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 […]
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 […]
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 […]
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 […]
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 […]
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 […]
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 […]
Complexity is lazy. Engineers do it first: they spin up a dozen microservices on day three of a startup, feel brilliant for designing something “future-proof,” and then spend the next two years maintaining a distributed Rube Goldberg machine. Leaders fall for the same trap. It’s shockingly easy to grind a company to a halt not […]
Everyone talks about how “change is hard” in software. We dread migrations, refactors, and rewrites. But let’s be honest: software is built to change. That’s literally in the name. What’s brittle isn’t the code, it’s the people and the structures around it. If your team can’t change direction without six meetings, your bottleneck isn’t technical. […]
Many senior leaders view themselves as “realists.” But this so-called realism is often just cynicism in a suit. Being optimistic doesn’t mean being naive. It’s a strategic advantage for those aiming above the obvious. It’s the hidden skill no one teaches executives. The Comfort of Cynicism Let’s admit the truth. For many, the cynical take […]