Human Inquiry in the Age of Algorithms

A review and discussion guide for System Error, required reading for technologists and citizens alike.

Gabe Kleinman
6 min readNov 3, 2021


Jeremy Weinstein, Hilary Cohen, Mehran Sahami and Rob Reich of Stanford. Photo Credit: Christie Hemm Klok

In early 2014, the war was on for software engineering talent.

I was Head of People at Medium, and we were losing the fight to Uber, Airbnb, and Big Tech incumbents. At first I thought this could only be due to compensation and/or our lack of aggressive language promising untold riches (e.g., blitzscaling, hypergrowth, “get on the rocket ship,” etc.), but there was something more that our software engineers pointed out.

They spoke emphatically about how the best engineers only wanted to work on hard problems.

Weren’t we solving a hard problem? The future of discourse, depth of knowledge, and thoughtful connection?

Turned out I was missing the point. The problems they were referring to had little association with the purpose of any company, let alone Medium. These problems were technical, coding challenges only. How to optimize for a passenger-in-a-hurry getting matched with just the right driver at just the right time in just the right location. How to ensure that a would-be vacationer got served up the most beautiful rental in an idyllic location at the perfect price. And so on.

These were difficult software engineering challenges, no doubt.

But few of us at the time stopped to ask: What was the higher order social or economic problem these companies were addressing? What were these companies actually optimizing for, apart from user growth and engagement? What were the real world impacts of these decisions?

Were these problems worth solving, and at what opportunity cost?

System Error: Where Big Tech Went Wrong and How We Can Reboot deconstructs the relationship between how engineers are educated, how venture capital is deployed, and the state of our democracy. Authors Rob Reich, Mehran Sahami, and Jeremy Weinstein — a leading contemporary philosopher, a famous computer science professor, and a former Obama policy wonk, respectively — take these topics head on in an approachable way that forces soul searching in us all, technologists and citizens alike.