• How do you judge the value of a creative act?

  • What’s worth fighting for?

  • What kind of conversations do you want to have more of?

  • What’s the relationship between sensing and knowing?

  • What’s the difference between innovation and invention?

  • When’s the last time you backed up your computer?

  • What does it feel like to be part of a movement?

  • What’s your biggest vice?

  • What’s the most beautiful thing in the world?

  • When are you most at ease?

  • How do you question authority?

  • What’s the relationship between opportunity and responsibility?

  • What’s the best story you’ve ever told?

  • How do you share what you know beyond words?

  • What do you respect yourself for?

  • What’s the question you’re trying to answer?

  • What inspires you to think simpler?

  • What’s the difference between what you want to achieve, and how you spend your time?

  • When are you free to play?

  • Who values your work?

  • What kind of conversations do we need more of?

  • How do you seek out your blindspots?

  • How do you define courage?

  • How do you actively create your own reality?

  • What allows you to trust someone?

  • What makes vulnerability a strength or a weakness?

  • How do your colleagues know they’re important to you?

  • When do you feel the most clarity between your values and your actions?

  • What’s the last mental model that you put aside?

  • What do you want to be known for?

  • What do you need to leave behind?

  • What is the difference between vulnerability and honesty?

  • How do you express the tension between what is and what ought to be?

  • What’s the biggest sacrifice you ever made?

  • What’s the best book you’ve ever read?

  • When’s the last time you spoke up for yourself?

  • What do people respect you for?

  • What are you most proud of?

  • What’s the question you keep asking?

  • Is thinking a form of feeling?

  • What’s the best advice someone ever gave you?

  • What do you need in order to create?

  • What’s your relationship to chaos and order?

  • How do you see the world differently than those around you?

  • What do people value about you?

  • What do we need more of?

  • What is the value of vulnerability?

  • What inspires you to think bigger?

  • What helps you to reflect?

  • What keeps you up at night?

  • What are you willing to get arrested for?

  • When are you most creative?

  • What size group do you feel most comfortable working in?

  • What’s your theory of change, and how do you apply it?

  • What relationships do you value most, and why?

  • Who’s the best storyteller you know?

  • Where do you hold tension?

  • When are you most yourself?

  • When do you find you’ve gone too far?

  • What do you gain and what do you lose by being vulnerable?

  • What moves you to create?

  • What’s worth your time?

  • How do you allow others to trust you?

  • How do you define innovation?

  • How does fear of failure influence your decisions?

  • When’s the last time you updated your computer?

  • What’s the most fearless thing you’ve done?

  • What kind of conversations do we need less of?

  • What does it feel like to know something beyond words?

  • What did you have to give up to be where you are now?

  • What’s your creative blind spot?

  • What is the relationship between trust and integrity?

  • What’s the most important thing you’ve ever lost?

  • What’s the best decision you ever made?

  • What are the inherent values that drive your work?

  • What is the relationship between vulnerability and courage?