn’t on my radar. Coming out of healthcare, with the purpose and the connection with saving lives, helping people, it’s easy to connect to. Financial wasn’t, for me. But one of the executive search firms said to me, when you interview, the biggest question hanging over your head is going to be, could you be successful elsewhere because you grew up in J&J. You had advocates, you had influence, you knew the industry. It’s like your deck was stacked for you. Could you do all that when you’re a nobody coming off the street?

So when the CIO role opened at State Street, I interviewed — and talk about being your authentic self. I had already done all this transformation, I already knew the outcomes, I knew everything I did was always enterprise and always end-to-end transformation. And because I wasn’t really vying for the job, I was having this conversation with the CFO and saying, “Here’s what your organization is lacking, here’s the noise you’re going to hear, do you really have the appetite for it?” And “I’d like talk to the COO and see if they’re ready to hear this about the value chain. I may not know your problem yet, but I guarantee it’s one of these three things.”

I was testing their advocacy of, do you really want to transform? Are you ready? Because you have to own this. I can’t take accountabilities for your organizations. I can help you get there. I’m an enabler for you, but you have to own it. And it was a very different interview. By the end of it, I loved Ron [O’Hanley, State Street Chairman and CEO] and his whole team. I took the job on the leadership and the person more than the industry, and it was very successful.

I followed the same recipe when I went to Verizon. Those were big growing moments. They were risky, they were very uncomfortable, but it was the biggest growth that I’ve ever had.

Whether it’s a tough message to the C-suite, a difficult conversation with peers, or helping teams make sense of uncertainty and change, you tell people the truth in a way they can hear it. How can other leaders develop that ability to take people on the journey, especially when the message isn’t easy?

Skirting a problem is not the way to solve it. I’ve never been the person to say what you want to hear. I’ll tell you how you get there, and I’ll get you the results you want, but I’m going to be super honest because I want to manage the expectations of what we have to achieve.

What I’ve learned as a leader is to take accountability. Say what you’re going to do, then do it, and if you hit a roadblock, be the first to call it. That gets you access, because people see it as a calculated risk. Anybody in the C-suite has resources and budget, but the earlier you signal and don’t waste money and resources, the more access to people and resources you will have.

The greatest lesson I learned from one of the leaders in my path was: If you can’t say it in an elevator, and you can’t say it on one slide, you’re talking too much. So, think about it as one slide: What is it you need? What are you going to achieve? What are the risks? What are you taking accountability for? How will you measure it? It doesn’t matter what the message is when you can be that succinct. You’ve got them laser-focused on what it is. You gave them just enough of the periphery to know how you got there, and then it’s their belief in you that you can do it if they give you the money and resources, because that’s what you’re looking for.

It sounds so simple but putting things together succinctly is hard work. You have to take all the unnecessary noise out, and keep the conversation focused. You don’t want their mind wandering, wondering where is she going, or what are they doing? Give it to them upfront and tell them what you need.

You’ve spoken about entering corporate environments early in your career feeling intimidated by people with more traditional credentials or educational backgrounds. What advice can you give rising leaders about battling imposter syndrome?

Take the time to figure out what makes you uncomfortable, what makes you feel like an imposter, or what in that meeting you dread going in where you’re not acting like yourself. Are you more quiet than usual? Are you not asking the question you’d normally ask? Figure out what those issues are, and then address the things that make you uncomfortable. I went to college later because that bothered me. Those credentials do matter. So I addressed it and got my degrees and certifications.

The other thing is to find people you trust, people whose opinion you respect, and bring them on the inside of what you’re working on. Maybe it’s dealing with a difficult business partner. You may not particularly want to be friends with them, but you’re going to have to work with them. Find the people that work effectively with them. You do this with high integrity — this is not about talking about that person — but find the allies that work with them. Nine times out of ten, they feel the way you do, but they found a way to work with the person. Pick their brain. Bring them in the fold and say, “I need this alliance. I can’t get there, and quite frankly, I know I’m resisting because maybe I just don’t like them. How did you get there?”

People are generous. Ask their opinion, ask how they’re showing up. “Am I creating the trigger? Is there something I’m doing in that meeting or in that room that I’m not coming out with a decision or whatever I needed?”

The greatest gift is feedback. There’s feedback you do something with, and there’s feedback you don’t, but either way, it’s a gift. Somebody’s giving it to you. It’s not personal; it’s business. And those things really help build your confidence and leadership style.

In an era increasingly shaped by automation and disruption, Jane Connell believes the most enduring competitive advantage may come from something deeply human: the ability to inspire confidence, curiosity, resilience, and possibility in others. For more advice from this Hall of Fame CIO, tune in to the Tech Whisperers podcast.

See also:

• Mastering the chess of IT leadership today
• Developing a customer-first culture for IT
• Coherence: Where leadership and AI success intersect

In many teams, dependency security still happens after the most important trust decision has already been made. A package is added, the lockfile changes, the feature moves forward, and only later does the pipeline ask whether the application should have trusted that code in the first place.

That workflow made sense when dependency security was mostly viewed as a compliance check. Run a scanner. Produce a report. Fail the build if the risk crosses a threshold. Let someone decide what to do next.

But the modern Node.js ecosystem has changed. The risk no longer begins in CI. It begins earlier, at the moment a developer decides to trust a package.

That is why the next phase of Node.js security cannot be limited to better pipeline enforcement. It has to move closer to the developer workflow, before dependencies become part of the application, before a pull request becomes someone else’s problem, and before a build log becomes the first moment anyone realizes that something important has changed.

Every install is a trust decision

The npm ecosystem is built on trust at an enormous scale. Every install is a trust decision. Every transitive dependency extends that decision to maintainers, packages, scripts, release pipelines, and infrastructure the application team may never inspect directly. This model gave JavaScript its incredible velocity. It also created one of its deepest security weaknesses.

Recent npm supply chain incidents show why this matters. In March 2026, malicious Axios versions were published to npm through a compromised maintainer account. Microsoft later described how those packages attempted to retrieve a second-stage payload during installation. In May 2026, TanStack published a postmortem explaining that 84 malicious versions across 42 npm packages were published through a legitimate release pipeline after an attacker abused GitHub Actions behavior and runner trust boundaries. Security researchers also reported broader Mini Shai-Hulud activity across the npm ecosystem in May, including hundreds of malicious package versions published in a short period.

Not every one of these incidents is a traditional CVE. Some are malicious package compromises. Some involve CI/CD credential theft. Some involve maintainer or pipeline compromise. But they all point to the same larger issue: dependency risk is now part of everyday software engineering, not something that can be pushed entirely to a downstream security process.

The problem is not the scanner. It is the handoff.

Ubiquitous dependency risk changes what developers need from security tooling.

The problem is not that teams lack scanners. Many organizations already run security checks in CI. The problem is that the output of those checks often arrives too late and speaks the wrong language for the person expected to act on it.

A pull request fails. A long vulnerability report appears. The report may be technically accurate. It may contain the right advisory IDs, affected versions, dependency paths, severity labels, and references. But the developer still has to comb through the output and reconstruct the actual engineering decision from the evidence provided.

That reconstruction is rarely simple. The developer has to understand which package introduced the issue, whether the vulnerable dependency is direct or transitive, whether the fix is actually within the application team’s control, and whether the recommended version is safe to adopt. They also have to determine whether the dependency is used in production or only during development, whether the update might break the application, and whether the fix belongs in the current pull request or requires separate engineering work.

That uncertainty is where security work often slows. The scanner has detected risk, but the developer has not been given a clear path from detection to decision.

Security needs to move closer to engineering judgment

This is not a criticism of scanning. Scanning is necessary. CI enforcement is necessary. Centralized security platforms are necessary. But they are not sufficient, because they often operate after the trust decision has already been made.

The real architectural question is this: where should dependency security live in the software development life cycle?

If it lives only in CI, it becomes an interruption. If it lives only in dashboards, it becomes someone else’s queue. If it lives only in periodic audits, it becomes a backlog. But if it lives at the moment a dependency is introduced, upgraded, or reviewed, it becomes part of engineering judgment.

That shift matters because modern JavaScript development is becoming faster than human review can comfortably handle. Developers no longer add dependencies only by reading documentation and choosing libraries manually. AI coding assistants can suggest packages, generate install commands, modify package files, and rewrite code around third-party APIs. Agentic development workflows can make dependency changes as part of broader automated refactors.

AI makes the trust boundary harder to see

That acceleration is useful. It also changes the risk model.

When a human developer adds one package, the team can review the decision. When a coding agent modifies several dependencies as part of a larger task, the trust boundary becomes harder to see. The package file changes, the lockfile changes, the application still runs, and the pull request may look like a normal feature update. But the real security question may be hidden inside the dependency graph.

This is where Node.js teams need a different mental model.

Dependency adoption should not be treated as a small implementation detail. It should be treated as an architectural decision with security consequences. A new package is not just code reuse. It is a new trust relationship.

That does not mean developers should stop using packages. The npm ecosystem exists because reuse works. Most teams cannot and should not build everything themselves. But convenience should not erase visibility. If a dependency becomes part of the application, the team should understand what was added, what changed in the lockfile, what risk comes with it, and what action is available if something is wrong.

Developers need confidence, not just reports

The same applies to remediation. Developers do not want a wall of vulnerability text. They want confidence. They want to know what action reduces risk, what version should be targeted, whether the change is safe, and whether the fix is actually under their control. A vulnerability report that leaves the developer uncertain may satisfy a process requirement, but it does not necessarily improve the speed or quality of remediation.

That is the gap many teams feel today. Security tools are often very good at saying, “There is a problem.” They are less consistent at helping the developer answer, “What should I do next?”

This is the broader problem I have been exploring through CVE Lite CLI, now an OWASP project. The point is not that one command-line tool solves Node.js security. It does not. The larger idea is that dependency security has to move closer to the developer’s moment of decision. A useful developer-side security workflow should not merely report that risk exists. It should help the engineer understand whether the issue is in their control, what change is available, and whether the fix actually reduces risk.

The future is decision support, not just detection

That distinction is important. The future of Node.js security is not just more detection. It is better decision support.

Security teams still need policy. Enterprises still need dashboards. CI still needs gates. But developers need something more immediate: a way to reason about dependency risk while the code is still fresh in their mind. That is where the ecosystem has to evolve.

We already accept that testing belongs close to development. We accept that linting belongs close to development. We accept that formatting, type checking, and build validation belong close to development. Dependency security should follow the same path. It should not be treated as a mysterious report that appears at the end of the process. It should become part of the normal rhythm of engineering work.

Before adding a package, developers should understand what trust relationship is being introduced. Before accepting an AI-generated dependency change, they should inspect what entered the graph. Before merging a pull request, teams should understand whether a vulnerability is direct, transitive, fixable, or blocked by another package. And before treating a CI failure as noise, organizations should ask whether the workflow is giving developers enough information to act confidently.

Node.js security will be won, or lost, before CI runs

The Node.js ecosystem will not become safer by slowing down all development. That is unrealistic. It will become safer when security work is placed where developers can actually use it.

The next generation of Node.js security will be won or lost before CI runs.

It will be won when dependency decisions are still small enough to understand, fresh enough to review, and close enough to the developer for action to feel natural.

That is the shift teams need to make now. Not from insecure to secure in one step, but from late detection to earlier judgment. From vulnerability reports to engineering decisions. From trusting packages by habit to understanding trust as part of software design.

Enterprises that use AI in hiring and firing decisions continue to be under scrutiny, and this time it’s Meta under the microscope.

A legal complaint filed on July 13 in a US District Court in California alleges that Meta used AI systems that unfairly and illegally selected workers for termination while they were out on protected leave.

More than two dozen anonymous plaintiffs are seeking a preliminary injunction that would prevent the company from finalizing their separations or altering their compensation, benefits, or protected leave status.

Meta has countered that the claims lack merit and that its workforce decisions were, and continue to be, made by people, not AI.

An important lesson

These allegations should serve as an important lesson to other businesses using AI in their HR decision-making, analysts note.

“Enterprises must begin by rejecting the convenient assumption that AI improves workforce decisions simply by touching them,” said Sanchit Vir Gogia, chief analyst at Greyhound Research.

There is “scant independent proof” that AI makes layoff choices more accurate or more lawful, he said. “It makes them faster, and faster has never been shown to be fairer.”

The claims against Meta

The complaint states that, on May 20, 2026, Meta began notifying roughly 10% of its workforce (around 8,000 employees) that they had been selected for termination. The company also announced that several thousand more would be reassigned to new AI initiatives. But this came even as Meta reported record revenues in Q1 2026 ($56.31 billion, a 33% year-over-year increase), and pledged to spend upwards of $100 billion on AI this year.

In addition to questioning the need for staff cuts, the filing alleges that Meta used a “constellation” of internal AI systems to score, rank, and select employees for termination. These tools included Meta’s internal AI coworker, “Metamate,” employee-trained “second-brain” agents that replicated their output, algorithms tracking keystrokes and other digital activity, and AI token usage dashboards.

“Meta did not assemble the termination list through the considered judgment of managers who knew the work,” the complaint claims.

The 26 plaintiffs, all current or former employees, requested, took, or were approved for “statutorily protected” leave within 24 months of the workforce reduction, and claim they were “disproportionately selected” for layoff based on scoring that essentially penalized them for exercising their legal right to take leave.

These practices are prohibited by federal and state law; The US Family and Medical Leave Act, for one, prohibits the use of protected leave as a “negative factor” in employment decisions. Further, the plaintiffs allege that Meta violated the US Worker Adjustment and Retraining Notification (WARN) Act that requires employers with 100 or more employees to provide written notice 60 calendar days in advance of mass layoffs.

This notice gives employees reasonable time to seek alternate employment; however, the complaint argues, an employee undergoing “significant medical treatment” or providing “around the clock care” for a “weeks old newborn” or other loved ones “cannot also be told that during this exact same time period they must look for new work.”

In one scenario, according to the filing, a scientist was identified for termination just two days before she gave birth while on pregnancy leave. In another, an engineer’s manager tied his performance rating to “broken time” when an injury prevented him from working. In a third, a researcher was called out after requesting time off following a medical diagnosis.

The plaintiffs are seeking a preliminary injunction pending an independent audit of the “algorithmically assisted selection process” and “resolution of the merits of their claims” in arbitration.

Once terminations are finalized, the harm to plaintiffs “cannot be undone by money damages alone,” the complaint states. For employees out on leave, “every day that goes by constitutes additional harm, in that Meta is taking away the entire purpose of a protected leave.”

Considerations for enterprises

Any system that materially influences who keeps a job is not an HR tool, Gogia noted. “It is high-risk enterprise infrastructure.”

An “AI-determined” process delegates the outcome to the system, while an “AI-assisted” one gives the system the ability to rank, recommend, and summarize, with a human formally making the final decision. Exposure arises in either model, Gogia pointed out, because the output has often been compressed and eliminates detail by the time of executive approval.

There must be one non-negotiable role in the process, Gogia said: A single executive with the authority to halt the process, suspend the model, and delay decisions when evidence does not hold. This person should be “a meaningful reviewer [who] understands the model’s limits, knows the actual work, and holds the authority to challenge the recommendation, with every override visible and reviewable,” he said. At the same time, the objective is to “govern the machine and the manager together,” since human judgement brings its own “risks, favoritism, and proximity” bias.

Gogia advised enterprises to retain fixed memory for auditing, determine who chose the auditor, what was excluded, and whether the result can be reproduced. They should also inventory every source feeding the model and its origins, and run adverse-impact analysis before making any firing decisions.

Leave details must never be identified as inactivity or weak adoption; a protected absence is not ordinary missing data, and the system has to be informed of this. Rather, these circumstances belong in an “independent review lane,” where human reviewers get enough context to “neutralize” the period without receiving specific leave details, Gogia said.

He pointed to another important question: What should the “second brain” AI agent that ingested the employee’s communications and documents to replicate the employee’s output be allowed to do when humans are away, and who owns that output?

Ultimately, said Gogia, “the safest position is not to ban AI from workforce planning. Used with discipline, it can expose duplicated work and inconsistent assessment, and it can challenge human bias rather than automate it.”

How employees can protect their rights

Employees, for their part, need a genuine window in which to challenge inaccurate data before separation becomes “irreversible,” and they should “fight the record, not the algorithm,” Gogia advised.

That means that, while the model cannot explain itself, documented evidence can. Employees should lawfully retain their own reviews, leave approvals, and severance documents, and build a chronology of events: When leave was requested, when performance language changed, when new metrics appeared, Gogia said.

Impacted workers should ask in writing which criteria were used in the decision, whether automated systems materially influenced it, how protected leave was treated, and what information about them influenced the result and how that information was verified.

Further, it’s important to take note of deadlines; the federal discrimination window is typically six months, although that is extended to 10 in many places, and internal processes are “not obliged to respect it,” said Gogia.

His ultimate advice for workers: “Preserve the lawful record, and protect the deadline.”

This article originally appeared on CIO.com.

Enterprises that use AI in hiring and firing decisions continue to be under scrutiny, and this time it’s Meta under the microscope.

A legal complaint filed on July 13 in a US District Court in California alleges that Meta used AI systems that unfairly and illegally selected workers for termination while they were out on protected leave.

More than two dozen anonymous plaintiffs are seeking a preliminary injunction that would prevent the company from finalizing their separations or altering their compensation, benefits, or protected leave status.

Meta has countered that the claims lack merit and that its workforce decisions were, and continue to be, made by people, not AI.

An important lesson

These allegations should serve as an important lesson to other businesses using AI in their HR decision-making, analysts note.

“Enterprises must begin by rejecting the convenient assumption that AI improves workforce decisions simply by touching them,” said Sanchit Vir Gogia, chief analyst at Greyhound Research.

There is “scant independent proof” that AI makes layoff choices more accurate or more lawful, he said. “It makes them faster, and faster has never been shown to be fairer.”

The claims against Meta

The complaint states that, on May 20, 2026, Meta began notifying roughly 10% of its workforce (around 8,000 employees) that they had been selected for termination. The company also announced that several thousand more would be reassigned to new AI initiatives. But this came even as Meta reported record revenues in Q1 2026 ($56.31 billion, a 33% year-over-year increase), and pledged to spend upwards of $100 billion on AI this year.

In addition to questioning the need for staff cuts, the filing alleges that Meta used a “constellation” of internal AI systems to score, rank, and select employees for termination. These tools included Meta’s internal AI coworker, “Metamate,” employee-trained “second-brain” agents that replicated their output, algorithms tracking keystrokes and other digital activity, and AI token usage dashboards.

“Meta did not assemble the termination list through the considered judgment of managers who knew the work,” the complaint claims.

The 26 plaintiffs, all current or former employees, requested, took, or were approved for “statutorily protected” leave within 24 months of the workforce reduction, and claim they were “disproportionately selected” for layoff based on scoring that essentially penalized them for exercising their legal right to take leave.

These practices are prohibited by federal and state law; The US Family and Medical Leave Act, for one, prohibits the use of protected leave as a “negative factor” in employment decisions. Further, the plaintiffs allege that Meta violated the US Worker Adjustment and Retraining Notification (WARN) Act that requires employers with 100 or more employees to provide written notice 60 calendar days in advance of mass layoffs.

This notice gives employees reasonable time to seek alternate employment; however, the complaint argues, an employee undergoing “significant medical treatment” or providing “around the clock care” for a “weeks old newborn” or other loved ones “cannot also be told that during this exact same time period they must look for new work.”

In one scenario, according to the filing, a scientist was identified for termination just two days before she gave birth while on pregnancy leave. In another, an engineer’s manager tied his performance rating to “broken time” when an injury prevented him from working. In a third, a researcher was called out after requesting time off following a medical diagnosis.

The plaintiffs are seeking a preliminary injunction pending an independent audit of the “algorithmically assisted selection process” and “resolution of the merits of their claims” in arbitration.

Once terminations are finalized, the harm to plaintiffs “cannot be undone by money damages alone,” the complaint states. For employees out on leave, “every day that goes by constitutes additional harm, in that Meta is taking away the entire purpose of a protected leave.”

Considerations for enterprises

Any system that materially influences who keeps a job is not an HR tool, Gogia noted. “It is high-risk enterprise infrastructure.”

An “AI-determined” process delegates the outcome to the system, while an “AI-assisted” one gives the system the ability to rank, recommend, and summarize, with a human formally making the final decision. Exposure arises in either model, Gogia pointed out, because the output has often been compressed and eliminates detail by the time of executive approval.

There must be one non-negotiable role in the process, Gogia said: A single executive with the authority to halt the process, suspend the model, and delay decisions when evidence does not hold. This person should be “a meaningful reviewer [who] understands the model’s limits, knows the actual work, and holds the authority to challenge the recommendation, with every override visible and reviewable,” he said. At the same time, the objective is to “govern the machine and the manager together,” since human judgement brings its own “risks, favoritism, and proximity” bias.

Gogia advised enterprises to retain fixed memory for auditing, determine who chose the auditor, what was excluded, and whether the result can be reproduced. They should also inventory every source feeding the model and its origins, and run adverse-impact analysis before making any firing decisions.

Leave details must never be identified as inactivity or weak adoption; a protected absence is not ordinary missing data, and the system has to be informed of this. Rather, these circumstances belong in an “independent review lane,” where human reviewers get enough context to “neutralize” the period without receiving specific leave details, Gogia said.

He pointed to another important question: What should the “second brain” AI agent that ingested the employee’s communications and documents to replicate the employee’s output be allowed to do when humans are away, and who owns that output?

Ultimately, said Gogia, “the safest position is not to ban AI from workforce planning. Used with discipline, it can expose duplicated work and inconsistent assessment, and it can challenge human bias rather than automate it.”

How employees can protect their rights

Employees, for their part, need a genuine window in which to challenge inaccurate data before separation becomes “irreversible,” and they should “fight the record, not the algorithm,” Gogia advised.

That means that, while the model cannot explain itself, documented evidence can. Employees should lawfully retain their own reviews, leave approvals, and severance documents, and build a chronology of events: When leave was requested, when performance language changed, when new metrics appeared, Gogia said.

Impacted workers should ask in writing which criteria were used in the decision, whether automated systems materially influenced it, how protected leave was treated, and what information about them influenced the result and how that information was verified.

Further, it’s important to take note of deadlines; the federal discrimination window is typically six months, although that is extended to 10 in many places, and internal processes are “not obliged to respect it,” said Gogia.

His ultimate advice for workers: “Preserve the lawful record, and protect the deadline.”

This is Part 2 of a series on tech worker unionization. See Part 1: “A brewing battle: More IT workers want unions. The industry doesn’t.”

The best time for tech workers to unionize was 20 years ago, when they had plenty of leverage. The second-best time is now, when they don’t.

Mass layoffs, AI-driven displacement, corporate surveillance, workplace disillusionment have created conditions that have made organizing compelling for tech professionals. But the federal labor board that has historically protected workers’ right to organize has been weakened, and the companies that once feared it are openly defying it.

Here’s how organizers and labor experts describe the pros and cons to organizing — and how you can get started.

What unions can — and can’t — do for you

The single biggest benefit of a union contract for most tech workers isn’t pay — it’s protection against arbitrary termination, especially in the wake of recent mass layoffs in tech. In the United States, nonunion “at-will” workers can be fired at any time without a stated reason, while unionized workers negotiate protections written into their contracts.

“That fear of the company letting you go for anything at any time…with a union they just can’t do that,” says Zak Thompson, a senior software engineer at Kickstarter and union steward at Kickstarter United. Now that Kickstarter employees are unionized, people are less worried that saying something negative will result in termination.

“I’ve been shocked at the willingness of my co-workers to speak up against what they see as poor or controversial business decisions,” Thompson says.

Beyond job security, unions can deliver concrete material gains. Kickstarter United was formed in 2020, although getting there wasn’t easy: two employees were fired during the organizing campaign — which itself became a galvanizing event. And while the union hasn’t been able to prevent layoffs, it did negotiate better terms: four months of severance pay and four to six months of continued health insurance, versus the two to three weeks per year of work that management had initially proposed.

Other benefits include a four-day work week; AI protections; a minimum pay floor; and standards for raises, promotions, and time off for the company’s 59 employees.

Unions can give tech workers a voice in decisions that affect their daily work — including how AI tools are deployed. “Nobody I’ve spoken to is against new technology or getting trained in it,” says Max Belasco, a business systems analyst at the University of California Los Angeles School of Law and co-chair of the UCLA chapter of the University Professional and Technical Employees/Communications Workers of America (UPTE-CWA) Local 9119.

“But when new technology is being implemented, we want to know: what’s the five-year vision, the 10-year vision? Are we implementing this in a way that betters staffing, increases efficiency, or eases the lives of people already working? Or are we trying to take away jobs, automate people out of their pension or paycheck?” Belasco says.

The challenges are real. Tech professionals are less inclined to leave their jobs in the current market because wages haven’t been increasing as fast as they once were, and it can take longer to land another job.

“Tech moved from a very tight labor market in 2022 (1.85% unemployment rate) to a noticeably weaker one in 2024–2026 (3.49%),” although that’s still better than the national unemployment rate of 4.36% through May of this year, says Liya Palagashvili, senior research fellow and director of the Labor Policy Project at the Mercatus Center at George Mason University.

Flexibility is a concern. The more substantive challenge, raised by economists including Palagashvili, is that traditional union contracts impose uniform terms across an entire bargaining unit, limiting the flexibility that many tech workers — and their employers —currently enjoy. Tech firms need to move fast, adjusting teams, products, and roles on the fly.

“Collective bargaining agreements can make those adjustments much more difficult, whether by making them slower, costlier, or inconsistent with the contract,” she says.

Workers skeptical of unions in a survey of 1,900 tech professionals conducted by the career site Blind cited specific concerns: that unions are “not meritocratic,” “prevent innovation,” and “hold back earnings of top performers.”

Thompson from Kickstarter United pushes back: “We have nothing in our contract about ‘you can’t bend down and pick up a piece of trash because that’s someone else’s job.’ The company is free to give bonuses and individual raises as much as they like. This is all just up to the people who are bargaining the contract from the union side.”

Organizing carries potentially serious personal risks. During negotiations for a second three-year contract in 2025, Kickstarter United went on strike for 42 days. A few months later, the company announced layoffs.

“They let go strong union leaders, including a person who had bargained our last contract,” Thompson says. The union appealed, and the issue is now going to arbitration.

If you form a union, don’t expect much support from the National Labor Relations Board, the agency that certifies US labor unions and protects workers’ right to organize, in terms of prosecuting complaints of unfair labor practices, Thompson warns. “We’re in a political moment in this country with a pretty weakened NLRB. You have to be ready to organize and withhold worker power without any guarantee of safety.”

Organizers are up against an enormous union avoidance industry. Organizers can expect fierce pushback as soon as the business discovers that organizing is underway.

“There’s a multi-billion-dollar industry in union avoidance,” says Alan McAvinney, a Google software engineer and organizing chair, Alphabet Workers Union-CWA, a 1,400-member minority union of Alphabet employees. (Google is a subsidiary of Alphabet.)

US employers spend roughly $1.7 billion a year on union avoidance consultants and law firms, according to a May 2026 report by the Economic Policy Institute and LaborLab.

Expect hardball tactics. Management may play hardball during the time between when organizers announce their intention to unionize and the actual vote. For example, management can threaten to fire foreign-born workers in the US on H-1B visas if they support the union. Those workers would then have just 60 days to find a new sponsoring employer or lose their H-1B status, according to a recent Tech Workers Coalition blog post.

And at venture capital-backed startups, investment agreements sometimes require management to attest there is no union activity — meaning a public organizing drive can trigger funding withdrawal. Or, if a unionized company is acquired, the new management can dissolve the union overnight by reclassifying unionized workers as new hires.

With these sobering facts in mind, here is how organizers who have done it describe the process of creating a union.

Step 1: Start a conversation with your co-workers

At the University of California, a two-tier system had evolved where some tech workers were unionized and some weren’t, Belasco says. Management created new titles that fell outside the union even though they had similar job descriptions and responsibilities to those in the union. Those nonunion employees received lower pay and benefits than their unionized peers, which created resentment and instability.

Belasco and other organizers wanted to eliminate that division by bringing everyone under the same contract. But when they began their unionization drive, “the biggest barrier we faced wasn’t management opposition — it was that people felt this was just the best-case scenario realistically available: ‘We have this job at the university, we have concerns about automation and layoffs, but what can we really do about it?'” he says.

The antidote to that fatalism, organizers say, is simple: “Just start talking to your immediate co-workers. Are they experiencing the same challenges you are experiencing?” says McAvinney. “There’s no need to start talking about a union at this point.”

Just get a consensus and start building a group of like-minded individuals, Thompson advises. “Always start with one-on-one conversations, and that’s what you should do the whole time. That’s the key to organizing,” he says.

Tech workers often think they’re a special case, says Thompson, and therefore that unionization isn’t a good fit. “You’re not special. You are a company of workers, you are organizing, and there is a playbook for that. Trust the process, because it tends to work pretty well,” he says.

Step 2: Who’s on board, and who’s not? Map your workplace, but keep it quiet

Once there’s a consensus, continue to grow your network. Keep a list of everyone you’ve spoken with and note their disposition: “Is this person union-friendly or anti-union? Would they be a strong organizer?” Thompson says.

Maintaining secrecy early on is essential, because anti-union tactics will start immediately, and that can stop union organizing before it can gain momentum.

“Generally, employers do not want to share power with their workforce,” McAvinney says. Employers will deploy every means at their disposal to stop organizing efforts and peel away potential yes votes.

“If you look at historical examples, having 70% approval before the employer finds out about you results in a high percentage of wins when you actually cast the vote. Historically, that’s an effective buffer,” he says.

There’s a real threat of firing and layoffs. The traditional tech worker belief that job mobility makes collective action unnecessary is now being tested by a tighter job market, McAvinney says, noting that workers who many believe were fired for speaking out back in 2019 were a galvanizing factor in his union’s formation.

“You generally don’t want to be in a situation where the employer feels comfortable firing everyone. Part of that is thinking from a cynical standpoint about what the consequences would be to the employer if they did fire everyone,” he says.

One-on-one conversations that include personally asking co-workers to keep conversations confidential are key to keeping things quiet, Belasco says. When 2,100 UC tech workers voted to unionize in May, 96% voted in favor. To stay out of earshot of managers, avoid employee surveillance tools, and sidestep conference calls that could be recorded, organizers met with workers in their homes.

“That tactic is probably what made the difference between winning the election and getting the majority we got,” he says.

Step 3: Find the right union affiliation or go it alone

“Running a campaign against major employers requires the resources and expertise of the larger labor movement, even if workers publicly present as independent,” says Kate Bronfenbrenner, director of labor education research and senior lecturer emeritus at Cornell University’s School of Industrial and Labor Relations.

Options include the Communications Workers of America (CWA), Service Employees International Union (SEIU), and the Office and Professional Employees International Union (OPEIU), among others. Another resource, the Tech Workers Coalition (TWC), provides training on organizing tactics, AI-in-workplace issues, and contract negotiation, and can match workers to the right unions for their needs.

The Alphabet Workers Union decided early on to affiliate with CWA. “They gave us a bunch of support early on in our campaign with no strings attached,” McAvinney says.

Kickstarter is organized through OPEIU, Thompson says. “They’ll usually have resources and staff that can help you through the next steps: collecting signatures in support of a union, bringing that to management, holding a vote — the more formalized things that interact with US labor law. They’ll also help with organizing along the way,” he says.

For workers at institutions where a union already exists, there may be a faster path. Organizers at UCLA did what’s called a “unit modification,” aligning with UPTE. By organizing under UPTE, the workers didn’t have to negotiate a new contract from scratch — they joined an already-negotiated contract covering existing UPTE tech members, which put them in “a much stronger position” than starting fresh, Belasco says.

Step 4: Choose your union model: majority vs. pre-majority or minority

Assess what’s practical for your organizing effort. In a majority union, more than 50% of all workers in a defined bargaining unit must vote to join the union through an NLRB-supervised election in the private sector, or a Public Employment Relations Board (PERB)-supervised election for public sector workers.

The NLRB must certify the union, which then operates under its legal protections. This means, for example, that the employer must bargain, negotiated contracts are enforceable, violations must go to the NLRB or arbitration, and workers can’t be dismissed without just cause.

A pre-majority or minority union is a minority labor organization operating without NLRB protections or collective bargaining agreements. “Pre-majority means that workers are able to demonstrate majority support — through signed cards, petitions, a walkout, or everyone wearing solidarity T-shirts — without going through a formal election,” Bronfenbrenner says.

The Alphabet Workers Union-CWA (AWU-CWA) formed as a pre-majority union because achieving majority status across a globally distributed workforce of over 100,000 was not a realistic near-term goal. “An underground model where you try to reach 70% support across a workforce of over 100,000 people isn’t realistic,” McAvinney says.

A pre-majority union can still make a difference, he says. For example, the Alphabet Workers Union-CWA convinced management to offer voluntary exit packages — buyouts — prior to announcing layoffs.

For smaller organizations, a majority union may be the more practical option — it’s more attainable, McAvinney says. “I don’t think [the pre-majority union model] is the correct thing to do in all situations. I certainly would not recommend it to a 200-person shop.”

Kickstarter, which had fewer than 100 employees, was able to form a majority union, with 55% voting to organize.

Ultimately, says McAvinney, “there’s no inflection point where you go from being able to win nothing to winning everything, even with a contract and a supermajority. But the more people you have who are willing and able to fight for what they want, the more you’ll be able to get.”

Step 5: Who should — and should not — be in your union?

Belasco’s situation at UCLA illustrates a broader strategic choice that every organizing campaign must make. He had been in a union position in educational technology when he was told his role would be reclassified as a non-union position.

“I was given a choice: apply to the new non-union position to continue doing the work I’d trained for, or stay in my union position doing service desk work I wasn’t used to,” he says. “Essentially, it was a choice between job security and career progression.”

Belasco joined a “wall-to-wall” union, which represents a broad range of university professional and technical employees across the UC system rather than a single job category, such as engineers or tech professionals.

Kickstarter United is another example of a wall-to-wall union. “It’s not just the engineers who are unionized, but also customer support, designers — everyone,” Thompson says.

Wall-to-wall unions are more powerful, but they’re also more difficult to achieve. Under US labor law, “professionals have to vote separately on whether they want to be combined with other workers,” says Bronfenbrenner. “You can never have a wall-to-wall unit without giving professionals the chance to decide whether they want to be separate.”

The law’s “professional employees” category includes roles like software engineers and developers but not necessarily others. For example, customer support specialists and QA analysts would fall into the “non-professional workers” category.

“For decades, the pattern was either to organize everybody except the engineers, or manage to organize the engineers and fail to bring in everybody else — neither of which builds real worker power,” says Simone Robutti, an organizer with Tech Workers Coalition Global, an international branch of TWC based in Berlin.

Step 6: You won the vote. Get ready for what comes next

Winning a union vote means having a seat at the table, says Thompson. “Once the workers have come together and agreed they want that seat, you bring that to management, and they have a chance to voluntarily recognize a union,” he says.

But in most cases employers contest the results, which must be certified by the NLRB or PERB. That process, in which the employer uses various tactics to challenge the legitimacy of the outcome, can take weeks or months.

Unfortunately, the legal framework that is supposed to protect workers during this process has been significantly weakened in the last few years. In a potentially more ominous development, SpaceX, Amazon, Trader Joe’s, Starbucks, and the University of Southern California have in separate legal actions challenged the constitutionality of the NLRB, arguing that the agency’s structure violates the separation of powers. The Fifth Circuit Court of Appeals upheld injunctions against the NLRB in SpaceX’s case in August 2025 — a serious challenge to the agency’s authority.

In the meantime, some companies may disregard negotiated contracts, which can lead to lengthy legal appeals or extended arbitration.

“The NLRB can still force an election, but it can’t force a contract, and companies are saying they simply won’t comply,” Bronfenbrenner says. This is where the expertise and resources of affiliation with a major union can help, she adds.

As a result, contract negotiations can take far longer than workers might expect. At Kickstarter, for example, two years and four months elapsed from the time of the union vote to the first contract, and that was at a 59-person company with a relatively cooperative employer. At larger companies with more aggressive legal teams, the timeline will be longer.

Forming a union is hard work, Robutti says. “It’s not a service you pay for and they protect you. It doesn’t happen spontaneously, and it doesn’t happen magically. It’s the choice to take responsibility for improving your workplace.”

Generative AI is a kind of artificial intelligence that creates new content, including text, images, audio, and video, based on patterns it has learned from existing data.

Today’s generative models are typically built on foundation-model architectures such as large-language models (LLMs) and multimodal systems, enabling them to carry on conversations, answer questions, write stories, generate code, and produce images or videos from brief prompts.

Generative AI is different from discriminative AI, which draws distinctions between different kinds of input. Where discriminative AI answers questions like “Is this image of a rabbit or a lion?”, generative AI instead responds to prompts such as “Describe to me how a rabbit and lion look different from one another” or “Draw me a picture of a lion and a rabbit sitting next to each other” — and in both cases produces text or imagery that, while grounded in the AI’s training data, isn’t just a copy of something that already existed.

Just a few years ago, generative AI was once a novelty focused on chatbots and artistic image generation. Today, it has become a core enterprise technology, and powers everything from content creation and software development to customer support and analytics workflows. But with that power comes a new set of challenges — from model alignment and hallucination to governance and data-integration hurdles.

In this article, we’ll look at how generative AI works, explore how it has evolved into the foundation-model era, examine how to implement it effectively, and offer best practices for getting value out of it, today and in the future.

How does generative AI work?

For decades, early artificial-intelligence efforts often focused on rule-based systems or narrowly trained models that were built for one task at a time. While these efforts produced useful systems that could reason and solve human tasks, they were generally a far cry from sci-fi visions of thinking machines. Programs that could talk to people never seemed to get very far past the level of ELIZA, a “computer therapist” created at MIT in the mid 1960s; even Siri and Alexa after much fanfare were revealed to be fairly limited.

The big structural shift that gave birth to modern generative AI came with the concept of a transformer, first introduced in “Attention Is All You Need,” a 2017 paper from Google researchers.

Using a transformer architecture as a basis, you can build a system that derives meaning from analyzing long sequences of input tokens (words, sub-words, bytes) to understand how different tokens might be related to one another, then determines how likely any given token is to come next in a sequence, given the others. In AI lingo, we call these systems models. Because a model analyzes very large datasets and parameter counts, it can pick up on statistical patterns and knowledge implicitly embedded in the data.

This is all easier said than done. The process of adjusting a model’s internal parameters so it gets better at predicting the next token in sequences is called training. During training, the model repeatedly guesses the next token in a given sequence, compares its prediction to the actual one, measures the error, and updates its parameters to reduce that error across billions of examples. Over time, that process teaches the model the statistical relationships that will allow it to generate coherent language (or code, or images) later.

What is a foundation model?

You’ll often hear the word large used for transformer-based models of these types, like the LLMs we mentioned earlier. Large in this context refers to the large number of internal numerical values that the model adjusts during training to represent what it has learned, along with breadth and diversity of data used to train the model and the underlying compute resources powering this whole process.

This is in contrast with the narrow models of the earlier era of AI/ML, which werebuilt for one purpose and trained on a limited dataset. For instance, a spam filter may be very good at what it does, but it’s only trained on email data and all it can do is classify emails. Large models, by contrast, serve as what’s known as foundation models. They’re trained broadly on diverse data (text, code, images, or multimodal data) and then adapted or specialized for many downstream tasks.

These foundation models are the basis for most of the popular generative AI tools and services on the market today. They can be specialized in several ways:

• Fine-tuning: Giving a foundation model further training on a smaller, task-specific dataset
• Retrieval-augmented generation (RAG): Giving the model the ability to pull in external knowledge when asked a question
•  Prompt engineering: Tailoring a query so the model gives the sort of answers you’re looking for.

How do AI systems write computer code?

One of the surprising discoveries of the gen AI era was that in recent years was that foundation models trained on natural-language text can also, when fine-tuned with code examples, also write computer code — often better than many purpose-built systems. Still, it makes sense, when you think about it — after all, high-level computer languages are designed by humans and ultimately based on human language.

This 2023 InfoWorld article highlights how models like PaLM, LLaMA and other transformer-based systems fine-tuned on code repositories propelled this shift, but since AI giants like OpenAI have moved into this space. This all matters because code generation (or code-assisted productivity) has become a key enterprise use case of generative AI — perhaps the key use, given the industry’s enthusiastic adoption of it.

What are AI agents?

So far, we’ve been talking about chatbots, writing assistants, image-generation tools. They respond to prompts, output text or images, and then stop. A new category of tool called agentic AI goes further: it plans, executes, and in many cases learns as it works.

Because large models already understand language, code, and even structured data to some extent, they can be repurposed to generate not only descriptive text but operational instructions. For example: an agent might parse the intent “generate a sales-report”, then format internal calls like getData(salesDB, region=NA, period=lastQuarter), and then call an API, all by generating text that’s interpreted as instructions. The MCP framework standardizes the “language” of those instructions and the plug-points into tools and data so that the model doesn’t need bespoke integrations for each new workflow.

These kinds of autonomous agents have several enterprise use cases:

• Software automation: Agents that generate code, call unit tests, deploy builds, monitor logs and even roll back changes autonomously.
• Customer support: Instead of simply drafting responses, agents interact with CRM APIs, update ticket statuses, escalate issues, and trigger follow-up workflows.
• IT operations/AIOps: Agents monitor infrastructure, identify anomalies, open/close tickets, or auto-remediate based on defined rules and context from logs.
• Security: Agents may detect threats, initiate alerts, isolate compromised systems, or even attempt to manage threat containment — though this raises new risks.

How can you implement generative AI in the enterprise?

We’ve now touched on what generative AI can do. But how can you make it work reliably in your business. The difference between a pilot and full-scale deployment often comes down to systems, structure and governance as much as to models themselves. InfoWorld’s Matt Asay offers a deep dive into enterprise gen AI essentials, but here are some important points to keep in mind:

Choosing between API, open-source or custom fine-tuned models. One of the first major decisions for any enterprise project is: do you use a model via an API (e.g., from a vendor like OpenAI or Anthropic), deploy an open-source model internally, or build/fine-tune a custom model yourself? Each has trade-offs.

APIs offer speed and minimal setup, but may expose data, limit customization or accrue high cost — and will leave you at the mercy of your vendor. Open source allows internal control and may ease fine-tuning, but requires infrastructure, expertise, and support. Custom fine-tuning gives you the tightest alignment to your use-case, but lengthens time to value and increases risk.

Governance, data privacy and compliance. Deploying generative AI in an enterprise setting raises new governance, privacy and regulatory issues. For example: Who owns the data that’s ingested? How is proprietary data protected if you call a third-party API? What traceability exists for model outputs—a huge question for regulated industries? One useful framework is covered in “A GRC framework for securing generative AI” Data governance must adapt for the new era,  and new frameworks are evolving to help.

Human-in-the-loop review. Even the best models make mistakes and cannot simply be put on autopilot. You need a human-in-the-loop (HITL) process: real people need to review outputs, validate for bias, approve high-stakes content, and tune prompts or models based on feedback. Incorporating HITL checkpoints helps mitigate risk and improve overall quality.

Integration with existing systems and RAG pipelines. Retrieval-augmented generation, which we touched on earlier, connects foundation models into business workflows, systems, and enterprise data stores. RAG can bind LLMs to your organization’s internal knowledge bases, thereby reducing hallucinations (which we’ll discuss in a moment) and increasing the relevance of gen AI output.

What causes AI hallucinations?

Probably the biggest limitation of generative AI is what those in the industry call hallucinations, which is a perhaps misleading term for output that is, by the standards of humans who use it, false or incorrect.  

Every generative AI system, no matter how advanced, is built around prediction. Remember, a model doesn’t truly know facts—it looks at a series of tokens, then calculates, based on analysis of its underlying training data, what token is most likely to come next. This is what makes the output fluent and human-like, but if its prediction is wrong, that will be perceived as a hallucination.

Because the model doesn’t distinguish between something that’s known to be true and something likely to follow on from the input text it’s been given, hallucinations are a direct side effect of the statistical process that powers generative AI. And don’t forget that we’re often pushing AI models to come up with answers to questions that we, who also have access to that data, can’t answer ourselves.

In text models, hallucinations might mean inventing quotes, fabricating references, or misrepresenting a technical process. In code or data analysis, it can produce syntactically correct but logically wrong results. Even RAG pipelines, which provide real data context to models, only reduce hallucination—they don’t eliminate it. Enterprises using generative AI need review layers, validation pipelines, and human oversight to prevent these failures from spreading into production systems.

What are some other problems with generative AI?

Generative AI has proven to be such a disruptive technology that’s stoking near-apocalyptic fears that it will result in a superintelligence that will enslave or destroy humanity. Meanwhile, in the present day, increasingly troubling reports of so-called AI psychosis are emerging, where people have mental health episodes triggered by the uncanny and sometimes sycophantic ways chatbots affirm whatever you talk to them about and try to keep the conversation going.

Compared to such existential questions, the following business-related problems may seem petty. But they’re real issues for enterprises considering investing in AI tools.

• Data leakage and regulatory risk. When a model is fine-tuned or prompted with sensitive information, that data may be memorized and unintentionally reproduced. Using third-party APIs without strict controls can expose proprietary or personally identifiable information (PII). Regulatory frameworks like GDPR and HIPAA require explicit governance around where training data resides and how inference results are stored.
• Prompt injection occurs when an attacker manipulates a model’s instructions—embedding hidden directives or malicious payloads in user input or external content the model reads. This can override safety rules, expose internal data, or execute unintended actions in agentic systems. Guardrails that sanitize inputs, restrict tool-calling permissions, and validate outputs are becoming essential.
• Copyright and content ownership. Many foundation models are trained on data scraped from the public internet, creating disputes over copyright and data provenance. Enterprises using generated output commercially need to confirm usage rights and review indemnity terms from vendors.
• Unrealistic productivity expectations. Finally, organizations sometimes expect generative AI to deliver instant productivity gains. The reality, it turns out, is more mixed. Enterprise adoption requires infrastructure, governance, retraining, and cultural change. The models accelerate work once properly integrated, but they don’t automatically replace human judgment or oversight.

The current generation of enterprise AI systems includes several layers of defense against these risks:

• Guardrails that constrain model behavior and filter unsafe outputs.
• Model validation frameworks that measure factual accuracy and consistency before deployment.
• Policy layers that enforce compliance rules, redact sensitive data, and log model actions.

These safeguards reduce—but don’t remove—the inherent uncertainty that defines generative AI.

GenAI: essential for the enterprise

Generative AI has evolved from a novelty into a core layer of enterprise technology. Foundation models and agentic systems now power automation, analytics, and creative workflows — but they remain fundamentally probabilistic tools. Their strength lies in scale and adaptability, not perfect understanding.

For organizations, success depends less on chasing model breakthroughs than on integrating these systems responsibly: building guardrails, maintaining oversight, and aligning them with real business needs. Used wisely, generative AI can amplify human capability rather than replace it.