This is an outline of how I approach having 1-on-1s with my direct reports. I think of 1-on-1s as my primary tools for connecting with an individual and working on their morale, engagement, productivity and growth.
I usually like to find out if my report wants to lead the conversation. You might start with a simple question. Do you have an agenda or something that's on your mind? If not, then I think about which one of the major points below I want to get into.
These are the high level areas I like to hit, and I've listed some relevant questions/prompts with each one. This isn't meant to be comprehensive, and it's not meant to be a script. I like my 1 on 1s to be more organic and I'll jump around these topics depending on how the conversation goes.
How are you doing? (every 1-on-1)
1. How's your project going?
2. Are you struggling with anything?
3. Can I help you knock down any barriers?
4. Are there places I can step in and help facilitate communication with others?
I've got some feedback for you. (Positive or negative. As often as needed)
1. I've observed these things you've been doing
2. I've gotten this input from people you've worked with
3. This is how you did on recent projects
4. Let's talk about this scenario where you did good/needed improvement
Let's talk about what's happening around the org. (At least once a month. Definitely when significant changes have happened.)
1. Can I address any recent changes that you're curious or concerned about?
2. Can I address any rumors or things that worry you?
3. Let me tell you what the leadership team has been talking about that may affect you.
4. Let's talk about the wider org direction and make sure you're connected to what our business goals are.
Let's talk about your career path. (Once a quarter at least. You can do this in smaller more frequent iterations too)
1. Let's set some goals for the next few months
2. Let's check in on the goals we set for you
3. How can I create opportunities for your growth?
4. Let's talk specifics on what's going to get you to the next level
5. Let's talk more long term. Where do you wanna be in a few years?
Let me tell you my thoughts on the direction of the team. (How often you do this depends a lot on your team and how your company operates)
1. Here's what I think the priorities are for our team right now.
2. Here's where I think we're doing well and where we have challenges.
3. I'd like to get your opinions on these things and talk about where I think you can help move things forward.
Keep in mind that there is an implicit number zero here which is connecting on a personal level. Ideally I'm always building rapport and trust throughout 1-on-1s and in other scenarios. I find time to talk about family, recent events, hobbies, future plans, etc. I'll sometimes even let this conversation take up significant time in the 1-on-1. I don't like to make people feel rushed or that there's always something intense that we need to talk about.
There is some initial onboarding into 1-on-1s. The first several are going to be about getting to know my new report and finding out what they need from me. That requires some more targeted information gathering. Here’s a great post by Lara Hogan that focuses on that. Questions for our first 1:1