📋 Questions

What’s a vulnerability of yours that you believe has actually served you well in business?

Source: Andrew Wilkinson

Who are you neglecting the most in your life to run your business/es?

Source: Andrew Wilkinson

What s the most cutting piece of criticism you’ve ever received? How did it affect you, and how did you respond?

Source: Andrew Wilkinson

What’s one thing in your business that you would keep doing even if you didn’t have to?

Source: Andrew Wilkinson

How many days can your business function without you?

Source: Andrew Wilkinson

Who are you most jealous of?

Source: Andrew Wilkinson

What personal sacrifice has haunted you the most on your path to success?

Source: Andrew Wilkinson

What is the craziest thing you have done for your business?

Source: Andrew Wilkinson

What are you most excited about these days?

Source: Andrew Wilkinson

When was the last time you asked for help?

Source: Andrew Wilkinson

What keeps you up at night?

Source: Andrew Wilkinson

Who has been your greatest mentor, and what is one lesson from them you often find yourself revisiting?

Source: Andrew Wilkinson

Who is your biggest energy drain and brings you down?

Source: Andrew Wilkinson

Who is your biggest booster? Who lifts you up?

Source: Andrew Wilkinson

Is there anyone you feel you might need to fire, but have struggled to do so?

Source: Andrew Wilkinson

Which competitor do you admire the most and why?

Source: Andrew Wilkinson

What aspect of the future of your industry intimidates you the most?

Source: Andrew Wilkinson

What’s a lesson you learned the hard way?

Source: Andrew Wilkinson

Beyond financial gain, how do you personally define success in your entrepreneurial journey?

Source: Andrew Wilkinson

In what personal areas are you still seeking growth and learning, despite your business success?

Source: Andrew Wilkinson

Questions for Co-founder Alignment

Source: Sam Parr

What is something that I think about in the shower?

What is something that you have spent 5+ years on that you can translate to others in significantly less time?

What is something that you have done that 95%+ of the population hasn’t done?

What’s their Hammer?

Source: Andrew Wilkinson

Am I getting the person excited?

Source: Wes Kao

Am I explaining in a way that’s easy to understand?

Source: Wes Kao

Are you willing to devote atleast the next 5 years of your life to solving this problem?

Source: Arindam / NextLeap

What would this look like if it was easy?

Source: Tim Ferris

Am I leaning into my absolute strengths and unfair advantages to its theoretical max?

Source: Shaan Puri

What do you see me do that is easier for me than it is for other people? 

What silly story am I telling myself?

Source: Shaan Puri

What would you do today that you would be happy you did tomorrow?

Source: Jimmy Carr

Here is all my context. What would you do?

Source: Unknown

What would 12 out of 10 look like? / Who is doing this as a 12 out of 10?

Source: Shaan Puri

What do our worst customers all have in common?

What’s the obvious thing you’ve noticed as an insider but isn’t obvious to everyone else?

Source: Shaan Puri (MFM)

Why now?

Source: Wes Kao’s Newsletter

What’s the frequency and magnitude of this problem?

Source: Wes Kao’s Newsletter

How will this save money or make money?

Source: Wes Kao’s Newsletter

What’s the worst that could happen and can I handle that?

Source: Stephen Barlett

Can I control or influence this situation?

Source: Stephen Barlett

Is this issue going to matter in a year or five years from now?

Source: Stephen Barlett

If we could never talk to our customers again, how would we figure out what to build?

What would be the most fun thing to build?

If you were never allowed to provide tech support, in any form, what would have to change?

If all our customers vanished, and we had to earn our growth and brand from scratch, what would we do?

If you were forced to increase your prices by 10x, what would you have to do to  justify it ?

What's one thing I can do today that I'll be thankful for a year from now?

What common ground can we find in this situation to move forward constructively?

If we were to start our business from scratch today, what would we do differently?

What's the most daring choice we could make right now, and what would be the potential payoff?

How can we leverage individual team members' passions to drive our project forward?

What 'busy work' can I eliminate or delegate to focus more on what truly matters?

What if I replace judgement with curiousity?

Source: The Book of Beautiful Questions by Warren Berger

What would I try If I knew I couldn’t fail?

Source: The Book of Beautiful Questions by Warren Berger

What if this isn’t a yes or no decision?

Source: The Book of Beautiful Questions by Warren Berger

Why do I believe what I believe?

Source: The Book of Beautiful Questions by Warren Berger

Is this a reversible or irreversible decision?

What date would you be surprised by if this project wasn’t done by then?

Source: Shaan MyFirstMillion

Who have I helped this year and how?

Who do we need buy-in from in order for this to move forward?

What's the hard part?

What would success look like?

Who is this for? What is this for?

How can we test this idea in the smallest, lowest-overhead way possible?

If we had to completely reinvent our product/service, what foundational change would we make and why?

What recent changes in our industry can we view as opportunities rather than threats?

How can we as a team improve in providing specific, sincere praise and constructive, kind criticism?

In what areas do I need to be more open to hearing harsh truths about myself, and how can I encourage others to provide me with honest feedback?

What new approaches could we consider that we haven't tried before?

What do you feel are your most significant strengths, and how can you use them more effectively in your role?

How can I move the needle on this idea/goal in the next hour?

What are reasons not to do this?

Can you walk me through your thought process on how you approached this challenge?

Source: Quiet Leadership by David Rock

How do you feel your work contributes to the team's overall goals?

Source: Quiet Leadership by David Rock

How can I approach this with less seriousness and a little more sincerity?

Source: Feel Good Productivity by Ali Abdaal

What would it look like if I was confident in this?

Source: Feel Good Productivity by Ali Abdaal

What would this look like if it was fun?

Source: Feel Good Productivity by Ali Abdaal