I had an interesting conversation once with a friend, another CTO who has a lot of management experience. He sheepishly admitted to me that he didn’t like doing regular 1-1s because he himself had always resented being forced to do 1-1s with managers that he felt he didn’t need. “Regular 1-1s are like going to a psychiatrist when you’re fine and discovering you have depression.” I bow to his experience. It is absolutely true that every person and team is different: they need different things, have different communication styles, and focus on different things. That being said, if you’re not a CTO with years and years of management experience, you should probably start by assuming that you need to do regularly scheduled 1-1s.