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September 22nd, 2019

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If you enjoy this article, see the other most popular articles

If you enjoy this article, see the other most popular articles

If you enjoy this article, see the other most popular articles

Software developers often fail when they try to become managers

(written by lawrence krubner, however indented passages are often quotes). You can contact lawrence at:, or follow me on Twitter.


Rosie (all names are composites of multiple employees) is the strongest engineer on the team. She can navigate any part of the stack. And when people have questions about the code base, they ask her for help — after all, she wrote most of it. Sometimes she’ll patiently answer, but sometimes, if it’s faster, she’ll just roll up her sleeves and do it herself.

Rosie is fast. She gets things done. I can always count on Rosie.

So as the team grows and needs a manager, I ask Rosie if she’s interested. She seems reluctant at first, but she wants to help her team. And she’s never backed off from a challenge. She takes a couple days to think it over, and eventually, she says yes.

She seems fine initially, riding a wave of excitement and renewed confidence. But over the next few weeks, I can sense her energy dropping. She’s less on top of things. Her enthusiasm and confidence fall and she seems agitated. The rest of the team notices she’s far less effective as a manager than she was as an engineer — and even worse, things don’t seem to improve over time. I’ve fallen victim to the classic trope of losing a top engineer and gaining a mediocre manager.

Over a series of conversations with Rosie, she acknowledges that things aren’t going well. I offer my support and my confidence that if she wants to, we can make this work. Instead, she asks if she can transition back into a purely technical role. I agree, but even after her transition, her enthusiasm never recovers, and a few months later she accepts a technical role at a different company.


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"I wish I could go back," said Anna. "I guess I thought it would always be there, and I could go back and learn more when I was older. But now I'm older and it's gone."

"All the great art scenes are like that," said Mariah. "Renoir's career was half over before the term Impressionism caught on. And Fitzgerald and Hemingway had given up on the Left Bank long before the place was overrun by talentless hacks who wanted to imitate the Lost Generation lifestyle. And the Beats had mostly left San Francisco before busloads of visitors started to do tours of the Haight-Ashbury. When Johnny Rotten couldn't work with the Sex Pistols anymore, he left and the London punk scene began to die. Later on, he said he regretted his decision to leave. Everyone thinks they can go away and come back later, but they never can. When Joan Didion and her husband left New York, she quipped that some other couples were staying too late at the party, but that gets it all backward. The party ends whether you want it to or not, and it takes an unusual arrogance to celebrate the end of an era that some people will remember as the best years of their life. Hemingway lived in Paris during his twenties, but he didn't write about his experience in Paris until he was in his sixties. No one ever knows they're part of an art movement; it's something you only see afterward."

"But if we only see it in retrospect, then how can we find the next great art scene?" asked Anna. "What do I look for?"

Also read this true story about a startup I worked at in 2015:



September 22, 2019
3:17 pm

By Just An Observer

Common failure mode for salespeople as well.

Exceeded quota 40 quarters in a row, let’s make them the district manager.

They drown in paperwork and babysitting their staff.

As you probably know since Celolot or its real life equivalent actually dealt with aversion to paperwork.

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