Thoughts on finding the hidden gems in early-stage startup hiring.
One thing I'd add re: "non-obviousness." There are also tarpits; people who make you think "I can't believe my luck! How has the market missed someone this good!?" At this point, I have enough scar tissue that I immediately doubt my first instinct here. If someone is amazing on paper/in interviews and they aren't working somewhere more prestigious than my corner of the industry, there is often some mitigating factor: an abrasive personality, an uncanny ability to talk technically about systems they can't actually implement, a tendency to disappear from time to time. For these candidates, I try to focus the rest of the interview process on clearing all possible risks and identifying any mitigating factors we may have missed while getting the candidate excited to work with us assuming everything comes back clean.
Do you find that in the tarpit scenario they will typically have a work history hinting at these quirks?
One person had 3-4 positions out of college, all between 8 and 14 months. Turns out they would join a large company, do nothing, and wait until they got let go. Not sure why they tried this at our smaller org, where the behavior was much more obvious.
Another flag for me is when an earlier-stage candidate claims deep expertise in multiple not-closely-related technologies. We hired one person who had deep ML, databases, and cloud services expertise - we have people like that on staff, so no problem, right? Turns out they struggled to do any of those (despite great performance on the take-home and really good, almost textbook-y answers in the interviews - this was before FinalRound and similar, so I assume they just prepped really well and had help from a friend). Now, I try to tease out the narrative of how they developed expertise in each area (e.g. "I started as a business analyst making dashboards, but then I got really interested in how databases worked and ended up building my company's first data warehouse"), which tends to be pretty illuminating in its own right. This sounds a little obvious, but a surprising number of candidates will explain their work history without ever mapping it to the skills they developed at each role unless prompted.
There were a few with really good resumes who got caught out during the interview process. Testing explicitly for humility in the interview helped a lot with this.
Personally, I think my biggest gaps are around "hunger" and "agency"... I have these things at times, sporadically, but I have difficulty sustaining them long enough to become a really high performer at most jobs. Eventually I get kind of burnt out and stop really giving my all, then transition to something else within a year or so.
I have a high-pedigree CV, so people generally want to hire me, but I often don't live up to their expectations because of this.
Any tips on how to cultivate these traits?
For example, if you're feeling comfortable and handsomely compensated at your current job, and you have the sense of security that you'll keep being hired forever, why would you burn the midnight oil and go the extra mile? Is your lifestyle going to change at all if you get to that next level? You might work longer hours, experience more anxiety and stress, and get barely any upside in return.
My hunch is that the human brain is efficient. It won't make you work any harder than you need to if you have obtained the thing you already want.
Maybe the real question here is whether you truly desire to be this aspirational high-performer, or if that's an idea you're romanticizing, something you feel you should aspire to, but you don't genuinely crave it. You end up fighting between the idealized you and the practical you. Which may explain why you're burning out and losing steam eventually, you can only force yourself to do something you don't feel like doing for so long before the body rebels.
It’s possible that I just have the wrong personality to be a high-performer, and I should embrace being a somewhat overpaid flâneur. Or maybe I just haven’t found the right environment.
For now, I’ll keep following Derek Sivers’s advice [0] to relentlessly steer towards the things which give me that spark of excitement and motivation.