hiring

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.

Revisiting ideas: Promotion from Within

Ages ago a friend of mine wrote a rather seminal post on "promotion from within". It is interesting to go back and read this post through the lens of hiring and leading a team for a few years. It is a great post, but I think that one major point often gets overlooked, and this point causes many companies who follow its advice to fail. That point is this:
2) Using either the few experienced managers you've been able to internally promote or failing that, outside executive coaches, intensely mentor your more inexperienced managers to develop their skills. Typically, because many of your management candidates were less than fully-qualified, they will demonstrate potential but still be unsure in their new roles. Until they are comfortable and practiced in their roles, both they, their peers, and their teams will exist in a state of some distress. 

This is problem I have seen both at my own company and also observed at others': We promote from within, but provide no mentoring or guidance to those so promoted. Great managers are truly not born. They are made, and usually made through both being sat down and patiently taught the ways to effectively lead projects and people, but also through observing both successes and failures.  They are also made by being called to task on their own personal failures, something that many startups are unwilling or unable to do. The cult of personality around founders and early employees can work against the one thing necessary to make "promote from within" successful: some form of external help.

Most of us in the startup world are working amongst people that have very little experience managing. And we've taken these ideas that Yishan so eloquently voiced, that culture is paramount, and elevated them to high status, while forgetting that there is a lot to learn to be a successful manager. I know that I came into this job two years ago thinking that given my natural willingness to be in charge and my strong technical skills I would be a great manager. Haha! Truthfully I'm only now getting to the point where I have an inkling of all the things I don't know, and a large part of that is thanks to a ton of coaching. I would not be able to lead my team successfully without coaching, and even with my own coach, I need a coach to help the managers that report to me.

So, promote from within. But don't cheap out on the process by forgetting that these new managers and leaders need help, need training, need to be held responsible for both the good and the bad that they will inevitably produce in their first months and years as managers. Otherwise you might as well hire experienced external managers, because my hunch is that the payoff is actually equivalent, risking culture vs risking unguided learning.

Moneyball

The first thing they always do is quiz you. When big tech companies look for employee prospects, the first test is always basic knowledge. The Googles of the world have a checklist. "Coverage Areas" is what they call the talents they're checking for in a candidate. The big three are Coding, Algorithms and Analysis, Systems Design. Maybe they will also care about Communication skills, and Cultural Fit. They put you through the paces. Can she code? Does she know her Big-O analysis, her data structures? Can she design a distributed system to mimic Twitter? Tick, tick, tick. Pass enough of the checkboxes, and they'll make an offer. Nice salary, great benefits, the chance to work on big problems with these intimidatingly smart folks. When it comes to the deep pockets and well-oiled recruiting machine of a big tech company, it can be hard for a startup to compete for talent. 

I was thinking about this a lot as I watched Moneyball last night. It got me thinking. I wish there was a sabermetrics for developers. After all, what is a startup but a cash-strapped team trying to win against the Yankees? This is an imperfect analogy, but let me break it down.

First a step back for those of you that haven't watched the movie and don't give a flip about baseball. Sabermetrics is basically a system that tries to predict, through past performance, how well a player will do in the future on certain metrics. In contrast to tests of basic skills (running, throwing, fielding, hitting, power) that talent scouts look for, sabermetrics focuses on the statistics of a player's actual game performance. Instead of going broke on a couple of big-name players, as many teams would, or gambling on hyped up fresh "potential", the Oakland As used this system to draft cheap players that together ended up forming a competitive team against the A-list roster of the New York Yankees.

The thing about baseball that makes it a useful analogy for many startups is that baseball is a team sport where the size of the team is fixed and the potential of the team in aggregate matters. The same is true for a tech team. We see so many stories about how you should only hire "A" players, that they attract other A players, and they out-perform other developers 10-1 (or 50-1 or 100-1 depending on how grandiose you're feeling). But how do you find these A players? The Derek Jeters are probably settled, and cost more than you can afford. Google and its kin have deep enough pockets to hire anyone that ticks off all the "Coverage Areas", know that they will get lucky and find some natural As in that bunch, train up some more, and the rest will be good enough to take on the mountains of other work needed at such a huge company.

The thing that Google intentionally neglects, and the thing you absolutely can't afford to ignore, is past performance in the game. What is the tech equivalent of on-base percentage? Product shipped. This is why everyone drools over open source developers as hiring potential. You can see their work, you can know that they've shipped. Teasing this out of others is a tough process. We don't have visibility into the work that most people have done. Writing code for you proves that they have the tools to deliver, and is an essential part of the interview process, but it's not enough to show that they actually have delivered. All we can do is ask them, as a detailed part of their interview, what they have done. 

I realize that relying on reports of past experience as part of the hiring process is fraught. I would never suggest you neglect technical vetting in favor of experience. It's easy to get burned by someone whose personality you like and who sounds smart, only to find out they don't have the basic skills to succeed. And even with the best interviewers in the world, it's always possible that you will still hire someone that chokes at the plate. In the case where you find yourself with a player that isn't shipping, you have to take to heart the other thing that you can do more easily than Google: get rid of underperformers. It sucks, and no one enjoys letting people go, but a startup cannot afford to keep people that aren't delivering.

Will this result in your team being full of A-list all stars? Maybe. Or you may find yourself with a team where few people are exceptional standouts, but everyone delivers. When everyone in your roster can reliably get on base, you're winning. You're shipping. And that's what the game is about.