How to have better one-on-ones

Illustration by Molly Magnell for this article.

The value of a good one-on-one meeting is nearly immeasurable.

It's a time to sync on things in a format you can't get any other time or in any other medium. You don't have an audience waiting in the wing to jump into the conversation, nor distractions to pull your attention away from the other person. I believe a great one-on-one is where your best work often gets done.

To make your one-on-one's more effective:

  • Define and agree upon their purpose together
  • Be clear about the schedule
  • Use the time to sync on anything you can't anywhere else
  • Work to keep things casual

Define and agree upon the purpose up-front

First-and-foremost, you'll want to set a clear plan or purpose for your one-on-one meetings.

The plan can be high-level (e.g. "Catch up on everything that happened over the last week in our lives.") or focused (e.g. "Discuss a decision I need to make tomorrow around Project X."). The key is to have a clear purpose or agenda both parties understand before the meeting. Whether you're meeting for the first or hundredth time: get aligned on the purpose and plan of the time.

What do you each want to get out of the time? What would a successful sync look like for both people? What is most valuable to the relationship? Even if you spend time catching up, that's an important use of time for teammates to have.

Be clear about the time and recurrence

It's not enough to agree on the purpose of your one-on-ones. Both people should know in advance just how much time will be dedicated to the meeting and how often they will occur.

Some people use 1:1s as a way of getting updated on work. Others use it as a chance to chat and get to know the other person casually. In either case, the amount of time required will play a part. Discuss and agree on how much time you'll need to fulfill the sync's purpose and how often you should be meeting.

Consider how close your relationship is to the person: weekly is the right cadence if you work very closely. If more casually, as far out as once a month can suffice. It will vary for every person you meet with and the purpose. Staying in-sync on personal goals can be less regular than meeting to stay connected about the work.

Use the time to discuss things you can't elsewhere

Email, group posts, Slack chats, and more are all excellent ways to stay up-to-date with your peers about ongoing work, in asynchronous methods more often than not. You may not have the ability to sync on more personal or pressing matters with a level of emotion or nuance to them in these methods, however. One-on-ones are for things you can't say in the other means or something that may not be suited for those channels.

Focus on the individual, the working relationship, or things that may impact others but need to be figured-out in-person, in advance. Consider the value of any one-on-one as being able to discuss these crucial subjects on a micro level, without interference or the ears and eyes of a larger audience.

Ask yourself (and the other person): "What conversations are we not having elsewhere?" Those are what your one-on-ones are for more often than not.

Keep it casual and human

It's worth noting: one of the best aspects of one-on-ones is you have them in real-time, usually face-to-face, with one other person. Meaning: you can see the person, you can better understand what they're saying or how they're listening, how they're responding to what's being said (in real-time), and you can interject the conversation with questions or ideas on-the-fly as necessary.

The work we do as teams ultimately comes down to the work we do as individual human beings. Often when we get buried in project scope documents, design mocks, and customer feedback requests, it can be hard to remember we're all people functioning together.

Keeping one-on-one conversations as casual and friendly builds the working relationship and enables you (as a team) to better tackle work subjects.

One-on-ones can be awkward or time you wish you were spending doing work, but ultimately the investment made in a good conversation with one other team member can pay immense dividends. A good one-on-one is any one-on-one where both people understand the purpose of the time, where they have agreed on how long and how often the time should be spent, and where each person uses the time to connect at a human, casual level.

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