The higher you go at work, the lonelier it gets.

You’re expected to make faster decisions with fewer inputs.

Manage risks no one else sees.

And hold a space for everyone else’s uncertainty, while simultaneously having to manage your own.

But here’s what’s rarely talked about… Even the best leaders find it difficult to think clearly in isolation.

And yet, that’s exactly how many of us make our biggest calls: alone, under pressure, without enough time or perspective.

But for some leaders, that’s quietly starting to change with the help of AI, if they permit themselves to use it differently.

Not as a task tool. Not to generate content or create slide decks. But as a thought partner.

You don’t need more advice. You need a place and the space to think.

AI can’t lead for you. It won’t replace your judgment. But when used well, it can become an unbiased partner for complex, nuanced decisions.

Not the tactical ones. And also not, “What should I name this program?” or “How do I word this email?”

Use it for the meaningful ones. The ones that ask:

• “Do we optimize for short-term revenue or long-term trust?”
• “Do we scale what’s working or explore what’s next?”
• “Do I challenge this stakeholder or protect the relationship?”

These are the kinds of decisions that shape teams, cultures, and outcomes. They deserve more than a late-night, often agonized gut check, even when there’s no one else around to ask.

The best thinking doesn’t come from a blank page. It comes from tension.

Here’s what most people get wrong: they use AI like old tech. Put in a prompt, get a response. Move on.

But leadership isn’t only about answers. It’s about asking better questions, exploring the edges, and thinking through the tradeoffs carefully.

That’s one of the ways I use AI. I don’t ask it to tell me what to do. I ask it to argue with me, to stress-test my logic, to show me what I might be missing.

I’ll say:

• “Be honest with me.”
• “Assume I’m wrong. Why?”
• “What are the risks if this fails publicly?”
• “What would my critics say in a boardroom or at the dinner table I’m not at (it’s not just for work :)? ”

It responds. I push back. It improves. I adapt. Not (necessarily) because it’s smarter than me, but because it helps me see more clearly.

This is about leadership improvement. Mental clarity. Decision quality.

If you’ve ever wanted a sounding board at 7 am before a tough call, If you’ve ever walked into a meeting knowing your strategy had weak spots, If you’ve ever worried about a decision with no one to vet it with…

This is your chance to try something different.

Not because it’s trendy. But because YOUR leadership is too important to do in a vacuum.

Your turn: Try this with one decision this week

Pick something real. Not urgent, but important.

Block 20 minutes. Lay out the stakes, your current thinking, and the real tension points.

Then ask AI to challenge you. Not solve it, but challenge it.

At the very least, you’ll walk away thinking more clearly. At best, you’ll change your mind or deepen your conviction.

Either way, you’ll decide better. And that’s never been more important for leaders.

If this helped clarify something for you, consider sharing it.

Or send it to someone who’s managing the weight of difficult decisions alone.

For more practical insights on clarity, conviction, and leading well, subscribe to On Leading Well or follow me on LinkedIn for weekly ideas on human-first leadership in the age of AI.