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 […]
Do you know how “one size fits all” really means it fits no one well? The same occurs when we try to lead everyone in the team the same way. Making the adjustments—from either side—will help ensure your efforts pay off and your team takes off. Here are the most common tweaks I’ve found helpful […]
If not me, who? That quote from two millennia ago still holds true for anyone who wants to keep growing regardless of the organization around them not being perfect or their boss being a lousy coach. Especially as you get more senior leadership roles, the onus is on you. Here’s how you can start taking […]