Essay

Essay

Long-form thinking on leadership, engineering culture, and the craft of building high-performing technology teams.
09
Mar
Code Used to Be a Moat

Code Used to Be a Moat

The economic protection of software was always reproduction cost. AI collapses that cost. Any business whose moat depended on software being expensive to reproduce is now structurally exposed.
3 min read
02
Mar
The Typewriter Defense

The Typewriter Defense

Atlassian won’t vanish overnight—but inertia isn’t a moat. In an agentic world where software is cheap and specs replace tickets, workflow tools built for human task tracking face structural risk. The need for coordination remains. The shape of it doesn’t.
7 min read
09
Feb
Planning in the Agentive Era

Planning in the Agentive Era

Agentic dev breaks planning. Work finishes before tickets get written. Estimates don't apply. But orgs still need dates. The fix: plan outcomes, not tasks. Artifact in the repo where agents read it. Ranges, not commitments. Most orgs aren't ready. Figuring it out live.
9 min read
02
Feb
Humility breeds success

Humility breeds success

Self-awareness is a form of self-knowledge that emerges when you know your strengths as well as your weaknesses. A self-aware leader knows when he can succeed as well as when he's licked. Such a leader has the strength of character to step aside in favor of a better alternative.
4 min read
12
Jan
The Junior Engineer Paradox

The Junior Engineer Paradox

Engineering capability was earned through friction. You wrestled with syntax. You paged at 2 a.m. You learned why certain patterns were bad because you lived inside their failure modes. That friction is gone. But the struggle isn't. It's simply moving up the stack.
3 min read
05
Jan
What AI-Powered Development Requires from Leadership

What AI-Powered Development Requires from Leadership

In the agentic era, execution is cheap but decision latency kills velocity. The solution isn't more coordination—it's architectural strategy with enough logic density that engineers can make good calls independently. Duplication beats meetings. Build the framework before you unleash the agents.
8 min read
29
Dec
GenAI Product Doctrine: Products of Counsel

GenAI Product Doctrine: Products of Counsel

Products of Counsel advise humans toward outcomes, not just answers. The moat isn't chat UI or data access—it's accumulated user context, domain judgment, and encoded expertise. Sycophancy and false confidence kill trust. Win by being worth believing, not by being liked.
5 min read
22
Dec
GenAI Product Doctrine: Products of Judgement

GenAI Product Doctrine: Products of Judgement

Products of Judgment feed Products of Consequence. If your output is derived, not retrieved, the doctrine applies: confidence as first-class output, structured uncertainty, reasoning legible enough to investigate. Agents can't muddle. Make your signal good enough to act on.
8 min read
15
Dec
The Dawning of the Age of the Arbiter

The Dawning of the Age of the Arbiter

Organizational distance, layers between intent and execution, drove specialization for decades. AI agents collapse that distance, letting one engineer direct many without translation loss. The human role shifts from doer to arbiter: steering, judging, staying close to the craft.
5 min read
26
Nov
The Coming PR Tsunami

The Coming PR Tsunami

LLMs broke the code production bottleneck, and now review is the constraint. The fix: small atomic PRs, LLM-generated summaries that compress comprehension time, and engineer-owned calibration. Teams that adapt stay ahead. Teams that wait drown in their own queues.
3 min read