What questions do you ask your team?

Woman asking questions to sales managerWhen people ask me what I do as an executive coach, I often say, “I ask questions.” Yes, I get paid to ask questions. Often times the CEOs I work with struggle to answer the questions I present to them. That’s good. It’s a starting point for learning, growth, and development.

The same is true for you and your leadership team. Do you ask them questions?

Over the past six months I have been working on a leadership development guide for Founding CEOs. It is intended to help you become a great CEO. What’s one of the top skills I suggest all Founding CEOs work on? Asking better, more effective questions.

Asking questions serves you, your team, and your company in many ways. But, I won’t go into them in this blog entry. It’s the start of a new year and I would rather help seed your thoughts with questions that your fellow Founding CEOs ask their teams.

I try to ask CEO guests on the “From Founder To CEO” podcast about their best questions.

The question I ask them is: “What is one of your favorite CEO questions that gets powerful results from your team?”

I’ve compiled their questions for you. You might want to try some of these in 2016. They are good!


  • “How do we take this thing and make it exceptional?”  (Joshua Dorkin)

Moving Things Forward:

  • “If you could only do one of these things, what would you do?” (Tope Awotona)
  • “Is there anything getting in your way right now?” (Caitlin MaGregor)
  • “Is there a bottleneck?” (Caitlin MaGregor)
  • “What is the one thing that you need to get done today?” (Joshua Dorkin)
  • “Are you focused on the right things today, to produce the things that need to be produced?”  (Joshua Dorkin)
  • “What are the three big take-aways from our meeting?” (Joel Heath)

Being Supportive:

  • “Is there something we can do to make your life better and what would that be?” (Caitlin MaGregor)
  • “Is there something you are struggling with?” (Caitlin MaGregor)
  • “What is the one thing you are thinking about today?”  (Joshua Dorkin)
  • “How are things going?” [Do it in a certain scenario…pick the time and situation where they can really open up to you.] (Andrew Krebs-Smith)
  • “What is your Rose?” [The thing that is going really well or that you are most proud of.] “What is your Bud?” [The thing that is on the horizon that you are most excited about.] “What is your Thorn? [The thing most frustrating you.] (Mattan Griffel)
  • “What are the struggles that you are going through, and how can we get around them?” (Joshua Dorkin)

Encouraging Problem Solving:

  • “What do you think of the results yourself?” (Steinar Henskes)
  • “How would you make this decision if you were the CEO?” (John Bodrozic)
  • “If there is a resource constraint or time constraint, what would you do, and why?” (Tope Awotona)

Probing Further:

  • “What’s the one thing I didn’t ask you that you are glad I didn’t ask?” (Bryan Miles)

Goals & Priorities:

Do you have questions that serve you well?

What do you you ask your leadership team?

Share them below so we can all benefit from them.

Happy New Year!

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