Guest Post by  Glen Hellman

– previously posted  on Glen’s Blog

Great executive leadership coaches should be judged more by the questions they ask than the advice they provide. People are more likely to buy-into and successfully execute solutions that they have divined on their own than by advice that is handed to them. Therefore great questions are the key to a good coaching relationship.

Here’s are just a few great questions:

  1. Situation: Client is blaming everyone else for failures.  Question: So if everyone else wasn’t to blame who else could be responsible?
  2. Situation: Answer to a tough question, “I don’t know.”  Question: What would you answer if you did know? (I don’t know is a cop-out).
  3. Situation: Client is controlling the conversation, telling stories and talking about trivial surface level issues.  Question: What questions are you hoping I won’t ask you today?
  4. Situation: Client is talking about something that is making them angry.  Question: Where, do you feel this anger? Where in your body? How big is it? What color is it? (get them to really get in touch and embrace the anger in order to motivate them to act)
  5. Situation: Client is stuck on an issue.  Question: If you could wave a magic wand, how would you fix this? (let them brain storm, start with ridiculous and to start towards an answer)
  6. Situation: Client is telling a story packed with details, facts, assumptions.  Question: Can you break this down for me into known facts and assumptions? (start writing down the known facts separate from the assumptions to gain clarity)
  7. Situation: Client asks what they should do.  Question: What do you think I’d do? (You could tell them what you would do and that would work for you. they’re not you)
  8. Situation: Client is stuck. Question: What is currently impossible to do that, if it were possible, would change everything? (Another starting point or way to move from an impass)
  9. Situation: Conversation starter Question: What do you know about your company that you are pretending not to know (9 times out of 10 the answer is I don’t know, in which case go to #2)?
  10. Situation: Client responds to a question with a weak answer.  Question: What else (continue asking what else until you start getting silly answers. You’ll be surprised how many nuggets will be unleashed)?
  11. Situation: Client uses the “can’t” word (major red flag).  Question:Can’t? (say no more…… wait, let silence do the heavy lifting)

Glen Hellman is a former hired-gun, turn-around CEO working for Venture Capitalists. He’s a leadership coach, angel investor and a board member of the University of Maryland, Dingman Center for Entrepreneurship.  You can connect with Glen at

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8 thoughts on “Great Coaching Questions for Leaders

  1. Mike Marquardt says:

    Another great blog!

    1. Mike coming from you – the author of the book “Leading with Questions” that really got me started on this journey of Leading with Questions that is HIGH PRAISE! Thank you so much for your encouragement! You are a good man!

  2. Pam Smith says:

    Love these questions! Sitting here with another coach discussing a challenging client and these questions are in the mix.

    1. Pam my hat goes off to Glen Hellman for sharing what I am sure is just a drop of his incredible coaching wisdom! So glad that Glen’s “Guest Post” provided you with “Just in Time” input for your next coaching appointment!

  3. Bob, thank you for sharing my blog. I’m glad that it was well received and only hope it helps us all do a better job of achieving our missions.

    1. Glen it was my pleasure! On Monday night I passed out printed copies of your post to all of our Executive Leadership Team Coaches who are coaching 16 of our U.S. National Ministry Directors. Thanks for helping all of us!

  4. Jan Bouch says:

    Love the questions

    1. Bob Tiede says:

      Thanks Jan for your encouragement!

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