7 Keys to Asking Better Questions (What I’ve Learned From My Leadership Podcast)

better questions

If you want to become a better leader (and who doesn’t?), the key is simple: learn to ask better questions.

I wish I knew that 25 years ago when I started.

I thought leadership was about giving answers, not asking questions.

I still have to reign myself in from talking too much and listening too little, but I’ve worked hard on the art of asking questions over the last few years.

In mid-2014, I became immersed more deeply than ever before into the art of asking questions as I prepared to launch my leadership podcast (you can subscribe for free here).  (Thank you to everyone for making the podcast so amazing!)

One of the surprisingly consistent questions I get is how I come up with the questions for my guests.

People seem to notice the approach I take and want to know how I prepare the questions.

The reality is I haven’t known how to answer that question except to say “I don’t know, I just do it.” Not very helpful.

I also get interviewed frequently these days, and I’ve come to the conclusion that there are better lines of questioning, and not-so-great lines of questioning.

So I sat down to try to figure out the principles behind the art of asking better questions.

Here’s what I’ve come up with. I think the principles work whenever you are interacting with someone…whether it’s the foyer on a Sunday, in a meeting, or for a podcast or show.

Asking better questions is foundational to better leadership.

So how do you learn to ask better questions?

I want to keep growing in this field, but here are 7 things I’m discovering.

Asking better questions is foundational to better leadership. Click To Tweet

1. Put yourself in their shoes

You may be getting together to discuss an issue, but behind every issue is a person.

When you speak to the person behind the issue, not just the issue, you always have a better conversation.

How do you do that?

Start here: imagine what it’s like to be them.

This is true if you’re talking to Andy Stanley or whether you’re talking to a college student anxious about what’s next after graduation.

People have emotions, fears, dreams, hopes and experience everything else you do.

A great way to access this stream of thinking is to imagine the questions you would have if you were them.

Imagine launching a church that grows exponentially. What would your hopes, dreams and fears be?

Sure, the person you’re speaking with might respond differently than you would (and be open to that), but this at least gets you into the same emotional ball park.

If you can imagine what it’s like to be them, your questions will not only become better, but they’ll like you. Why? Because you just showed interest and empathy. And we all respond better to an interested, empathetic person.

When you speak to the person behind the issue, not the issue, you always have a better conversation. Click To Tweet

2. Avoid putting people on the defensive

Most people heading into an interview or conversation are a bit worried—whether that’s a job interview, a podcast or TV interview, or a meeting where you’re asking questions.

They’re afraid they’re going to say something they’ll regret. Or afraid you’re out to make them look bad.

People sense right away whether you’re trying to make them look bad. And they respond to you accordingly.

Any cheap press or momentary victory you get from a controversial quote is in my view, so not worth it.

I never want to make anyone look bad. Even if I disagree with a person.

I just want them to tell their story…and if you put them at ease, they will.

“But what about the truth?” say the suspicious among you.

Well, that doesn’t mean you don’t ask real questions. But in fact, when someone is at ease, they’ll often tell you far more than they would if you put them on the defensive.

If you want to listen to a couple of very authentic interviews on very controversial topics, you can listen to my conversation with Justin Dean on the collapse of Mars Hill Church in Seattle, or Aaron Harris on what it’s been like for him to grow up in the church as gay man.

People sense whether you're trying to make them look bad. And they respond to you accordingly. Click To Tweet

3. Ask what it felt like

I’m a logical guy. I think a lot. I’m a law school graduate. Most of what I do these days boils down to thinking, solving problems and then figuring out how to communicate what I’ve learned.

As a result, I constantly process principles behind why things are the way they are, and why people do what we do.

But deep down, we’re all emotional creatures. I am. You are.

So is anyone you talk to.

If you really want to connect with the person you’re speaking with (or interviewing), when they tell you about a critical moment in their life (good or bad) ask them what it felt like.

What was it like to learn you had cancer?

What did it feel like to have half your church walk out overnight?

What did it feel like for you as a leader to go from 100 people to 1000 people attending your church overnight?

What were you feeling when you failed out of college and had to go home to tell your parents?

In those moments, you move from head-to-head conversation to heart-to-heart conversation.

And those are my favourite conversations. That’s the kind of stuff around which friendships and bonds form—both between you and your guests, and your guests and any listeners.

Heart-to-heart conversation is always better than head-to-head conversation. Click To Tweet

4. Look for the counter-intuitive or exceptional

Lots of counter-intuitive things happen in life.

Follow that trail.

Exploring the counter-intuitive usually leads to great places because it attacks widely held assumptions. For example, people assume you burn out with things are going poorly, not when things are going well.

In a similar way, people are surprised that successful people struggle.

In my view, that’s what made the interview I did with Passion Ministries founder Louie Giglio so riveting. He talked openly and honestly about how success led him to break down and how he battled back.

Bottom line? If something surprises you, chase it.

5. Drill down

Our world is filled with 2-minute sound bites.

The best conversations in my view never happen in 10 minutes or between commercial breaks. They happen long after people have used all their sound bites and pushed past their ready-made answers.x

I took a risk in doing long-form podcasting when I launched (the average episode is around an hour). The reason I chose that path is because meaningful real life conversations tend to be longer, not shorter.

Taking your time also allows you to drill down on key issues.

Whether it’s my podcast, a meeting, or even a job interview I’m conducting, most of my questions are unplanned. I always write questions out ahead of time, but you can’t really anticipate the good stuff.

When you hear something someone says that piques your interest, drill down on it.

Go further. As in:

What do you mean by that?

Fascinating…tell me more.

What happened next?

What…say that again? What happened?

That kind of questioning opens up the floodgates for new insights and principles.

If you just move onto the next question, you usually lose a goldmine in the process.

6. Be curious

Curiosity is your best friend as a leader.

When you’re interviewing, act more like a 6-year-old than a 36-year-old.

Ask why…a lot.

If you’re genuinely curious, ask:

Why did you think that?

Why do you think that happened?

Why didn’t you quit?

Why did you make that decision?

‘How’ is another amazing curiosity question:

How did you even think that was possible?

Wait, how did that happen?

How did you possibly think that might work?

Even in a meeting setting, you will learn so much more about the person you’re talking with or the issue you’re studying if you stay curious.

The best leaders I know are insatiably curious.

They want to know how and why things work, and they want to know more about the things they don’t know about.

So…be curious.

The best leaders are insatiably curious. Click To Tweet

7. Forget about yourself

Too many leaders are interested in making a point rather than asking a question.

And that’s a critical mistake.

If you’re always trying to show how smart you are, you accomplish the opposite.

If you're always trying to show how smart you are, you accomplish the opposite. Click To Tweet

When I started my podcast in the fall of 2014, my wife listened to the first few episodes and said (in a very loving way), “You talk too much.”

I felt like saying, “It’s MY podcast!”

But she was right.

Since that time, I try to talk less than 10% of the time in an interview (unless the interview is designed to be a two-way conversations, as a few have been).

I’ve tried to talk a lot less in my daily leadership as well. It’s way too easy for me to dominate meetings and I have to put a constant check on my tongue and brain.

After all, leaders, when you listen first and speak second, people are far more interested in what you have to say.

When you listen first and speak second, people are far more interested in what you have to say. Click To Tweet


What Do You Think?

Hopefully asking better questions leaves you and whoever you’re talking with feel amazing after a conversation. That’s my goal whenever I talk to a leader, on-air or off-air.

If you want unlimited free access to my podcast, you can subscribe for free here on any of these channels:




In the meantime, what helps you ask better questions? Scroll down and leave a comment!

7 Keys to Asking Better Questions (What I’ve Learned From My Leadership Podcast)


  1. Rich Huisman on May 3, 2021 at 4:27 pm

    Really enjoyed this Carey. As a leader that likes to talk, I really appreciated your insight into talking less and listening more. Love this.

    • Carey Nieuwhof on May 5, 2021 at 4:37 pm

      So glad to helps Rich!

  2. Rosie Osborne on May 3, 2021 at 9:03 am

    I loved this article! Some of these things are things we know but forget. It was a great reminder. I especially liked the advice to “Drill Down”. I tend to rush and move on. I need to slow down and get to the good stuff.

    • Carey Nieuwhof on May 3, 2021 at 12:54 pm

      So glad to hear that Rosie!

  3. Tom Sharpe on May 3, 2021 at 8:51 am

    My favorite listening to you interviews is “what is your head talk like?”

    • Carey Nieuwhof on May 3, 2021 at 12:54 pm

      Yes! Love that question.

  4. Alan Rathbun on May 3, 2021 at 8:43 am

    Thanks for this post Carey! Very valuable insights. I especially liked the “Ask what it felt like” tip and “Be curious”.
    From another perspective, I have found that my conversations are more open when I don’t use “why”. I have found that “why” can make people defensive, but if I phrase “why” questions using “what” instead, they can stand outside their situation with you and look at it more objectively. So instead of asking, “Why did you make that decision?”, I would ask “What led you to make that decision?” It’s amazing the big difference that small change can make in opening a conversation.

    • Mara Marsman on May 3, 2021 at 12:14 pm

      Absolutely right, Alan!

  5. Grant Erickson on May 3, 2021 at 8:33 am

    Great article! I found it interesting that the URL address mentions ‘5-keys…’ Wondering what two got added?

  6. Kelli on May 2, 2021 at 1:39 pm

    1. Thank you, Carey & team—for this post and for consistently sharing content that helps holistically. I unabashedly rave, use & share your stuff like a zealot. I’d buy a t-shirt if you sold them. Friends & colleagues laugh a little at my enthusiasm…until they check it out themselves; then the “wows” roll in.
    2. Any suggestions on how to “grow” or re-ignite curiosity if you’re not naturally so, or feel stuck in survival mode?

    • Carey Nieuwhof on May 3, 2021 at 1:03 pm


      This is so encouraging to read. I’m going to bring this to our staff meeting on Wednesday and read it to everyone. Thank you so much for being such an avid supporter!

      What you do is SO important, and I’m glad that we can assist you in it. 🙂

  7. Lorie Hartshorn on May 2, 2021 at 10:17 am

    Really good approach to asking questions Carey. You set such a good example in this. I’m trying to apply these principles in the short TV interviews that I do. I’m always longing for more time to go deeper, so thank you for doing long form interviews. They are enriching and cause the listen to lean in more.
    I consider you a mentor through your excellent interviewing skills. Thanks for unpacking this for us.

    • Carey Nieuwhof on May 3, 2021 at 1:08 pm

      Lorie, I’m so glad to hear this.

      TV is so hard, but I’m glad to help as I can!

      Cheering for you!

  8. Sarah R on May 2, 2021 at 9:11 am

    I love this post! I recently started an interview podcast for grad students and I am learning to ask questions well. It’s tough!! Thank you for sharing your insights!

    • Carey Nieuwhof on May 3, 2021 at 1:08 pm

      So glad to help!

  9. Kenny Jahng on May 2, 2021 at 7:57 am

    Great points.

    I personally like question set number #3 above.

    When I use the StoryBrand copywriting approach for asking for testimonials, the same type of questions about how it made them feel before and after the problem was solved. I find that it turns the testimonial from a cookie cutter statement people gloss over like they have banner ad blindness to an actual story that draws people in.

    Same dynamic is happening here in interviews. Love it!

    • Carey Nieuwhof on May 3, 2021 at 1:08 pm

      Love it Kenny!

  10. Alex on April 20, 2016 at 11:54 am

    Yet another excellent post, Carey. I like your opening statements, particularly one that resonated with me greatly: “I thought leadership was about giving answers, not asking questions.”. This was me a few years ago. I thought leadership in ministry was to provide answers, not ask more questions. Yet, I quickly learned that Jesus dealt with most of people’s queries with a question, that lead to a conversation (or the culmination of one).

    What many don’t realize is that the more answers we learn and provide, the more questions we have or come up with. I thought that by now I’d have most of the answers for the family, marriage and ministry. We’ve learned a lot in these three. Truth be told, the more I know, the more I realize how much I don’t know. :-).

    Leading with questions actually demonstrates great leadership of care, compassion and charisma leading to revealing to spontaneous answer. Thanks for a great post Carey.

    • Carey Nieuwhof on April 21, 2016 at 4:10 am

      Alex…thanks. You’re right…we’re all learning how much we don’t know. Stay curious. 🙂

    • Jeremy Van Langenberg on May 2, 2021 at 8:03 pm

      Thanks so much for this wisdom Carey. So true, about reaching out to a person’s heart & how they feel, and digging deep, and forgetting about yourself. I’m going to pay attention to these 7 points and evaluate how I go. Jeremy

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