10 Questions to Ask When Interviewing With a Startup

Lately, I’ve been helping several startups I’m involved with on the recruiting front. As startups move from the early stage to the growth stage, the amount of hiring really ramps up and there are several in that phase locally. When meeting with potential candidates, I like to think about the questions I’d be asking if I was on their side of the table.

Here are 10 questions to ask when interviewing with a startup:

  1. What’s the three year plan for the startup?
  2. What are the three most important things to accomplish in the next 12 months?
  3. How does this role fit in with the upcoming priorities?
  4. What are the three most important things to be successful in this role?
  5. What are the three biggest risks for this role?
  6. What’s working well in the business? Why?
  7. What’s not working well in the business? Why?
  8. When does the startup have to raise money again?
  9. What are the prospects that the startup raises money on good terms?
  10. What happens if the startup isn’t able to raise money?

Of course, the questions would differ based on the person and the role being contemplated. Regardless, it’s important for candidates to understand the big picture and how they would fit in with the organization.

What else? What are some other questions you’d ask when interviewing with a startup?

2 thoughts on “10 Questions to Ask When Interviewing With a Startup

  1. David, what questions do you like to ask your prospective LPs? What has been or would be most effective when having that conversation? How would you approach finding he best LPs for raising a fund and getting a mentors that have raised VCs funds?

  2. Why are you hiring for this position right now?

    An employee could have left due to a problem they saw. They may be growing and need the support. There could be any other less obvious reason. This question has always given me more insight on the opportunity being discussed.

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