Appendix A: 100 Most Powerful Questions

This appendix provides a curated collection of powerful questions organized by context. Use these as ready-made tools for specific situations, or as inspiration for crafting your own questions.

Personal Growth & Self-Discovery

“What would I do if I knew I could not fail?”
“What patterns keep repeating in my life, and what might they be trying to teach me?”
“If my future self could give me advice, what would they tell me?”
“What am I avoiding looking at in my life right now?”
“Which of my beliefs are truly mine, and which have I inherited without examination?”
“What would I do differently if I truly valued my time as my most precious resource?”
“What am I currently learning, and how is it changing me?”
“If my life were a book, what would be the title of the current chapter?”
“What activities make me lose track of time?”
“When do I feel most alive and engaged?”
“What do I need to say ‘no’ to in order to create space for bigger ‘yeses’?”
“What important truth do very few people agree with me on?”
“What would I most regret not having tried if I were looking back at the end of my life?”
“What am I pretending not to know?”
“How am I complicit in creating the conditions I say I don’t want?”

Leadership & Team Development

“What’s the conversation we’re not having that we need to have?”
“What would have to be true for us to achieve our most ambitious goal?”
“How might we make this challenge so interesting that people can’t resist working on it?”
“What permission do people feel they need but aren’t asking for?”
“If trust were our only metric of success, how would we approach this differently?”
“What could we do that would be impossible but would change everything if we could do it?”
“What is the story our team tells about itself, and how is that story helping or limiting us?”
“What is the most generous interpretation of their actions/statements?”
“What capability are we betting on to win in the marketplace?”
“How would our approach change if our primary goal was learning rather than performing?”
“What if we were designing this from scratch today—what would we do differently?”
“What are our non-negotiables, and what are we flexible about?”
“What perspectives are we missing at this table?”
“What is our relationship to failure, and how is that helping or hindering us?”
“What would our users/customers tell us if they were brutally honest?”

Decision-Making & Strategic Thinking

“What would we do if we had half the resources but the same goals?”
“What would we measure if we could only track one metric of success?”
“What information would cause us to completely rethink our approach?”
“What would this look like if it were simple?”
“How might we be wrong about what we think we know?”
“What are the second and third-order consequences of this decision?”
“What’s the opportunity cost of this commitment?”
“What would someone who completely disagrees with us point out?”
“If this strategy fails, what will be the most likely cause?”
“What question are we not asking that we should be?”
“If we could only accomplish one thing in the next three months, what would create the most value?”
“How will we know if we’re successful?”
“If we were advising someone else on this decision, what would we tell them?”
“What information feels uncomfortable or inconvenient that we might be avoiding?”
“What’s our plan B, C, and D if our primary strategy doesn’t work out?”

Creativity & Innovation

“What if the opposite were true?”
“How would a beginner approach this challenge?”
“What constraints can we add that would spark more creativity?”
“What would this look like in a completely different context or industry?”
“What would [specific person or organization known for innovation] do in this situation?”
“How might we solve this problem using only what’s in the room right now?”
“What if we had to deliver this in a tenth of the time?”
“What’s the most outrageous solution we can imagine?”
“How would a scientist/artist/child/engineer/chef approach this?”
“How might we use this existing problem as an advantage?”
“What would this look like if it were a delightful experience?”
“What if we combined two seemingly unrelated aspects of this challenge?”
“What assumptions are we making that limit our thinking?”
“What could we learn from nature about how to solve this problem?”
“If this were a journey, where would it start and where would it end?”

Relationship-Building & Communication

“What matters most to you, and why?”
“What’s something you believe that most people disagree with?”
“What are you learning right now that’s challenging you?”
“How can I support you best right now?”
“What does success look like for you in this situation?”
“What’s something you’ve changed your mind about in the past few years?”
“What are you excited about in your life right now?”
“What’s a question you’re living with these days?”
“What would feel like a meaningful use of our time together?”
“What’s an aspect of your work that others might not appreciate or understand?”
“What are you grateful for in this relationship/situation?”
“What’s something important about you that I might not know?”
“What boundaries would make this relationship healthier?”
“How do you like to receive feedback?”
“What’s a conversation you’ve been avoiding that might be beneficial?”

Problem-Solving & Troubleshooting

“What’s the problem behind the problem?”
“How would someone with a completely different background approach this?”
“What would need to be true for this problem to dissolve entirely?”
“What would change if we knew we couldn’t fail?”
“How might we break this problem into smaller, more manageable parts?”
“What patterns do we see across similar challenges we’ve faced?”
“What if the problem is actually an opportunity in disguise?”
“What would happen if we did nothing?”
“How might we reframe this as a design challenge?”
“What resources do we already have that we’re not fully utilizing?”
“What would the perfect solution look like, regardless of constraints?”
“Who else has solved a similar problem, and what can we learn from them?”
“How might we turn this obstacle into an advantage?”
“What’s the minimum viable solution we could implement immediately?”
“How would we approach this if we knew the answer was already within our reach?”

Meaning, Purpose & Values

“What would I do even if I never got paid or recognized for it?”
“How do I want to be remembered?”
“What breaks my heart about the world, and what might that reveal about my purpose?”
“What feels most meaningful in my life right now?”
“What values do I aspire to embody more fully?”
“When do I feel most aligned with my deepest values?”
“What legacy do I want to leave?”
“What would bring me a sense of fulfillment even if no one else ever knew about it?”
“What does success really mean to me, separate from others’ definitions?”
“What contribution do I want to make to the lives of others?”

How to Use This Appendix

These questions are not designed to be asked in sequence or used verbatim in every situation. Rather, they serve as powerful starting points that you can adapt to your specific context.

For maximum benefit:

Select thoughtfully: Choose questions appropriate to your current situation and the depth of relationship you have with those involved.
Customize: Adjust the wording to fit your natural speaking style and the specific context.
Give space: After asking a powerful question, allow ample time for reflection before expecting a response.
Follow up: Powerful questions often lead to initial answers that can be deepened with follow-up questions like “Tell me more about that” or “What’s beneath that for you?”
Document insights: Record meaningful revelations that emerge from these questions for future reflection.

Remember that the most powerful question is ultimately the one that generates insight, clarity, and possibility in your specific situation. Use these as inspiration, not prescription.

Next Page: Appendix B: Question Templates