Engineering Leadership
Building and running engineering organizations: hiring, scaling, culture, and the judgment calls that come with the CTO seat. 27 essays, from 25 years at the seam between the boardroom and the codebase. This is the thinking behind fractional CTO engagements.
How to Run Recovery Days Without Building a New Treadmill
Extra days off after heavy weeks work right up until people start chasing them. How I decide who gets one, and the rules that stop the policy from burning out the people it's meant to protect. Part 3 of 3.
Read →Why I Give Developers 3 to 4 Extra Days Off a Month
When a team delivers months of work in a single month, I give them extra days off, usually three or four. Yes, that's almost a full work week. The employer still comes out way ahead. Part 2 of 3.
Read →The Human Context Window Is Your New Bottleneck
AI lets one developer carry three to six tasks a day. The agents never get tired. The person holding all of those threads does, and it shows up in their mood long before it shows up in the output. Part 1 of 3.
Read →Do You Really Need a Chief AI Officer?
Probably not a full-time one. You almost certainly need the seat filled, which is a different question and a much cheaper answer.
Read →How to Hire AI-Native Engineers: Screen for Judgment
The profile of a great engineer has changed. What to look for now: taste, skepticism toward plausible output, and leverage with AI agents.
Read →A Turnaround CTO for Portfolio Companies Is a Different Job
PE-backed companies don't need a caretaker interim. They need someone who will take cost out aggressively, rebuild the work around AI, and answer to the thesis while doing it.
Read →How to Choose a Turnaround CTO Provider
Staffing firms, consultancies, solo operators. What each one actually delivers when a portfolio company needs costs cut and delivery rebuilt, and the questions that expose the difference.
Read →Is the Leetcode Interview Dead? What to Use Instead
Algorithm puzzles test exactly the work AI now does for free. Here's what a technical interview should measure instead, and what mine looks like.
Read →Do I Need a Fractional CTO? Seven Signs You Do
Patterns I see over and over in founder conversations. Recognize yourself in two or more and it's worth a call.
Read →Is the Resume Dead? What to Screen For in the AI Era
AI writes flawless resumes now. Every signal hiring used to lean on is gone, and most interview processes are still screening like it's 2019.
Read →When a Portfolio Company Loses Its CTO
The resignation lands on a Friday. Here's the operating partner's playbook for the first 48 hours, the month after, and the mistakes that turn a gap into a crater.
Read →The Economics of One CTO Across a Portfolio
Why funds that keep a single trusted turnaround CTO on call outperform the ones that source fresh every time a company runs hot. The math, and the part the math misses.
Read →Why Technical Skill No Longer Decides Who to Hire
For thirty years we hired engineers for what they could type. AI ended that. What actually predicts performance now is harder to test, and worth more.
Read →How Big Should an Engineering Team Be? Four Beats Twelve
AI changed the math of team size. Why the right hire count is smaller than your plan says, and what that does to roles, budgets, and recruiting.
Read →How Engineering Leaders Create Their Own Luck: 9 Habits
The luckiest people I've worked with weren't lucky. They built a surface area for luck to land on, then put in the work that made it stick.
Read →What Is Go Fever? How Groupthink Ships the Wrong Product
Go Fever and groupthink don't just ship broken products. They ship the wrong ones: the feature the room fell in love with and the user never asked for, defended past every signal that it didn't fit.
Read →How to Grow Engineering Leaders, Not Just Headcount
Scaling a team by hiring more bodies buys you headcount, not leverage. The durable move is to build leaders and make yourself replaceable.
Read →How to Lead an Engineering Team Remotely Across Time Zones
Remote technology leadership isn't a downgrade of the in-person version. Done deliberately, distance forces the clarity that good organizations need anyway.
Read →Who Should Own Engineering, Ops, Support, and Data? One Leader
Splitting dev, platform ops, support, and data into separate fiefdoms feels organized. It manufactures the worst failures. Single ownership fixes that.
Read →How to Fix Bad Company Data: Dashboards People Actually Trust
Most companies don't have a data problem. They have a trust problem. Turning scattered, untrusted data into visibility people act on is platform work, not a dashboard.
Read →How to Manage People in a High-Growth Company
In high growth the org chart, the product, and the headcount all move at once. Managing people through that is a different job than steady state.
Read →How to Run Internal and Outsourced Engineering as One Team
Internal product teams and external developers can ship as one accountable unit, or fail at the seam. The difference is who owns delivery.
Read →How to Build a Multi-Year Tech Roadmap That Survives Reality
A three-year roadmap that locks every quarter is fiction. One with no direction is chaos. The job is building the version that holds a line while reality keeps moving it.
Read →How to Scale a SaaS Engineering Team Without Breaking It
Scaling a SaaS org breaks more from added process than added people. The job is to grow capacity without grinding down the trust and speed that got you here.
Read →What Kind of CTO Do You Need? A Guide by Company Stage
The CTO who takes you from zero to one is rarely the one who scales you to a hundred. A field guide to matching the leader to the moment.
Read →What Is Operator Experience? The UX Nobody Designs For
Everyone talks about user experience. Almost nobody designs for the operator, and that is the experience that decides whether a software business can actually afford to grow.
Read →On-Prem to Cloud Migration With Under an Hour of Downtime
Big-bang migrations fail loudly. Here's the incremental, reversible approach I use to move legacy systems to the cloud while the business keeps running.
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