This week on First Round Review, we hold three conventional engineering management “anti-patterns” up to the light for a closer look.
Unexpected Anti-Patterns for Engineering Leaders — Lessons From Stripe, Uber & Carta
When Will Larson was CTO at Calm, he had to make the tough call to cancel a major product migration from the monolith to a multi-product suite. It ended up being a huge success for the company, so when he first got to Carta, also in the CTO’s seat, he had the instinct to try the exact same thing.
“I thought, if it worked at Calm, why wouldn’t it work here?” Larson says.
What he discovered later was that he was missing crucial historical context and different perspectives, things he only found out after getting obsessively close to the details on his team.
While conventional management wisdom told him, as a leader, to step away from the code, it was the dozens of conversations and days spent mining for context that clued him into all the reasons his strategy at Calm never would have worked at Carta.
“One of the biggest lessons in management over the last decade is that micromanagement is bad,” he says. “But I think this is an anti-pattern. Avoiding micromanagement creates disengaged and context-free leadership, and leadership can be so much more than that.”
Larson has always been drawn to the puzzle that is engineering strategy. His winding career has landed him in leadership roles at Stripe, Uber and Digg — and he’s scaled engineering teams from tens to hundreds of people. He’s meticulously documented the lessons he’s learned, penning widely-circulated essays on the topic on his blog, authoring three different books and even sharing some of his frameworks right here on the Review.
He returns today to drop more knowledge, this time focusing on conventional leadership practices that lead folks astray. “We have to have the openness to think through whether a different approach might make sense in a very specific case,” he says. “That’s a fundamental part of engineering.”
In this exclusive interview, Larson walks through three unexpected anti-patterns engineering leaders can use to elevate their team strategy. He lays out the case for why micromanaging can be a good thing, why execs shouldn’t bother spending too much time on metrics, and why managers shouldn’t shield their direct reports from reality.
While he speaks directly to an audience of engineering leaders, his advice goes far beyond that, and executives in any function are sure to find his advice useful.
Here’s a quick snippet of what’s inside:
- Don’t shy away from micromanagement: “New engineering managers are often advised to ‘step away from the code.’ But an extremely high-functioning exec understands the domain they are operating in at some level of detail,” he says. “As you get too far out of the details, you just become a bureaucrat. Too many well-meaning engineering managers end up as bureaucrats.”
- Measure imperfectly: “Often when people start measuring, there's always a concern that their measurement is flawed. And that's true for all functions,” he says. “But I’m a believer in measuring something imperfect, but useful, versus holding out for the perfect metric while measuring nothing in the interim.”
- Don’t be an umbrella: “In the past, I used to think I was energizing my team by sparing them the details. But now it feels like lying to them,” he says. On a tactical level, Larson adjusted this habit by buffering less information. “That means even if it’s disappointing for folks, I’d rather them process news bit by bit, rather than deal with a huge ocean of mess all in one moment.”
Thanks, as always, for reading and sharing!
-The Review Editors
P.S. If you’re hungry for more of Larson’s best leadership practices for eng teams, go deeper by listening to our podcast episode with him here.
Recommended resources:
-Will Larson’s latest blog post on making engineering strategies more readable.
-CTO and career coach Yue Zhao on what we get wrong about influence.
-This deep dive examines the growing specialization of product management.
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