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Leveraging Hybrid One-on-Ones for Better Connections



Alexandra Sunderland discusses why one-on-one conversations are vital for teams that aren’t co-located, and how to leverage them to build strong relationships and a healthy team.


Alexandra Sunderland is an engineering leader with over a decade of experience working in both hybrid and remote roles, at companies ranging from 10-person startups to public corporations. She is currently a Senior Engineering Manager at, where she is helping to build the future of work.

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Sunderland: I'm excited to be giving this talk as a part of the hybrid work track because I've been working in a remote and hybrid environment for the last 10 years, so I have many lessons, thoughts, insights, mistakes that I've made. My name is Alexandra Sunderland. I'm a senior engineering manager at the meeting management and productivity platform, I'm also the author of the new book, "Remote Engineering Management," where I do talk about one-on-ones and a bunch of other things related to remote management as well.

Why I Care About One-On-Ones

I want to start off by talking about why I care about one-on-ones so much, why this is something I decided to give a talk about. Really, what it boils down to is one-on-ones are the most important meeting that you can have with your direct report. At the same time, they're also the most misunderstood type of meeting. They're so critical, because they're the time where you help your direct report grow in their career. You build trust. You build the foundation of a relationship that's so important for everything else that you do at work, and has a big impact on their happiness. This goes all the way back to when I was an engineer starting out with my first one-on-ones with my manager. I remember I wasn't told what the purpose of them was. I didn't understand what sorts of topics we were supposed to be talking about. What ended up happening is that we would spend this time every week talking about what we were up to on the weekend, and what we were going to have for lunch. We weren't making the best use of the time together. I really want to make sure that everybody fully understands why they're important and how to make use of them in hybrid workplaces too.


The things that I want to cover include how to take advantage of that uniqueness of being in a hybrid and remote workspace when it comes to one-on-ones, because it might seem a little trickier to do one-on-ones when you're not seeing people in person. I actually think that remote one-on-ones are a little bit better than in-person one-on-ones. I want to talk about the purpose of one-on-ones, why we have them. How to have great one-on-ones, which is the most important thing here, just making sure that we're making the most of the time together in those meetings. Then we're going to end off with some types of one-on-ones that you might have, because there's more than just the typical manager, direct report type of one-on-one. Then, also, how to troubleshoot some of the most common issues and points of resistance that you might have when you're setting these up.

One-On-Ones Are Important in Hybrid Work

I think that one-on-ones are very important no matter where you're working in, but especially in hybrid work. The reason for that is that if you are doing hybrid, most likely, there are going to be some people on the team who are working in the office, some people who are working remotely. There's not going to be a very equal balance between how often you see everyone in person versus over a video call. That imbalance can really play out in interesting ways, especially when it comes to giving feedback and career progression and understanding the value that people are bringing to the team. Because people can tend to overvalue the things that they're seeing in person and the interactions they're experiencing in real life. I think that one-on-ones and hybrid work are especially important because it levels the playing field a little bit. It gives you a chance to talk with everyone on the team, understand what they're up to, and get dedicated face time with everyone, no matter whether they're working remotely and you're in the office, or whatever the situation is.

Why Remote One-On-Ones Are Great

Whether you're working remotely from home or working in an office and having one-on-ones over video calls with people who are themselves working remotely, I actually think that remote one-on-ones are the type of one-on-ones that are the best to have. There are a few reasons for that, a little bit controversial. I think that remote one-on-ones bring a lot of value to them. For example, if you're doing them from home, then you get to be in your own environment. I, for example, love sitting on my chair with my legs crossed, with a blanket and a mug of tea, and I might be fidgeting with whatever is on my desk. It's not going to look that good if I'm doing that at the office in person, having a one-on-one with someone. I get to do that in the privacy of my own home where they can only see my face and they don't get to see all of that stuff. Because I feel more comfortable, it's easier to talk about things going on. It's easier to give real feedback.

The other issue I've noticed now that I'm working a little bit more hybrid in the office is that you have a lot of privacy when you're in your own home, maybe not with other people who are living in your home, but privacy from your coworkers. One of the difficulties I've run into is when I'm having a one-on-one in the office, I find sometimes you don't know how thin the walls are and you have to start whispering if there's something really delicate coming up. If you're in your own house, that doesn't matter, you can be as loud as you need to be. Another benefit that I feel makes it a lot easier to have difficult conversations is that you don't feel like you're forced to maintain any eye contact with someone. When they're on the screen, you can look at the screen, you can look around the room, and it doesn't feel very awkward. If you're in a room with someone, and they're looking at you in your eyes and you're glancing around the room, it might feel a little bit stressful. I find that not having to maintain that eye contact makes it much easier to talk about some difficult things.

What Makes for A Great One-On-One?

What makes for a great one-on-one? Before getting to that, we have to understand the purpose of one-on-ones. At its core, the main purpose of one-on-ones is really to build trust between you and your team members. Building trust is so important because it means that it's easier to give each other feedback and talk about really difficult things when they come up. Building trust and creating this really great relationship as a foundation for everything makes everything about work so much easier. It's so much easier to collaborate and be honest with each other. One-on-ones are also great spaces to create alignment on things like company or personal goals and vision. Give and receive feedback about anything that is constructive and helps people grow, something you definitely want to do in private and not in public with other team members around. It's also a really great space to talk about anything that either of you want, so ideas, blockers, questions. The nice thing about it is that if you have one-on-ones that are set up recurring, so you always know when the next one is going to be, you get to put the topics that you want to talk about, any questions or things that come up throughout the week. You get to save those for the one-on-one and have a whole bunch of discussions at once that happen there.

There are a few things that I look out for to know whether my one-on-ones are going well. One of them, the most important one is really that both people are coming to the one-on-ones prepared with things that they want to talk about. Because if you don't do that, you're probably going to end up in a situation similar to me when I started out where you talk about your weekend and what you're going to have for lunch and things like that. That's not a good use of anyone's time. Both people knowing what they want to talk about and having specific things is a really good sign that they are taking the one-on-one seriously, and that it is a good use of everyone's time. Another big thing though, it's not enough to just bring topics, it's really important that the things you're talking about lead to deep, actual conversations. Bringing in questions saying something that just requires a very short answer, that's not a real topic. You want to do things like make sure that there are actual conversations being had, opinions being shared, discussions going on, and really diving into topics very deeply, because that is a sign of a great one-on-one.

How to Structure Hybrid One-on-Ones

How do you actually structure a hybrid one-on-one? There are three main parts to this: timing, location, and topics. These three things are the things that differ a little bit between remote, hybrid, and in-person one-on-ones. The first thing I want to talk about here is timing. There are two main components to how to structure your one-on-one with timing. That's both the time of day that it's been scheduled for and the length and frequency at which it happens. Time of day. I'm sure at this point, we're all aware of time zones. Another main thing though, is this whole manager versus maker schedule, where throwing a meeting onto a manager's calendar, no big deal because our time is meant to be interrupted and refined with all those little meetings happening all the time. Makers, though, engineers, need many long blocks of uninterrupted time to get work and deep focused on writing code. Throwing a one-on-one right into the middle of a big block of uninterrupted time that they have is not good, because it's going to break that flow state, and then they'll be less productive than they like to be. That's something to be aware of.

One of my favorite tips, though, is to avoid scheduling one-on-ones on Mondays and Fridays, specifically, because those are usually the days where holidays happen. Those are the days where either meetings will just get canceled or be squished into some point in the rest of the week. One-on-ones are meetings that you don't want to cancel very often. By avoiding having them on Mondays and Fridays, you're less likely to have to do that. For the length and frequency, I would suggest no shorter than 30 minutes for a one-on-one. I think that this is really important because 30 minutes is the minimum time required to get into the groove of things, get comfortable, and really get deep into conversation. Then 60 minutes is the upper bound there. There's a lot of variety in terms of how you can structure this, mixing length and frequency. At the very least, I think that 30 minutes every second week is appropriate for a lot of people. Very much depends on people's preferences, how often they feel they need to meet, how many topics they have. I have a mix of things going on right now where some people on my team we meet for 45 minutes every second week. Some people on my team we meet for an hour every week. It fully depends, and there's no one exact right way other than at the very least, 30 minutes biweekly.

Location for hybrid meetings is definitely an interesting one and a little bit more tricky, because for a hybrid one-on-one, does it mean that you are together in person at the office by chance? Are you both remote? Is one of you in the office and the others at home? What does that really mean? For the purposes of this, though, what I've found is that having a good mix of both in-person and remote one-on-ones for the same person is really good at getting a variety of topics to come out and a variety of ways of talking. For example, I'm more comfortable talking to people remotely because of not having to make that eye contact, getting to cozy up with my blanket and everything. Some people on my team are more comfortable talking in-person, because that's where it's easier to open up, and chat about things. I like catering to both of us so that we're able to have different types of discussions.

In terms of options, though, I think that there's so much more than just the default that we're used to, which are video calls and meeting rooms. For virtual calls, you can do voice only calls and not turn on your video. That sometimes also makes it easier to talk about certain topics when you don't see the person and you get to really focus on what it is that you're saying. In-person, meeting rooms are fine. I do find it a little bit awkward standing up from your desks at the same time and walking over and closing the door and sitting down and facing each other to talk. I really enjoy going for a walk outside, which also has a lot of those benefits of voice only calls because you're not staring at each other. You're facing forward. You have fresh air, new sounds, new sights. It makes things different. It can make it easier to talk about things. It can bring new ideas as well. In general, in hybrid, though, what I really appreciate about this way of working is being able to mix up all those options. I love doing a meeting room one week, a video call the next week, it just creates so much more balance between how people work.

In terms of topics, we're going to talk a lot about different things that should be brought up in one-on-one's, ideas for how to make the most of the time together. There are some topics that I think are very specific to hybrid work that should be brought up at least periodically to make sure that things are going well, because hybrid is very tricky. We want to make sure as much as possible that there isn't this like us versus them for people who spend most of the time in their office versus people who are remote. Because there's always going to be a feeling of, people who are working remotely feeling like they're missing out on conversations happening in the office, even if that's not actually happening. We want to get ahead of that and make sure that there's a lot of discussion happening around how people are feeling about that. Things like asking how connected they are with the rest of the team, is really good. Ideas on how to better collaborate between people who are in the office and people who are remote. Also, just giving them the chance to ask, is there something that happened in the office that I missed out on? That kind of thing. Even if the answer is like, no, you didn't miss it, or we posted the conversation here, or whenever we started talking about this, we invited everyone to join in on a call. Stuff like that is really good to reassure people that they're not missing out on things that are happening.

Also, very importantly, I'm a big fan of asynchronous communication. Focusing on things like recording videos and sending those back and forth, or writing things down, commenting, sending documents. Anything like that, where you're not required to be collaborating on something at the same time. Big fan of that. Makes remote and hybrid work so much better. Anytime someone has an idea of how to improve that, or even what processes or meetings could be moved asynchronous, that's something that's really important to talk about in one-on-ones as well. Outside of those hybrid specific topics, there are also many things that should be talked about on a regular basis, in one-on-ones too. For example, anything around career progression. How they could grow in their role, feedback about what they're doing really well but they could be doing better. Coaching them through new areas that they're learning. I really love to ask people opinions on things like, what could we be doing to improve the team? What do you want to work on next quarter? What ideas do you have for the company? What do you want to work on? Then, also, thoughts on like, what did you think of that recent announcement that happened? Or, how do you feel about this change that we've made? Things like that. People aren't going to bring up their opinions necessarily in team meetings, but if you ask them specifically about it, they probably have something really valuable to say, and that will lead to really big important discussions.

Importance of a Shared Meeting Agenda

Once you have those one-on-ones set up with the timing, the location, and you start to put some thought into the first few topics, the next most important thing to do is have a shared meeting agenda. I know that some people are big fans of having agendas for one-on-ones that are written by hand in notebooks, or stored on their computers, only accessible to them. I don't think that's quite good enough. It's a great start, but I really think that there's so much value in having the agenda shared with other people, ahead of time, and collaborating on it together. Not just letting them know a few minutes before, what topics you want to talk about. The biggest value that I personally get out of having a shared meeting agenda, where we're collaborating together, is that it gives the other person or me in particular, more time to think about the topic and how I want to respond. I'm the type of person where if you ask me something, spur of the moment, what my opinion is, I'm not going to have a very good answer. I need at least a few minutes to go and think about what it is that I want to say. In one-on-ones, if somebody has written ahead of time, "I want to talk about how to progress to the next level of my career." I'm going to have a much more thought-out and useful answer, if I know that ahead of time that you want to talk about that, and get to put some thought into it so that by the time we're going into that conversation, I know exactly what I want to say and we can talk based on that answer. We get much deeper discussions based on that.

Also, because we have the shared agenda, there's this historical record that's shared about the types of things that we talked about. It makes sure that we have alignment on decisions that were made. Because if I type out, maybe you did ask, how to get to the next level in your career, and I write out some answers. You being able to see those answers means that if I wrote something incorrect, you'll know that there was a misunderstanding, and we'll be able to correct each other right then and there. Which is always better than finding out later on that you weren't aligned on what it was that you actually talked about. Shared agendas are also great because it shows the other person that you value their time. It shows that you're putting effort into the time you're going to spend together. It also allows for this thing called batch communication. Instead of me bugging my manager 20 times a day with the many things that I want to talk about and creating a lot of distractions for him, I'll put those 20 things every day into our shared meeting agenda, where we will get to talk about those things all in one batch. I know that he has an hour dedicated, just talking with me about the things I want to chat about. That makes better use of both of our time, so we're not constantly interrupting each other.

Having a shared meeting agenda is a very good first step, but there are some key things that make it go from good to great. The first one is that it's actually collaboratively set by both parties, because it's no fun if only one person is ever contributing topics to the agenda, or if there's only one person contributing and then the other person doesn't even read them until the meeting actually starts. That's just not very collaborative, kind of defeats the purpose of it. Making sure that both people are really on top of adding topics and checking the note throughout the week before the meeting happens is very important, and a sign of a great agenda in a one-on-one setup. I also really like having headings within the note that are recurring, that aren't super prescriptive about exactly what should be talked about, but still get people thinking. For example, instead of just having a blank note every single time, which is a little bit daunting, it might be nice to have something like a section that's just called feedback. That gets people thinking throughout the week, what feedback do I have that I could add to that meeting note? It's a great way of guiding your thinking and creating topics without specifically saying, you have to add feedback to this, or what feedback do you have for me?

I think it's also very important to order topics by importance in the note, because you want to make sure in the limited time that you have together that you hit the most important things first. If there's anything smaller that maybe doesn't even have to be talked about out loud together, it could be done at the very end of the meeting. What I like to do is have a to-do asynchronously section. Topics that go there are ones that are still important to need discussing, or answers to them. They could be resolved by writing in the notes or chatting on Slack, or whatever it is, afterwards, and don't necessarily need to be talked about during the meeting when there are other things to go over.

On top of having meeting agendas, which is the list of things that you're going to talk about. There are also meeting notes, which is the historical record of what it is that you did talk about and the decisions that were made. Lots of distinguishing things here about what makes notes really great. The main one here is also same as with the agenda, that they're written collaboratively, because it's no fun where it's always the one person writing all the notes because it's hard to talk when you're writing notes for things. That goes for one-on-ones, and any type of meeting really. You want to make sure that people are taking turns writing notes, doing it collaboratively, and not just always pushing it off to the same person to do that. They shouldn't be writing down absolutely everything that's being said. The meeting note shouldn't be a transcript of the call. If you want to do that, then recording calls is much more efficient. They should capture the key points, so decisions made and ideas that people had so that it's enough information to jog your memory about what the conversation was about and any outcomes from that.

The one exception that I have to writing key points instead of entire conversations when it comes to one-on-ones is when it has to do with feedback that I'm giving. Any time I'm giving either positive or constructive feedback, this is valid for both, I like to deliver that verbally with people on a call and talk about it there. Then I know that I personally, I absorb information much better when I see it in writing. My memory sometimes fails me, so I like having a historical record to go back to, for anything that's discussed. For feedback, in particular, especially if there's anything related to outcomes people have decided on, steps that you're going to take or are expecting for people to get better and level up, it's really important to have that written down in the notes so that they can absorb it verbally, when they hear it directly from you. Then refer back to it as well, so that you aren't having any misunderstandings between what people are remembering.

Types of One-on-Ones

Next, I want to talk about some of the types of one-on-ones that you'll probably have, because not every one-on-one is equal, not every one-on-one has the same structure. There's some that have a very particular connotation to them, and also require discussing some things. First one that you're probably going to encounter is the first one-on-one. Whether this is somebody who is new to the company, or just new to your team, the first one-on-one that you have with someone on your team is going to be very special. In that first one-on-one, some of the core things that you're going to be doing are getting to know each other, both on a personal level, outside of work, learning about hobbies and stuff, but also learning about each other and how you work. There's a lot of setting expectations on both sides about how you expect them to be working, and what sorts of things they're expecting from you, as a manager. Lots of context going on here. This is also an important one-on-one because it sets the tone for how the rest of the one-on-ones that you have together are going to be run. If you show up to this first one-on-one, and there's no agenda, no set of topics, it's just all up in the air, then that makes it seem like the rest of them are going to be run like that, too. If you come to these one-on-ones prepared with a collaborative agenda, ready to go, take meeting notes during the one-on-one, then that's setting them up to understand what it's going to be like to have these one-on-ones and puts them in the right mindset for doing those same things as well.

Specifically, some of the topics that I really like to cover in these first one-on-ones include hobbies and life outside of work, because social things are super important for building trust between people. You spend so much of your time together with people that you work with, so why not get to know them as humans too. Making sure that expectations on both sides match, very important that this is double-sided, and not just setting up your expectations for them. I like to ask some specific things, like how they like to receive feedback or praise. Because, for example, not everybody likes getting public shout-outs where you're saying, "Great job, this person, for doing this thing," and they prefer to receive that in private. That's a really important thing to know, before you start doing it publicly. I also like to ask how they like to communicate, because some people really prefer communicating over Slack, just having quick written back and forth. Then others like having video calls and are better communicators that way. That's very good to know ahead of time.

Hybrid-specific, understanding their balance of remote versus office work, probably going to be very dependent on the company and the setup that you have. That sounds like something very important to understand as well, and to share how others in the team are doing that as well. Lastly, I really like ending the call, or the in-person meeting, or whatever it is, with understanding how I can be the best manager possible for them, and understanding what value they like to get out of one-on-ones. What specific things I can do to make sure that they're happy at work going in their career and doing well. There are so many other things that could be asked and I linked inside to a blog post by Lara Hogan,, with just a whole bunch of questions for first one-on-ones. It's a really good resource to check out.

The next type of one-on-one that you'll probably have is the feedback one-on-one. The feedback one-on-one isn't necessarily an entire one-on-one dedicated to just feedback. Feedback is obviously something that should be talked about in other one-on-ones as well, just as a regular thing whenever you have feedback, sharing that with people. Once in a while, there are one-on-ones, for example, if you do a quarterly review, end-of-year review, whatever it is, there's usually some formal review performance process. Those meetings where you talk about that, I think should really happen in one-on-ones. Because one-on-ones hopefully by the time you're getting to this place are spaces where you build trust with people on your team, and they're nice, safe spaces to talk about what's on your mind without fear of repercussion. For feedback one-on-ones, if you schedule an entire separate meeting that's just called like performance review, or something like that. That makes that meeting scary and it's not that same regular space at the same date and same time as people are used to for the normal one-on-ones. It gives a bit of a different air to it and might make people feel a little bit more on guard. I really love doing feedback one-on-ones in the normal one-on-one recurring cadence.

Hybrid one-on-ones actually do have a bit of a key twist to them as well. For example, if you're working mostly in the office with other people, and there are remote people who don't come into the office, very often, you might see their work and view their contributions differently, because you'll be physically exposed to the other people and seeing the things that they're doing. While the work that the remote people are doing might be a little bit more hidden and might be happening in channels that you don't have access to, or you don't check very often, and people might be doing things that are very important, but you don't know. It's possible that feedback that's being given, is skewed more favorably towards people that you work in person with. One of the ways around this that I found I really love doing is, in my one-on-ones in every agenda, automatically gets added this one heading that says, "What have you done in the last week that I do not know about, or I probably don't know about?" This is giving people permission to brag about things that they've done that I wasn't involved in. Because I've found when I was even working just fully remotely with everyone on the team, there were things that people were doing that I wouldn't find out about until the year-end review process when their peers would write, "I admire that this person is doing all of this work." I would have no idea. It's not through any fault of my own, it would be happening in channels that I wasn't a part of.

I found that giving people this explicit expectation for them to brag to me about the things they're doing, really make sure that that stuff comes to light and isn't getting hidden. That starts to level the playing field a little bit more when it comes to giving people feedback and understanding what they're doing, and helping them grow in their careers. Another aspect to this as well is that hybrid one-on-ones are very important to continue doing, because if you have people on the team who are working fully remotely, then you need to make sure you have these one-on-ones so that you're building up trust with them and getting to know them, and spending that dedicated time alone with them. Because it's really hard to give people constructive feedback if you don't have that foundation of trust already. Having that trust is going to make that feedback hit very differently. I really think that having recurring one-on-ones with everybody makes things better.

The next type of one-on-one you might have is a coaching one-on-one. Coaching is a very specific thing, which is when you're helping someone develop a new skill and maybe showing them the ropes and making sure they understand how to do it, and answering any questions when they run into blockers. It also involves actively checking in with them and making sure that they're progressing, and seeing if they need help with anything. This is a really good thing to do to help people grow and learn new skills. It's also something that can be difficult to do unless you have recurring check-ins where you can see how people are doing, because otherwise, both parties have to remember to talk about it with the other person, and it can add yet another meeting to calendar. I love using one-on-ones as this specific time slot, where coaching is one of the topics that comes up and we can talk through whatever it is that people are learning about. It's a really good way of staying on top of that and not letting it fall through the cracks.

The next type is a social one-on-one. There's a lot of advice online that says that one-on-ones should always be work related and work topics. I know that, at the start, I was also saying that it's very important to not just go into meetings and say like, how was your weekend? What are you eating for your lunch? I do agree with that in principle, but I think that there's a really good balance to be had of having productive one-on-ones where you are talking about very work related topics with the start of social time built into them. It's perfectly fine to also have entire one-on-ones where you're just talking about your personal life, your family, your hobbies, and things like that. It's not for everyone, not everyone likes to talk about their personal lives with people at work and likes to keep a little bit more of that separation. I don't think it's something that should be forced if people are uncomfortable with it. All I have to say on this is that I do think that it is ok to have entire one-on-ones where you are just talking about this, as long as it's not the norm.

After that, peer one-on-ones are also something that are very common for managers to have with each other. As a manager, your team is just the engineers who are on your team and report to you. The people that you work with directly cross-functionally are your immediate teams, so your peers. For example, for me, that would be head of design, head of customer success, head of marketing, and all these people who lead these other functions in the business. They're the ones that I have to collaborate with so that we can make sure that projects are getting done and that everybody knows what's going on. It's very important to have dedicated time with all of those people so that you can talk about things, like what your priorities are. As an engineering manager, it helps me so much to understand what would be helpful for the sales team, or what kinds of issues the customer success teams were running into that the engineers can help solve. Things like current priorities. Things that we could do in the future to collaborate, or projects that are coming up that we might need to focus on and work together on. Also, just how we can work better together. There are so many things there that are important, because the better you collaborate with the cross-functional leaders that you work with directly, the better the members of each of your teams will work together as well.

Troubleshooting Common One-On-One Issues

There are a few common issues that happen to pop up pretty often with one-on-ones. I know, I've definitely run into my fair share of issues over the years, and I want to address a few of them, to make sure everyone understands how to avoid them, or how to fix these. The first one, and probably one of the most common ones is that people are a little bit resistant to having one-on-ones in the first place. I've definitely run into this where maybe somebody at a previous company didn't have a very good time with one-on-ones because they weren't useful, didn't really get anything out of them. They felt like a waste of time. They think that all one-on-ones are going to be like that. When you try to set them up with them, they are a little hesitant to actually follow through with them. Maybe they'll say something like, "We don't have to have one-on-ones. I'll let you know if there's anything I want to talk about. We'll chat then." Which I don't think is quite the right way of going about creating that trust and that relationship with them.

There are certain ways that you can try to fix this issue. The most valuable one really to understand is making sure that they understand the purpose of one-on-ones, because that's often something that just hasn't been communicated to them. Same as when I started one-on-ones, and I was never told why we were having them. I think that if they understand the value that they could be getting out of them and the types of things that should be discussed, then that will go a long way towards creating the willingness to go through with them. I recommend even just having like a go-to document saying this is why we're doing it that you can share with anybody new who joins the team. Another thing you can do is if you have weekly one-on-ones with everyone on your team, maybe don't start with weekly with them and start instead with biweekly. Because when you have a biweekly cadence, because there are two weeks that elapse between every time you have these meetings, there's just more stuff that accumulates that you could be talking about. The one-on-ones that you do have might be a little bit more dense, and dense with topics. If you're talking a lot during these, then it will seem more valuable than even if it's the same number of topics, but spread out across two different meetings.

Also, very important is for the first few agendas, you might have to put a little bit more effort into adding most of the topics to them. Especially if they aren't really bought into the concept of one-on-ones, you're going to have to add topics that solicit ideas from them, solicit opinions, and really get the conversation going so that you're not sitting there awkwardly on the call just waiting for the time to run up. I recommend also asking a lot of questions when you do that. Write a lot of notes to demonstrate to them. It's a very good visual way of understanding like, we did talk about a lot, and this was a good use of our time. Those notes are things that are very good to refer back to later on. For example, if you ask someone, what do you think about this process, and they tell you what they think and they have an idea for making it better. Then coming back to them at the next one-on-one saying like, "Your idea was great. We went and implemented it. Here you go. This is how things are better now because of that conversation we had," which might not have happened outside of a one-on-one. That's going to show immediate actionable value that has happened from this one-on-one, and will increase buy-in.

The next very common one as well. Even if people are bought into the idea of having one-on-ones and agree that they should happen and understand their value, they still might come to them and say, I actually don't have anything to talk about. On the same page, as with the last issue, a really good way of going about solving this is by asking a lot of open-ended questions that solicit their opinion on things. I really like to have a set of questions every week that I can always fall back to even if there are topics that are added to the agenda, and we happen to run through them really quickly. I really like asking things like, what did you think of the announcement that the company made last week? Or, what do you think that the product and engineering team could be doing better to increase collaboration? Just open-ended questions where many opinions are possible, there's no wrong or right answer. Those types of things will get people talking, and it will make them feel good that you're asking them their thoughts as well because everyone likes to feel heard. Earlier, I mentioned how one-on-ones could also be used as a good time for coaching. This is a great use case for it too, where if there's nothing that people are really talking about, you can come up with a career goal with them, or something they want to learn, some new skill, and use the one-on-one time to work towards that goal. Ask them questions, see how they're progressing, and see if they need any help with building up that new muscle. This is a really good time to spend doing that.

The next issue, emotional overload. This is actually an issue that I don't have a terrific solution for. I just wanted to call it out specifically as something that happens, to point out that you're not alone if this does happen. It is very difficult as a people manager, because people share very awful things that are happening in their lives and very happy things that are happening in their lives, too, which is great. It's very difficult in one-on-ones to go through this emotional whiplash, where you're hearing about really awful things that you can't solve in their personal lives, which is very hard when we're used to solving things for them at work. It's hard going from hearing something very sad in one call to maybe going and seeing someone in-person talking about something super happy, and having to react appropriately in both situations while trying to internalize what's going on. I don't have any great solutions for that. It is difficult.

Another thing that I hear often is that people in senior positions don't need one-on-ones. I don't believe that this is true. I think that it is true that people who are in senior positions won't necessarily need as much day-to-day support in their jobs. Maybe they don't need as much face time with their manager for understanding how to deploy code, how to write certain things, how to go about working together. They still do need a lot of support in terms of making sure that their feedback is heard, asking them for their opinions, giving them context. Making sure they're aligned. Helping them progress in their career. There's so much about one-on-ones that isn't related to helping people directly with questions that they have about their job. I don't think that senior people should be left out of that, because it's very important to continue spending time in developing the careers of people who are doing really well.

The last issue is something that is a little bit more hidden. It's something that I started to discover a little bit more recently, but differences in cultural expectations. I read this book a while ago called, "The Culture Map," by Erin Meyer. It talks about how different cultures have different ingrained views about things like how to communicate. What actually is effective communication? How to go about making decisions. Who should make decisions? What the manager's role is. Especially, in a hybrid and remote environment, teams are very often made up of people from all around the world. At one point, my team, every single person on the team was from a different country. That means that there are very different opinions on how things should be done. The best way of addressing this and making sure that everyone's on the same page is to create a common team culture and have that written down for many key aspects so that everyone knows what's expected of them specifically. I do recommend reading the book to get the full picture, because it's very interesting, what types of things come into play when you look at culture.

How to Get Started

If you're brand new to one-on-ones, and you're starting them out for the first time, or you want a bit of a reset on them and realign expectations with everyone, here's what you should do to get started. Number one thing is, communicate the purpose of the one-on-ones. Make sure that everyone's on the same page and understands that. Say it verbally. Write it down. Just make sure that people truly understand why you're doing these. Also understand for yourself, why you're doing them, because it's one thing to have people understand what value they can get out of them. It's also very important for you to know why you want to do them so that you have your own list of topics and goals in them, and ways that you might want to guide the conversation so that you're making the most out of them with your team as well. After scheduling them, make sure that you're also contributing to the agenda collaboratively with them, not just having your direct reports constantly come up with the agenda entirely on their own every single time. Add a few topics so that it kickstarts the conversation. Then, after a period of time, ask for feedback about how they could be more useful. It takes a lot of iterating to get these right. If you ask for feedback about what you could do better, what should be changed, what would make them more useful to them, you're going to get to the ideal version of one-on-ones much faster.

How to Know if One-on-Ones are Useful

Once you've been having these one-on-ones for a while, you're also going to want to know, are these actually useful? To do that, my biggest tip is just ask them, do you enjoy your one-on-ones, or do you dread the interruption? Because even if you're not talking about work, even if you're only having social time, every single one-on-one, if they at least enjoy that time with you, then you're building trust and building up that relationship, which is what really makes people work better together. That's at least a core component of the purpose of one-on-ones. If people dread the interruption and would rather focus on whatever it is they're working on, something key is not working and you need to take a step back and reevaluate how the one-on-ones are going.


To recap everything, how to have an effective hybrid one-on-one. Number one, most important, understand their purpose and value, and communicate that purpose to your team. Make sure you have them often. Try to cancel them as little as possible. Contribute to the shared agenda, both of you, not just the direct report. Ask a ton of questions, solicit their opinion so that they feel heard. Use one-on-ones as a space for giving them feedback and providing coaching so that they can grow in their career. Most important, though, is iterate on the format. If something's not working, don't just stick with it and see if it gets better. Also, don't be afraid to personalize them to each person. Different people, especially at different levels in their career, are going to require different things from you. It is perfectly ok to run one-on-ones completely differently between different members of the team. It's nice to start off from one common format, but then don't be afraid to iterate and personalize them.


For more information on how to build trust with your team members, have great one-on-ones, and learn more about the stuff in general, I recommend these three books, which are amazing: "The Making of a Manager," "Resilient Management," and, "Effective Remote Work." My book, "Remote Engineering Management," is also now available wherever you buy books.

Questions and Answers

Stanier: Could you elaborate on how to get better feedback from one-on-ones, when my manager is not involved with the team's day-to-day activity? It's a very common thing. What I often hear from a manager is, yes, everything's fine. It's all good. When the manager is not involved with the day-to-day team, how do you get that content in?

Sunderland: That can be so frustrating. I find, no matter what, even if your manager is involved, day-to-day with your work, just asking them point blank for feedback isn't usually going to get very good results. What I do, because my manager also isn't directly involved with what I do very often, is just saying, what do you think about how I approached this particular situation? Or, here's what I'm thinking, do you agree with how I'm going to go about this? Do you have any thoughts on what I could do differently? Just being really specific about what I want feedback on, is going to make them think more about examples and be better at giving that direct feedback. Also, just letting them know that that's something that you want, will put them on guard and make them look out for instances that they can give you feedback. I find that to be really helpful.

Stanier: Have you ever had difficulty with getting your direct reports to share their own topics in one-to-one agendas rather than you coming up with them yourself? If so, what would you do to encourage your reports to be more proactive in sharing their topics to make it less one sided?

Sunderland: Because even once you get to the one-on-one, even if you as the manager are able to come up with discussion topics and get them actually talking, it can be tricky to get them to think of adding their own topics to the agenda in the first place. My suggestion here would just be to be, make it really explicit that that's an expectation that you have of them. Let them know that you want for them to come to every one-on-one with at least one topic and that you expect to see that written down on the agenda. That way, they'll think about it more often. They'll start doing that, because maybe it's unclear that that's really why you expected them. That's how I normally get people to start thinking about it a bit more.

Stanier: Do you also keep private notes, or do you keep all the notes shared?

Sunderland: I keep most of my notes shared. I'm really big on transparency. I want to make sure that if I write down something about someone, they can see it so that in case I misunderstood, they're able to correct me and make sure that I have the right information about what it is we discussed or decided. I do have some private notes, because I find my memory can be a little bit embarrassing. Sometimes, I know somebody has a dog, I'm not going to remember the dog's name. I'll keep a private note just so that I can look at that quickly, and remember those little facts about them, so that at the end we're able to have more normal conversation. For things like that, private notes are great, but otherwise, I would recommend keeping everything public so that they know exactly what's going on.

Stanier: Is it ok to ask your manager to cancel a one-on-one, if there really is nothing to talk about?

Sunderland: Yes. A lot of advice often says cancel. Even in my talk, I said cancel them as unfrequently as possible. I think that there's always nuance in situations, there's always room for going against the grain. I've canceled many one-on-ones with my manager, because sometimes I just really need the deep focus work or I just don't feel like talking that day. I just need time to like go take a nap instead. It is definitely ok with canceling one-on-ones, no matter who you are.

Stanier: What if your manager is not interested and doesn't put anything on the agenda?

Sunderland: You can send them my talk, and hopefully there are some ideas there about why one-on-ones are so important and why the manager does have to contribute a lot to them, as well. As a manager, your job is to be there for your team and be asking questions and be giving feedback to people, and doing all this stuff. Yes, I think communicating why it's really important to you that you do have these conversations and what you're hoping to get out of them, might make them understand why it's so important to be doing these.

Stanier: I love the idea of having clear expectations to different types of one-to-ones that you have. What's your strategy to decide what format you use for your next session? How do you draw the cards?

Sunderland: It's not so much that I decide on my mind, this one's going to be about coaching, and this one is going to be about feedback. Feedback may be like right now we're at the end of the year, and so we are having actual end of year performance conversations. I like to have a cadence of when certain conversations happen. Feedback, for example, like very efficiently happens every six months at Fellow, and things like coaching and career planning, I like to do once every two months or so. Otherwise, whether it's a social one-on-one, or you're just asking a lot of questions, and talking about work, really depends on what's going on in the company and the team at the time, and what kinds of topics people are bringing to agendas. The topics, or the types of one-on-ones I outlined are more so just like, buckets of topics that you can pull from. It could be a one-on-one that is an amalgamation of all of those things at once.

Stanier: You mentioned a lot of collaborative shared notes. What do you recommend for structuring your one-on-one content?

Sunderland: I work for We're a meeting management productivity software. Basically, the nice thing about Fellow is that we're purpose built for meeting notes. We connect directly to your calendar and your meeting notes are associated with that calendar event. If you have a recurring one-on-one, all of your notes are one on top of the other, so it's really easy to keep a history of those. You can save a template that you like. I like structuring my one-on-ones where it's pretty much freeform, but I like asking specific questions each time, and those get automatically populated. Using even Google Docs, or Evernote, or whatever note taking tool you use, anything is better than paper and pencil, which was just shared with nobody, and only for your eyes. Anything is great. I definitely think meeting-specific tools like Fellow are really helpful for making sure that topics are remembered, that you're getting reminders to add topics as well, and it keeps agendas and notes top of mind.


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Recorded at:

Apr 14, 2023