When something breaks or shifts in the org, most leaders reflexively rush to regain balance, to restore things to how they were. But what if that’s the wrong move? What’s the rush? In chess, experts learn to maintain the tension. Just because there’s a threat on the board or a possible trade, it doesn’t mean […]
Most leaders don’t really know what they’re doing. They wing it. They handle most issues on a case-by-case basis. Even those who have gained experience seem to operate based on muscle memory, as opposed to having given things some extra thought. While your instincts might be enough to achieve ok results, this approach rarely supplies […]
Your team didn’t mess up. You didn’t ship a bug. You didn’t blow the budget. You didn’t miss a deadline. You just missed the wave. While others were pivoting, launching, or riding the momentum—you were still “prioritizing” or “waiting for clarity.” And it’s the most dangerous kind of failure: the kind no one notices until […]
Your engineering team is likely obsessing over DevEx, sprint efficiency, and engineering velocity—at least, you’d better hope they are. But here’s the harsh truth: focusing exclusively on engineering velocity means missing out on potentially 10x the impact elsewhere in your company. It’s not just about speeding up your developers; it’s about spreading internal superpowers everywhere. […]
Here’s a little secret: your CEO doesn’t want to call all the shots. What they really want is a leadership team that can run most of the company without them. People who spot problems, propose solutions, and take charge. But what do most executives do?They wait.They “align.”They play the role of middle-manager-on-steroids: more meetings, more […]
Teams don’t fail because they’re lazy or incompetent. They fail because no one actually defined what success looks like. I’ve seen it too often: a CTO frustrated that their team isn’t improving, yet swearing they’re “doing all the right things.” A manager giving an underperformer “one last chance”—solely within their own head—without ever stating what […]
Your second startup is just as likely to fail as your first—only in dumber, more frustrating ways. You think you’ve learned. You think you’re smarter this time. And that’s exactly why you’re about to overcorrect yourself into oblivion. Almost twenty years ago, I first read The Mythical Man-Month, and learned about the concept of the […]
You think you’re leading, but are you just leaning? Too many tech executives rely on crutches—rigid processes, feel-good metrics, office presence—to prop up their leadership. These habits make you feel in control but actually hold you back. Real leaders don’t hide behind structure or autopilot decisions—they make the hard calls, shape their organizations, and drive […]
Congrats! You’ve worked so hard to get your team running, only to find out you’ve embedded mediocrity as a cultural tenet. When we don’t get enough external criticism, it’s easy to lose sight of the slow deterioration in a team’s robustness. Let’s help you learn from a bunch of real-world examples I’ve seen over the […]
Every CTO wants to believe they are steering their company in the right direction. However, in the pursuit of success, many fall into self-deception, repeating comfortable lies that sound logical but ultimately undermine their leadership and their teams. These lies come in different flavors—some are internal justifications, others are strategic misalignments. The problem? They feel […]