The Messy Middle of AI Culture Change: Navigating the Toughest Phase

I have a confession to make: I love the messiness of transformation.

That probably sounds strange. Most leaders crave certainty and clarity. We want neat roadmaps with clear milestones. But after working with organizations on digital transformation for 15+ years, I've learned that the most important work happens in what I call "the messy middle."

This messy middle is where we find ourselves right now with AI culture change. It's that uncomfortable space where the old way is dying but the new way hasn't fully taken shape. There's no orderly, linear path through it—just a backwards, forwards, all-around journey of trying, learning, and adapting—which you can read more about here.

When I talk with leaders implementing AI, I hear the frustration in their voices. They want clear playbooks. They want proven steps. But the messy middle doesn't work that way, especially with technology evolving as rapidly as AI.

The Culture-Strategy Disconnect

Here's something I've observed time and again: you can have the most brilliant AI strategy, but if your culture isn't ready to embrace it, that strategy will fail. It's like planting seeds of innovation in barren soil—if you don’t fertilize, water, and nurture that ground, nothing will grow.

Peter Drucker was right when he said "culture eats strategy for breakfast" every single day. A great culture with an okay strategy will always win over a great strategy with a dysfunctional culture. Why? Because a healthy culture will figure out how to make any strategy work. (If you’re worried that your strategy is in need of a little help, though, you can get a free AI strategy audit here) 

But for many organizations, AI presents a unique cultural challenge. We're facing what I call the FOMO-FOGI tension: fear of missing out versus fear of getting in. 

The Cultural Headwinds Against AI

A recent Stanford AI study revealed something fascinating. In China, 83% of people believe AI will be more beneficial than harmful. In the United States? Just 39%.

Think about what this means for your AI strategy. If you're leading an American organization, the majority of your team likely believes, at a deep cultural level, that AI will do more harm than good. You're pushing against powerful cultural headwinds before you even begin.

This isn't just about technology adoption; it's about overcoming deeply ingrained cultural beliefs about whether this technology is even good for us. That takes a lot of work (you can learn more about it in my talk, “A Leader’s Guide to Artificial Intelligence,” which you can find here. 

Five Beliefs of an AI-Ready Culture

Through my research for my upcoming book with Katia Walsh, I've identified five core beliefs that separate AI-ready cultures from those that struggle with transformation:

1. Speed over perfection
AI changes too quickly for traditional analysis paralysis. Your teams need to prioritize momentum and decision-making over perfection. I've studied these technologies extensively, and I'm still constantly surprised by new capabilities. Waiting until you "master" AI means you'll never start.

2. Focused experimentation
The options for AI exploration are overwhelming. Cultures that thrive don't try to learn everything—they focus on doing a few things better. Remember that strategy is about choices, both what you will do and what you won't.

3. Questioning assumptions
The most dangerous phrase in business is "that's how we've always done it." AI-ready cultures constantly ask "why?" and test their assumptions. Even when you establish effective AI practices, keep questioning: could there be a better way?

4. Continuous learning
The humility to recognize what you don't know and the discipline to keep learning is essential. The landscape changes weekly, and yesterday's best practice might be tomorrow's cautionary tale.

5. Shared purpose
Without a clear, shared purpose, everyone defaults to their pet AI projects for their team, department, or customers. AI-ready cultures maintain laser focus on the transformational initiatives that move the entire organization forward.

That’s why I’m so excited to share our forthcoming book, “Winning with AI” with you. It will be your comprehensive guide to mastering AI within a strategic framework tailored to your organization's purpose and values. 

Why Traditional Change Management Fails with AI

If you've led change initiatives before, you might be tempted to apply traditional change management approaches to AI adoption. I've seen this fail repeatedly, and here's why:

Traditional change management assumes you're going from point A to a well-defined point B. With AI, we don't know precisely where we're going. We have a direction, but no fixed destination.

The impacts are unpredictable. We have ambitions and set corresponding targets, but we're navigating uncharted waters.

The pace outstrips traditional change cycles. By the time you implement phase one of your change plan, you're already pivoting because the technology has evolved.

This isn't a short-term change—we're talking about sustained transformation over months and years, which brings me to perhaps the biggest challenge:

Change fatigue is very real. When people are constantly changing and never feel like they've "arrived," exhaustion sets in. The genuine effort they're putting in seems endless without clear wins to celebrate.

Changing Your Culture's Underlying Beliefs

If your culture is holding back AI adoption, how do you change it? I've found a systematic approach that works, though it's far from easy:

1. Make the hidden beliefs visible. Gather your team and have everyone write down what beliefs they think are holding the organization back. What behaviors reflect those beliefs? Put everything on the table (literally) and sort through them together.

2. Identify which beliefs no longer serve your future. These are the ones you need to change.

3. Reframe each outdated belief with a new, empowering alternative. When you see the old belief exhibited in behavior or conversation, gently redirect to the new belief.

4. Measure whether behaviors are actually changing to reflect these new beliefs. This is your evidence that culture is truly transforming.

I watched this process transform a century-old global company that wanted to become more customer-centric. They created a culture manifesto of new beliefs, and each leader identified one fundamental belief to change in their division. By focusing intensely on just changing that one belief, they achieved remarkable transformation within six months.

One of my favorite examples comes from an organization that had a core value of "respect." Over decades, this value had morphed from the founder's original intent (that good ideas could come from anywhere) into an unspoken rule that no one could disagree with the most senior person in the room because that would be "disrespectful."

As you can imagine, innovation had ground to a halt. To reframe this value, they returned to the founder's original meaning and instituted new behaviors: leaders would speak for only the first five minutes of meetings and then actively encourage dissent and different perspectives. They set a 12-month timeframe for this change, with intentional rituals and stories to reinforce the reframed value.

Embrace the Messy Middle

Changing culture for AI readiness is gut-wrenching work. Your palms will sweat, and you'll face resistance. That's how you know you're doing it right.

But the organizations that embrace this messy middle, that have the courage to examine their beliefs, reframe them, and nurture new behaviors, are the ones that will ultimately harness AI's transformative potential.

This work is indeed messy. It's also absolutely worth it.

Your Turn

What beliefs are holding your organization back from embracing AI? Which of the five beliefs of an AI-ready culture is most challenging for your team?

What I Can’t Stop Talking About 

• The entrepreneurial readiness myth. "I'm not ready" is the phrase I hear most often from aspiring entrepreneurs. But here's the truth: you will never feel fully prepared. Being a founder means embracing uncertainty while shouldering responsibility for everyone's paycheck. Here's why waiting for readiness might mean missing your opportunity entirely.

• A powerful poll on AI perception. I mentioned that a fascinating Stanford study reveals that 83% of people in Asian countries believe AI's benefits outweigh risks, compared to just 39% of Americans. This stark contrast isn't random—economic context shapes our technological outlook. Share your AI perspective here. 

• Are you bringing your whole self to work? How much of yourself do you leave at the door when you go to work? Being "integrated" doesn't mean being identical in every context—it means staying true to your core while adjusting which aspects you emphasize based on the situation. The key is clarity about who you are at your core—those are the dials that should never change.Read more about it here. 

My Upcoming Appearances

• May 8: LinkedIn Office Hours, Webinar, Virtual

• May 16: Private Executive Retreat, Portland, OR

• Jun 10: Betterworks Webinar, Virtual

• Aug 29: Indy SHRM, Indianapolis, IN 

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If this information was helpful, there’s plenty more! Sign up for updates and early access to my upcoming book, co-authored with Katia Walsh, which is all about creating a winning generative AI strategy.

Catch my most recent LinkedIn courses:

“The Manager's Guide to Integrating and Managing AI Agents." In this brand-new course, I offer practical approaches for effectively managing both AI agents and human employees as a unified team. Ready to lead with confidence? Get the course here.

"Transforming Business with AI Agents: Autonomous Efficiency and Decision-Making." I provide a comprehensive introduction to autonomous AI agents, explaining how they differ from other AI products, boost productivity, and enhance decision-making while addressing key ethical considerations. Explore the course here.

Join me and Andreas Welsch on May 8th for a candid discussion where we'll discuss agentic AI and break down the hype and explain what decision-makers need to know about this rapidly evolving space.

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