The Trials and Temptations of the New Leader: "Cool Factor"

Being a new leader at a startup is hard for many reasons. You think you're good at a lot of things, only to discover that you're not. You were fooled by success gained inside of a company with hidden structures that helped you succeed, the invisible backpack of big(ger) company privilege.

One very common area of weakness is recruiting. When I started to lead engineering at Rent the Runway I fancied myself pretty good at recruiting. After all I had done it well in prior gigs, I was friendly and engaging in interviews, so I'd be fine! Of course I quickly realized that startup recruiting is enormously different than at a company with a whole recruiting department sourcing candidates, making sure the process goes relatively smoothly, and of course, paying them fat industry++ salaries. Outside of this structure you experience a world where you reach out to so many people and get nothing but silence, blank stares, or polite dismissals. Your CEO tells you that you've gotta sell, and asks for your sales pitch. And often, faced with a string of failures and pressure to grow, you land on the need to do something "cool" with technology to up your "cool factor."

You know what I mean. Chase the buzzwords: microservices, Go, big data, event-driven, reactive, functional, etc etc etc. The only way engineers will want to come work for me on my relatively straight-forward application development is if I give them the carrot of Cool New Technology!

I have learned a few things over the years, and one of those things is that usually engineers that are only interested in Cool New Technology are not going to stick with your Boring Business Problem for long enough to be worthwhile, or worse, they'll stick with it long enough to leave a trail of one-off solutions that no one else on the team understands before they walk away and leave you holding the bag.

If you're tempted to reach for Cool Tech, then I'm going to guess that you're not at a company where the primary challenge is purely technical or scaling. Instead, the interesting problem that your company is solving is almost certainly a combination of a) figuring out how your business, possibly the first of its kind, is going to survive, and b) growing, changing, and evolving to create a functioning organization. Once your company is successful, many of the problems that seemed trivial become surprisingly challenging to solve at scale, but in the early days oversolving with cool tech only leads to distraction from tackling the real challenges.

So resist the urge to adopt any technology for the cool factor of recruiting. Instead, look for people who want to own big parts of the system, who are interested in the business, who are really passionate about the customers you're serving, who are looking for leadership opportunities. Don't undersell the opportunity you have just because it isn't Cool New Technology. Be honest with yourself about the real problems that make you excited about the business that you're in, and that's where you'll find your best sales pitch.