If You’re Interviewing With a Startup, Here Are Three Questions To Ask Their Investors

I’ve Spoken With Hundreds Of Potential Employees, Most Don’t Ask Everything They Could

The other day I was sitting in a New York City park, talking to a senior engineer who had an offer from an early stage startup we backed. His questions of me were pretty comprehensive — trying to understand our rationale for investing, getting a VC’s perspective on what they needed to accomplish for the next financing, and most importantly, gut-checking some important cultural attributes which mattered to him. Two days later, he accepted the offer to join!

I’ve written before about how much I enjoy participating in the hiring process and how I try to make it about the candidate picking the company, not the other way around. The candidate I mentioned above did one other thing, which I often employ when I’ve referencing an individual or doing diligence on a company. Finish up with the open-ended “is there anything I didn’t ask about but should have?” (another way of phrasing when trying to get smart about an industry, “If you were doing investor diligence on this company, what questions would you be asking that I failed to raise?”).

I paused for a moment, and verbally ran through the stuff the engineer *did* ask about, to make sure we both had a sense of what was covered. Then I suggested there were three questions that might be of use to him, that he didn’t ask, but which I’d offer up and answer.

  1. Has There Been Any Attrition At The Company?

Obviously the bigger and older the company, the more this question needs to be tuned for specifics, but at a young startup (say under 20 people), it’s fine to start with just “has anyone left” and see what the investor says. You’ll learn whether there have been any transitions, and whether they were ‘regretted’ or ‘unregretted.’ It will shine light on their hiring philosophy, how quickly they correct mistakes of fit (if applicable), and so on.

2. When They Raised Their Series A [or whatever their last round was], Did Any VCs Pass and If So, For What Reasons

Here you can understand whether there was a lot of competition and demand for their fundraise, and whether the investment community say it through the same lens. Or whether it was a polarizing deal with firms passing for similar (or different) reasons. This is an “outside-in” view of what the startup needs to accomplish, while similar questions of the exec team should provide you “inside-out” perspectives.

3. Do You Think The Current CEO Can ‘Go the Distance’

While it’s still quite early in the company lifecycle, you can get a sense of how the earliest investors project not just the current competency of the CEO, but their pace of growth and maturity as well.

You’ll notice I didn’t include a whole bunch of basic questions here about the company’s financial details. It’s my opinion that the founders should be the one to share company-specific data, and I trust they are doing so responsibly. I don’t want to erroneously contradict something they’ve said since they’re closer to the day-to-day numbers. One exception is that if a startup I’m repping has fewer than 9-12 months of cash on hand, I need to be able to convey the risk profile adequately to a candidate and share my perspective on how funding will go. From my perspective, it’s irresponsible to bring a team member on board if they don’t know the company will need to fundraise in the coming quarters, regardless of whether they ask directly or not. Many candidates are fine with this risk, especially when the company is doing well and insiders want to put more money in regardless.