Interview questions to ask a startup CEO

Let’s dig into the kinds of questions I like to ask startup CEOs during interviews. They fall into three categories: 1) situational context; 2) existential company risks; and 3) culture fit.

1. Situational context: These are questions that help me get a lay of the land, to get a sense for what we’re working with, and to help me sniff out what questions from the next two categories are worth asking.

   1. How big is the team? In total, Product only, Engineering only? I’m trying to get a sense for PM:Eng ratio¹ and if the build org is big enough, relative to company size and company needs.²

   2. Who is on the exec team? This tells me who has influence and hints at company culture.

   3. Why hire a CPO now? Why not a Director-level head of product or keep doing it yourself?

   4. What’s the next big company milestone? What’s the most important problem to solve in order to get there? This tells us a lot.³

2. Existential company risks: These are questions that tell me how safe I should feel, and for how long.

   1. What’s our runway? Does that runway assume we hit our financial projections? What would our runway be at today’s revenue level?

   2. Do we have PMF? What makes you believe that is true?

   3. (If more funding will be needed) What will it take to get our next fundraise? What do we believe must become true for that to happen?⁴  

3. Culture fit: These are questions that help me gauge if I’ll be happy there.

   1. When the answer isn’t obvious, how do you and the exec team make decisions?

   2. What was a time when you thought you were right but it turned out you were wrong?

   3. How does the company do quarterly planning?⁵  

   4. If you had the best product team in the world, how often would their product launches be successful?⁶

Obviously, there isn’t time to ask all of these questions. Pick the ones that seem most critical to uncover. The rest you may be able to get out of your other interviewers, or ask for a follow up call if things are going well.

The Workshop

This is a newsletter-only section where I share a half-baked idea in hopes that y’all who are smarter than me can work it out with me.

Newsletter is already long given all the footnotes, so I’ll keep this brief.

You may have seen news over the last few weeks or months of various content companies licensing their data to OpenAI, Google, or similar companies. The most recent news is Shutterstock (Bloomberg, $104M last year), before that was Vox and The Atlantic (Variety), Financial Times (Reuters) and before that Reddit (Reuters, $60M per year). I believe there are others.

On the one hand, I get it: making extra revenue on the side for content that they were making anyway is just pure profit at a time when profits are scarce.

But it also seems like they are hastening their own demise?

I’m not the first to make this comparison, but it definitely reads like how Hollywood licensed their content to Netflix in the early days of streaming, only to find that they helped Netflix grow into what is now an existential threat to their business models.

Maybe the argument is: the apocalypse is coming no matter what we do, so we might as well make some profit along the way.

Is there a bull case here that I’m missing? I’d love to hear from you.

1  1:4 - 1:8 is a good range. Less than 1:4 basically never happens (if it did, I would be questioning how they even define the role of PM because something is very wrong there.) Greater than 1:8 is concerning and would cause me to dig in to whether Product is strategic or mostly project management.

2  Build Org:Company Size & Needs ratio isn’t very scientific. Mostly I’m trying to get a sense for if the build org is dramatically under resourced (say, < 25% of total employee count) and/or if the goals that have been described are achievable with the available resources (incl. budget for hiring). If the team is too small, relatively, that could mean there is a ton of tech debt accrued, that the teams have been feature factories and lack strategic thinking muscles, that the CEO is wildly unrealistic about what it will take to achieve their goals, that this is a tech-enabled business and not a tech business.

3  First of all, if they don’t know, that’s concerning. Second, I like to ask this same question to other members of the Exec team that I interview with, to check for alignment. Third, it starts to map in my mind what kinds of problems the build org would be solving, and I can use the answers to the prior questions to gut check if it seems feasible.

4  This is a strategy check, and a jumping off point for follow up questions. They may say things like “we need to grow ARR to $x”, and we can follow up with “how’s retention looking?”, which can help us understand if the product is actually good and just needs more customers or not. There’s a chance they have a bad answer, which isn’t a deal breaker but does give you insight into the fact that part of your value could be in crafting a better company strategy.

5  I realize this is not obviously a culture fit question. But it helps me understand how much of planning 1) happens at all, 2) is dictated by the founder, 3) is output vs outcomes oriented.

6  I think my answer would be something like 60% of the time, assuming prior to launch we were doing lots of discovery, feedback via design prototyping, etc. I’m not counting A/B testing, which kind of avoids the point of the question. If their answer is 80+% of the time, you may be in a situation of unrealistic expectations.