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Interview prep for CEOs: sample questions and audio quality

I want you to stand out during the interview.  To help you prepare, below is a list of sample questions I commonly ask. Keep in mind the conversation often jumps around a little and we may go off on tangents depending on your answers!
If you give these questions and topic areas some thought beforehand the interview will be a total breeze and the audience will remember you as thoughtful and compelling, interesting and amazing.
I encourage you to think about stories, anecdotes, and learnings others might be surprised by. This will make our discussion come alive and engage our listeners.

Sample questions


  • If I was a CISO, how would you answer my question “what does YOUR COMPANY do”?
  • Who buys this?  
  • What problem do you solve for them?
  • What business outcomes do customers get from this?
  • What is the big innovation?
  • How did you decide this was a company worth starting? Take us back to that moment.

[I will definitely ask this one]  What are 3 big takeaways about getting your first 10, real, paying customers?  (that were not from friendlies) eg, learnings, stories (!), mistakes, how long it took to get them, where the leads came from, special deals you had to cut, deals you lost, etc.


  • Tell me about your sales team right now.
  • When did you bring the first of them on?  How did you know it was the right time?
  • What roles did you hire for first? Why?
  • How did you transition from founder-led sales to sales team-led selling? What did you get wrong?
  • Did you consider PLG? What made you choose it or not choose it?
  • What have you learned about pipeline generation?  What's working for you?
  • What role do partners play for you? Why?
  • What’s the biggest challenge for the GTM team right now?
  • Getting attention in the market is really hard, how do you do it at your company?
  • Differentiating is tough; what are you doing so people understand and remember why you are different?

Audio Quality

Audio quality is super important.  People don't listen to crappy audio! 

Airpods, built-in laptop mics, and the microphone on your phone are not good enough for podcasts. 

Please let me know if you want me to send you a good microphone. I will send you a good microphone at no charge (if you are in the US), and you can keep it.  No need to go through the hassle of sending it back.  It will upgrade your audio on zoom calls.

Or, if you want to buy your own, these microphones are great too...

Audio-Technica ATR2100 USB

Audio-Technica AT2020 USB

Jlab Talk USB