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A Year in Reading, 2025

Well here we are. Another year has gone by. Each year, it goes by quicker and quicker. Each year, it grabs a hold of me and whispers, “you’re on a one-directional ride, buddy!” I’m now a quarter of the way through — no, scratch that, almost halfway through, actuarially

Learning Without the Lessons (In Pursuit of Uncertainty)

We’ve been asking the wrong questions in every retrospective and assigning the wrong endings to every story for the past century. ‘What did we learn?’ assumes a lesson exists to be learned, and that a certainty about the world can be extracted. What if there isn’t?

Are You Treating ChatGPT Better Than Your Coworkers?

Here’s a 🌶️ spicy take: I think practice at human/LLM interactions can lead to better human/human interactions. Over the last few months I've watched colleagues spend considerable time crafting and sharing LLM prompts for different projects—complete with context, examples, and success criteria. Then I'd see them turn

Appendix to "Identifying Signals of Expertise"

In "Identifying Signals of Expertise", I ended up cutting almost 2000 words to keep things succinct and focused. But that stuff was useful! If you're looking to upskill your interviewing skills further and dive deeper into identifying signals of expertise, read on; I've included three sections that were previously cut:

Identifying Signals of Expertise

One of the most useful questions I've used for evaluating expertise during a hiring interview is: Tell me about a time when you did something you thought was right, and later it turned out to be a mistake. That kicks off a series of additional questions and followups: * What was

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