Using Agents is literally engineering management
Managers understand what's going on with AI better than ICs. The whole job of management is getting heterogeneous intelligences with incomplete context to coordinate toward a goal.
Jack Danger
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Committing Prompts, promptlog.md
The whole industry is figuring out how to review AI-generated code. One pattern that might help is committing prompts to git.
The Reach Pattern
Your AI coding assistant can see your code but not your organization. The Reach pattern is a personal CLI that borrows your real browser sessions to call web APIs on your behalf.
Good Bosses, Bad Bosses
Bad bosses break feedback loops. Great bosses deliberately manufacture them. All it takes to be a bad boss is to break feedback loops about your own behavior.
A Pyramid-shaped Career
Getting a high-status role early in your career can limit you. You start to associate success with status, and anything that looks like a 'step down' feels like losing ground.
Big Bets
A 'Big Bet' is a rapid push into a new market space. These initiatives often fail and come with hidden costs like draining morale and neglecting other key products.
Managing Underperformers
Kind managers address underperformance early and accurately. There are two unrelated causes of underperformance: Refusal to Align and Failure to Execute.
Technical Coherence
Software development slows down over time. Technical Coherence is a process any engineering leader can apply to reverse this slowdown, mostly achievable in a single meeting.
Technical Debt Financing
Technical debt is one of the most powerful tools a CTO has. It only hurts us as an organization when we miss the larger picture.
Infrastructure Gravity & Domain Engineering
Product Engineering is 'stuff the whole company wants' and Infrastructure is 'stuff the engineers say we have to do.' Where you draw the line between them changes everything.
Explore, Experiment, Invest
Every product initiative develops through three distinct stages. Confusing them is the primary source of product failures.
You must not measure individual software engineer performance
Effective engineering is a collaborative and creative discipline where the team is the performative unit, not the individual. Attempting to reward or discipline individuals throws the team off balance.
A reference guide for fintech & small-data engineering
A reference guide composed while leading Infrastructure at Gusto, covering fintech and small-data engineering principles.
The Four Interfaces of SaaS product suites
There needs to be a handbook for migrating a monolithic application into a service-oriented SaaS product suite. This covers the four interfaces that matter.
The Upside Down Org Chart
A corporate org chart is drawn with the CEO on top and individual contributors at the bottom. What if we flipped it upside down?
Design Doc Template
A design doc template developed in the early days of Square and iterated by several companies including Gusto and Pathstream.