Update: Since first publishing this article, we’ve moved our advice on 1:1s into a dedicated page in Remote Work Playbook.

I read a great interview with John Milinovich recently on First Round Review in which he talked about how important he felt running regular 1:1s were. This routine allows him to keep up-to-date with how his team is feeling, leading him to be a better manager. If you haven’t read it yet, it’s well worth a look as is the rest of the content on FRR–there are some fantastic insights on there from some very smart people.

As Milinovich says:

"The best question to start a one-on-one is often just, ‘Where’s your head at?’ You’d be surprised by the range and depth of responses you’ll get to that simple question...”

“... Sometimes people want to dive very specifically into what they’ve been working on. Sometimes they’ve had all this angst bottled up about not doing as good of a job recently because of something going on in their lives or with their relationships or health, and we give them a chance to talk about that and be honest. A lot of times people just don’t know how to get over a certain hump or out of a rut. If that’s the case, we want them to tell us with zero reservation what’s going on so we can help."

I never scheduled regular 1:1s for a long time at Hanno. Initially, this was largely down to the fact that we were a team of just 2 or 3 people a few years ago and we talked constantly. So, generally we had a pretty good handle on how people were feeling. I first introduced 1:1s to allow me to keep up-to-date with the team on a constant basis as we’ve grown–introducing this more structured form of appraisal and team review has prevented me from slipping into infrequent reviews and leaving my team unsupported.

Now that we’re a little bit bigger and will potentially be growing even more in the next few years, that ‘keeping up face-time’ role that we get from a 1:1 has become all the more important. It will be interesting to see how this evolves with a larger team and how our priorities shift. However for now I think the trigger of having a monthly chat and feedback session (which is a lot more frequent than some companies do performance reviews), plus the setting of OKR goals once a quarter during 1:1s has been a positive move for us. It has certainly left me in a better position to help my team to grow.

1:1s can be a deeply personal thing, which will probably be handled differently by every team lead. Even so I figured I’d pass on a few specific tips and tricks that have worked for me to help others navigate through this 1:1 road:

What structure do I use?

For now, I set up all the 1:1s on the 1st (or the nearest working day) of the month as a recurring monthly calendar event. I’ve surprised myself by how fun they’ve turned out to be – even for everyone involved. It’s a really great way to kick off the month and we all look forward to our sessions.

I also have a recurring Asana task in my schedule to “Prepare 1:1 feedback for [team member name]”. This is due a couple of days ahead of the session. The content of this feedback evolves monthly as we figure out the best structure. Nevertheless, it loosely amounts to the following, under the heading of What happened this month?

  • Strong positives: I try to counter a natural tendency of mine to not provide as much positive feedback as possible by opening on a positive note – because to be honest people nearly always have a positive month. There are always plenty of things to highlight and acknowledge here.
  • Things to discuss is a set of topics that I’d like to bring up and often includes things that I know the individual has struggled with. I provide a little extra feedback and maybe hint at some ways we could look at to improve matters. It’s a good opportunity to bring up the not-so-pretty points from my end and helps them assess how they think the month has gone by. It also serves as a helpful mini-agenda for the discussion, keeping things on track.
  • Recap on last month’s targets is where we drop a little screenshot in, showing progress towards the current OKRs.

To come up with all of this I tend to look through:

  • The month’s set of weekly 15Five feedback: one of the questions here is ‘What were your biggest wins this week?’, another is ‘What did you struggle on?’. Both of these are very helpful.
  • A few other places to review progress on monthly goals and recap, including WeekDone.
  • I also read through the previous month’s 1:1 document to recap on what we identified as weak points last month and evaluate any improvement. It’s a great way to spot recurring issues that you don’t necessarily notice otherwise from the ground level.

I then send this over as a Google Doc and ask them to read it through. They’re welcome to add comments to it and sometimes we have a brief chat with a few comments in the Doc, particularly if there’s anything they flag up that I haven’t explained clearly that they’d like to hear more about. I like to get this sent to them a few days ahead of our chat, allowing them some time to reflect on things themselves.

So, what do you want to talk about?

This is the big opener from me and there are 2 main reasons for that:

First, it gives them the floor and lets them lead the discussion, forcing you to listen. You’ve provided feedback and this has hopefully been read and understood. Now it’s their chance to talk about what’s on their mind instead. If what’s on their mind happens to match the feedback document contents, then that’s what we’ll talk about. But that doesn’t have to be the case–it’s for the individual to dictate.

To take another quote from Milinovich:

“Sometimes the most effective thing you can do is just give someone your full attention and make it clear to them that this is their time no matter what else I might have going on or how busy I might be.”

Secondly, I really want everyone on my team to take ownership of their own careers and to be proactive about bringing up potential problems.

Even if you don’t have any big issues or worries to discuss, it can just be a great opportunity to chat without others being around. This can turn out to be a rare occurrence if you’re not careful to create the opportunity. From my own experience, there has always been something new and interesting that has come out of every 1:1. They’re consistently enlightening, even when it’s just a rambling chat.

Finishing up with goal setting

Since we’re all trying to self-improve and we’ve just spent an hour talking about the strong and the weaker points of the last month, the outcome of the chat usually leads to identifying a set of positive steps to improve things. I mentioned a minute ago that the final section of the 1:1 Doc had a table listing of a set of OKRs–that’s where this comes in.

Originally, we set goals on a monthly basis. But the problem here was that they were simply too short-term, and easy to put off. A heavy week, or a personal situation, could throw the whole month’s goal progress away. By setting quarterly OKRs, we can instead have bigger targets to work towards, and spend our monthly 1:1s talking through progress on these.

That makes the 1:1 the perfect opportunity to coach and mentor people on the progress they’re making towards their OKR goals, both personal and professional. It also helps to avoid a situation where people put off an OKR, and that doesn’t get caught until the end of the quarter. It’s impossible to ignore OKRs if you’re having review sessions every month.

And a few tips and tricks that work well for me

I hate the idea of conducting a formal “review” by sitting across a table and discussing KPIs. So, I try to keep it as relaxed as possible, allowing us to have a proper conversation with the right mentality:

  • Shake it up wherever possible. I’m a particular fan of doing it over a decent meal–breakfast or something interesting elsewhere. It becomes something to look forward to, not a chore. Also, I always pay for the food myself (it doesn’t matter if it’s a taxable business expense or not–it’s worth paying out of your own pocket). We’ve also had some fun reviews while doing a 6-hour hike up some mountains in Hong Kong (no place to hide!) and while sitting in a park in Spain, and on a beach in Bali. I try to do whatever I can to avoid sitting on opposite sides of a table during 1:1s.
  • When possible, I try to do it in person. This is not exactly the simplest of tasks when you’re leading a distributed team, but when we can make a 1:1 happen in person, it’s always a more rewarding experience. I schedule 1:1s with everyone during our team retreats.
  • Make it routine and don’t skip it. Make a recurring calendar appointment. This can be rescheduled a week or two beforehand if someone is travelling for example. But not by more than a day or two to avoid disrupting the routine. Under no circumstances should you as the manager, cancel it or change it at short notice. It’s one of the most important things you can do in your job and it should take priority over almost everything else that could come up.
  • Try to be aware of any tendencies on your part to be the one constantly talking. Particularly if you’re doing the 1:1 by video chat, snack on something like a watermelon or drink a pot of tea. Since my hearing is very poor (I’m deaf), I’ve found that I sometimes have a tendency to talk more, so I’m able to get away with needing to hear less. Obviously this is counterproductive and if you’re the kind of person who just likes to talk, you might find this helpful too. Regardless, you should probably learn to listen better and check that inclination!

What am I learning from it?

  • Motivated people really really want feedback. Remember when you used to get your school report card at the end of each term? I don’t want to make the process seem juvenile, but I was always desperate to see mine and how I’d done – this is no different. We can’t all self-improve solely by ourselves and it’s unusual to receive this kind of completely honest feedback elsewhere in our lives.
  • On the flip side, if you don’t make the time to do this, it’ll get swept under the carpet and your team will likely start to get frustrated at the lack of feedback. There are arguments for having longer-term goals, which we try to achieve in other ways. Nonetheless, just as we try to iterate constantly on products by getting regular feedback and running shorter cycle times, the same principles apply here. 3 months is too long to wait to hear a little tip or piece of feedback. You just might run the risk of something minor simmerring up to become a much bigger problem.
  • It is way more fun than you might expect. After all, you like your team–right? What could be better than having a chat about how they’re feeling and being able to help them improve?
  • I learn as much about myself and the way I’m able to help my team and improve the way I manage as they learn from me. As I said, these sessions always bring up great talking points. They allow us to dig a bit deeper on something a person on the team might curious about.

How do I think it’ll change in the future?

I don’t think we have the perfect process and I don’t think a 6 person team is the same as running a team of 20 or 30 people. But I do think that for a young business or small team in particular (even more when you have less-experienced people on your team), doing these sessions can be one of the most positive steps you can take.

The big question is clearly how it will scale. Obviously a big part of a 1:1 is the mentoring and feedback role, which at present probably holds most value when it comes from me. But if we grow that won’t necessarily remain the case. It’ll be interesting to see what solutions we figure out for scaling appraisals–always a tricky thing to do really well. Perhaps in the future we’ll extract the ‘assessment’ and goals bit from the 1:1 and keep it totally in the informal style that URX does theirs.

There’s still plenty to be discovered!