Hi Mozar! Good for you on trying to go in with a plan! I have these kinds of meetings with my employees and I vastly prefer that the associate drive the conversation so it's clear that they're engaged.
I am a lead in a large IT organization, so my perspective is surely influenced by that. I generally do project-based work with multiples teams, and I have a handful of people who report to me but I'm not a manager.
So my suggestions given my limited experience:
Think about what you would like to get out of this one on one time, and if possible try to communicate that directly to your manager. Ask if your goals are in alignment, or if he has something different in mind (in addition to, or instead of what you were thinking.) Show respect for his time by sending an agenda ahead of each session if possible.
Here are a few examples of my recent agenda items with my manager:
- expectations: what I see as my top 3 priorities right now, is her view the same, discuss any differences
- process improvements I'm piloting with my team/ outcomes
- project roadblocks, risks, and things to get ahead of. Sometimes it's an FYI so she knows what I'm managing, and sometimes it's so I can ask her to step in.
- people: this is generally a run down of my direct reports, who is working on what skills, who may be ready for promotion soon, and how my mgr can help me get each person the right opportunities for their growth
- growth: skills I'm working on, feedback areas I'd like her to pay specific attention to, her observations on my interactions and need for improvement
- is there anything she is doing that I can take off her plate? How can I make her job easier?
- What unplanned or unimportant work are we doing as a team that we can try deleting? (I try to come with suggestions but sometimes the open ended questions get interesting too)
- reinforcement: I try to mention one or two things she did that I appreciated, especially things that make my life easier or that I want her to keep doing. Managers are people too :-)
- career: less frequently, I include an agenda item for a look back at the goals were outlined earlier in the year and how I think I'm doing, whether I'm on track, where I see myself in the future
I'm interested to see what others have to say too. Best of luck!