Archive - Ilya Sterin's Newsletter

Evaluating feature robustness across contexts

I was in NY for work a week ago. I come here a lot, especially in the last year. I usually stay at the same hotel. About 6 months ago, the hotel started…

Feb 3 •

January 2024

The primary hindrance to agility

People tend to divide into sides on many topics, like emacs vs. vi, product-driven vs. engineering-driven vs. sales-driven, and agile vs. waterfall…

Jan 8 •

November 2023

Lost in flexibility

I often hear people in product and executive roles say, "Let's make this feature flexible and customizable." In my experience, this is a product/design…

Nov 24, 2023 •

September 2023

Fat-tailed distribution of project risk

This weekend, I'm diving into the book "How Big Things Get Done". It explores the concept of a fat-tailed distribution in project outcomes. After…

Sep 4, 2023 •

July 2023

Managing strategic work in the whirlwind of small and urgent tasks

As we further adopt Shape Up, I’ve heard numerous teams struggling to understand how to adopt Shape Up in the context of how they currently work. One…

Jul 29, 2023 •

January 2023

Forgetting (Book Review)

For most people, forgetting is a cause of anxiety. But forgetting is the brain’s routine for optimizing storage, consolidating thoughts, and building…

Jan 15, 2023 •

November 2022

Engineers who navigate optionality (going uphill)

As we think about audacious goals for next year and how to organize teams for success, we’re thinking about the skills required for team flow. If you’re…

Nov 25, 2022 •

April 2021

In software development, synchronous processes are easy to reason about; they are sequential, more deterministic, and require less integration testing.

Apr 28, 2021 •

November 2020

The economics of product tradeoffs

The word tradeoff has become ubiquitously overused and misunderstood in product development.

Nov 27, 2020 •

July 2020

Your artificial brain

A couple of months ago I stumbled on something which stopped me in my tracks. I realized that the way I consume and retain information and…

Jul 10, 2020 •

June 2020

B2B buyers have emotions, too

When I first learned about Jobs To Be Done from Bob Moesta and Chris Spiek, one of the core concepts that stuck with me was the emotional…

Jun 1, 2020 •

August 2019

Turn your guesstimates into estimates

Our process of scoping work, and estimating the time it will take, is fundamentally broken.

Aug 9, 2019 •

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