Sarcasm and vitriol wrapped in a twee bow.
Close Enough to Influence, Independent Enough to Be Honest Recently, four people I mentor brought me different versions of the same problem in the span of a few days. One CTO was dealing with a founder-developer who still had strong opinions about how software should be built. Another had an operator CEO who was hands-off Continue reading "Working with the CEO"
What Your Organization Sees When You Go Quiet A few weeks ago, I was talking with Pawe?, someone I’ve been mentoring as he works toward a director role. He’s doing a lot of things right: growing his scope, delegating more, building roadmaps. But in the middle of the conversation, he surfaced a dynamic I recognized Continue reading "Don’t Let Your Boss Do Your Job"
Most leaders develop systems thinking by accident. Here’s how to build it on purpose. I emphasize learning systems thinking, but I haven’t explained how to build the skill. I often highlight its importance, yet I rarely give people actionable steps to develop it. My systems thinking is intuitive now, and most senior leaders I know Continue reading "Every Organization Is a System. Are You Designing…
Why the leap from Director to CTO is really three distinct shifts, and how to start making them before you have the title If you want to move from Director to CTO, the real secret is this: you don’t make one giant leap. You make three distinct shifts: to your focus, your horizon, and your Continue reading "The Director to CTO Path: How to Follow It, or How to Mentor It"
Why being understood matters more than being right When I was starting out at Microsoft, I nearly derailed my first executive presentation over the word “avatar.” We were building virtual world software, and I used “avatar” the way the industry did. The VP stopped me, insisting it wasn’t the right term based on its dictionary Continue reading "Talking to Executives: That s Not a Derailment, That s…
From managing work to managing context One of the most abrupt transitions in a leadership career is the moment you stop managing a team and start managing managers. It rarely happens gradually. One day, you lead a small group and their output. The next, you oversee an organization whose work you can’t directly touch. You Continue reading "The Shift to Managing Managers"
What happens when your role outgrows your technical background One of the guarantees of career progression in technology leadership is that, eventually, you will outrun your own resume. Most technology leaders start as specialists. Frontend, backend, SRE, QA, mobile, data. Your first leadership role is often managing a team you used to be on, doing Continue reading "Leading What You’ve Never Done…
At the start of every year, leaders are encouraged to look back and look forward. Most of us nod along, then immediately get pulled back into execution. Meetings stack up, priorities collide, and the reflection part quietly disappears. That’s a mistake. Reflection isn’t something you do when you have spare time. It’s what keeps you Continue reading "Reflection is a Crucial Leadership Skill"
Process is one of those topics that reliably creates tension in growing engineering organizations. Too little of it and everything feels chaotic. Too much of it and nothing moves. Most teams I work with aren’t confused about whether process matters. They’re struggling with when to add it, how much to add, and how to tell Continue reading "Process Is a Tool, Not a Virtue"
What tech debt actually tells you about your team and your system Tech debt comes up constantly: in mentoring conversations, consulting work, conference Q A, and inside my own teams. I’m always a little surprised by how often it’s treated as a moral failure rather than what it usually is: a set of trade-offs made under Continue reading "Tech Debt Is a Signal, Not a Sin"