Deeper Thoughts

Long-form essays on technology, leadership, and the craft of building

Six ascending platforms representing the levels of an engineering leadership career

The Six Levels of an Engineering Manager Career — and Why They Matter

July 21, 2024

A framework for understanding the fundamentally different jobs at each rung of the engineering leadership ladder — IC, Manager, Director, VP, C-Level, and CEO. Being promoted isn't doing your current job better; it's a new job with new skills, new mindsets, new success criteria, and new failure modes.

An open letter on culture — title cover from the original draft

An Open Letter on Culture to Product and Engineering Organizations

October 15, 2022

Eight cultural guidelines for product and engineering organizations, written during my 18 months as CTO at MongoDB. Topics: balancing non-functional requirements with features, treating tech debt as a choice, pride in your work, trust, Conway's law, Dunbar's number, experimentation, candor and context for accountability, and avoiding unnecessary approvals.

Cover image — A blog about multi-cloud I never published

How to Stay Competitive and Flexible in a Multi-Cloud World… and How Not To

August 15, 2022

An argument against the false fairy-tale of cloud-agnostic abstractions. Why letting the workload dictate the cloud, taking advantage of best-in-class services where you can, and focusing teams on being great on every environment they deploy to beats commoditizing yourself across the lowest common denominator. From conversations with many CTOs during my time at MongoDB.

The Council of Values — five robed wizards in a starry purple chamber, each holding a banner of glowing runes

Leadership Principles from Various Companies (under construction)

June 22, 2022

A curated set of leadership principles from companies I've worked with or admired — with my commentary forthcoming.

A single unified backlog of work and life items, woven together

A Single Prioritized Backlog

January 17, 2021

About 70% Clay Christensen, 30% me. The case against balancing work and home as two separate budgets — and for integrating them into one prioritized list for your whole life. Licensed Apache 2.0 so others can adopt it.