Long-form essays on technology, leadership, and the craft of building
Making Good Decisions via Memos and Meetings
March 15, 2025A company succeeds or fails based on the speed and quality of the decisions it makes. Slides hide weaknesses in reasoning; documents expose them. My guidelines for writing good memos, the key questions for each meeting type, and how to run a meeting that ends in a decision instead of a follow-up. Licensed Apache 2.0.
How to Run an Incubation Process
March 1, 2025A pro forma process for incubating new ideas alongside the regular flow of a product engineering org. Four phases — research, ideation, incubation, productization — with three decision gates between them. Drawn from variations I've used at NASA, Oracle, NewsCorp, Grab, MongoDB, and dbt Labs.
The 5Ds: Discover, Debate, Decide, Declare, Deliver
January 1, 2025A working framework for thinking about every decision in five distinct phases. Originally a scratchpad I wrote as CTO at dbt Labs while thinking out loud about how to make and communicate decisions better — sharing here as a work in progress.
The Motive of Leadership
November 17, 2024On Patrick Lencioni's *The Motive*: rewards-based leadership vs. value/team-based leadership, and why senior leaders never change because they're told to — only because they change what they value. Originally a note to my engineering managers.
The Six Levels of an Engineering Manager Career — and Why They Matter
July 21, 2024A 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.
When a Rating Isn't Enough — My Dimensions of a Leader
June 1, 2024A single-dimensional performance rating loses a huge amount of information about most humans. Eight dimensions I factor in when looking at leaders — and why lack of self-awareness about where you stand on them trumps all of them, and is a criteria for exit at director-and-above levels.
The Six Stages of Change — A Framework
May 1, 2024Sometimes people need to change to adapt to the company, and we're not sure of the journey or how to help them. Six levels from unaware-of-the-gap to changed-and-maintaining — and a warning about the 3-4-5-3-4-5 cycle that can fool you into thinking someone has actually changed.
Reorgs — Some Thoughts
April 1, 2024Reorganizations are hardly ever viewed as positive by the troops. As a leader you've been sitting with the new structure for weeks; for everyone else, it lands as a surprise. The job isn't moving boxes — it's running the announcement like a well-orchestrated Broadway play, where the unpopular things are called out as the plot, not ignored.
LIFE Metrics — A Way of Thinking Deeper About Customer Experience of Availability
February 1, 2024Fleet uptime is a fine starting point, but it doesn't represent the customer experience. The LIFE framework — Length, Impact, Frequency, Experience — is how I think about availability NFRs in a way that actually maps to what customers feel.
Cascading — A Key Part of Being a Leader
January 1, 2024Cascading isn't just forwarding emails. It's the practice — and discipline — of synthesizing, filtering, editorializing, and sometimes deleting the information that comes at you as a leader, then deciding what your team needs to know and how they need to know it. Originally written as a leveling note for my direct reports.
A Single Prioritized Backlog
January 17, 2021About 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.
Under Construction
Drafts and works-in-progress — published as I work on them, with finishing edits and commentary still to come.
An Open Letter on Culture to Product and Engineering Organizations
October 15, 2022Eight 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.
How to Stay Competitive and Flexible in a Multi-Cloud World… and How Not To
August 15, 2022An 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.
Leadership Principles from Various Companies
June 22, 2022A curated set of leadership principles from companies I've worked with or admired — with my commentary forthcoming.