My Favourite Questions

It’s surprisingly hard to ask the right question, at the right time to the right person but when you get it right it unlocks doors and ways of thinking you didn’t even know were possible.

This is an evolving list of my favourite questions, broken into those I see as absolute gold that I use all the time and the still tasty ones that I use less frequently but still find useful.

The Coaching Habit

  • What’s on your mind?
  • And what else?
  • What’s the real challenge here for you?
  • If you’re saying yes to this what are you saying no to?
  • What was most useful for you?
  • How can I help?
  • What do you really want?

Dare to Lead

Okay, some of these are statements to open with rather than questions but it still counts.

  • What does support look like?
  • What’s my part?
  • I’m curious about…
  • The story I’m telling myself is…
  • Tell me more.
  • Help me understand…
  • What problem are we trying to solve?
  • Walk me through…
  • Tell me why this doesn’t work for you.
  • I’m working from these assumptions - what about you?

TASC - accountability and success checklist

  • Who owns the TASK?
  • Do they have AUTHORITY to be held accountable?
  • Do we agree they have the time/resources/clarity to SUCCEED?
  • Do we have a CHECKLIST of what needs accomplished?

The 5Cs of Strategic Thinking, Decision Making and Delegation

  1. Colour
    • Set a clear intention
    • Assign a level of importance
    • Answer ‘what does done look like?’
  2. Context
    • What’s happening in other areas that will impact or be impacted by this decision or deliverable?
  3. Connective Tissue
    • How does this plan/strategy/decision/deliverable solve or amplify what’s already happened or happening now?
    • Or how does it lay the groundwork for what hasn’t happened yet but is part of the future vision?
  4. Cost
    • What will it cost up to do this in money/time/bandwidth/focus/priority shifts?
    • Is this cost tolerable/expected/agreed/controversial/communicated?
    • What’s the cost of not doing it?
  5. Consequence
    • What are the consequences of not doing this?
    • What’s at stake?
    • What are the consequences of getting it wrong?
    • Are there any unintended consequences we can anticipate or solve for now?

Leading With Questions

  • What can we learn from this?
  • What would you do in my position?
  • What gets in the way of doing your job?
  • What brings you joy in your work?
  • Are there any questions that I have not asked you that I should have asked you and, if so, can we discuss them now?
  • What are you afraid I’ll do?
  • What suggestions for improvement do you have for yourself?

Questions to manage conflict

  1. How can we separate the people from the problem - diagnose the cause of the conflict?
  2. What goals are in conflict?
  3. What does each side want?
  4. Do all sides have a clear understanding of the issue?
  5. How can I encourage them to view the conflict from the other side’s perspective and to practice active listening?
  6. What are the common areas of interest?
  7. What are the issues?
  8. How can each side get what it wants?
  9. What are the issues that are incompatible between the two sides?
  10. What are the most important goals of each side?
  11. How can we generate options that can be used to solve the problem?
  12. What objective criteria will we use as a basis for our decisions?
  13. How can we disagree in an agreeable fashion?

Still tasty

  • How do you view your performance?
  • How does your work contribute to our success?
  • What does our leadership team do that gets in the way of your job?
  • How could we communicate management decisions more effectively?
  • What have you done today to improve your leadership skills?
  • What makes you proud to work for our organisation?
  • What can the rest of the team do to help you on this project?
  • What is not working in how we deal with each other?
  • Do you have anything to add?
  • What did you hear and come away with from that meeting?
  • I’ve observed X. What are your observations, how do you feel about my observations?
  • Could you say more about…?
  • If this change is relevant and meaningful, what opportunities does it offer?

Leaders Who Coach

  • I heard you mention X things - which one would you like to focus on?
  • What have you already considered?
  • Do you have a goal/outcome in mind?
  • What would make you feel like this was an hour well spent?
  • What would you like to explore?
  • Help me understand why this is important to you.
  • What do you think is reasonable to explore in the X minutes we have?
  • How do you want to tackle this?
  • Where are you at with this?
  • Where do you need to get to by the end of the session?

From my own coach

  • What intention would you like to set for this session?
  • How would you like to feel?

My own

  • How can I make 1:1s most useful for you?
  • How do you like to receive praise?
  • How do you like to receive critical feedback?
  • How will I know when you are having a bad day? How can I help?
  • What does good look like in a manager for you? What does not good look like?