I am not a very organized person, and 1-1s with strict requirements for to-do lists don’t resonate with me. I’m happy to adopt these requirements if my reports want them, but I prefer a more fluid style. My goal in a 1-1 is first to listen to anything my direct reports want to discuss. I want the meeting to be driven by them, and I want to give them space to bring up whatever they feel is important. I view a 1-1 session as much as a creative discussion as a planning meeting. The downfall of the rambling 1-1 is that, if it’s left unchecked, it can turn into a complaining session or therapy. Empathetic leaders can sometimes allow themselves to get sucked into an unhealthy closeness with their direct reports. If you start focusing a lot of energy on hearing reports’ complaints and commiserating, you’re quite possibly making the problem worse. You don’t have to have a to-do list, but problems in the workplace need to be either dealt with or put aside by mutual agreement. There is very little value to repeatedly focusing on drama.