Challenging Projects Build Strongest Bonds

Engineering leaders often treat engineers like children rather than capable adults who can handle difficult problems. This protective approach actually limits engineers' growth and prevents them from taking on senior leadership roles where they could truly thrive.

When hiring and retention were the primary metrics for evaluating middle management, leaders tended to coddle engineers to avoid losing team members. This created a paradox: we couldn't hold engineers fully accountable, which meant we couldn't put them in truly senior roles. The current market shift allows us to treat engineers as peers, give them hard problems, and hold them accountable—enabling them to grow into the senior positions they've been seeking all along.

This perspective extends to how we approach engineering strategy. Good strategy often involves boring but powerful constraints that focus energy on what truly matters. At Carta, they defined a "standard kit" of tools engineers could use, which frustrated some who wanted more freedom. At Stripe, they maintained a Ruby monolith, and at Uber, they ran their own data centers instead of using cloud services. These constraints weren't popular with all engineers, but they aligned teams with company priorities.

The goal of good strategy isn't to appease everyone but to dictate how limited capabilities are invested in the problems that matter most. When engineers complain about boring constraints, remember that these limitations often enable the organization to move faster on customer-facing innovations rather than spending energy on internal tooling variations.

For engineering leaders, this means being willing to make unpopular decisions that focus team energy on business priorities. For individual contributors, understanding these strategic constraints helps you direct your creativity toward solving customer problems within the established guardrails rather than fighting against them.

When facing challenging situations, remember that the most difficult experiences often become the most valuable. As Will notes about his time at Dig during a catastrophic rewrite: "You would never voluntarily take on these really challenging things, but sometimes when they show up, you're with a group of people you really respect and love working with, and you want to overcome together. That's a really powerful experience."