The Most Natural Question in the World (And Why it’s the Wrong One)

A reader named Layne, a CMO with 20+ years in startup tech, wrote something in her review that I keep coming back to:

“I thought good coaching meant having better answers. This book showed me it means asking better questions.”

That one sentence is the whole paradigm shift.

Most of us were trained, implicitly or explicitly, that our value comes from what we know. The higher you go in your career, the more you’re expected to have the answer. Someone brings you a problem, and your brain immediately starts solving it. That’s what good leaders do, right?

Two weeks ago I wrote about why advice doesn’t work, even when it’s good. Last week I was unplugged in Costa Rica. This week I’m back with a question for you:

If you’re not supposed to give the answer, what are you supposed to do instead?

Ask a better question. But not just any question.

The Most Natural Question in the World (and Why It’s the Wrong One)

Have you ever had a tense conversation with someone, and then hours later you’re in the shower or at the gym, and the perfect thing to say just pops into your mind? That happens because you cannot solve a problem while focused on the problem. Your brain doesn’t distinguish between “I’m thinking about a problem” and “I’m in actual danger.” Both activate the same defensive wiring, which blocks creative thinking. The insight only arrives once you’ve relaxed enough for your brain to shift into a different mode.

Now think about what happens when someone says, “My coworker is pissing me off.”

Your response, almost certainly, is: “What happened?”

Workout felt terrible? “What happened?” Missed a deadline? “What happened?”Frustrated with a direct report? “What happened?”

It’s the most natural, compassionate-feeling response in the world. We’re biologically wired to scan for problems. We’ve been culturally trained that good leadership means understanding what went wrong. And our empathy drives us to meet people in their emotional space.

Here’s the problem: “What happened?” will lead you both into at least ten minutes of detail and drama about the problem. Your colleague or employee will recount every frustrating moment, every person who made things worse, every reason they couldn’t succeed. And you’ll nod along, taking notes, feeling like you’re being helpful by “really understanding the situation.”

But you’ve just wasted ten minutes that could have been spent actually moving forward. And worse, you’ve pushed their brain deeper into defensive mode, where creative problem-solving is neurologically unavailable to them.

Two Words That Change Everything

Instead of “What happened?”, try: “What’s ideal?”

Feel the difference? That question doesn’t ask someone to look backward into the problem. It asks them to look forward into possibility. And when the brain is oriented toward a desired future, something shifts: shoulders open, gaze lifts, breathing deepens. That’s not just “feeling better.” That’s the nervous system downregulating and the prefrontal cortex coming back online. Now they can actually think.

Here’s what the shift sounds like in practice:

“So and so is driving me crazy.” → “What is it that you want them to do?”

“My workout felt like crap.” → “When you finish a workout feeling great, what’s different?”

“I keep missing deadlines.” → “What are the most important deadlines to hit right now?”

“I keep failing at this.” → “Tell me about a time you succeeded. What was different?”

Each of these redirects the brain from threat to possibility. From defense to discovery. From rehashing to reimagining.

Going Deeper: “What Else?”

Once you’ve asked a good question, there’s a second move that most people skip.

When someone gives you their first answer, that answer is almost always the automatic one. The thing sitting on the surface. The rehearsed response.

The real insight is usually one or two layers beneath that.

So after they answer, ask: “What else?”

Not because their first answer was wrong. But because their brain hadn’t finished thinking yet. “What else?” is an invitation to go further. And what comes next is almost always more honest, more specific, and more useful than what came first.

The Conversation You’re Having with Yourself

I wrote this book about how to show up better for other people in conversation. So one of the things that has surprised and moved me most is how many readers are telling me it changed the conversation they’re having with themselves.

One reader wrote that she picked up the book to become a better manager. What she didn’t expect was that it transformed how she talks to herself. By shifting from rehashing what went wrong to exploring what’s ideal and when she’d succeeded before, she moved out of self-doubt and into clarity, creativity, and confidence.

That quiet pressure to always have the right answer? It starts to lift when you realize your job was never to provide the answer. It was to ask the question that helps someone find it. And that someone might be you.

Try This Week

The next time someone brings you a problem, resist the pull to ask what happened. Instead, try:

“What’s ideal?”

And when they answer, follow it with:

“What else?”

Then notice what shifts.

I’d love to hear what you discover. What’s your go-to question when someone brings you a problem? Tell me in the comments.