Stop Caring So Much About Your People

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 […]

Dumbest Default: Functional Teams

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 […]

Squeeze Failures Dry

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, […]

Business Thinking for Tech Executives

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, […]

Conveying Competency

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 […]

Gardening Organizations

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 […]

Foolproofing Teams

Caution isn’t excellence; it’s drag. Retros won’t fix fear. Cut risk at the source, and your team stops tiptoeing and starts sprinting. I’m going to assume your team is holding regular retrospectives to learn from mistakes and successes. One major source of potential improvement that often goes unnoticed is recognizing fear and combating it. The […]

Exploiting Mistakes

We’re all human, and to err is human. I can guarantee that you and your team will be making heaps of mistakes. However, I cannot say how much you’ll learn from them. Are you letting all those learning opportunities go to waste? A World of Difference Between the teams that utilize their errors and those […]

Learning to Learn

Knowledge and expertise are similar to capital. If you don’t make deposits regularly, you’ll miss out on most gains. Your team—and you—should be learning regularly, not just once a year during a “hackathon” or when things are on fire and demand learning rapidly. Let’s learn how the best teams learn. Learning Disorder Being able to […]

Hype Escaping Velocity

As tech leaders, we’re destined to always be in some sort of limbo when it comes to adopting new technologies and combating the hype cycle. You might as well learn how to manage this battle well. You cannot over-hype; that’s like consuming heaps of empty calories. Similarly, avoiding all novelty entirely will lead to innovation […]