Issue #671, 3rd October 2025

This Week's Favorite


Tips for Probabilistic Software
7 minutes read.

"deterministic software has edge cases, while probabilistic software has long tails." -- Thinking in probability is a skill where many software engineers, even veterans, are beginners in this new world of building on top of LLM models. Jason Liu offers practices and questions for building a product that is non-deterministic in nature, while we want to provide deterministic value to our users.

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Culture


CTO When CEO Announces the 5th Pivot of the Year
1 minutes read.

My humble effort to help you start the weekend with a smile on your face.

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The Static Risk Fallacy
6 minutes read.

"Make accumulation visible" is a powerful tool to demonstrate to technical leaders and relevant executives the real risk impact of the decision, or as Chris Beckman writes it: "The static risk fallacy isn’t just about math. It’s about how we make decisions under uncertainty. Each “yes” feels independent and disconnected, but real exposure steadily increases."

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From Managing People to Managing AI (Video)
96 minutes read.

"Diagnose with data, treat with design." — Choosing which areas to work on is art, not a science. Determining whether we took the right path can be enhanced with rigorous scientific methods.

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Shipping Products When You Don't Know What They Can Do (Video)
19 minutes read.

Every role is going to change in the next few years. Ben Stein guides us through the journey of product management when boundaries and requirements are no longer deterministic. This will make our jobs a hundred times harder yet also more interesting. It’s moving everyone into a builder in an open-world game, where the character can decide their path in millions of different ways while interacting with other players.

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Peopleware


I Have Built Around 300 Agents. Here's What I Learnt So Far
4 minutes read.

Sai Yashwanth is spot on: "Working with 5 startups showed me that the technology is only part of the story. The culture around experimentation, speed of iteration, and clarity of vision matter even more. An average agent usecase in the right hands can create real value; a brilliant agent usecase in the wrong hands goes nowhere. [...] In the future, every product will likely have agents running behind the scenes, coordinating tasks, personalizing experiences, and handling complexity humans don’t want to deal with."

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The New Code (Video)
21 minutes read.

I love the notion of defining specs that can point to test examples to verify intent and outcomes: "Engineering is the precise exploration (by humans) of software solutions to humans problems. [spec is] One artifact, three roles: communicate intent, adjudicate compliance, and evolve safely." For engineers, letting go of unique languages and reverting to English may be the most challenging part. There is pride and craftsmanship that people will hold on to. Talking at different abstraction levels. It’s like telling painters that they’ll start writing English instead of using a brush. Effective and efficient, yes, but is it enough? The question Sean Grove ended with was an opener for me, “what is the next IDE? Maybe it’s ITC - integrated thought clarifier?”

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Five Years Ago Today, I "Retired" From Amazon. Here Is What I Have Learned and What I Wish I Had Known Back Then
4 minutes read.

Ethan Evans shares some of his learnings after a long career at Amazon (15 years). A career should be planned like a great product - with a heavy investment in the mission, user experience, and measuring what's truly important to you.

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Inspiring Tweets


@thejustinwelsh: The most brilliant life hack is very simple: Decide what matters and ignore everything else. Then, execute on that daily until reality catches up with your vision.

@AditiRajasthan: Go workout. Tell no one. Go for a run. Tell no one. Eat clean. Tell no one. Read a book. Tell no one. Travel. Tell no one. Whoever guards his mouth and tongue keeps his soul from troubles.

- Oren

P.S. Can you share this email? I'd love for more people to experiment and improve their company's culture.

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