Tech Leadership Right Now: Experimentation, Not Answers

We’re in a genuinely different moment. The pace of change means that what works today might not work in a couple of months. Let alone what worked so far in your career. This isn’t the usual “things are changing” platitude. Things are actually shifting substantially. What should you do as a tech leader? Stop Trusting […]

Tech Capital Renaissance

For several years, I’ve been advocating for engineering teams to stop obsessing over tech debt and start looking for ways to increase tech capital. Those who have done so saw the dramatic impact it had on organizations. And lately, we’ve finally seen what this approach can really provide. Are you sitting on your hands? What […]

Personal Progress: Don’t Weigh Down Your Team

Working on my CTO Assessment (more on that below), I’ve been talking with many tech leaders. Having them go through it, many mention skills where they have large gaps, that they say are critical, yet haven’t really worked on. What do you expect to happen? You must know by now that problems aren’t likely to […]

Your Team Structure Is a Constraint

Many CTOs treat velocity as an execution problem. Hire better, process better, align better. But they actually have a shape problem. A significant portion of your friction isn’t caused by what your team does. It’s baked into who they are and how they’re arranged. You can’t fix your way out of inherent structure friction by […]

Change Management in Tech Organizations

Effectively driving change is a core skill for any leader, and that can set you apart from the rest. Each change is another step towards a better team. Just as your team iterates on the product, so should you iterate to drive growth. To do it easily, let’s go over the Change Algorithm. The Algorithm […]

Soft-Skill Upgrades for Tech Leaders

We obsess over optimizing our tech stack and tools while ignoring the operator who runs it all. The result? An illusion of progress that tries to cover for a weak foundation. Self-improvement for tech leaders has massive compounding effects, both personally and across the entire org. Can you upgrade yourself? While a coach accelerates progress, […]

Making Engineers Autonomous

I have to say that I often chuckle to myself when I see people write so much about autonomous agents writing code. So many leaders are barely able to delegate and trust their senior engineers; am I supposed to believe they’ll be fine with LLMs doing it? Let’s talk about making teams more autonomous, so […]

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. […]