The remote manager's guide to one-on-one meetings
Summary
One-on-one meetings are an excellent way for managers to connect and manage their remote team members.
Avoid task specific conversations and paired work in such meetings
Instead use the meeting to discuss well-being, ideas, concerns, feedback or to identify where you can help each other.
So you don’t lose track of important topics, maintain a tracker for such discussions.
When you lead a remote-first team, maintaining cohesion is likely to be one of your primary concerns. One-on-one meetings are one of the most effective tools at your disposal, to connect with and manage your direct reports. I recommend meeting each person in your team, for 30 minutes to an hour each week. Even if you don’t manage others, one-on-ones can be an effective way to stay in touch with your colleagues.
But what should these meetings cover, especially if you’re a manager? If you only have an hour each week, you must use it prudently, shouldn’t you? So in today’s post, let me tell you how I recommend you spend this time with your colleagues.
Topics you can avoid
If you’re working remotely, you must manage all of your work asynchronously. In effect, that means you must have a team task board, that tracks your team’s work - past, present and future. Your tool of choice may vary; Jira, Asana, Trello or whatnot; but transparency is the common sentiment, regardless of the tools you employ. Anyone should be able to look at the task board and tell what any member of a team is up to at any time. If you’re lining up work for someone, this is where you do it. If you want to know what someone has done in the last few weeks or months, your task board should help you find out.
Don’t do status updates. And so, if you maintain an up-to-date task board, you needn’t address status updates in your one-on-one meetings.
Don’t do task reviews. If a team member wants you to review some of their work, do it asynchronously and as long as the feedback isn’t contentious, you must share it asynchronously too, via the task board.
Don’t do paired work. You may also need to pair up with your teammate to work on something together. But resist the temptation to reuse your one-on-one meeting for this purpose. Set up a separate pairing session for such real-time collaboration.
By taking status updates, task reviews and paired work out of scope for your check-ins, you make room for other, higher-order conversations. But what might those conversations be?
Topics you should address
Your people are more than the work they do and the tasks they complete. They’re human beings with ambitions, constraints and life that work fits into. I recommend using the one-on-one meeting to connect with those human beings. I’m not asking you to be their BFF. Friendship is sometimes counterproductive to being an objective manager. But remember that you can know your people and be empathetic towards them without losing your objectivity. Indeed, if you know your people well, you’ll structure their roles in a way that gets the best out of them.
Here are some topics I enjoy addressing in my check-ins with colleagues.
Life and well-being. I spend some time, especially at the start of every check-in, with a “how are things?” The key here is the willingness to dive deep and not make this a formulaic question. Give it the time it deserves, even if it can be all the time you spend in the meeting. Ask why people feel a certain way and if you can do anything to help. This is a chance for you to show that you care about them and not only their work.
Ideas you want to bounce off each other. While I love team task boards, every activity may not originate there. Sometimes people need the safety to discuss ideas with each other before they write them up on the task board for others to see. Use the safety of the one-on-one meeting to feel each other out with ideas you’re unsure about.
Stuff that may bother either of you. Humans make up teams and humans are imperfect. There are bound to be occurrences or patterns that upset people. If one can’t address such perceived annoyances, silence can often build up a feeling of simmering discontent. Create an open environment in your check-ins, where both of you can express your frustrations to each other, even if you don’t have immediate solutions. Sometimes, just knowing that another person will listen, can be comforting.
Help each other. While the one-on-one isn’t a place to do paired work or task reviews, it is a place where you can identify opportunities to collaborate. Think of this communication channel as a two-way street. Both you and your direct report should be able to ask each other for help. Resist the temptation to complete the task in the meeting though. Agree on who helps whom and by when, and if you must help each other in real-time, set up a separate time to do so.
Share candid feedback. At some stage, you’ll review your team member’s performance. That performance review should never be a surprise. They should have had feedback throughout the performance cycle to know how they’ve fared. Feedback is also a two-way street. Be sure to ask your direct report for feedback. Exchanging effective feedback is a crucial managerial skill. If you haven’t read the book already, I recommend learning about effective feedback skills from Kim Scott’s excellent book - Radical Candor.
You won’t cover all these topics in every meeting. The key, however, is to build a shared understanding with your team members about the scope of your one-on-one meetings and the topics that you’ll discuss. That way both parties can also plan for such interactions.
Preparing for one-on-ones
Without enough planning for one-on-ones, you may end up discussing only the topics that are on the top of your mind. That way you risk ignoring simmering, long-standing issues that may not be urgent but are important.
I find it useful to track one-on-one discussion topics just like we track backlog items on a task board. People have many topics they want to discuss with one another, but they can’t keep all these thoughts at the front of their heads. Not all topics are equally important either. This is where a one-on-one tracker comes in handy. The idea is simple.
Log everything. Whenever you or your direct report think of a topic to discuss, you add it to the tracker, with the details you have in mind. Adding details is important, because if you see only a headline after a week, you may not recollect what that topic was all about.
Think of priorities. If you can, prioritise your discussion topics so you always discuss the most important items first.
You can use any tool to implement such a tracker. Trello offers a template where both managers and team members can log their discussion topics and actions they’ve committed to each other. With some effort and AI help, you can even create such a tracker using a generic spreadsheet.
Track your discussion topics using Trello
The beauty of tracking discussion topics this way is that you can sometimes address certain topics even outside the one-on-one meeting. If you describe the topic well enough, the other person can read it before the meeting and address it asynchronously. That frees up time in the meeting to address topics that need fast, back-and-forth interaction. Writing up the topics you have in mind, also gives the other person a sense of what to expect in the conversation. That mental preparation can often make one-on-one meetings more effective than otherwise.
And that, my friend, is my advice for how to run your one-on-one meetings. It’s a recipe that’s worked well for me over the years. I’d love to know how it works for you though. What topics do you bring to your one-on-ones? How do you track them? What part of my suggestions do you agree or disagree with? Share your thoughts in the comments below. I’m keen to learn from you too!