58 essays

Writing

What AI changes in how teams build, and what it doesn't. Notes on AI-native products, platforms and operating models, from twenty years of building technology that pays its way.

ai native
Latest

The Software Factory Died Twice. Here Is What Has to Be True for the Third Time.

Software factories were tried in 1980s Japan and again across US Defense. Both fell short in the same way. The agentic version in 2026 is different in one specific respect, and it is not the agents.

5 September 2026 · 10 min readRead

All writing

22 August 2026 · 5 min read
The Illusion of Learning

I asked an AI to summarize a book about how people learn. It took me a second to notice what I had just done, and longer to work out why it bothered me.

Read
14 May 2026 · 10 min read
What to Kill in Your Engineering Org This Quarter

Most engineering orgs added AI but kept the rituals built for a slower era. Here are eleven things to retire this quarter, and what to replace them with.

Read
ai native
2 May 2026 · 12 min read
AI-Native Engineering Cadence: What Replaces Sprints

Most teams added AI to sprint workflows that no longer fit. Here's the new cadence AI-native teams run on: rituals, rhythm, and the metrics that anchor it.

Read
engineering management
22 April 2026 · 14 min read
The Engineering Manager Job Just Split in Two

The Engineering Manager role used to be one job. It is now two, and most orgs have not noticed. Here's the split, the second role, and how to staff it.

Read
5 April 2026 · 10 min read
Block Has a Theory, Most Companies Just Have a Spreadsheet.

Block made an honest case for removing the middle management layer. Most companies copy the conclusion without the work. That gap is where careers get ended.

Read
engineering team structure
4 April 2026 · 11 min read
AI Engineering Team Structure: Smaller Teams Win in 2026

Your AI rollout did not move delivery because your org chart is built for 2020. The fix: smaller teams, senior-weighted, fewer handoffs. Step-by-step inside.

Read
29 March 2026 · 12 min read
Incremental vs. AI Transformation: What CTOs Actually Choose

Most CTOs frame this as a technology decision. It isn't. The choice between incremental AI and full transformation is determined by four business constraints, not technical preference.

Read
27 March 2026 · 7 min read
The Forward Deployed Engineer

Palantir built a role in 2015 that most companies had never heard of. One engineer, full ownership, deployed directly into the client's problem. AI didn't create the role. It made it possible at scale.

Read
25 March 2026 · 6 min read
Anthropic Built a Three-Person Team. They Called It a Harness.

Anthropic's engineering team published a technical deep-dive on multi-agent harness design. What they actually published was an org chart, and it explains exactly why most AI initiatives produce underwhelming results.

Read
24 March 2026 · 6 min read
Your AI Tools Are Working. Your Ownership Model Is Not.

Teams frustrated with AI ROI share a common pattern. The tools are working. The work is getting done faster. The business outcomes have not changed. That is not a tools problem.

Read
ai adoption
21 March 2026 · 8 min read
The AI Adoption J-Curve Repeats at Every Level

Most teams survive one AI productivity dip and call the transformation done. The AI adoption J-curve does not happen once. It happens at every level of maturity, and the teams that know this build differently.

Read
fractional cto
20 March 2026 · 7 min read
Fractional CTO in Singapore: Technology Leadership for Growth-Stage Companies

Singapore's growth-stage companies are well-funded and technically ambitious. The technology leadership gap they face is not about capability in the market. It is about finding the right engagement at the right stage.

Read
claude code
18 March 2026 · 8 min read
Claude Code vs Cursor vs GitHub Copilot: What I Actually Use and Why

Three different tools with three different design philosophies. Here is an honest comparison from someone who has used all three in production, and the framework for deciding which one belongs in your workflow.

Read
ai adoption
17 March 2026 · 11 min read
Healthcare Teams Can't Copy Big Tech's AI Playbook

Healthcare engineering teams face constraints that make the standard AI adoption playbook dangerous. The maturity model still applies, but the sequence and risk tolerance are different.

Read
ai native
16 March 2026 · 8 min read
Context Engineering Is the Skill That Separates AI-Native Engineers from Everyone Else

Prompt engineering is about what you say. Context engineering is about what you build. It is the emerging discipline that determines whether AI tools produce consistent, accurate output or confident-sounding nonsense.

Read
15 March 2026 · 10 min read
How Engineering Teams Win in the Age of Agents

Agents made execution cheap. The bottleneck moved to context and verification. Here's the operating model engineering teams are using to win.

Read
fractional cto
15 March 2026 · 6 min read
Fractional CTO in Malaysia: What Growth Companies Actually Need

Malaysia's growth companies face a specific technology leadership gap: too early for a full-time CTO, too complex for a part-time advisor. Here is what the right engagement looks like and how to evaluate it.

Read
claude code
14 March 2026 · 9 min read
A Practitioner's Daily Workflow with Claude Code

The default way most engineers use Claude Code leaves significant value on the table. Here is the workflow pattern that consistently produces better output with less friction.

Read
agentic engineering
13 March 2026 · 8 min read
The Agentic Coding Workflow: How to Structure Development When AI Does the Work

Agentic coding is not vibe coding with a longer leash. It is a specific way of structuring development work so that AI agents can execute reliably within defined boundaries. Here is what it actually looks like.

Read
product management
13 March 2026 · 1 min read
AI Will Not Kill PM. It Will Expose Fake PM.

When building gets cheap, the bottleneck moves to problem discovery and outcome ownership. The PM who writes tickets gets exposed. The PM who owns the outcome gets stronger.

Read
12 March 2026 · 9 min read
The Next SDLC Is Defined by Terrain, Not Stages

Most engineering teams are running AI on the wrong terrain. The Greenfield, Brownfield, WhiteField framework explains why results disappoint and what to change.

Read
engineering
11 March 2026 · 9 min read
AI Generated Code Broke Your Code Review Process. Here Is How to Fix It.

AI tools increased PR volume by 98% on some teams. Code review processes designed for human-paced output cannot handle that. The bottleneck is now review, not production, and the fix is not reviewing faster.

Read
engineering
9 March 2026 · 8 min read
AI Is Quietly Collapsing the Junior Engineer Pipeline

Entry-level engineering roles have dropped significantly since AI tool adoption accelerated. Most engineering leaders are not paying attention to this. They should be.

Read
engineering leadership
8 March 2026 · 8 min read
How Engineering Leaders Should Evaluate AI Coding Tools

Most AI coding tool evaluations are run by individual developers and optimised for developer experience. That produces a different answer than an evaluation optimised for team outcomes. Here is how to run the right evaluation.

Read
7 March 2026 · 9 min read
AI Didn't Change Software Engineering. It Exposed It.

For 30 years, writing code was the bottleneck in software. AI removed it. Now teams can see which engineers had judgment, and which had execution.

Read
claude code
7 March 2026 · 10 min read
The Four Layers of Claude Code: A Mental Model for Engineering Teams

Claude Code is not just an AI chat window in your terminal. It has a four-layer architecture that determines how it behaves. Understanding it changes how you set it up and what you get out of it.

Read
engineering leadership
6 March 2026 · 7 min read
What Engineering Leadership Actually Means in the Age of AI

AI changed what execution costs. It did not change what leadership requires. But it did change what leadership looks like, and most engineering leaders have not yet made that adjustment.

Read
ai native
4 March 2026 · 12 min read
AI-Native Engineering: The Complete Guide

AI-native engineering is not using AI tools. This guide covers what it means, the four capabilities required, and the L1-L4 maturity model that separates real transformation from tool adoption.

Read
fractional cto
4 March 2026 · 10 min read
What Does a Fractional CTO Do? A Founder's Guide

A fractional CTO is not a part-time CTO. This guide explains what the role covers, when to hire one, and how to avoid an engagement that ends with advice and no real change.

Read
ai maturity model
3 March 2026 · 9 min read
AI Maturity Levels for Engineering Teams: L1 to L4 Explained

Most teams using AI tools are stuck at L2. Here are the four AI maturity levels, how to assess where your team sits, and what the move to L3 actually requires.

Read
ai native
3 March 2026 · 8 min read
The Hidden Cost of Low AI Adoption on Engineering Teams

Teams not using AI tools consistently are not just missing productivity gains. They are accumulating a competitive disadvantage that compounds month by month.

Read
fractional cto
3 March 2026 · 8 min read
Fractional CTO in Southeast Asia: What's Different

Fractional CTOs in Southeast Asia face a different context: a distinct talent market, different AI adoption stage, and a specific advantage most founders miss.

Read
fractional cto
2 March 2026 · 11 min read
Fractional CTO: Most Engagements Are Just Expensive Advice

Most fractional CTO engagements end with a roadmap in a Google Doc. The ones that work install something durable. Here's how to tell the difference.

Read
ai native
1 March 2026 · 11 min read
The Velocity Trap: AI Is Making Teams Faster and More Broken

PRs are up. So are incidents. The 2026 data shows a pattern I've watched play out across engineering teams, and the fix is not what most leaders expect.

Read
ai native
28 February 2026 · 9 min read
Moving an Engineering Team from L2 to L3: A Playbook

L3 AI maturity is achievable in four to twelve weeks. Most teams do not get there because they try to do everything at once. Here is the sequence that works.

Read
fractional cto
28 February 2026 · 8 min read
The First 30 Days With a Fractional CTO: What Should Happen

By day 30, a good fractional CTO engagement produces something tangible, not a strategy document. Here is the week-by-week of what should actually happen.

Read
claude code
27 February 2026 · 9 min read
Why Claude Code Breaks Down on Large Repositories (And How to Fix It)

Claude Code is excellent on small, well-structured codebases. On large repositories, it degrades in specific, predictable ways. Understanding why tells you exactly what to fix.

Read
fractional cto
27 February 2026 · 8 min read
How to Structure a Fractional CTO Engagement

Most fractional CTO engagements fail not because of who you hire but because of how scope is set. Here is how to structure an engagement for real outcomes.

Read
ai native
26 February 2026 · 8 min read
How to Measure AI Adoption ROI on Engineering Teams

Most teams measure AI adoption with velocity and tool licences. Both metrics miss the point. Here are the six metrics that actually show whether AI is working for your team.

Read
build app with ai agents
24 February 2026 · 11 min read
Build App with AI Agents: What Three Days Taught Me

Build app with AI agents and the bottleneck is no longer code. I shipped a production assessment tool in three days. Here's what that actually required.

Read
fractional cto
23 February 2026 · 7 min read
Fractional CTO Pricing: What to Expect in 2026

The fractional CTO market rate ranges from $2,000 to $20,000 per month. Here is what drives the price, what each tier actually buys, and how to evaluate whether you are getting value.

Read
ai native
22 February 2026 · 8 min read
CLAUDE.md: What It Is and Why Your Team Needs One

CLAUDE.md is the single highest-leverage thing an engineering team can do to make AI tools work reliably. Here is what to put in it, what to leave out, and how to keep it alive.

Read
fractional cto
20 February 2026 · 8 min read
Fractional CTO vs Full-Time CTO: How to Decide

The question is not which is better. It is which one matches your current problem. Three criteria that tell you clearly whether to hire fractional or full-time.

Read
ai native
20 February 2026 · 9 min read
Vibe Coding Is Over. Here Is What Comes Next.

Vibe coding was a useful first phase. Generate, accept, ship, repeat. It worked until it didn't. The teams that figured out what comes next are operating in a different gear entirely.

Read
ai native
19 February 2026 · 8 min read
AI-Native vs AI-Assisted: How to Tell the Difference

Three diagnostic tests that reveal whether your engineering team is truly AI-native or just AI-assisted, and why the difference determines what you should do next.

Read
software agency ai disruption
17 February 2026 · 10 min read
Software Agency AI Disruption Is Already Here

Software agency AI disruption is reshaping who wins development work. A solo builder with the right stack out-ships agency teams on most standard projects.

Read
claude code
13 February 2026 · 8 min read
Claude Code Hooks: The Safety Layer Most Engineers Skip

Claude Code Hooks are deterministic callbacks that run before and after every agent action. They are the difference between an AI tool you can trust in production and one that occasionally does something you did not ask for.

Read
engineering team productivity
10 February 2026 · 10 min read
Hiring Engineers Won't Fix Your Delivery Problem

Slow delivery is a systems problem, not a staffing one. Adding engineers to a broken system makes it louder, not faster. Here's what actually fixes it.

Read
claude code
6 February 2026 · 9 min read
Claude Code Skills: The Feature That Changes How Your Team Works

Claude Code Skills are reusable, auto-invoked knowledge packs that make AI tools work consistently across an entire team. Here is how they work and how to build them.

Read
ai agents
3 February 2026 · 11 min read
AI Agents Don't Fail in Dev. Your Repo Does.

AI agents fail in production codebases because the repo isn't built for them. Four layers separate agent-ready codebases from the rest.

Read
engineering management
29 January 2026 · 11 min read
What Engineering Managers Actually Do Now

The EM job was written for a world where engineers were the bottleneck. AI changed that. Most EMs are still optimising for the role that no longer exists.

Read
engineering
24 January 2026 · 10 min read
The Org Chart Didn't Change. The Work Did.

Engineering teams adopted AI into org structures built for slow execution. Coding is no longer the bottleneck. The structure is. Here is where to start.

Read
ai native
21 January 2026 · 10 min read
The Security Debt AI Is Quietly Creating

69% of organisations found security vulnerabilities in AI-generated code. PR volume doubled. Security review capacity did not. The debt is accumulating.

Read
ai strategy
16 January 2026 · 10 min read
Your Board Is Asking the Wrong AI Questions

Every board is asking 'are we using AI?' It's the wrong question. CTOs who win this conversation reframe it: not adoption rate, but what the business can now do.

Read
ai native
13 January 2026 · 10 min read
AI Makes Vague Requirements Expensive

AI requirements planning doesn't fix vague specs, it accelerates them. Teams now build the wrong thing faster, with more confidence, at a higher cost to undo.

Read
ai native
7 January 2026 · 11 min read
DeepSeek Lowered the Cost. Not the Problem.

DeepSeek R1 made AI dramatically cheaper for engineering teams. Most leaders took the wrong lesson. Cost was never the bottleneck. Here is what actually is.

Read
offshore engineering
15 December 2025 · 11 min read
Replacing an Offshore Engineering Team Without Killing Velocity

The cost-arbitrage era of offshoring is ending. AI changes the math. Here's how to transition from a large offshore team to a smaller, faster onshore one.

Read