When Resistance Is Futile

His timing couldn’t have been better. I opened the package and clapped my hands in delight. Inside was a black felt beret, along with a note. 

“Keep fighting the good fight. Long live the resistance!”

Gleefully, I put it on and took a few photos with my team before we headed out for lunch. An hour later, I’d announce my resignation. 

The months leading up to this moment were fraught with a tension most software developers can recognize. The business execs wanted an ambitious project delivered on an even more ambitious timeline. Concerned about the quality of the delivery, the technical team attempted to negotiate a more reasonable deadline. Instead of finding a productive middle ground, we locked in a stalemate.

We’d worked so hard to build up the courage to have conversations within the team about what was possible and where we were experiencing challenges. When we brought these issues to the executives, we were met with disappointing responses.

“Work always expands to fit the time allowed, so just cut the estimates in half,” they’d offer. 

Ah yes, Parkinson’s squeeze. 

“But have you considered Hofstadter’s Law?” I countered. “You know, the one that says work always takes longer than you think, even when you account for Hofstadter’s Law.” 

The humor–and the point–had been lost.

“Stop spending all this time talking about what you’re doing and just code something. Be scrappy!” 

Mumbling to myself that scrap is a synonym for waste, I’d concede another battle lost and turn my attention to helping the team make the best of a bad situation.

The problem with a toxic environment is that you can’t stay in it for long before you start feeling unwell. I’d noticed how tense and angry I was during the day, and how helpless I felt when I saw my team working long hours and getting criticized for not meeting deadlines they couldn’t possibly achieve and never agreed to.

Although I’d been hired as a technical project manager, I’d assumed a de facto Scrum Master role with the team. My raison d’etre quickly shifted from delivering the impossible to supporting the team and trying to make their voices heard. I don’t believe I succeeded in either point. The only thing I perhaps achieved was becoming the face of the resistance (hence the beret from my conspiring coworker). 

So I quit. The team carried on and delivered the project eventually (a year after the supposed “drop-dead” date). 

On my last day, one of the execs attempted to join the team retrospective, carrying two six-packs of beer. I thanked him for the beer and showed him the door. One of the developers thanked me later, saying that even on my last day, I still supported the team. I felt proud of that at the time.

Years later, I see this situation differently. Though my intentions were noble – protect the team! – my actions did little to improve their situation or help the company meet its goals. My resistance, perhaps, was futile.

As I’ve tried to make sense of this experience, I’ve often wondered how things might have been different if we’d found a way to trust one another. What made it difficult for these leaders to trust that their team wanted to do their best work and help the company succeed? And what made it so difficult to build a bridge so we could work together?

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Coach the Person, Not the Paper