Admit You Don't Know: Reverse Mentorship With An AI Sherpa

Here's what most leaders get backwards: they think credibility comes from always having the answer. In the AI era, it's the opposite. Credibility comes from admitting you don't know—and doing something about it.

Those three words—"I don't know"—might be the hardest for any leader to say. I wrote about this years ago after catching myself being unwilling to admit ignorance to a student. But when I finally said it, something magical happened: the whole class came alive with ideas, resources, and energy that would have never surfaced if I'd pretended to be the sage expert.

That's the paradox: pretending to know shuts down learning. Admitting you don't know opens the door.

The Leadership Paradox

Senior leaders face a double bind when it comes to AI. Their time is so valuable that the opportunity cost of learning feels astronomical. Yet as Geoff Woods pointed out on Beyond the Prompt, most organizations are using AI to get more efficient at the 80% of activities that drive only 20% of value, instead of being strategic about the 20% of activities that drive 80% of outcomes.

Guess who spends most of their time in that crucial 20%? Senior leaders.

So we've got executives who could 10x their impact through AI collaboration, but they're the last ones to make time for it. Meanwhile, they're supposed to drive organizational AI adoption and hold teams accountable for metrics they don't understand themselves.

Here's the thing: you can't require what you won't do. Period.

David Long from the Portland Trail Blazers put it bluntly: "If they're not on board, how are they supposed to hold their entire department to a standard of AI use? The whole building crumbles."

The Credibility Hack

This is where humility becomes a leadership superpower. At a recent keynote I gave for PCCP, LLC, one of their senior leaders told me something that stopped the room:

"I raised my hand and asked for a mentor, even though I run the firm. I got one one of the younger folks to be my mentor on the AI thing. We're collaborating like crazy, and we're loving it. Everybody has seen how much enthusiasm and joy it’s brought me, and it’s really broken down the fear of the unknown."

When Don publicly spoke up about his “reverse mentorship” arrangement shared this at their company conference the following week, several other senior leaders stood up asking for AI mentors on the spot. Don’s humility sparked a movement.

Find Your Mentor (The 15-Minute Discovery)

Here's how to identify your AI mentor in real time:

In your next team meeting, when a challenging question comes up, say: "I don't know the best approach here—does anyone know how AI might help us think through this?" Then sit back and watch.

The person who immediately jumps in with suggestions? Who pulls up ChatGPT and starts demonstrating? Who gets excited about the possibilities? That's your mentor candidate.

You've just discovered who on your team is already fluent—and you've modeled the humility that makes great leaders. Two birds, one stone.

Enter the AI Sherpa

Not every leader is ready to raise their hand for a junior mentor. That's fine. The alternative is what I call the AI Sherpa, which is basically a personal, dedicated dream weaver for senior leaders—temporary capacity expansion for executive learning.

Here's the offer (and frankly, it's irrefusible): Dedicate an AI-knowledgable coworker for the purpose of AI discovery on the leader’s behalf. Sherpa shadows the leader for 2-3 days. Listen to their meetings, understand their workflows, identify the AI opportunities they can't see. Build custom GPTs for their specific challenges. Make them fluent, enthusiastic users.

Think about it—if an AI-forward innovator spends three days with a senior leader as their AI shadow, creates three relevant GPTs, and ensures they know how to use them... it's really hard to imagine they won't keep using them. And once the leader is using AI daily, they have both the credibility and the data to drive organizational accountability.

As Don Corleone might say: make them an offer they can't refuse.

A Transformation Litmus Test

The beauty of this positioning is that the offer of an “AI Sherpa” to augment senior leaders is so obviously beneficial and so low-friction that growth-oriented leaders would be foolish to decline. When making a sherpa available—and this is important—make the stakes clear.

If a time-constrained leader opts out of world-class AI mentorship designed to make them a credible practitioner who can drive cultural transformation? That's valuable data about their commitment to organizational change. That's just cause. Let's leave it at that.

This gives you an unassailable position: you're making an incredible offer, and they'd better take it.

The A-A-A-A Playbook

Whether you opt-into a reverse mentorship, or roll out the AI Sherpa model as a service, the rhythm is the same:

Admit — Say out loud: "I don't know how to do this yet."

Apprentice — Invite a younger staff member (or external Sherpa) to shadow your work and show you the ropes.

Apply — Let them build you 2-3 custom GPTs or workflows you'll actually use.

Amplify — Model your use publicly so your teams see you're walking the talk.

This isn't weakness. It's leadership.

The opportunity cost of learning isn't nearly as expensive as the opportunity cost of staying ignorant while your competition races ahead.

In the age of AI, those three words—"I don't know"—may be the only way to become a credible leader.

Related: Admit You Don’t Know
Related: Beyond the Prompt: Geoff Woods
Related: Catalyze AI Success: The Power of Dedicated Innovation Capacity

What's stopping you from making (or accepting) this offer? Reply and let me know - I'd love to hear what you try.