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To listen well, get curious

source A common piece of interacting-with-people advice goes: “often when people complain, they don’t want help, they just want you to listen!” For instance, Nonviolent Communication:1 It is often...

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My favorite essays of life advice

I start each of my weekly reviews by re-reading one of my favorite essays of life advice—a different one each week. It’s useful for a few different reasons: It helps me get into the right reflective...

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What I've been doing instead of writing

I’ve been too busy with work to write much recently, but in lieu of that, here’s a batch of links to other stuff I’ve been doing elsewhere. The thing I’m most excited about: Wave raises $200m from...

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Searching for outliers

Shortly after I started blogging, because I was a college student and had nothing better to do, I set a goal to write every week. I started in September 2013 and wrote around 150 posts between then and...

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10x (engineer, context) pairs

People have big arguments over whether “10x engineers” exist or not. Pro: The differences are not minor—it is rather like Salieri and Mozart. Study after study shows that the very best designers...

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Be less scared of overconfidence

When I was deciding whether to work for Wave, I got very hung up on the fact that my “total compensation” would be “lower.” The scare quotes are there because Wave and my previous employer, Theorem,...

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Staring into the abyss as a core life skill

Recently I’ve been thinking about how all my favorite people are great at a skill I’ve labeled in my head as “staring into the abyss.”1 Staring into the abyss means thinking reasonably about things...

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Why and how to write things on the Internet

Recently I noticed that most existing “why you should write a blog” articles (e.g.) have at least one of two shortcomings, according to me: They mostly focus on counterarguments to not starting a blog,...

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Leaving Wave, joining Anthropic

Last Friday was my last day as CTO at Wave, capping an incredible ~8 years filled with more professional and personal growth, joy, and meaning than I could have hoped for. This was the hardest decision...

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Some mistakes I made as a new manager

This post was adapted from a “management roundtable” I gave at Anthropic. I had an unusually hard time becoming a manager: I went back and forth three times before it stuck, mostly because I made lots...

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How I build and run behavioral interviews

This is an adaptation of an internal doc I wrote for Wave. I used to think that behavioral interviews were basically useless, because it was too easy for candidates to bullshit them and too hard for me...

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Trust as a bottleneck to growing teams quickly

This is an adaptation of an internal doc I wrote for Anthropic. I’ve been noticing recently that often, a big blocker to teams staying effective as they grow is trust. “Alice doesn’t trust Bob” makes...

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Categories of leadership on technical teams

This is an adaptation of an internal doc I wrote for Anthropic. Recently I’ve been having a lot of conversations about how to structure and staff teams. One framework I’ve referenced repeatedly is to...

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