Elevate Your Leadership by Asking These Three Questions

Here’s how smart leaders harness the power of curiosity to build trust and solve problems

I have a question for you!

Do you ask a lot of questions?

Statistically speaking, most of us don’t. 

In fact, the number one complaint people have after a conversation is something along the lines of, “I can’t believe they didn’t ask me any questions!”

Everyone wants to be noticed and heard, and that’s exactly the gift you give others when you ask them a question and truly listen.

This was a big theme in a recent conversation I had with Michael Bungay Stanier. He’s the founder of the leadership company Box of Crayons and the author of The Coaching Habit, a book that has sold over a million copies.

In his words, “Questions are the kindling of curiosity.”

When you embrace your curiosity as a leader and start asking the right questions, that’s when the magic happens!

A thoughtful question at the right time to the right person has all kinds of benefits. It can:

  • Unlock a problem by probing deeper into the issue at hand

  • Spark innovation by allowing others to offer creative and original thinking

  • Eliminate ambiguity by clarifying a situation or point of view

  • Boost engagement as people feel included and develop more ownership

  • Build trust as your team sees how much you value their input

Unfortunately, most leaders are less prone to ask questions and more prone to give advice—to try and have all the answers. And that can cause teams to feel shut out and unheard. 

The great leaders I know don’t have all the answers. Instead, they know how to ask the right questions.

Today, I want to share three specific questions you can ask to up your leadership game, starting today. Let’s jump right in!

Question #1: “What would you do if you were me?”

A big part of my job at Yum! Brands was visiting our Pizza Hut, KFC, and Taco Bell restaurants around the world.

I really needed to know what was working and what wasn’t, so I asked questions. And my favorite question was this: “What would you do if you were me?”

I’d ask it to anyone: the general manager, the line cooks, and even the teenager working the drive-through.

The answers I heard always helped me understand what was important to each of them. 

I got to hear what systems they wanted to fix. What was getting in their way. What customers really cared about.

It was a goldmine of information—and the source of some of our best ideas and biggest wins. 

If you want to tap into the expertise of everyone around you, start asking this question!

Question #2: “And what else?”

Asking questions is vital if you want to uncover problems and engage your team. 

But you know what’s just as important as asking good questions? Getting the best answers.

I want to reference my conversation with Michael Bungay Stanier again because it was just so full of insights on this topic. 

Michael told me that “[people’s] first answer is never their only answer. And it's rarely their best answer.”

To dig deeper, he relies on a simple three-word follow-up question: “And what else?”

Often we don’t know what we truly think until someone gives us a chance to articulate it.

By asking “And what else?” you’re giving the people around you the chance to refine their thinking and find a more substantial answer.

Michael calls it a “multiplier” question to draw out knowledge that might not otherwise surface.

It also helps you raise the leadership skills and ownership levels of everyone on your team as they’re forced to explore their own solutions and ideas more fully.

What might your organization be missing out on by relying on the default answers?

What could happen if you started to test those initial responses and really dig into their substance?

Consider the meetings and one-on-ones you’re a part of. If you want to find better answers while also empowering the people around you, incorporate this powerful follow-up question some time this week!

Question #3: “How can I help?”

Some leaders hesitate to ask questions because they don’t want to be perceived as weak or unprepared. 

But others may avoid it because they fear putting team members on the spot or making them feel uncomfortable.

That’s why I love this question that Brian Cornell, the CEO of Target, asks his employees.

When he shows up to a store for a site visit, his go-to question is, “How can I help?”

This question puts people at ease instead of making them feel like they’re under scrutiny.

As he told me on my podcast, “I always try to make sure I start by asking ‘How can I help,’ because I'm there to make sure I support them.”

This is a powerful question for two reasons.

First, it helps you spot problems. Think about it: the places where someone could use your help are likely the places they’re experiencing trouble. They’re clues to the bigger issues you need to be aware of.

Second, it signals your posture of service to your team. Like Brian points out, your job as a leader is to recognize and remove the obstacles that get in your team’s way so everyone can excel.

You’re there to support the people you lead, and this question frames the conversation accordingly. Asking “How can I help” communicates that you care.

This question would be a powerful part of your regular check-in meetings with your direct reports. It can also help you “manage up.” Try posing this question to your boss and see what happens! 

In the words of the scientist Claude Levi-Strauss, “The wise man doesn't give the right answers, he poses the right questions.”

As tempting as it can be to share your own advice and experience, try asking more questions as you lead. You’ll help others uncover their own insights, and you’ll have a stronger sense of what’s really going on in your organization. 

But I need to offer a word of caution, too.

Asking questions is just the beginning. You’ve got to genuinely be curious about the answers. You’ve got to care enough to listen to the responses. And you’ve got to follow through on what you hear. That’s key to keeping the trust and engagement of your team.

But I hope these three questions give you a practical path forward. I know they will help you and your team unlock innovation, strengthen relationships, and ultimately get BIG things done together!