Like the author, I have had some ongoing 1:1s be incredibly productive. Like really changing my life. Unlike the author, I wouldn’t broadly recommend them. They’re so easy to do in a way that isn’t productive. I think that’s the default, really. So if I was going to tell people to do them I’d be very explicit that you need to do something different than you probably think. Here are exacts steps and characteristics, if you don’t follow these then it won’t work and don’t come to me about it.
The overall general trend of why they’re not effective is they’re too surface level. You say some updates to your boss in a way that doesn’t get you fired, maybe complain about some stuff. You kinda just talk about things.
It needs to be a time when there is some work really happening. It’s metawork, but it’s still work. Like “what were the things that distracted you last week?” and you write them down, there in the meeting. Not “anything distracting you lately?” “nope I’m fine”. It’s a much more vulnerable, interactive process. This is probably why a 1:1 with your boss isn’t the most effective person. Too much image to maintain.
I think the sports model is better. In baseball, the Manager (coach or head coach in other sports) makes decisions about who is playing. Coaches (aka assistant coaches or trainers) are skill experts who help you get better. You can be more vulnerable with them. I think some industries, especially software, would do well to have more of a manager/coach model.