Playing to Win: Becoming the Champion is a book published back in 2006 on the mentality of competing and winning at the highest levels, framed around a trifecta of dorky games: Street Fighter, Chess, and Magic: the Gathering. Of course—as a kid from the 90s who has totally played these games on the playground and in dimly-lit arcades—I can at least relate to being on the losing side of the competition. That said, I keep the short paperback on my bookshelf despite its focus on video games1, because the author’s salient point still resonates all these years later: that in a competitive and high-skill environment, winning behaviors evolve ultimately from the defined rules of the game.
Which is, intent and some fuzzily-defined sense of honor and the spirit of the game matter less than actually just winning. For instance, in fighting games, players are called “cheap” if they employ repetitive attacks which become aesthetically boring, but are so advantageous in the matchup that they are hard for the opponent to overcome. In Playing to Win, the author cites an example from a tournament game, where they secured victory by just repeating a basic move—Chun Li’s low forward kick—against an opponent who just could not figure out a way to counter the tactic. Despite the boos from the audience upon the realization that this was essentially all there was to the match, they persisted and eventually won the game, even if it meant losing a few fans along the way.
Similar dynamics play out in other sports as well. For the last couple of years, NBA players have incrementally refined their skills to draw fouls, fooling both defensive players and the referees to get easy points from free throws. It got to a point where these types of moves were deemed “non-basketball moves,” and in the beginning of the 2021–22 season the league instituted a rule change meant to discourage foul-baiting. For the players who were most affected, their free throws per game did indeed go down when rule was initially instigated, only to normalize back to their career change rate throughout the course of NBA season.
I was reminded of that book when I came across this article:
The advice—that it’s to a senior engineer’s benefit to understand what their engineering organization values to maximize their own chances of promotion—is apparently considered a bit controversial. I’m guessing that much like fighting game enthusiasts or NBA fans, engineers want to believe that by following general best practices, implementing the “right way” to build software would be intrinsically rewarded. Yet, the author is of course correct: careers are built only via recognition from others, and such recognition are most visible when aligned with an organization’s culture and values.
How this manifests in practice differs by team and company2. When I worked for Google a decade ago, it was common knowledge within engineering that the easiest way to build your promotion packet and have it approved was via product launches, doubly so when working on the hottest areas of the company at the time: Google+ and Android. Facebook was and is known to value infrastructure work, and for a little while Yahoo pushed for mobile development above everything else. Within a team, there’s always a few areas of focus that are particularly valuable and practitioners get disproportionally rewarded. Fixing gnarly bugs, prioritizing exec requests, helping land a major partnership, specializing in domains complementary to the founders; I’ve seen colleagues fast-track their way to high positions within organizations by identifying and optimizing for what management cared about3.
Then again, it’s also worth asking: is this a game worth playing to begin with?