Use when
You want deeper founder, operator, or executive conversations without making the main question finder too broad.
External resources
Question banks worth exploring next.
These resources are separated from the main Level Up question finder so the homepage stays focused and attribution stays clear.
Back to Level Up questionsAlisa Cohn
Conversation prompts and leadership resources.
A useful source for founders, operators, and leaders who want better conversations around growth, hard moments, and leadership judgment.
Original public source
Shaan Puri
Common question versus better question.
Useful when someone is stuck asking a broad question and needs a more precise prompt for decisions, conversations, or business judgment.
Before
I'm not sure... what should I do?
After
What would I do if I weren't afraid?
Before
How can I make this succeed?
After
What would make this certainly fail?
Before
I can't decide. Which path is the right path to pick?
After
Which path makes for the best story?
Before
Long time no talk, what's new?
After
I remember you were really into ____. How has that been going?
Before
What advice do you have for others?
After
What are the less obvious reasons you've achieved X?
Before
Tell me about yourself. What's your story?
After
What's the kindest thing someone's ever done for you?
Before
Tell me about yourself. What's your story?
After
What's a promise you want to keep to yourself this upcoming year?
Before
What are all the things we need to do this week?
After
If we only had 2 hours a week to work on this, what would we spend it on?
Before
Hiring: does this person have any weaknesses?
After
Hiring: what are this person's extreme strengths? Are they incredible at 1-2 things?
Before
We lost $X. How can we make it back?
After
Do we need to make the money back in the same avenue we lost it?
Before
How do we get more customers?
After
Who are our all-star customers, and how do we get more of them?
Before
What should we do?
After
What would _____ do in this situation?
Before
What if this fails?
After
If the worst case scenario played out, could we live with that?
Before
What should I complete from my to-do list first?
After
What one thing on this list would make everything else much easier or irrelevant?
Tim Ferriss
The 11 Tribe of Mentors questions.
Best for reflective conversations where you want people to share lessons, beliefs, habits, failures, and operating principles.
- What is the book, or books, you've given most as a gift, and why?
- What purchase of $100 or less has most positively impacted your life in the last six months?
- How has a failure, or apparent failure, set you up for later success?
- If you could have a gigantic billboard anywhere with anything on it, what would it say and why?
- What is one of the best or most worthwhile investments you've ever made?
- What is an unusual habit or an absurd thing that you love?
- In the last five years, what new belief, behavior, or habit has most improved your life?
- What advice would you give to a smart, driven college student about to enter the real world?
- What are bad recommendations you hear in your profession or area of expertise?
- In the last five years, what have you become better at saying no to?
- When you feel overwhelmed or unfocused, what do you do?
Arthur Aron
The 36 questions for closeness.
A classic resource for conversations designed to build closeness. Because the tone is more personal, use it intentionally and with the right room.
Use when
The group has consent, enough time, and a context where more personal answers are welcome.