First-Principles Debugging for Leaders

Problems crop up all the time. That’s a rule of nature. The question is how we address them. Many leaders get tunnel vision and rush to get the thing sorted out. Sometimes, that’s a surefire way to keep seeing that problem repeat itself. I’ve found that we can uncover a lot of issues so much […]

180 Observations and Thoughts from 180 Days in Rome

It’s been six months since we moved to Italy. I’ve been collecting different thoughts and thought I’d share some of them. Disclaimer: This is what we’re seeing in our nice neighborhood in Rome. Our private experiences. YMMV. Italian kisses-on-the-cheeks have a specific order Kids tend to eat lots of sweets in their food boxes for […]

CEO-CTO Therapy (Part 2): Measuring Engineering

This time, we’re continuing this series about improving the relationship and alignment between the CEO and the tech executive. You don’t have to feel like you have nothing to show, that your value isn’t understood, or that you don’t know what to do. As a tech leader, you can bring more clarity to the situation. […]

OKRs for Tech Teams: Doesn’t Have to Suck

It’s that time of the year when we start seeing people lamenting their objectives and planning processes. Were you handed OKRs that you don’t really understand? Objectives you plainly don’t believe in and know will be changed by the time you’re back from the New Year’s vacation? You’re not alone, and it doesn’t have to […]

10 Observations from 2025 for Eng Leaders

Every end of the year, I sit down to do some personal reviews, as well as collect my notes. Since I have hundreds of meetings with founders and tech leaders worldwide every year, looking at it all from a higher altitude helps me notice themes and trends. This year, I decided to share those that […]

The CTO Scrooge

Let’s exploit the fact that this weekly article goes out on Christmas for a light read. Did you allow yourself to become a grumpy tech leader? Without planning it, you’ve ended up in a position where you’re actually not really having fun? Let’s quickly see how it happens to many good people. One of the […]

CEO-CTO Therapy (Part 1): Communication

Working with tech executives, one thing becomes obvious very quickly: the CEO relationship is the most important one you have, second only to Product. And yet, it’s often fragile, strained, or quietly dysfunctional. Even among co‑founders. It doesn’t have to be that way. This is a problem I’ve dealt with repeatedly in client work. Not […]

Deliberately Shaping Engineering Organizations

Your team’s running along and getting work done. You’re busy supporting all of that, which is great. But don’t lose sight of the longer-term leadership work of shaping the org, or you’ll waste the current momentum. Leaders obsess over product roadmaps but treat their future org chart like weather: we’ll look out the window in […]

The Shallow Leadership Crisis: Practical Steps to Lead With Depth

Most leaders I meet are shallow. Not because they lack care. They’re shallow because they’ve stopped treating their role with the same urgency, curiosity, and responsibility they had as engineers. As ICs, they were obsessed with mastering their craft: learning, experimenting, improving. As leaders, far too many settle for “keeping things afloat.” A new year […]

Leadership Stances: Are You a No-Op Leader?

Working with many tech leaders, I’ve come to realize that while each one of you is a unique and special snowflake, if you squint, you can notice certain archetypes of behavior. One of the most critical aspects of that categorization is your stance: how you comport yourself with the CEO and the executive team. I’ve […]