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Don’t Reward Too Early

Years ago, as a CIO, I hired an engineer who wowed everyone in the interviews. In week three, I gave him a spot bonus. Just for showing up strong. Six months later, he was the least engaged person on...

Starting Over Is Not a Strategy

I once had a senior engineer rewrite the same integration four times in three weeks. Each version looked cleaner than the last. None of them worked. When I asked what was wrong with version three, he...

The Hidden ROI of Developing Your Own Rock Stars

I used to chase rock stars. The polished resume, the proven track record, the person who could walk in and deliver immediately. On paper, it always looked like the smarter, faster move. But after...

Your Blindspot

TL;DR: Most of your decisions aren’t decisions. They’re old code running in the background. Subroutines you installed years ago, still executing today. Until you see them, they decide your...

The Skill of Reinventing Yourself

The email lands on a Tuesday. Your role has been eliminated. So you do what everyone does. You polish the resume. You send it out fifty times. Then a hundred. Nothing comes back. Is anyone even...

Retirement might never come for you

I was out for dinner last week. Nothing special, just a local place I like. A few tables over sat a guy, maybe mid-forties, the polished kind you see in IT leadership. He was there with his wife and...

It’s about the person.

When I started out, I thought leadership was a checklist. Skills. Commitments. Accountability. Outcomes. I ran my teams like a system diagram, all boxes and arrows. Twenty years in, I barely lead...

Nobody starts out great.

One of my business partners asked me a question a couple weeks back that stuck with me. “What does it actually take to hire the rockstars everybody brags about? The Spotify, Netflix, Anthropic...

Let the ink dry.

Three months in. Two solid clients. A real pipeline. And she wanted to scrap the whole thing. I was working with a former Fortune 100 VP last fall. Smart. Senior. She had finally landed on a...