Good startup questions for interview podcasts

After more than 30 episodes of my interview podcast, The Connecting Dots Podcast, I collected a big amount of startup questions. Let me share what questions worked for my interview podcast:

The importance of follow-up questions!

Those questions below just offer a gateway into stories, experiences and points of view that you have to take. This is what makes long-form interview podcasts like mine much more interesting than the superficial podcasts consisting of 15-30 mins/ep. In longer conversations you can get a feel for the interviewee: Is (s)he more risk averse or more risk friendly? What are his/her ambitions? How does their upbringing influence their work (if at all)?

Those follow-ups are not 'what?'-questions but 'how?'-questions: Not what did you do but how did you do that? Another example: When did you start your company? In 2015? Ah ok, now lead me through the first 6 months of founding your company. Some more good follow-ups: What was your thought process like when pivoting to X? How did you feel with the pressure of this big investment round on your back?

Another reason why I'm happy to have those standard questions below: I always feel more relaxed having so many questions that I can ask if a conversation stagnates or I don't know what to ask next.

Questions for startup founders

on startups

  • What is the core idea of your startup/business?
  • What's the business model?
  • What distinguishes your startup/business from other startups/businesses?
  • What will give your startup a competitive advantage in the next 2-3 years?
  • What is the 3-5 year vision for your startup/of your work?
  • What is the "end goal" of your startup?
  • Bootstrapped or getting investors on board?

on co-founders

  • What (skills, knowledge, personality) were you looking for in a co-founder?
  • How are the tasks shared between you and your co-founder?

lessons learned

  • Biggest learning(s) as a founder?
  • Biggest lesson in pitching your startup? And what did you do wrong at first? What did you do well from the beginning?
  • Most rewarding and most frustrating startup experiences?
  • How did a failure or apparent failure lead to success (or something positive)? So, for example: Some people get fired from a job only to find out that they then have great other opportunities like working for themselves.