This blog post is a sample chapter from my book:

How to Hire and Manage Remote Teams

The term one-on-one evolved to refer to a specific type of meeting and does not mean any general meeting that has two people on it. One-on-ones are the regular meetings between a manager and each of their reportees. One-on-ones are always important but in a distributed team they become critical – mainly because you are not going to be able to run into your reportees on the hallways and have a quick meaningful conversation opportunistically.

A one-on-one has several goals and I recommend the relevant chapters on The Hard Thing About Hard Things (Ben horowitz) and High Output Management (Andrew Grove) in order to understand more about how to conduct them and their importance.

The main and most critical role of the one-on-one is to identify problems, or potential problems, as early as possible. By the time one of your employees tells you they have another job offer, more often than not, it’s way too late to do anything about it. The issues leading to their moving posts will have started long before, perhaps months, and the opportunity to address them will have been when it first arose. If you’re not aware, and not providing the opportunity for your worker to make you aware, a problem can fester beyond the point of salvation. The one-on-one aims to reduce this possibility.

A one-on-one is the time when an employee can bring up small issues:

  • I’m not happy with our project.
  • Work is boring.
  • I feel my ideas are ignored.
  • This person is being rude to me.
  • The way we work just sucks.

And from that information it is your job to start fixing it. 

However, it is unlikely your employee will feel empowered to say any of this unless they already trust you. For this reason, one-on-ones should not be reserved for only dealing with critical issues, or when you suspect there could be a problem. Routinely meeting is an exercise in building the rapport that will be required for the worker to bring up any real problem.

For those uneventful one-on-ones, it is important that you keep a balance between listening and sharing. If you don’t share anything at all, you’ll end up coming across as an interrogator. It is through sharing that you show them that you are listening and empathizing with what they are saying.

The opposite tends to be a bigger problem. If you as the manager go into long monologues during the one on ones most of your employees will respectfully listen and hate every minute of it. Many of us tend to have a bias that means that if we feel we spoke for 50% of the time, we actually spoke 70% of the time, so you might need to rein it in.

Since you are doing this remotely, you could get a stopwatch and during a couple one-on-ones measure how much you talk or how much they talk. Don’t worry about getting too precise (for example, when switching back and forth quickly during clarifying questions). This is just a rough approximation. Your performance during those one-on-ones will be distracted, so this isn’t something to do regularly, but it can be a useful self-test to show yourself your baseline.

To achieve a good balance, here’s a recipe you can follow:

  1. Start with the pleasantries: How are you? Fine, you? Fine. This is neither sincere nor useless. It’s a protocol to start communicating, it establishes cadence, tone of voice. Don’t ignore it, but also don’t take it at face value.
  2. Ask one or two questions to let the worker become comfortable talking. “How was this week?” or “That was a good release, wasn’t it?”
  3. Re-ask them how they are doing: “Now, really, how are you doing? All good in your life?”. Now is when you need to start practicing silence.
  4. Ask them if they have any questions for you. Continue practicing silence.
  5. Ask them what was the best or worst part of the week. Again… silence.

When I say practice silence, what I mean is that you ask the question and then shut up. Different people take different amounts of time to start talking. Especially if they need to bring up a difficult subject, which can require mustering some courage. Give them time and space. This will feel uncomfortable, but it’s a skill you need to master. There are some stereotypes that introverts are more comfortable with silence than extroverts, but I’m not sure how true it is. If you are a manager, you are probably more comfortable talking than the worker (if they are developers for example), so you might need to put up with more discomfort.

The initial “How are you?” question is part of the protocol of starting a conversation. There are some studies that show that it establishes speed cadence, tone of voice and other aspects of communication. What it’s not is a sincere question of how someone is doing. Don’t expect people to answer it truthfully; if they do, great! But most people need to be asked twice. But… avoid asking twice in a row. When we are asked the same question twice in quick succession, it engenders the feeling of being accused, as though we are lying or are being unreliable – so most of us will dig in our heels and avoid changing our answer. Most of us need to warm up to a conversation before we can answer truthfully. So ask some other benign questions, and then circle back round to it. 

If at any point during that recipe your worker takes off on a tangent that is useful, as in it’s providing you with the information you need about their wellbeing, drop the recipe and follow their lead. The recipe is there for the cases where a worker is being more passive, which is likely to be true when you are just starting to work together.

I recommend taking copious notes during the ones-on-ones and following up on things that were happening. These notes should be strictly private.

I tend to run one-on-ones in two different schedules:

  • Weekly but optional.
  • Every other week but mandatory.

Every other week but mandatory is the default way I use to schedule one-on-ones. Weekly but optional is a scheme that I use under many special circumstances:

  • The employee and I don’t know each other well.
  • The employee is new to the team.
  • I am new to the team.
  • There’s an ongoing issue or conflict.
  • They are a junior employee needing more guidance.

The optionality has limitations: we can skip one, if they are being productive and have no pending issues to discuss in the one-on-one. Once it’s skipped one week, the next week it becomes mandatory.

Normally I book one-on-ones to last 25 minutes with five minutes for me to finalize my notes. If someone reaches the end of the one-on-one and there are pending issues to resolve, book another meeting straight away to continue working on it (this rarely happens).

It’s very easy for one on ones to become status reports. It’s something easy for the worker to say, and it’s something easy for the manager to consume, but the one on ones are not about performance or what got done. To drive that point: imagine the situation in which the line manager and the project manager are different people, the line manager does the one-on-one but the project manager cares about the status reports of what has been done. 

Instead, I suggest you just say something along the lines of: “This is not about a progress report, but was there anything you enjoyed or that annoyed you this week?”

That last part of the question allows the worker to do a retrospective and instead of talking about having achieved tasks A, B and C, they can talk about how whilst doing C they had a conflict with another worker; or how they loved doing B and wished they were doing more of that. Those are important signals for you.

The one-on-ones cannot be extremely transactional. It takes time for someone to be comfortable to tell you about a problem they have. This is normal: people literally go to the doctor, where their confidentiality is protected by law, and still procrastinate on sharing something because it’s uncomfortable. So don’t expect that a worker will just show up and tell you there’s a problem because you have an “open door” policy. You need more than that. You really need to prove yourself approachable proactively, and that happens through repeated positive small interactions.

If, like me, you have a terrible memory, write down the names of their spouses, children, pets, birthdays, what’s going on with their lives and ask them about it the next time (“how was your holiday to Mallorca?” or “How was [daughter’s name] school play?”). These are notes that I consider extremely private; not to be shared with employers or other managers. I don’t even write them on a medium they could gain access to (normally I use paper). For me, it’s the same as with any other friend: I have a calendar with their birthdays, because it’s important that I don’t miss them.

In Summary: one-on-ones are often neglected or perceived as only necessary when something is already wrong. In fact they are a vital means of establishing rapport with your team and keeping on top of what’s going on with your employers. This is really the only way you’re going to be able to identify minor issues before they become big problems, and has knock-on effects on employee retention, team morale, and productivity.

This blog post is a sample chapter from my book:

How to Hire and Manage Remote Teams


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