Hey folks, welcome to The Imposters Club, the podcast for misfits in tech. You know who you are? Who am I? I'm your host, Teddy Kim. I'm a director of software engineering at a SaaS startup, here in Minneapolis. But I wasn't always a techie, I was a coach for about five years, and it was an amazing experience. I got to work with elite athletes, soccer moms, little kids, as well as para-athletes who had to overcome huge obstacles in pursuit of their dreams. Coaching has become part of my latticework of mental models, and I connect those skills every single day in my current gig.
Now, one tip I picked up along the way goes like this, there are two kinds of athletes, some need to feel good to play good. The rest need to play good to feel good. And it's the job of a coach to understand who fits into which bucket and to create conditions where both can succeed. Now I'm going to give you a narrow example. If I observe that an athlete has an elaborate pregame ritual, or that she psyches herself up before the game begins, then I know she needs to feel good to play good. With her my job is to stay out of her way and make sure she has the time and space she needs to get her head right. So when the game begins, she can access her flow state.
But other athletes respond to the immediacy of the game. They don't need elaborate preparation before the game begins. They need to play good. Playing good satisfies a very deep emotional need, which allows them to feel good until the next game anyway. So here's a fun thought experiment. Depending on who you believe, the failure rate of tech projects is somewhere between 50 and 70%. Wow. For the sake of argument, let's take the rosier figure and say that 50% of tech projects fail. That's still a lot, but we're going to go with 50%. Now, there are two types of employees, some of them need to feel good to play good. The others need to play good to feel good. So if 50% of tech projects fail, then I think we can reasonably conclude that 50% of the industry feels like shit at any given time. Because whether winning is a cause or effect, at least 50% of the industry isn't winning, which is appalling. But it goes deeper, so much deeper. Because the odds of project success are so low, it is possible, if not probable, that you will go the majority of your career without ever being on a successful project. That might sound far-fetched, but it's not.
I spent the first five years of my career on two multi-year projects. One was two years the other lasted three years. Both projects tanked. Now, my next project was a winner, luckily, but I'd already been in the industry for five years at that point. Sure, I learned a lot of stuff, but I didn't learn how to win until I'd been in the industry for five years. So here's where we are. Take a deep breath. Look around you. Everyone in tech is either a serial loser or at best an occasional winner, and at least 50% of the industry feels like shit at any given time.
And how has the industry responded? Well, as far as I can see, there are two responses. The first is to provide free snacks, beanbags, safe spaces, unlimited vacation, and other perks. That approach is really meant to placate the people who need to feel good to play good, but it doesn't work. Your team doesn't really want to eat Chex Mix while lazing around on a beanbag. Your team wants to win and to pretend otherwise infantilizes everyone. The other approach is to crack the whip and try to have better processes, tighter deadlines, and management by numbers. That approach is meant for people who need to play good to feel good. That approach unfortunately doesn't work either because it creates an environment where an entire team's emotional state revolves around things that can't be controlled, or for that matter even properly understood.
Listen, all experienced coaches know that feeling good and playing good are actually inextricable and interdependent. The job of a manager is to understand who fits into which bucket and create systems where both can succeed. That's how you get the wins. Unfortunately, that coaching mentality seems to be largely absent in the modern tech scene. You don't find coaches like that; the types of coaches who care about winning. The closest thing we have is the Agile coach, but that doesn't quite fit the bill. In practice, most Agile coaches perform an oversight role, where adherence to agile formalisms is more important than winning. That's not coaching, at least by my definition.
So how do real coaches get the wins? There are many coaching competencies, but here are a few that I think are the most important. First, a coach understands individual team members' intrinsic motivations. In other words, aside from a paycheck, what motivates your team member to show up for work every day? Is it a feeling of autonomy, a sense of service, or just recognition? If you don't understand intrinsic motivators at an individual level, as a manager, you just can't motivate people to do their best work. Second, coaches are chemists. They've put people together into squads and teams to create human chemistry. Good team design can produce force multiplication effects that are awesome to behold and it's not always pretty. Remember how Phil Jackson put Jordan and Pippen together with the championship Bulls and Shaq and Kobe together with the championship Lakers. Yeah, there was tension between the players, but you can't argue with the wins.
Finally, coaches prepare their teams to face the right opponent at the right time. If you're running a build team at an early-stage startup, you don't really care about your team's ability to scale distributed systems. You don't have any customers yet; scaling is not your problem. No, you want to prepare your team for the specific challenges of fast product iterations and market experiments. Prepare your team to solve the problem that's in front of you. Simple right?
Well, if it's so simple, why isn't everyone doing it? Remember at least 50% of tech projects fail. Everyone in tech is either a serial loser or at best and an occasional winner and at any given time, at least 50% of us feel like shit. We need to get better. But how? Well, as individuals, we need to decide to stop losing, we need to stand athwart the long downward slide to Loserville yelling "STOP". To quote the great coach, Vince Lombardi, "Winning isn't everything but wanting to win is"
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