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The Rabbit Hole is written by Blas Moros. To support, sign up for the newsletter, become a patron, and/or join The Latticework. Original Design by Thilo Konzok.

Key Takeaways

  1. Diagnostic questions
    1. Broad to narrow
    2. What’s wrong?
    3. How do we know?
    4. What are we not seeing?
    5. What should we do?
  2. Strategic
    1. What are you trying to do? Why?
    2. What difference will it make?
    3. Can you define “success”?
    4. Have you calculated the costs, benefits, risks, rewards, and alternatives?
    5. What is the extent of the problem?
    6. What will it take to succeed?
    7. Are we up to the challenge?
    8. What is the timing and sequencing of initiatives?
    9. What resources are needed?
  3. Empathy
    1. Leave running room
    2. Listen beyond words
    3. Establish intimate distance
    4. What are you most concerned about?
  4. Bridging
    1. What motivates you?
    2. What are you thinking?
    3. Are you dangerous?
    4. Tell me more
    5. Explain that to me
    6. Go on.
    7. That’s remarkable
    8. Fascinating
  5. Confrontational
    1. Accusatory, accountable, risky questions
  6. Creativity
    1. Set sights unreasonably high
    2. How would you do this differently?
    3. What’s your new idea?
    4. How might Disney engage with our customers?
    5. What would you change?
    6. What if there were no limits?
    7. What is your dream?
    8. What if you were CEO?
    9. Future test – it’s 5 years from now, we achieved what we wanted. What does that look like? What are we doing? What are we proud of?
  7. Mission
    1. Identify your mission, share values, play a role
    2. What interests you and gets your attention?
    3. What prompts you to respond?
    4. What do you care about? What do you stand for?
    5. What are your passions in life?
  8. Scientific
    1. Observe a problem, frame a question
    2. Offer an explanation
    3. Put your hypothesis to the test
    4. How can I test my idea?
    5. How might my idea be wrong?
    6. What do you see? What do you know?
    7. What are you trying to explain?
  9. Interview
    1. Why are you interested in this position?
    2. What do you think you can do for us?
    3. What makes you qualified and unique?
    4. Why should we hire you?
    5. What’s the most successful project you’ve run?
    6. What is it about this job that interests you most?
    7. How does this job connect with your larger professional aspirations?
    8. What questions do you have for me?
    9. What’s one thing you want everyone to know about you?
    10. What do you like about what you do?
    11. What’s the wildest idea you tried to turn into reality?
    12. What’s the biggest setback you’ve had and what did you do about it?
    13. What motivates you?
    14. What are you trying to achieve?
    15. What would a perfect job look like for you?
    16. What is obvious in your world that to the rest of us may be extremely unobvious?
  10. Entertaining
    1. What is 1 thing that blows you way?
    2. Who’s the most inspiring person you’ve met and why?
  11. Legacy
    1. What are you proudest of in life?
    2. What’s one story you’d like me to tell my grandchildren about you?
    3. What is meaningful to you?
    4. What brings you meaning at this time in your life?
    5. What is the most important lesson you have learned?
    6. What is your unfinished business?
    7. What is your story?
    8. What is a lesson you’d share from a mistake you made?
    9. How do you want to be remembered?

What I got out of it

  1. A beautiful list of questions across a wide range of domains