What to talk about in a first one-on-one

Your first one-on-one (aka 1:1) with a new report is a great time to set the stage for your relationship. It is the perfect time to start building mutual understanding and, eventually, trust.

Here is an annotated set of prompts I use in my first one-on-one meeting with a new report:

• Start by explaining what you hope to accomplish with this 1:1.
  • In my case, it is about starting to know each other, establish a cadence of regular conversations, sharing mutual expectations.
• “This transition is happening because …”
  • This part is not always necessary. For example, if your new report is a new hire, then they are the ones that triggered the transition and you don’t need to elaborate on it. In cases when there’s been a re-organization or there’s been a change in management for some other reason, it helps to start with an acknowledgement that a change is happening and making space to talk about that.
• Thoughts on my role as a manager and relationship with my reports and team.
  • Here I try to share as concisely as possibly how I see my role as their manager. In my case this is me talking about how I see my role as being in support for them, both to help them execute on work, and also to help them grow in the ways they want to grow in.
  • I always try to ask if they have reactions to what I said, if it sounds familiar or surprising, or if they have any concerns.
  • Make space for the other person to talk about how do they view your relationship. You can ask something like: “Is there something that you expect from me that I haven’t mentioned yet?” Realize that some will hesitate to answer openly this early in your relationship; that’s normal and ok.
• What do you need, want, expect from me, as your manager?
  • Some people have never have been asked this question, and so might not have a ready answer. This is especially true for less experienced folks. Give them some time to think, and recognize that this question will really be an ongoing conversation throughout your relationship.
  • For folks that don’t have anything that comes up, here are some more specific questions you can use to help them start uncovering their own answers:
    • What conditions do you work best under?
    • One possible variant of this is asking about their favorite past team or work situation, and why was it so good.
    • What management style do you prefer? (For example, do you prefer a coaching style, or a more directive style.)
    • How do you describe yourself when you’re at your best?
    • What communication channels and styles do you prefer?
    • How do you prefer to receive feedback?
• How do you prefer these 1:1s to happen?
  • Here I go into the weeds of what specifically works best for them for this kind of meeting:
    • Do you have a preferred time of the week or day for meetings?
    • Do you want to keep a shared agenda document? Do you want us to take shared notes from these meetings? (At this point I always clarify that I will take my own personal notes in any case, to help me keep myself accountable and to not forget anything.)
    • Do you like to do walking meetings, or do you prefer to always use a meeting room?
• If possible, offer a more tangible proof of my commitment to support.
  • My goal here is to show that I intend to walk my talk. For example, if they have already asked for my help with something, I proactively bring up my next step to help with this thing. Or if they said something like “I hope to get promoted to XYZ in the next N time”, then I talk about how we’ll work together throughout our weekly meetings to get there.
• End with “anything else?” or a similar question that gives them the floor to bring up anything that is on their mind.

These ideas are not a script. A 1:1 is always a conversation, and I let it lead us to wherever is relevant in that particular moment. Often the dialogue around these ideas will extend for several of our conversations.

This list itself is, in a sense, a conversation. It is a constant work in progress, where I add, remove and refine ideas as I learn what works for me.