Are you afraid of anything at work? Why?

What does your ideal day look like?

Imagine you are on your deathbed, what do you wish you did more in your life?

Have you seen something recently and thought to yourself ‘I wish I had done that’?

Is there any part of your life you wish you had more influence on?

Is there anyone in your network you wish you could apprentice under for a few weeks?

Who is someone you really admire?

What are habits you wish you had?

What is the most impressive thing that you have built or achieved?

What's not working in your life right now?

What are three things you are currently worried about?

Who made you smile today?

What are you most looking forward to?

In a typical day, what is the activity that makes you feel most energized?

In a typical day, what is the most energy draining activity?

If you could pick up a new skill in an instant what would it be?

What tasks are you procrastinating?

What piece of advice would you give to your older self?

How could you be more useful to those around you?

What is something you can apply to your life from the book you are reading now?

If you were to die tomorrow, who would you spend today with?

Is there something you should measure in your life that you currently don’t?

When do you feel most productive at work?

A genie appears in front of you and offers you one wish, what would that wish be?

Where do you see yourself in 6 months from now?

If you are the average of the 5 people you spend the most time with, who should be those 5 people?

Have you seen someone recently do great work that’s gone unnoticed?