Writing on leadership

How to Talk to Your Board About Technical Debt

The conversation always fails because CTOs speak architecture and boards hear cost. Here's the translation — and why you should never say "debt" in a board meeting.

Coding was never the real work

The review you're tempted to skip — because the AI built it and it looks right — is not a check. It's a teaching moment you are quietly handing to no one.

Be a gardener, not a mechanic

Engineers are trained to find root causes and fix things. That instinct will work against you when the thing in front of you is a person.

Then Why Am I Paying You?

My CEO thanked me. I said the team did it all. He said: then why am I paying you? On the brag log every senior leader needs — and why deflection isn't humility.

Your First 90 Days as CTO: What to Ignore, What to Fix, What to Watch

The first 90 days are not about fixing things. They're about understanding what you've walked into — and not destroying what was working while you do it.

What Training For An Ironman Taught Me About Coaching CTOs

An Ironman taught me what good mentoring actually delivers — cognitive quiet, not heroic effort. The senior move is hiring help before the wheels come off.

They Think You're Smart. They Just Don't Think You Get Business.

They know exactly how smart you are. What they don't believe is that you get business. Here's what that costs you — and how to change it.

Why Are You Asking Me This Now?

The question isn't rewrite or iterate. It's why you're asking right now — and the timing tells you almost everything.

If the CEO Isn't in the Room, You Don't Have a Roadmap

A roadmap is not a delivery plan. It's a negotiation. And like all negotiations, it only works if the right people are in the room.

Executive Presence on a Screen

Your board is in three countries. Your team is distributed. The investor deck goes on Zoom. The fundamentals of compelling communication don't change — but the mechanics do.

Using Visual Aids Effectively in Presentations

Visual aids are an essential component of effective presentations, providing a means to support and enhance the verbal message.

The Narrative That Moves a Room

The mechanics of storytelling are the same whether you're on a TED stage or explaining a roadmap decision to a non-technical board. Here's what actually works.

When the Room Goes Quiet and Everyone Looks at You

Board meetings, investor calls, all-hands after a hard quarter — executive presentations have real stakes. Nervousness isn't the problem. What you do with it is.

PowerPoint Isn't Bad for Business. It's Just That You Don't Know How to Use It.

Every CTO has to present to a non-technical board. The tool matters far less than people claim. Here's what the evidence actually says.