12 Questions Thriving Leaders Ask Their Team

Guest Post by Jeffrey Hayzlett

Have you ever heard that you should never ask a question for which you don’t already know the answer? Maybe I read that in a John Grisham novel. While that may be true for an attorney who’s cross-examining a witness, for executive leaders, it is quite the opposite.

We often have the misconception that the leader is supposed to have all the answers. When I was a new leader, I certainly bought into that idea. I worked so hard, because I never wanted to admit to team members that I didn’t have an answer to one of their questions. I put in overtime, trying to overcompensate for my shortcomings. It may have taken me a while to get it, but I realize that the best leaders don’t have all the answers.

It’s Simple – the Greatest Leaders Ask the Best Questions

“The greatest compliment that was ever paid me was when someone asked me what I thought and attended to my answer.” Henry David Thoreau

Demanding, commanding, or ordering will neither engage nor empower your team members. Asking for their input? Now that’s where you’ll really learn something!

Asking great questions is a powerful technique for garnering more information about a problem or situation, for seeking feedback on your performance as a leader, and for getting input and finding new opportunities to serve your customers.

Over the years, I’ve worked with leadership teams to help them to all start “rowing and growing” in the same direction. Asking questions is a big part of what I do. I liken it to when you go to a concert and the performer tosses a beach ball out into the crowd and then watches the crowd volley it back and forth. I ask a question of the team – often a tough and sometimes uncomfortable question, step out of their way, and let them volley it back and forth. Quality information, deep thoughts, and feelings are shared, problems are solved, turf wars are abandoned, and departmental silos are torn down. Simply because I asked a few carefully crafted questions.

I REPEAT: Carefully crafted questions. You only get answers to the questions you ask, so learn how to ask powerful questions!

So let’s get to it. Here I’ve compiled a list of

12 Questions Thriving Leaders Ask Their Team

  1. What makes you proud to work here?
  2. What do you think we should do in this situation?
  3. Is there anything that I’m doing that is getting in the way of your success?
  4. How do you see me as a leader?
  5. What lessons have you learned through this experience?
  6. What should I be doing more of? Less of?
  7. What do you think you/we could have done better/differently in this situation?
  8. How would you rate my communication skills and why?
  9. What aspects of your job do you love most? What aspects of your job are most challenging?
  10. What ideas do you have to improve our business/grow our organization?
  11. What are our customers saying?
  12. Are we doing anything that is no longer effective and that we should stop doing?

Adjust these questions to fit your particular situation. The one thing they all have in common is that none of these can be answered with a ‘yes’ or ‘no’, and, in fact, none can be answered with a one-word response. That is by design. By crafting and asking open-ended questions, you will prompt more information and gain greater insight from your team member.

Finally, I’d be remiss if I didn’t mention the most important facet of asking great questions. I say this with deepest affection, but please, for the love of God, Shut up and listen to their responses! This can be the trickiest part. Even though I am a big talker, I finally learned there’s a time to talk and a time to zip my lip. I encourage you to do the same. (Too bad I didn’t learn that until after I was out of school!) But, it’s a skill worth practicing.

Make room for silence. Sometimes your colleagues are quiet because they are taking time to formulate their answer(s). Sometimes your team members are quiet because they’re hoping you’ll jump in and save them from having to answer. Don’t do it. Let there be silence and patiently wait for the other person to answer.

Voltaire says,

“Judge a man by his questions rather than by his answers.”

Dare I presume to paraphrase Voltaire? I dare. I say,

“Judge a leader by her questions rather than by her answers.”

Dare to ask questions for which you don’t already know the answers. Develop your ability to craft questions that will extract information, input, and insight. It is a power-full tool to have in your toolbox.


  • What is one question you are asking your team each day?
  • What are your best techniques for engaging team members?
Jeffrey Hayzlett 


Jeffrey Hayzlett is the host of the award-winning All Business with Jeffrey Hayzlett on C-Suite Radio. Hayzlett is a global business celebrity, Hall of Fame speaker, Chairman and CEO of C-Suite Network, home of the world’s most trusted network of c-suite leaders and best-selling author.


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