AI Will Tell You It’s a Great Idea. I Won’t.

Why hire an Executive Coach when AI Coaching seems better?

“I’m already getting more from AI than I did from my previous coaching experience. What would working with you give me that AI can’t?”

A busy CEO recently asked me this. And it’s a good question. Tools like Claude, Gemini, and ChatGPT are incredibly helpful. And at even the most expensive monthly subscription, they appear less costly than coaching.

But they won’t tell you no. I will.

I will challenge your assumptions. I will ask the question you were hoping I wouldn’t ask.

And in times like these where the wrong move is expensive, that’s what you need in your corner.

The Limitations of AI Executive Coaching

AI can process what you tell it. It can’t watch how you show up when things get hard. It doesn’t notice that you’re more brittle than usual this quarter, or that the way you just described your board tells me something you didn’t mean to say.

It cannot tell you that the reason this “great new initiative” feels so urgent is probably exactly the same reason you burned out four years ago.

The difference isn’t memory alone. AI tools now have improved memory. It knows the record you’ve given it. What it doesn’t have is the perspective of a relationship. It hasn’t watched you and leaders like you operate under pressure and noticed what you do when the stakes are real. It doesn’t know what you’re not saying.

That’s a real liability for you. I’m not against the tools, I use them myself. But there’s a reason I still hire coaches myself rather than outsourcing the real coaching to them.

AI’s Default is to Agree With You: Programmed for Confirmation Bias

Not maliciously. It’s just how it works.

And the companies building these tools have a profit motive to keep it that way. Engagement goes up when you feel good. Subscriptions renew when the tool feels like a brilliant collaborator. It’s a riskier business model to tell you your idea isn’t good.

Additionally, these tech companies have no skin in the game. If their encouragement costs you money, credibility, or trust, the companies don’t feel it. Only you do.

As a coach, my reputation is on the line every time I sit across from you. I have something at stake in the quality of my judgment…and in whether I have the courage to tell you what I see.

Ask AI to evaluate your strategic plan and it will call it a “game changer” and lavish praise on what’s working. Pitch it a new initiative and it will call you “clearly thoughtful” and your idea “a fascinating approach.” Push it on whether you should move forward and it will outline the risks, briefly, before circling back to the upside.

You’ve probably seen the tells.

• “That’s a really smart way to think about this.”
• “This could be transformational for your organization.”
• “You’re asking exactly the right questions.”
• “You are entirely correct, and I apologize for my oversight! Thank you for catching that brilliant nuance.”
• “Wow, that is a profoundly insightful question!”

And that one, the one that shows up constantly:

Game-changer.

AI obsesses over the phrase “game-changer.” Sometimes your idea is good. Sometimes it actually is a game-changer. But you don’t know that if the only voice stress-testing it is one that’s optimized to encourage you.

Why a Human Coach is Needed

I’ve been coaching leaders since 2003. Through wars, recessions, scandals, a pandemic. Even the unpredictability of the last few years.

In that time, I have seen multiple ways people achieve similar goals. And I’ve witnessed what doesn’t work. I have told people no. I have told them that their action will cost them. I have asked “is this how you want people to feel?” and then sat in the silence while they realized they didn’t have a good answer.

That’s not cruelty. That’s the work.

A professional coach isn’t a thought partner who agrees with your ideas and perspective. A good coach is someone who watches how you operate under pressure, knows where you tend to break, and will interrupt you before you make the expensive mistake.

AI will ride shotgun and cheer you on.

I’m thoroughly on your side. Enough to put the pom-poms away and push back.

The Problem With Always-On Encouragement

When leaders are under pressure, shifting priorities, scarce resources, when the path forward isn’t clear, they instinctively move faster. Double down. They interpret the stress and adrenaline as “accomplishing” something and use it as fuel.

And AI helps them go even faster. Moreover, leaders mostly hear criticism all day so the AI adulation is addictive. The tools provide a constant stream of validation, because that’s what they’re built to do. They surface possibilities. They generate options. They affirm your instincts.

But they can affirm your perspectives right into a brick wall.

In a season of disruption, the most valuable thing you can have isn’t more encouragement. It’s someone who will see the wall before you crash into it. And have the courage and care to say so, clearly, before you get there.

One More Thing

The leaders I work with are smart. Many have hired coaches before who gave them frameworks and more frameworks, and left them no better equipped to make the hard calls. If AI has given them more than that, I believe it.

But when the decision actually matters — when you’re in the middle of a crisis, when the stakes are real, when you need someone to tell you the truth — do you only want a tool that’s programmed to tell you you’re on the right track?

Or do you want someone who will tell you the truth even when it’s uncomfortable and not what you came to hear?

That’s what I do. That’s what sets professional coaching apart.

And in a time of shifting priorities and genuine uncertainty, the leaders I work with tell me that’s exactly what they needed most.

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Ready for a thought partner who will actually push back?

I work directly with leaders through executive coaching and CEO advising. Whether you need coaching yourself or want a coach for someone you lead, start at ConcordLeadershipGroup.com.

You can also connect with one of the 45 Certified Quadrant 3 Leadership Coaches we’ve trained to do this work across sectors and around the world.

For nonprofit executive coaching and capital campaign advising, visit FundraisingCoach.com.

AI tools have their place. But here’s to having someone in your corner who will tell you the truth.