Powerful questions for mentoring conversations

These are powerful questions you can use in mentoring conversations to prompt new insights and ideas.


  Fast forward 10 years from now – what kind of life are you living?
  What would you do if you had all the resources necessary?
  If you lost everything you had, where and how would you begin?
  Who are you becoming?
  Who could you be?
  What will be your legacy to the world?
  What does life want from me?
  What will that get you?
  What is the cause that could get you out of bed every morning?
  What do you want to be remembered by?
  If no one judged you, who would you be?
  Where do you want to be in 5 years time? Why?
  What makes you forget about the world around you?
  What are you grateful for?


  Why do you want to achieve this goal?
  What do you really want?
  What is the question you should be asking yourself?
  What am I not asking you that you really want me to ask?
  What story is holding you back?
  What are you trying to prove to yourself?
  How does this decision match up with who you are?
  What are you waiting for?
  What are you trying to avoid?
  Really, what do you have to lose if you go for it?
  What is your big WHY?


  What do you really value in life?
  What is freedom for you?
  What is success for you?
  What is happiness for you?
  What does it mean to…

See opportunities

  In which ways can you turn this situation into a success story?
  In which way can it get better?
  What kind of opportunities are waiting to be discovered?
  What would your role model do?
  If I was in your shoes, what advice would you give me?
  What other angles can you think of?
  How might it work?
  How can you make it work?
  If you knew the answer, what would it be?
  Name someone successful that you admire. What would _____ do if they were in your position?

Create focus

  What problem are you actually solving?
  What do you need to make it happen?

Take action

  What is the #1 thing holding you back?
  What do you need to let go of?
  What is the #1 thing you should start doing to have a massive positive impact on your life?
  What do you need to hang on?
  If you were given an extra hour today, what would you do with it?
  What are you waiting for?
  When will you start?


  What happened? (facts only)
  What went well?
  What would you do differently, if you could do it again?
  What did you learn about yourself?
  What would help you succeed in the future?
  What do you think the moral of that story is?
  What are the positive outcomes of this situation?
  How do you choose to interpretate this situation?
  What has been your major learning, insight or discovery so far?
  What has your life taught you about…

Extra video: 4 tips for setting goals

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