Ilya Sterin's Newsletter

Mental Models for Product Strategy and Roadmaps

Prioritizing product features is more art than science. Here are several models I've found helpful throughout my career to help inform strategy or…

Apr 27 • 

Ilya Sterin

5

Integrated vs. Modular experiences

I've been thinking a lot about product philosophies lately, particularly the tension between integrated vs.

Apr 20 • 

Ilya Sterin

2

Design for Robustness

Complex systems are inherently unpredictable.

Apr 13 • 

Ilya Sterin

1

2

December 2024

February 2024

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, 2024 • 

Ilya Sterin

5

1

January 2024

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 • 

Ilya Sterin

5

1

September 2023

Fat-tailed distribution of project risk

This weekend, I'm diving into the book "How Big Things Get Done".

Sep 4, 2023 • 

Ilya Sterin

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.

Jul 29, 2023 • 

Ilya Sterin

4

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 • 

Ilya Sterin

1

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.

Nov 25, 2022 • 

Ilya Sterin

4

2

April 2021