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 […]
The mistake about mistakes? Everyone says they learn from mistakes, but don’t. The truth: leaders don’t have time to actually reflect. They just move to the next quarter, sprint, or fire. It’s not the catastrophic failures that hold us back—it’s the unexamined small ones. Stop failing on repeat. Leadership Autopilot We’re usually rewarded for momentum, […]
Many of us geeks need glasses—I know I do—but that’s not an excuse to let yourself be myopic also in your attitude. If all you do is manage the tech people, you’re not an executive—you’re a glorified team lead with a bigger paycheck. Like it or not, you’re part of a grander business. Your organization, […]
One of the recurring patterns I see in my work with CTOs and VPEs is the creeping tension between them and their CEOs. It’s natural: CEOs are wired to be antsy about performance, and in tech organizations that tension often centers around the performance of the tech leadership team. When there’s no technical co-founder around […]
Mindful and deliberate actions for leading your team and encouraging the desired growth are crucial. Left to their own devices, organizations tend to lose focus, become entangled in unnecessary complexities, and slow down. Yet when I ask leaders about their current gardening or coaching priorities, many respond with blank stares. Let’s fix that. In this […]