Executive AI Fluency: The Missing Link in Transformation

Author

Charlene Li
September 15, 2025

Here's what I keep hearing from organizations: "Our AI initiatives aren't delivering the results we expected."

But when I dig deeper, I discover something fascinating. It's not the technology that's failing. It's the leadership approach.

Most executives treat AI like any other enterprise software rollout. They delegate it to IT, approve the budget, and expect results in quarterly reports.

The problem? AI isn't like implementing a new CRM. It requires strategic thinking, workflow redesign, and cultural change that can only be driven by executive leadership.

Yet when I ask these same executives how personally involved they are in their AI strategy, the responses are remarkably similar: "That's not really my area" or "I leave that to the technical teams."

This mindset is precisely why AI stays trapped at the efficiency level instead of becoming transformational.

The Real Issue Isn't Technology, It's Leadership

Here's what I've learned: You can't create AI transformation without executive AI fluency.

Think about those Silicon Valley "AI safaris" where companies bring executives to meet with OpenAI and Anthropic and expose them to a slew of AI start-ups. Executives get excited, they ooh and ahh, then they go home and... nothing changes. It's innovation theater, not real transformation.

The Three-Step Framework to Executive AI Fluency

After working with hundreds of executives on technology adoption, I've discovered there are three critical steps to getting your top leadership truly AI-fluent.

1️⃣ Make It Personal

Generic AI training doesn't work with busy executives. You have to connect AI to one of their top three strategic objectives—the things they're already laser-focused on achieving.

Don't try to add AI as a fourth priority. Instead, show them how AI can help them achieve those existing priorities better, faster, cheaper, and with less risk.

Common executive pushbacks I hear:

  • "It's not my job, it's IT's job" → Actually, accelerating growth IS your job

  • "It's too early, moving too fast" → Speed is the new moat in AI

  • "Show me the ROI" → What's the value of reaching your strategic goal six months sooner?

  • "I don't have time" → This will save you time, your most constrained resource

2️⃣ Give Them Hands-On Experience

This goes way beyond prompt writing. Last year, I ran a workshop with 15 CEOs where we created custom GPTs for each of them using their own presentations and company information.

The difference was remarkable. Even minor customizations gave them confidence that AI could be specifically relevant to their work, rather than just providing generic assistance.

But here's the crucial part: You must address trust first. Use what I call the AI Trust Pyramid—just like Maslow's hierarchy, you can't address higher levels until the foundational concerns about safety, security, and privacy are handled.

3️⃣ Build AI Into Daily Routines

This is where the magic happens. AI fluency isn't a one-time training—it's about integrating AI thinking into everyday leadership practices.

Try these approaches:

  • Start meetings by asking: "How did you use AI to prepare for this meeting?"

  • Request AI first drafts: "What insights did AI contribute to these recommendations?"

  • Weekly check-ins: "Share one task where you used AI to improve quality or efficiency."

  • Challenge assumptions: "Did you run this through AI to stress-test our thinking?"

  • Development discussions: "How did you use AI to grow in your role this quarter?"

The Vulnerability Factor

Here's what makes attaining AI fluency particularly challenging for executives: Learning AI means being a beginner again.

For leaders who are expected to have all the answers, experimenting with AI can feel vulnerable. They're making mistakes, getting imperfect results, and learning in public.

But that's precisely where they need to be.

The mindset shift is crucial: Instead of having all the answers, executives need to get really good at asking great questions. They need to model continuous learning and embrace what leadership coach Barry O’Reilly calls a "hunch mindset"—trying experiments based on hunches rather than certainties.

This discomfort isn't a bug; it's a feature. When executives feel a little uncomfortable and uncertain, that's a sign they're learning and growing.

Making It Measurable

One organization I worked with created AI fluency dashboards for all departments. They tracked time spent using AI tools, the number of interactions, and the estimated percentage of work enhanced by AI.

When the legal department realized they were orders of magnitude behind other departments, it initiated the right conversation—not about shaming, but about providing support and training to enhance their AI fluency.

Set the expectation: Everyone should be AI-fluent within six months. If AI fluency and adoption is truly a priority for your organization, dedicate the resources to make it happen.

The Bottom Line

Your executives aren't inhibitors because they're "old dogs." They become inhibitors when they don't see AI as strategic, when they haven't experienced its power personally, and when they haven't been made to feel safe to learn from it.

But when you make AI personal, hands-on, and routine? They transform from skeptics to advocates, from inhibitors to momentum builders.

Because here's the truth: You can teach an old dog new tricks. And I've trained my cat to do over a dozen tricks. Cats aren't expected to do tricks, but with the right motivation (food and love), they absolutely can learn.

Executives are highly motivated by achieving their strategic objectives. Connect AI to those objectives, and you'll be amazed at how quickly they become your biggest AI champions.

🗨️ Your Turn

How are you getting your executives AI-fluent? Are they facilitators or inhibitors of your AI initiatives? I'd love to hear about your experiences—and your challenges.

What I Can’t Stop Talking About

  • Your spreadsheets won't save you from 50 MPH winds. At Burning Man, I watched people's responses to uncontrollable disruptions. The most resilient didn't rebuild what they had; they adapted and created something new with the remaining pieces. That's leadership in disruption.

  • 78% of companies are using AI, but only 27% have formal policies. That's like letting people drive without traffic lights; crashes are inevitable. You can't build AI governance when the crisis hits. The foundation needs to be in place before disruption strikes.

  • Looking for your AI brain trust? If you’re wrestling with finding value from AI and want a high-signal group of peers—not vendors or hype merchants—check out our Samudra community. We’re adding a few more leaders this month. Most members are C-suite or VP-level and show up ready to challenge, share, and evolve. Limited seats. North America-based meeting times.

My Upcoming Appearances/Travel

If you found this note helpful, please forward and share it with someone who needs the inspiration today. If you were forwarded this, please consider subscribing.

Join me on Facebook, Instagram, LinkedIn, and Twitter.