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Struck in the Middle #39: Three Positions of Leadership
Most corporate leadership isn’t leadership. It’s positional authority wearing a leadership costume. There’s a notion of tech leadership as a grand pursuit where people knowingly follow you. In reality, most leadership in corporations is positional. You are set up in hierarchies where your “leader” is merely the person you’ve been assigned to and need to follow. I’m going to postulate

Stuck in the Middle #38: What Should We Do With Our Brains?
Brain science, as it usually shows up in coaching, is a random mix of neurological studies, pop science, magical thinking, and irreproducible psychology nonsense. And while there is science behind it, the application is usually nothing more than self-help with fancy jargon. One of the most common versions of this is the notion that you can rewire your brain. If

Stuck in the Middle #37: Stay in Character
You’ve tried to get AI to push back on your ideas. It works for a while, then it folds, and you’re frustrated. But what if it’s doing exactly what you’ve been training your team to do? Most people have noticed the sycophantic behavior of AI like ChatGPT, Claude, and Gemini. Every idea you have is amazing; every suggestion you make

Stuck in the Middle #36: Giving Feedback Up Without Killing Your Career
When you have become a director or VP at a tech company, you have probably realized a few things. This guide will give you a framework for understanding how (and when) to give feedback to your boss. It should be noted that there is more to managing up than giving your boss feedback; this is just one critical aspect. In

Stuck in the Middle #35: Against “A Players”
After we completed the interviews, I was convinced that the new PM we were about to hire was an “A Player”; he had all the traits we were looking for. And so 6 months later, when things weren’t going well, I was shocked. Was I wrong during the hiring process? Did he not really have the skills we needed? Maybe