The Why.

About the questions

First things first; thank you for taking the time to review this list of questions. It will give you an understanding on what style of questions that'll be asked during our interview. It is not such much a rubric as it is a guideline, these questions are there to naturally allow the conversation to flow.

Opening & Origin Story.

Before you started, what were you doing and what made you take the leap?
Did you have a backup plan?
What's your earliest memory of being interested in this type of work?
Did anyone in your life model this type of path for you?
Did anyone tell you this was a bad idea and if so, how did you handle that?
Were their concerns valid, were they projecting their fears?

The Why.

Why this? Why not something easier or more conventional?
What would you be doing if you chose the "easier" or conventional path?
If money wasn't a factor would you still be doing this? If so, why?
What keeps you going on your hardest days?
What do you do when motivation runs dry?
What impact do you hope to have that goes beyond just running a business?
How do you want peoples lives to be different because of your work?
What legacy are you building?
If you could be remembered for one thing, what would it be?
Has your Why evolved since you started?
What motivated you in the beginning versus now?
Did you discover new purposes along the way?

Challenges & Growth.

What's been the hardest part of this journey that you didn't expect?
How did you learn to handle it?
Are you still working on it, or have you conquered it?
Was there a moment when you almost quit? What changed your mind?
What skill or mindset shift has been most crucial to your growth?
How did you develop that skill or shift?
What's something you had to unlearn along the way?
Where did that belief or habit come from?
What was the cost of holding onto it?
How did you finally let it go?
What's the biggest sacrifice you've made?
Do you regret it or was it worth it?
What did you get in exchange?
Would you make the same trade again?
How do you handle failure and setbacks?
Can you share a specific failure that taught you something valuable?
How has your relationship with failure changed over time?
What's your relationship with fear like now?
What still scares you about what you do?
How do you move forward despite the fear?

Fulfillment & Meaning.

How has this journey changed you as a person?
Are you more confident, humble, patient, etc?
What would your younger self think of who you've become?
What parts of yourself did you have to develop that weren't there before?
What does success actually look like to you now versus when you started?

Practical Wisdom.

If you could go back and tell yourself one thing before starting, what would it be?
Would younger you have listened?
What pain could that advice have prevented?
Any lessons you've only learned through experience?
What's the best investment you've made in yourself or your work? Was it education, a coach, a tool, or something else?
What made you pull the trigger on it?
What was your ROI in that investment?
What's something you thought mattered a lot that actually doesn't?
Why did you think it was important?
What matters more than you realized?
What do you know now that you wish everyone starting out knew?
Why don't more people understand this?
How can someone learn this faster than you did?
What's your approach to work-life balance?
How has it changed over time?
What boundaries have you had to set?
What resources (books, mentors, courses, etc) have been game-changers?
How did you find them?

Looking Forward.

What's the next chapter you're excited about?
What needs to happen to get there?
What are you building toward?
How will you know when you've arrived?
If everything went exactly as you hoped, where would you be in 5-10 years?
What would your day-to-day look like?
What would you have created or accomplished?
What's something new you're learning/exploring right now?
Why that specifically?
How does this connect to your mission?

Closing Questions

What question d you wish I had asked you?
What's on your mind that we haven't touched on?
What do you want people to take away from your story?
What's the one thing you hope resonates?
How can people support you or connect with your work?
Where can they find you?
What's the best way to engage with what you do?