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5 steps to building an AI-ready culture before your next technology investment

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Technology is evolving at a relentless pace. Headlines proclaim the latest AI breakthroughs and generative models that promise to transform the way we work. Yet, when I sit down with leaders across industries, the conversation quickly shifts. The real questions are not about models, algorithms, or shiny tech investments; they’re about people. How do we equip our teams to thrive amid disruption – not just survive it? What practical steps move us from mere digitisation to lasting transformation?

These are the questions at the heart of a recent episode in our Decoding Business Transformation series. I had the pleasure of hosting Dr Sean Gallagher, founder of Humanova and one of Australia’s foremost voices on the future of work. The insights and recommendations below are drawn directly from that conversation, and I believe every boardroom should confront them head-on: In the era of agentic AI, culture will determine winners, not code.

The fancy tech is table stakes. People are the differentiator.

Let’s debunk a persistent myth: successful AI adoption is not a technology problem – it’s a talent and culture challenge.

Recent BCG research shows that high-performing AI leaders invest 70% of their resources into people and processes, with just 10% going to the algorithms themselves. Real value emerges when we empower individuals at every level – equipping them with the mindset, capabilities, and (crucially) the psychological safety to experiment with and apply new technologies.

As Dr Gallagher put it: “AI is a talent strategy, not just a technology play.” Transformation begins not with a new tool, but with a fundamental reimagining of how we nurture, develop, and inspire our people to explore, experiment, and adapt.

Why most AI projects fail: Ignoring the human element

Here’s a sobering truth, surfaced by Deloitte a decade ago: humans adapt to exponential technologies much faster than organisations do. The mistake? Leaders try to “bolt on” AI to outdated processes – putting a rocket on a jalopy, so to speak.

True transformation happens when we flip the script: empower employees first, technology second.

Frameworks such as the “Work Value Pyramid” can help organisations focus on shifting time away from repetitive administrative work and towards creativity, problem-solving, and strategic innovation. In practice, this means:

  • Resisting knee-jerk reductions in headcount. Your people’s tacit knowledge is invaluable capital.
  • Rewiring incentives and KPIs to reward learning, experimentation, and sharing.
  • Destigmatising “shadow AI” use. Bring your secret AI champions into the open, empower them as peer teachers, and build psychological safety for everyone to explore.

Flatten the org; Redesign the work

The blueprint for winning in the AI age is taking shape: Flatter, Faster, Fitter, Fewer.

  • Flatter: Remove unnecessary hierarchy. Push decision-making to the edges of the organisation.
  • Faster: AI is about more than simply doing things; it’s about doing them at the speed the market now demands.
  • Fitter: Build nimble, AI-literate teams who treat AI as a digital colleague – not a threat.
  • Fewer: Growth is not about increasing headcount; it’s about unlocking higher-value work for everyone.

Above all, resist the temptation to simply automate legacy processes. As McKinsey put it, “the fundamental redesign of workflows is the largest factor correlated with real impact.” Start with people and how work creates value – then let AI accelerate, not dictate, those improvements.

Measurement: Macro, not micro

Most companies focus on the wrong metrics: time saved per prompt, or “AI-powered” process widgets. That’s missing the point.

Instead, focus on:

  • Business-wide impact: Are you accelerating time-to-market? Opening new revenue streams? Raising the innovation bar?
  • Learning culture: Are teams sharing use cases and lessons? Is experimentation a norm?
  • Accountability KPIs: Prioritise experimentation, collaboration, and demonstrated learning over mere output.

In closing: The real transformation is human

If there’s one message from my conversation with Dr Gallagher, and from everything I’ve seen working with the world’s most ambitious brands, it’s this:

  • Invest deeply in your people – early, intentionally, and continuously.
  • Amplify the learning and experiments of your early adopters.
  • Model the behaviour you seek, starting with leadership.
  • Redefine productivity around effectiveness and innovation – not just efficiency.

Generative AI, and the new breed of AI “agents”, are rapidly becoming our digital colleagues. But only human curiosity, courage, and culture can unlock their full value. In this era, the ultimate competitive advantage is not code. It’s culture.

To learn more about Twilio, visit here.


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