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 […]
Several years ago, I refuted common thinking and made the case for preferring product engineers over principal engineers. As someone who was almost always capable of coding circles around anyone else in the room, I realized that what genuinely mattered was the ability to do the right thing for the business, not just be busy […]
The tech industry glorifies speed. Yet moving fast all the time will inevitably result in more damage than good. Some decisions, especially in tech, can be reversed easily. Others will haunt you for years. The real dangers aren’t in picking the wrong framework but in the structural decisions—people, teams, offerings—that create organizational drag. The Long […]
“No one ever quit!” “Look at our hackathon!” “We hard-allocate time to fight tech debt.” Ostensibly, good things. In reality? Just the advice to follow… if you want to lead a mediocre team. You’re often tempted to follow the “common” playbook as a tech leader. But what if that playbook is the very thing holding […]
I saw a few startups making plans for the new year ahead and allocating significant chunks of their time to tackling “tech debt” or “keeping the lights on.” Some resources claim that 50% of startups spend more than 40% of their time on this, while only the top 10% have this down to a whopping […]