/decision-making
Posts touching decision making.
30 posts
- April 5, 2026 4 min
What I got wrong in my first year as Head of Engineering and what I would do differently
Over-hiring before culture. Saying yes to everything. Underinvesting in developer experience. Staying hands-on too long. The common thread was not trusting the team.
- /engineering-leadership
- /career
- /decision-making
- /team-building
- /experience
- March 15, 2026 5 min
The real job of a Head of Engineering
Make throughput predictable and quality sustainable. Not hero-shipping. Not writing the most code. Build a system that delivers without depending on any single person.
- /engineering-leadership
- /career
- /decision-making
- /cross-functional
- /blog
- March 10, 2026 5 min
Architecture debt is usually a decision-quality problem first
The worst architecture debt comes from low-quality decisions made with plenty of time. Improving decision quality reduces debt faster than refactoring sprints.
- /architecture
- /engineering-leadership
- /decision-making
- /blog
- March 5, 2026 5 min
Engineering teams do not need more process. They need better defaults.
Every incident triggers a new process proposal. The real fix is better CI pipelines, better templates, and better linters. Better defaults scale. More process does not.
- /engineering-leadership
- /team-building
- /ci-cd
- /decision-making
- /blog
- March 1, 2026 5 min
How I evaluate build-versus-buy decisions at a 50-person startup
Build-versus-buy is not about cost. It is about where your team's attention goes. Build what differentiates. Buy the commodity.
- /engineering-leadership
- /architecture
- /decision-making
- /startup-life
- /blog
- February 28, 2026 4 min
What AI changes about engineering leadership
Code review matters more than code writing. Architectural taste matters more than implementation speed. Evaluating AI-generated code is the new critical skill.
- /ai-ml
- /engineering-leadership
- /hiring
- /decision-making
- /blog
- February 9, 2026 4 min
Opus 4.6 has a million-token context window and I am still not sure what to do with it
Feeding entire codebases into a single prompt for architecture review produced mixed results. The practical sweet spots are narrower than the capability suggests.
- /ai-ml
- /engineering-leadership
- /decision-making
- /learning
- February 2, 2026 5 min
Drizzle ORM crossed 32K stars and I still think ORM choice barely matters
Query patterns, migration discipline, and connection pooling matter far more than which ORM you choose. The ORM was never the bottleneck.
- /postgres
- /typescript
- /architecture
- /decision-making
- /blog
- January 5, 2026 5 min
The hardest conversation I had in 2025 was firing a senior engineer I had hired
He interviewed brilliantly but could not operate in a startup. Performance management is the most important and least taught leadership skill.
- /engineering-leadership
- /team-building
- /hiring
- /decision-making
- /experience
- December 15, 2025 4 min
How I budget engineering time and why I give 20 percent to platform work non-negotiably
Twenty percent of every sprint goes to platform work. The compounding cost of deferring platform investment is measurable in incident frequency and developer velocity.
- /engineering-leadership
- /decision-making
- /startup-life
- /blog
- November 3, 2025 4 min
Why your engineering strategy document is probably a wish list, not a strategy
A strategy is a diagnosis, a guiding policy, and coherent actions. Everything else is a roadmap pretending to be a strategy.
- /engineering-leadership
- /architecture
- /decision-making
- /blog
- October 20, 2025 4 min
I mass-deleted our internal wiki and started over. Twice.
The wiki grew to 400 pages that nobody read. The fix was not better organization. It was aggressive pruning and a decay policy.
- /engineering-leadership
- /team-building
- /decision-making
- /experience
- October 13, 2025 4 min
Managing up to a non-technical founder without losing your integrity
Business-outcome framing for every technical decision. Risk quantified in dollars, not story points. Never say "technical debt" without a customer impact number.
- /engineering-leadership
- /startup-life
- /cross-functional
- /decision-making
- /blog
- August 18, 2025 4 min
The founder said ship in two weeks. I said no. Here is what happened.
A major customer deal hinged on a feature in two weeks. I pushed for three. The extra week saved us on day four.
- /engineering-leadership
- /startup-life
- /decision-making
- /cross-functional
- /experience
- August 11, 2025 4 min
GPT-5 shipped and my team asked if we still need junior engineers
The answer is yes, but for reasons that forced us to articulate what junior engineers actually contribute beyond lines of code.
- /engineering-leadership
- /ai-ml
- /hiring
- /decision-making
- /blog
- June 30, 2025 5 min
Eighteen months in: the five things I would tell myself on day one as Head of Engineering at a startup
Delegate before you are ready. Learn compliance before it learns you. Your cofounder's priorities are not wrong, just different. Tech debt compounds faster than you think. And the hardest one: your job is not to write the best code.
- /engineering-leadership
- /startup-life
- /decision-making
- /career
- /experience
- June 23, 2025 4 min
Kubernetes 1.33 and the features that finally made me stop questioning container orchestration for small teams
Every six months someone says Kubernetes is overkill for a small team. Kubernetes 1.33 continued a trend of sane defaults and reduced overhead that invalidates that argument for teams deploying more than two services.
- /kubernetes
- /k3s
- /architecture
- /decision-making
- /blog
- May 12, 2025 5 min
Founder dynamics: when your technical opinion conflicts with the CEO's investor promise
The CEO told investors we would launch a new vertical by Q3. I told the CEO we needed Q3 for infrastructure debt. We were both right, which made it worse.
- /engineering-leadership
- /startup-life
- /cross-functional
- /decision-making
- /experience
- April 14, 2025 5 min
Why I stopped mass-applying "best practices" and started asking "best for what"
Microservices, event sourcing, CQRS, DDD. I had been cargo-culting patterns from companies 100x our size. The question "who benefits from this complexity" changed my architectural decisions.
- /architecture
- /decision-making
- /engineering-leadership
- /startup-life
- /experience
- March 17, 2025 4 min
Google's $32B Wiz acquisition and what it signals about security as a first-class infrastructure concern
Google paying $32B for a cloud security startup signals that security is no longer a checkbox but a competitive differentiator, especially in fintech where trust is the product.
- /security
- /aws
- /architecture
- /decision-making
- /blog
- March 10, 2025 5 min
Learning to delegate when every task feels faster to do yourself
For six months I was the bottleneck on every code review, architecture decision, and production deploy. Delegation felt slower because it was. The turning point was redefining my job.
- /engineering-leadership
- /team-building
- /startup-life
- /decision-making
- /experience
- February 24, 2025 5 min
When the sales team demos a feature that does not exist yet and engineering finds out from a prospect
A prospect called asking for help configuring a feature our sales deck showed but engineering had never built. The fallout was not the scramble but the trust erosion between teams.
- /cross-functional
- /startup-life
- /financeops
- /decision-making
- /experience
- January 27, 2025 5 min
DeepSeek R1 and the moment I realized open-source AI would change how we build internal tools
DeepSeek R1 shipped as a 671B open-source model matching GPT-4o benchmarks for under $6M training cost. Self-hostable reasoning models change the calculus for regulated fintech.
- /ai-ml
- /architecture
- /fintech
- /decision-making
- /blog
- January 6, 2025 5 min
AWS re:Invent announcements that actually matter for a three-person fintech team
Aurora DSQL, S3 Tables, Amazon Nova. re:Invent 2024 dropped a firehose of announcements, but most solve problems we will not have for years. Three that actually changed our roadmap.
- /aws
- /architecture
- /fintech
- /decision-making
- /blog
- December 16, 2024 5 min
The meeting where product, sales, and engineering all had different definitions of "real-time"
Product wanted sub-second dashboard updates. Sales had promised "real-time" reconciliation. Engineering was thinking about eventual consistency with 30-second polling. One word nearly derailed a quarter of work.
- /cross-functional
- /architecture
- /financeops
- /decision-making
- /experience
- November 11, 2024 4 min
What Payload CMS 3.0 taught me about choosing frameworks that grow with you
Payload CMS 3.0 shipped with native Next.js App Router integration, validating a framework evaluation approach that prioritizes embeddability over feature count.
- /react
- /typescript
- /architecture
- /decision-making
- /blog
- September 18, 2024 5 min
Making technology bets: how I evaluate frameworks when the wrong choice costs a year
At a startup, picking the wrong framework is a survival threat. Here is the five-criteria scoring model I use for every significant technology decision.
- /decision-making
- /architecture
- /startup-life
- /experience
- June 19, 2024 4 min
The AWS bill that made me rethink everything about infrastructure
Our third month AWS bill was 4x what I projected. The culprit was not compute. It was data transfer, NAT gateway charges, and CloudWatch log ingestion.
- /aws
- /architecture
- /startup-life
- /decision-making
- /experience
- June 5, 2024 5 min
Startup engineering culture when you are the only engineer
For the first four months I was the entire engineering department. No code reviews, no architecture discussions. Here are the practices I invented to stay honest.
- /engineering-leadership
- /startup-life
- /decision-making
- /experience
- April 3, 2024 4 min
Why I chose PostgreSQL over MongoDB and how it shaped our entire fintech stack
Every fintech startup I talked to was defaulting to MongoDB. I went the other way and bet on PostgreSQL with strict schemas from day one.
- /postgres
- /architecture
- /fintech
- /decision-making
- /experience