What are questions to ask in an interview with a startup? I work at a medium sized company that brings in ~$70m in revenue with decent health benefits and 401k. I’ll be interviewing with a startup that’s under 50ppl and from what I could find online makes ~$4m in revenue and received a second round of funding (but is in debt). What are smart questions to make sure the company would be a good fit and for me to know what risks I could face joining a startup?

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I think one of the biggest (and most frequently overlooked) things is understanding how hectic/chaotic the culture is. Young startups are truly hit or miss...if you’re comfortable in your current role, you should ask questions that try to understand how much support the product team has, and the team’s level of influence in the company.

Couple things I’d start with...

- Where does the product team source most of its feature ideas?
- How are features prioritized?
- How does the product team interact with leadership? (i.e., not product leadership)
- How far out does the current roadmap go? What are the big feature plans? What impact should they have on the product/why do they matter? (not sure if they’ll share that)
- What’s the relationship like between product and engineering?


This is just a start. The point is to try to understand how mature the product org is and what its true role in the company is. Do you have to deal with an overbearing CEO’s every whim? Are priorities constantly changing? Is there a contentious relationship with your developers? Do they have a plan in place for the next couple months or are you walking into an empty backlog?

I think you do want to try to understand how stable the business itself is, meaning is it on solid financial footing and is the business safe for a while...but I want to know what the culture is like and how it impacts your day to day experience.

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This is really helpful.

Chaotic can be an understatement as I’m finding

funny

Gracefully and subtly throw in a question about why the role has opened up and the growth of the team/any changes in structure etc. PM1, those are great questions, I'm stealing some.

helpful

I would ask them about their plan for growth, what they're currently focusing on in terms of product and the company strategy. What are they expecting from you - do they need a shift or to drive it further forward, and yes try to get some idea of turnover....Also your comp is a big deal. You need to lean more towards base than equity on this one.

helpful

What keeps you up at night?

If there’s one thing you could fix immediately, resourcing aside, what would that issue be?

What aspects of the business currently are you targeting to utilize the latest funding round for?

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