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 the team. I thought I was buying loyalty. I was actually setting a price. Here’s what […]
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 said “it just wasn’t right.” That was the whole answer. He couldn’t tell me what broke. He could only […]
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 years in the C-suite, I’ve learned the truth: investing in developing your own people almost always pays greater dividends in the […]
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 career for you. Here’s how to catch them. I once watched a brilliant VP turn down a promotion. Not because the role was wrong. Because a […]
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 reading these? No. Nobody is. Recruiters use AI to find candidates in 2026. If AI can’t find you, you […]
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 two kids. And the whole time, his phone owned him. Work, from the look of it. […]
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 anyone that way anymore. I used to lead the work. Now I lead the person. Early on, every conversation with my team was […]
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 kind of people.” My answer surprised him. Sometimes it takes money. But most of the time? It takes a shot at glory. […]
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 positioning that didn’t make her wince when she said it out loud. Fractional COO for early stage healthtech. We […]
“I just know I’m in the wrong place.”
“I know I’m in the wrong place.” This feeling resonates in many careers, where the gap between knowing and doing leads to despair. The more time we invest in a job, the harder it becomes to leave, even if it no longer fits. The real question is: what is staying costing you? If you feel stuck, consider reassessing your environment and seek what truly fulfills you. Let’s explore this together!