The Management High Road

Oooof. Tech Twitter lit up last week on the drama surrounding Basecamp and their announcement of new company policies, centering around a ban on societal and political discussions on official company forums. For those unfamiliar, Basecamp—the company—makes the Basecamp product as well as an email service HEY, and has been around for over 2 decades with a pair of outspoken founders at the helm1. This time though, their blog posts were met with widespread outcry, to the point that the founders followed Coinbase’s lead and offered severance packages for employees who wanted out. By the end of the week, it was reported that about a third of the employees decided to move on, an exodus of talent.

An important lead up to this saga involves why these policies were enacted in the first place; a rough retelling of events:

  • The company had kept an offensive “funny customer names” list around for a decade;
  • The founders owned up to its existence and apologized;
  • Some employees within the company’s DE&I council pointed out how seemingly innocuous fun can serve as a foundation more serious consequences and hateful behaviors, escalating all the way to genocide;
  • The execs thought that really took the discussion out of proportion, and took it a step further themselves by calling out an employee on their hypocrisy to the entire company;
  • Employees filed formal complaints to HR;
  • New policies were announced publicly.

In our current political environment, this is an entirely believable series of events that amp up the emotional stakes with every escalation. And while there are plenty of hot takes surrounding this entire episode and its fallout, the ones I found most reflective opined on how the founders should have handled the situation instead:

In other words, after the initial apology, it was possible to deescalate the situation by eating humble pie and unconditionally admitting fault. Since that didn’t happen, the obvious next question is—why not?

Well, the easy and probably correct answer is that the Basecamp founders are, by their own admission, opinionated about how they work and are often loud in sharing. They’ve been telling others “the right way to run a business” for over 2 decades, so it’s not as if they’re lacking in confidence and ego. At the risk of oversimplifying the entire episode, the CTO thought they were right and wasn’t willing to let the issue go.

I’m sad, but not surprised how this played out—as the above tweet alludes, many executives are just unable to exhibit this type of humbling, potentially humiliating leadership. This is doubly true of founder-execs, since they’ve stayed at the top of the organization the entire time and have had little incentive to compromise throughout. The Basecamp founders are somehow an even more extreme instance of “what we say goes,” codified now in official company policy.

I’ve recently written about the difference between advancing up the management track and executive leadership, and I wonder if someone who’s risen through the ranks of people manager and director would fare better. The curse of middle management is to be held accountable to outcomes, without having full autonomous authority to make decisions; much of the difficulty—and frustration—in these roles is having to explain to why something is happening without necessarily being the one who made that choice, managing effectively both upwards and downwards at the same time. Developing the necessary skill here requires humility, and making personal peace with situations where there’s no winning move2.

Letting things go is really hard when you think you’re right! Nobody builds a company or climbs the career ladder to the top without feeling confident in their own judgement, so taking the high road here really means suspending your own emotions to make a tradeoff between a painful L now, hopefully preventing more painful Ls in the future.

  1. One of whom created the Ruby on Rails framework.

  2. Mastering the Kobayashi Maru exercise.

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