"Have You Tried AI?" The Answer Every Leader Should Give

I was on a video call recently when Sonya, an executive vice president at a major publishing house, dropped a question in the chat: "Which tool is best for analyzing customer feedback at scale?"

I could feel my fingers reaching for the keyboard to answer. I know a few tools. I could rattle them off. Easy.

But here's what I typed instead: "Sonya, have you asked ChatGPT?"

You know what's funny? I had to resist my own instinct to just solve it for her. And that resistance—that tiny moment of restraint—is the entire point.

Why This Question Feels Risky (But Isn't)

Most leaders I work with tell me the same thing: asking "Have you tried AI?" feels like it carries a risk.

Doesn't it look like I don't know the answer?

And here's the deeper fear (let's be honest): Isn't this a relinquishment of my “leadership responsibility”?

I get it. I really do. But the truth is, that's only true if you want to always be the person everybody has to ask for everything.

If you would actually rather have them be able—which I think is what leadership is really about, unleashing the capabilities of others—then you want to get yourself out of the loop as much as possible. Not because you're lazy (though honestly, who doesn't want fewer interruptions?), but because that's not a model for scalable flourishing.

Even if you do know the answer, an exceptional leader may actually prefer to ask "Have you tried AI?"

Why? Because you're not just solving their immediate problem. You're building a muscle. You're creating a habit. You're helping them develop the reflex to turn to AI first, instead of always turning to you.

You don't want to be the bottleneck.

Three Ways This Question Serves Your Team

When you ask "Have you tried AI?" you're giving your team three gifts:

1. It Opens Their Mind

Most people honestly don't think to use AI for most tasks. (I mean, I literally have a post-it note on my screen that's been there for two years that says "Have you tried ChatGPT?" Because even I forget.)

They're stuck. They reach out to you. And you're reminding them: Oh right, I have this incredibly capable teammate available 24/7 that I completely forgot about.

2. It Gives Them Permission

Even if they have thought of it, there's often a question: "Is it irresponsible for me to use AI for this?" "Does my boss want me to?" "Should I?"

When you ask the question—when you explicitly suggest they try AI—you're not just reminding them. You're giving them permission. You're signaling: Yes, this is not only okay, it's expected.

3. It Creates a Learning Moment

Here's what most people miss: AI isn't a tool that gives answers; it's a teammate: an expert, a coach, a creative partner.

When a member of your team invites AI into a specific problem, they don't just get an answer—they discover how to work with AI as a teammate on this type of problem. They learn prompting. They learn iteration. They build capability. They learn how to be a good collaborator to AI.

That capability compounds over time.

Two Ways This Question Serves You as the Leader

But it's not just altruism. This question serves you in two critical ways:

1. It Gives You Success Stories to Share

Here's the move: When your teammate comes back with their work product, ask a follow-up question: "How did AI help?"

Then—and this is important—get them to share with others how AI helped them. Even better, brag on them publicly, yourself.

This is how you create a flywheel. Every time someone shares a success story, you're multiplying the impact. You're showing the whole team what's possible. You're making it normal to use AI, not weird.

At the National Park Service, there's a leader named Cheryl Eckhardt who's mastered this. She has monthly office hours where she spotlights community members sharing what they've built with AI. She doesn't answer questions—she amplifies the people who've already figured stuff out. That's brilliant leadership.

2. It Prevents You from Being the Bottleneck

A few years ago, I was in a course learning to build custom AI assistants. (This was before custom GPTs were a thing.) I paid several thousand bucks out of my own savings because I felt like I really needed to learn this stuff.

They had a Discord for asking questions. I'd be stuck on something—like, I couldn't figure out how to structure a certain API call—so I'd post my question to the TAs. Then I'd sit there. Waiting. Can't move forward because I don't have the answer.

It's usually late at night because I have a job, so eventually I'd think, "I guess I'll go to bed and check in the morning."

Inevitably, the next morning I'd have a message from the TA: "Have you asked ChatGPT?"

And I was like, I paid money for this?

Then I'd get stuck again. Post another question. Wait again. And again, the next morning: "Did you ask ChatGPT?"

It took me—embarrassingly—several rounds of this before it finally clicked: They're just going to keep asking if I've tried ChatGPT. I don't have to wait for the TA. The expert I need is already in my pocket.

That's the gift you give your team when you ask this question. You're teaching them they don't have to wait for you.

What to Do Right Now

Here's your action plan:

1. Put a reminder where you'll see it
Post-it note on your monitor. Reminder on your phone. Whatever works. Mine says: "Have you tried ChatGPT?" It's been there for two years because I still need the reminder.

2. Practice asking without embarrassment
The first few times will feel weird. That uncomfortable feeling? That's your old leadership paradigm dying. Good riddance.

3. Ask the follow-up: "How did AI help?"
Don't just ask if they tried AI. Ask how it helped. Get the story. Then share that story with the team (with permission, obviously).

4. Make it a pattern for 2-3 weeks
This isn't a one-time thing. It's a new habit. Do it consistently and watch what happens. Watch how the questions change. Watch how people start solving problems before they even come to you.

The Real Gift

When you ask "Have you tried AI?" it might feel like you're deflecting. But you're not.

You're giving your teammates three gifts: an idea they didn't think of, permission they were waiting for, and a learning opportunity they wouldn't have gotten if you'd just answered their question.

You're giving yourself two gifts: a steady stream of success stories to share and freedom from being the bottleneck everyone depends on.

And you're giving your organization the most important gift of all: a culture where the default instinct isn't "ask the boss" but "ask AI first."

Leadership isn't about always having the answer. It's about building the capacity of others to discover answers for themselves.

And sometimes, the most powerful thing you can say is five simple words: "Have you tried AI?"

Related:
Don't Keep the AI Expert Waiting
The Most Important AI Role Has Nothing To Do With Code
Take Your Own Job Before Someone Else Does

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