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 […]
They were supposed to bring wisdom and experience. Instead they weigh down the org and drag down your velocity. Rather than allowing a startup’s main advantage to thrive and create an environment that basks in nimbleness, agility, and simplicity, they try to age it overnight. Senior engineers who come from mature startups or big tech […]
Yeah, I said it. Stop caring so much about your people. Not stop caring. Stop over-caring. Stop acting like your team’s happiness is the company’s primary KPI. Because it’s not. You’ve been told for years that “people are your most important asset.” True. But lately, leaders are twisting that into something absurd: You’re optimizing for […]
If you’re still organizing your teams by frontend and backend in 2025, you’re doing it wrong. The fact that this even needs to be said is wild to me. How teams should be organized feels like one of those questions we, as an industry, should have solved by now. Everyone “knows” that end-to-end, cross-functional teams […]