At a certain point in junior high, I realized not everyone in class had to squint to see the blackboard. That’s when I asked my parents to get my eyes checked. I still remember the first time I stepped onto the street from the eyeglasses store. All of a sudden, trees weren’t just general green […]
Many ambitious eng leaders blame org charts and politics for their limited impact. It’s comforting to think that a lack of authority or a rigid hierarchy is the only thing keeping you from greater things. But far more often, the real barrier isn’t the organization. It’s the title on your business card, and how you […]
Nothing torpedoes a startup faster than a room full of geniuses sprinting in random directions. It really could be problematic for startups to have too many 10x (or highly skilled) engineers. That’s because having a power tool can really speed up your work, but can also be extremely dangerous in the hands of someone who […]
You’re not just watching the dance. You’re on the floor, stepping on toes. The question is: Are you willing to admit it? Spend five minutes with an exec team, and odds are you’ll hear some version of: “Our middle management layer isn’t strong enough.” “They don’t think like owners.” “They’re not proactive.” Sure. That might […]
I was very lucky to work with extremely bright and talented people over the last couple of decades. People who don’t shy away from a challenge. Those who find clever solutions. Who work extremely fast. Then came a point in my career where I realized that it can act as a double-edged sword, harming the […]
Tech debt burns money; feedback debt burns culture. When a codebase rots, you can demonstrate the expected ROI numbers, make the case to Product, and ship a fix. Every conversation you postpone, however, silently hardwires suboptimal behavior and erodes trust in ways no spreadsheet can capture. The longer you wait, the more each shortcut feels […]
You have so many things on your plate. There’s probably always something you know you’re not getting to. Some tech execs I see put out fires so often, I tease them with the Fireman Sam theme song. You might be even good at all those things. Yet that’s not doing leadership work, that’s just being […]
One of the clearest patterns I see in my work with senior tech leaders is this:The great ones are always upgrading. They’re not stuck. They’re not stagnant.They’re learning how to operate at new scales, adapt to evolving team structures, leverage AI, and stay relevant in companies that are evolving fast. If you think your role […]
You don’t run out of time.You run out of excuses. By the time you’ve explained why something still isn’t working for the fifth time, your team’s stopped listening. And maybe you should too. The Excuse Machine There are always perfectly logical, valid reasons why things are hard. Why your org isn’t moving faster. Why you […]
I’d wager that the title of this article seems odd. After all, we usually talk a lot about gaining momentum, not fighting it. In the rat race to get those flywheels going, who wants to have them stop, right? (Has anyone ever seen an actual flywheel?) Yet, when you need to evolve as a leader, […]