We’re Asking Leaders the Wrong Questions

When I was running for office, people kept asking me, “What do you think about this issue?” or “What would you do in that situation?”

And every time, I had the same thought: How could I possibly know?

I wasn’t in the role yet. I didn’t have access to all the information. And the truth is, any answer I gave would have been a guess—based on what I thought I knew at the time.

But here’s the problem: We do this in leadership hiring all the time. We ask nonprofit CEOs, executives, and board members to predict how they’d act in a tough situation instead of looking at how they’ve actually handled challenges before.

But leadership isn’t theoretical. Leadership is what you do when you’re in the seat.

What Have You Actually Done?

When I lead executive searches, I never ask candidates, “What would you do in this situation?” Instead, I ask:

“Tell me about a time when you were in this situation. Walk me through exactly what you did.”

Because anyone can recite best practices. Anyone can repeat what they’ve read in a leadership book or heard at a conference. But that doesn’t mean they know how to apply it when the pressure is on.

A Costly Mistake and a Priceless Lesson

Many years ago, I made a $10,000 mistake at work. The details aren’t important—but what is important is what happened next.

I could have panicked. I could have covered it up. I could have tried to fix it alone and made it worse.

Instead, I went straight to my executive director. I said, “I made a mistake. Here are a few possible solutions I’ve thought through. What do you think?”

He listened, asked questions, and ultimately agreed with my proposed solution. Then he said something I’ll never forget:

"Now go fix it. And then move on."

He recognized that I was being hard on myself. He could see I had learned from it. And he helped me take the right next step without letting the mistake define me.

That’s the kind of leader I want to work with. Someone who doesn’t just know the right answer but knows how to get to the right answer when it matters.

So, What Are the Right Questions to Ask Leaders?

So, what should we be asking instead?

Instead of: “Have you worked with a board of directors?”
Ask: “Tell me about a time when your board had conflicting viewpoints. How did you navigate it?”

Instead of: “What’s your approach to strategic planning?”
Ask: “Can you walk us through a time when you led a strategic planning process? What were the challenges, and how did you handle them?”

Instead of: “How do you handle conflict?”
Ask: “Tell me about a time when someone completely disagreed with your perspective. How did you approach the conversation, and what was the outcome?”

The first set of questions lets candidates guess at what they’d do. The second set forces them to prove that they’ve already done it and show what they are truly capable of doing.

The Real Test of a Leader

Great leaders don’t walk into a situation with all the answers. They walk in with the ability to ask the right questions, gather the right information, and make thoughtful decisions.

That’s what I want to see in a leader. Not someone who has memorized the “right” response, but someone who can say:

✔ Here’s how I’ve made tough decisions before.
✔ Here’s how I’ve sought out the right information.
✔ Here’s how I’ve handled difficult conversations and still maintained relationships.

Because once a leader is in the role, there’s no script. There’s no checklist. There’s only real-time decision-making—and we need leaders who have already proven they can do it.

Why The Right Questions Matter

When I was running for office, people wanted me to give a polished answer about what I would do in a role I hadn’t stepped into yet.

That’s not how leadership works.

If I were in that role today, I wouldn’t be making decisions based on what I thought back then. I’d be gathering information, talking to the right people, and making the best decision I could with the facts in front of me.

And that’s what we should be looking for in every leader we hire—not hypotheticals, but a track record of real decision-making, problem-solving, and critical thinking.

So next time you’re sitting across from a candidate, a board member, or even a potential elected official, don’t ask: “What would you do?”

Ask: “What have you done?”

That’s the real measure of a leader.