I recently came across an article discussing Riot Games’ anti-cheating division. All their games revolve around competitive multiplayer gameplay—the biggest and most famous being League of Legends—so it’s been a core area of focus for the company for a long time. What I found fascinating, beyond the kernel-level access and spy-like infiltration into hacker groups to destroy them from within, is the expressed strategy of letting some cheaters go on purpose. The idea is to allow some players to engage in a limited amount of low-level cheating, rather than banning them quickly and driving them towards more disruptive cheating mechanisms that would also be harder to detect.
This is the philosophy of intentional, or strategic, leniency. It turns out that if you deal in absolutes and ultimatums, if issues are collapsed into binary, black-and-white decisions, then any choice will likely ratchet up the intensity. Escalations abound, and there’s much more risk in suffering unintended consequences.
Sun Tzu warned against this in The Art of War, with cautionary advice about maneuvering:
When you surround an army, leave an outlet free. Do not press a desperate foe too hard.
It’s tactically better to leave some means of escape, leave an exit path available, and avoid pushing an already-defeated army to its extremes. Without any hope, resistance can crumble with a whimper, but it can also become desperate—where the opposing army has nothing left to lose.
Outside of literal battle, this is akin to letting an opposing entity down gracefully, acting magnanimous in victory, or allowing them to save face. As I write this post, the US and China trade representatives have stared each other down for weeks after a series of escalatory tariffs, with both parties taking absolutist positions and unwilling to budge lest they reveal weakness. Each side is so convinced of its superior negotiating leverage, and contributed to their side of the trade war with such conviction, that it’s become a global economic staredown1.
Meanwhile, I’ve been reading Ben Horowitz’s book, What You Do Is Who You Are. He writes about culture and values, using historical leaders and their accomplishments as analogues to modern-day CEOs of startups and major tech companies. Horowitz emphasizes the importance of drawing red lines, cultural tenets that are non-negotiable and sometimes require drastic actions on the part of the leader to set the right tone2.
It makes for dramatic storytelling, but less discussed was the equally important aspect of tolerating minor behavioral infractions. It’s the managerial equivalent of picking your battles; prioritizing and focusing on the most important areas, and allowing the less important behaviors some amount of leeway. This serves the dual purpose of underlining the importance and immutability of those cultural red lines, as well as providing an escape valve for the team to get away from the rigidity of heightened expectations. In other words, it’s better to let the small stuff go, rather than build discontent and resentment by over-imposing zero-tolerance policies.
Paradoxically, selective leniency keeps it contained and creates a natural stack rank that highlights which behaviors are truly important to uphold. I’ve opined on what makes for ineffective meetings and my evolved preferences on how to run my own, but I’ve decided that it’s counterproductive to set hard rules on meeting hygiene for the entire organization. That is, while it’s a personal pet peeve to participate in inefficient, poorly-run meetings, it’s also not bad enough to the point where pushing for massive, cultural changes in meeting hygiene is worth the organizational energy when so many other priorities exist3. On the other hand, having experimented with making policies around required agendas and trimmed participant lists, I then had to deal with downstream side effects: cancelled meetings because agendas weren’t created in time, or meetings that got rescheduled because the host was too conservative in invites, and rescheduling busy calendars took additional weeks.
Strategic leniency isn’t about being soft. It’s intentional enforcement and tolerance, accommodating some amount of deviation because the cost of perfect control is too high.
Since then, the countries have deescalated their tariffs, at least temporarily—though that move highlights precisely the need to have an “out” on both sides of the negotiating table.↩
One such example involved Sun Tzu, beheading two of the emperor’s favorite concubines who didn’t take his training drills seriously.↩
So far I’ve only heard of one company, Shopify, that has pushed this to their policy forefront.↩
