Look Over My Shoulder

Closing the gap between good and extraordinary.

As I mentioned recently, I used to think AI was basically Wordle. Now I think it’s the biggest technological shift since the adoption of the internet, and I’m grateful to be working with it professionally at this moment in time.

My team is piloting Claude Code for our client’s enterprise. Most of us have played with coding agents on personal projects, but no one has used one inside of a real team environment, with established conventions, shared pipelines, and other people’s code to consider. A few weeks in, our technical principal asked for a pulse check, which led him to schedule a “Clawd Mawb” to look over each other’s shoulders and watch how everyone is actually using the tool.

Our team is small and pairs frequently, but I’ve noticed cliques or at least strong preferences for who works together. It could be because of style, hours, location, or whatever, but we don’t circulate knowledge as well as we could. Some people have joined, dug in, and made it obvious internally and externally that they are genuinely exceptional. I’m afraid they are lionized, breeding disengagement and driving a wedge in the team.

I personally think it’s easy to be intimidated by someone who is so clearly brilliant that it feels impossible to ever be as good as them. As a business analyst, I can look at someone like Terri or Smitha or Karen or Kate and quietly decide that they are simply in a different category than me. That the gap is a feature of the landscape rather than something that moves.

Two of those women have devoted irrational amounts of time pouring into me, and it has shown me that the gap moves. I’ve been able to watch over their shoulders and see what good actually looks like. Proximity to people who let me watch them work has been the most valuable thing in my career.

I grew up in an area where that kind of proximity was available in a different form. Recently I caught up with my two closest friends from high school (a dentist and a successful startup founder), and one of them asked what the most enduring thing we learned there was. I answered before I’d thought it through.

It wasn’t anything from a classroom. It was being around people who showed me what was possible. Growing up, I could see who doctors, lawyers, architects, and engineers were up close. They weren’t categorically different people or even genuinely exceptional; they were human. If I was curious enough, I could ask a classmate’s parent to grab coffee, and they’d usually say yes…and pay!

Conventional wisdom says to find a mentor. Yes and! I’d add to find as many people as possible who will let you look over their shoulder.

My kids (thankfully!) aren’t old enough to think about careers yet, but I know that’s coming faster than it feels. I want to be someone their friends think to call when they’re starting to wonder what’s possible. Similarly, I want to keep finding people who are further along in their stories, pulling up a chair, and paying close attention.

The Clawd Mawb is a start, but it needs to molt into something bigger.