That's A Great Question!

(not in order)


Open Questions:

Were you closer to your mum or your dad?

How do you think that has changed over time?

If you could change anything about growing up - what would you ?

What would a perfect day for you look like ?

If you could have anyone over for dinner, who would you like?

What have you dreamed of doing but haven’t done ?

We've all been embarrassed, what do you think back to & cringe?


What do people get wrong about you when they first meet you?

What is a question you hope that I wouldn't ask? 

If you were a drink right now, what drink would you be?

What's left on your bucket list?

If you won the lottery, what would you do with the money?

If you could only keep three possessions, what would they be?

When you are old, what do you think children will ask you to tell stories about?

What are you interested in that most people aren’t?

If magic was real, what spell would you try to learn first?

What topic could you spend hours talking about?

What do you think you do better than 90% of people?

What keeps you up at night?

How do you get in the way of your own success?

How do you hope you’ll change as a person in the future?

If you had a billion dollars to give, what would you do with it?

What important truth do very few people agree with you on?

Have you ever traveled around another country alone?

Wouldn’t it be fun to chuck it all and go live on a sailboat?

What is your ex's version of that break up?

What do you love most about yourself?

If you were to write a book, what would it be about? 

'What takes most of your time in your everyday life?

What work would you do if you had enough money to not have to work?

What do people get wrong about you, maybe even your friends?

What do people who do not like you say about you?

Have you played a team sport?

What do you believe so strongly that nothing will ever change your mind?

What is your favourite memory?


Who is someone you admire ?

Do you think we should tip waiters? 

Have you used (fake software) program before? (honesty check)

What's the best piece of advice anyone's ever given you?

You find a magic lamp, what are your three wishes? 

If you know you will die in a month, what would you do with your time?

You are given a chance to learn a skill to mastery in a day - what would it be?

If the old you could see the new you, what would the old you say?


What do you think about that really gets you excited?

Tell me something that’s true that very few people agree with you on.

What will people who don’t like you say about you?

Questions for Interviewees:


Did the culture at your last company empower or disempower you?

Who was the best boss you've ever had & why?

What kind of feedback do you expect to receive in this role?


How often do you expect to receive feedback?  

What problem do you face every day that nobody has solved yet?

What is a great company no one has started?

If I gave you $100 million, what would you build?

Questions I ask myself: 

Does the question sounds smart, or does it seek to understand?

Is it a patient question or one that assumes an outcome?

Do my internal principles hold up against a desire to connect? 

Am I doing less and experiencing more? 

Am I connected enough with myself to connect with others? 

If you had all the resources to build anything you wanted what would you build?