How to Ask Better Questions — and Why That Changes Everything

It started with a single, careless question.

I was consulting with a restaurant team that had been struggling for months with a slide in sales and morale. The GM looked tired, the kitchen manager had one foot out the door, and the line cooks were going through the motions like ghosts of a once-proud crew. During a routine check-in, I asked the team, “What’s not working?”

Silence.

I pressed again. A few mumbled responses. Something about inventory. Something about guests not tipping. A nod to the POS system. It all felt... surface-level. Mechanical. Defensive.

While rethinking that interaction, as I replayed the moment over a late-night bourbon, it hit me: I had asked the wrong question. I had started in the wrong place.

The Power of a Better Question

Asking questions is easy. Asking better questions—questions that unlock insight, foster connection, and shift the trajectory of a conversation—that’s an art. It’s also a practice. A mindset. And it changes everything.

Better questions aren’t about gathering data. They’re about creating possibility – opening up consideration of all options. They don’t just inform; they invite. They don’t just get answers; they get truth.

Here’s the thing: Most leaders, owners, and managers spend a lot of time solving problems they don’t fully understand because they never ask the right questions to begin with. They ask to confirm their own assumptions. To check a box. To diagnose instead of explore.

But the best leaders I know? They ask questions that slow people down. That make people think. That make them think.

And the really skilled ones? They ask questions that change the room. And then they ask one more question.

Why We Default to the Wrong Questions

We’re wired for efficiency. Our brains love shortcuts. And in the chaos of hospitality—where time is a luxury and pressure is a constant—we tend to ask:

• “What went wrong?”

• “Who’s responsible?”

• “How do we fix it?”

These questions feel practical. Direct. Problem-solving. They can be…But they’re not always helpful. Not at first. They often trigger defensiveness. Or limit creativity. Or make people feel like they’re being interrogated instead of invited into a conversation.

When we lead with blame, judgment, or a need for control, our questions show that. And people respond accordingly. They retreat. They guard. They perform instead of reflect. They aren’t in the mindset to think deeper and wider.

It doesn’t matter if you’re the smartest person in the room. If your questions feel like traps, no one will step forward.

A Better Way to Begin

Here’s what I should have asked that day with the tired restaurant team:

• "What feels heavy right now?"

• "What’s one thing we used to love about working here that we don’t talk about anymore?"

• "What do we need more of — and less of — to do our best work?"

These aren’t magic. But they’re different. They shift the tone. They create space. Better questions don’t presume the answer. They lean into curiosity. They honor the human experience, not just the task at hand.

And in a people-driven business like restaurants, hospitality, or any business where you truly value your investment in people, honoring the human experience is the whole game.

The Anatomy of a Better Question

If you want to level up the way you lead, coach, or connect, you have to master the anatomy of a better question. Here’s what they often include:

1. Curiosity over certainty

   1. Ask to learn, not to lead. Listen to understand, not to respond.

   2. Example: Instead of, “Did you follow the SOP?” try, “What did you notice while walking through the new process?”

2. Openness instead of bias

   1. Avoid steering someone toward the answer you want.

   2. Example: Replace “Why didn’t that work?” with “What do you think got in the way?”

3. Emotionally intelligent phrasing

   1. Acknowledge the emotional landscape.

   2. Example: “What part of this feels most frustrating right now?”

4. Future-orientation

   1. Focus on what’s possible, not just what happened.

   2. Example: “What would great look like in this situation?”

5. Ownership and agency

   1. Invite action and reflection.

   2. Example: “What’s one thing you could try this week to move that forward?”

      
      

You don't have to ask all five in one conversation. Just pick one. Use it well. Then let the silence do the heavy lifting.

The Leadership Shift That Changes Everything

When you start asking better questions, a funny thing happens; people start giving you better answers. They open up. They lean in. They bring their insight, their vulnerability, and their perspective. And as a leader, that changes your entire operating system.

You move from being the fixer to being the facilitator. You shift from telling to listening. You stop directing traffic and start lighting the path. And it’s not just about getting more information. It’s about building trust. Creating buy-in. Fostering ownership.

Because each question you ask is a signal. It tells your team what matters. It tells them what you see. It tells them curiosity is a welcomed attribute. It tells them how safe they are.

Tactical Applications (and a Few Favorites)

If you want to make this practical, try this:

In your next one-on-one:

• "What do you wish I asked you more often?"

• "What are you holding back on sharing?"

• "What would feel like real progress to you right now?"

At the start of a team meeting:

• "What’s something you’re proud of this week?"

• "Where are we winning that we haven’t acknowledged yet?"

• "What’s one friction point we’re ready to outgrow?"

When resolving conflict:

• "What feels unsaid here?"

• "What’s your intention (desired outcome) in bringing this up?"

• "What would help you feel heard?"

When coaching a direct report:

• "What do you think is really going on beneath the surface?"

• "What story are you telling yourself about this?"

• "If your possibilities were limitless, what would you try?"

You don’t have to memorize them. Just get in the habit of staying curious. Of giving people space, silence, and patience. Of pausing long enough to see what really wants to be said.

One Final Story

Years ago, I worked with a chef-owner who couldn’t seem to connect with her team. Turnover was high, morale was low, and despite her culinary brilliance, the kitchen was chaotic.

She asked all the traditional questions: “Did you prep the mise?” “Why are we behind?” “Who cut the fish like this?”

But one day, during a quiet moment before service, I suggested something else.

"Ask your sous chef what he wants to be known for." She laughed, but then she asked. And everything shifted.

It was a five-minute conversation that unlocked five years of frustration. Because in that moment, she wasn’t just asking about tasks, process, and product. She was asking about legacy. About pride. About the story her team was writing together.

And once that door opened, it never closed.

Final Thought

Asking better questions won’t solve every problem. But it will reveal which problems matter most. It will deepen your connection to the people you lead. And it will turn your conversations from transactions into transformations.

If you want to change the way your business works, your culture feels, or your team performs...

Start by changing the questions you ask. Here’s the deal: what is true today could be incorrect tomorrow, but the more skilled you are at asking better questions, the closer you get to what is real.

Because the right question, asked at the right time, doesn’t just shift a conversation.

It shifts everything.