SE Radio 551: Vidal Graupera on Manager One-on-One Meetings with Direct Reports

Vidal Graupera, an Engineering Manager at LinkedIn, speaks with SE Radio’s Brijesh Ammanath about the importance of managers’ one-on-one meetings with direct reports. They start by considering how a 1:1 meeting differs from other meetings and then explore how a new line manager should go about introducing meetings with their team. Vidal describes the objectives that managers should aim to achieve, as well as what their direct reports should aim to achieve from these meetings. Key takeaways from the episode include an understanding of the typical structure and agenda for an effective 1:1 meeting, how to start and close the meeting, how to measure the meeting’s effectiveness. Graupera also describes some common challenges in real-life 1:1 meetings and offers recommendations on how to coach line managers to conduct better meetings.

Show Notes


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Brijesh Ammanath 00:00:16 Welcome to Software Engineering Radio. I’m your host, Brijesh Ammanath, and today my guest is Vidal Graupera. Vidal is an engineering manager at LinkedIn. He’s the founder of Managers Club, an online site that helps share resources and experiences to inspire and help managers learn and improve. Vidal is the author of many books, including the Software Engineering Manager Interview Guide, Engineering Leadership Interviews, and Time Management for Engineering Managers. Vidal also maintains a mega list of one-on-one questions on GitHub, and this is how I first came to know about all the brilliant work he was doing in this area. I’ll make sure we have a link to this in the show notes. Vidal, welcome to Software Engineering Radio.

Vidal Graupera 00:00:55 Thanks for having me on the show. Very glad, very happy to be here. Very happy to be here.

Brijesh Ammanath 00:01:00 We will be talking today about manager one-on-ones with the direct reports. We will cover the basics, understand what a one-on-one is, why it’s important, what should an ideal one-on-one look like, how do you measure the effectiveness of one-on-ones, and the common challenges faced by both managers and directs in conducting one-on-ones. While preparing for the session, I also reached out to some of my friends and peers and have a list of challenges they have faced on the ground while doing one-on-ones. We’ll close the session by going through this list and see what suggestions Vidal may have for these scenarios. Before we deep dive into the one-on-ones, let’s take a step back and look at meetings in general. What are the different types of meetings that one usually sees in the enterprises, and how would they classified, Vidal?

Vidal Graupera 00:01:46 Well, there’s lots of meetings, of course. There’s one-on-ones, there’s staff meetings, all-hands meetings. If you’re running scrum, you might have a bunch of agile ceremonies like end of sprint demo meeting, retrospective meeting, sprint planning and grooming meetings. Those are very common in software engineering. Those are, there might be meetings to review RFCs, technical documents, things like that.

Brijesh Ammanath 00:02:14 Right. So, what is a one-on-one, and how is it different from the other types of meetings?

Vidal Graupera 00:02:20 Well, a one-on-one is a very special meeting. I think it’s actually one of the most important meetings a manager can have every week with his direct reports, and it’s private. So that’s one thing. They’re not recorded; they’re not intended to be for other people. So, I think that’s one thing that’s very different about them. And the purpose of the one-on-one, a lot of it is to build connection, understand how people are doing, where the other meetings sometimes are very related to moving a project forward or communicating or downloading some kind of information. So, these meetings are much more personal.

Brijesh Ammanath 00:03:01 Right. And what makes it important? What’s the outcome that we’re looking out from a one-on-one meeting?

Vidal Graupera 00:03:07 There are several things I’m looking for. One, especially nowadays in the realm of people working remote and hybrid, is to build a connection with the direct report. I think it’s important to build a connection with them, find out how they’re doing, how are they feeling, how’s their family, things like that. I think that’s very important. Another goal would be to answer any questions that a direct report might have because sometimes people are afraid to ask questions in a group setting. So, this is a good place for people to ask questions that maybe they’re not comfortable asking in a group setting or just maybe personal to themself — like, what are my possibilities of getting promoted, or what do I need to do to get to the next level? Which leads into career conversation. So, a good part of the one-on-one can be about someone’s career and career progression. And then a one-on-one is also very good way or place to give feedback because it’s not really a best practice, or it’s not really good, to give people feedback in public. So, at a one-on-one you can give people feedback confidentially.

Brijesh Ammanath 00:04:20 Understood. Let’s move on to the next section where we’ll deep dive into the one-on-ones and try to get into the really flesh it out. So, let’s start from the beginning. If you are a new line manager introducing one-on-ones in your team for the first time, how do you go about doing it?

Vidal Graupera 00:04:38 Well, I would tell everyone that I’m going to schedule one-on-ones with you. And so, you could expect an invite. I would tell them my goal in it; my goal is to connect with you, check in with you, give you an opportunity to ask questions, give you feedback. So, I would kind of set a little bit like why I’m doing it. I would let them know it’s not optional. Like, I actually made this mistake when I was starting out as a manager: I made one-on-ones optional for people. I would make, it’s not an optional meeting. Things happen and sometimes you can’t have the meeting, but generally we’d want to have the meeting. So, that’d be another thing I would tell them. So, I would tell them and then I would schedule the meeting with them. See, a lot of — well, almost no engineers are kind of trained in how to do a one-on-one. Few managers are, so there’s actually some blog posts and some eBooks that I found that talk about how to do a one-on-one with your manager. So, I also share these resources with my directs. Some of them read it, some don’t. These are some ideas as to what they might ask or look for in a one-on-one.

Brijesh Ammanath 00:05:55 Right. You touched on quite a few points that we will branch out and there will be questions on those that I’ll come to later. But before that, can you tell me or walk me through a typical one-on-one and is that a recommended structure? Is there an agenda for the one-to-one, or what should be the content of the one-to-one?

Vidal Graupera 00:06:14 Sure. I think the ideal structure has three parts. There’s a part where we start with whatever questions the direct report has, or whatever they want to talk about. So, I usually start my one-on-ones after hello, how are you? Things like that. I might check in, you know, how’s your family? How are you doing? I might say, what do you want to talk about today? And so, this is the point where my direct report can ask any question they have under the sun. And I’m very honest and transparent — usually to a fault. So, they know they can ask me, and unless there’s some reason I can’t tell them, I’ll just tell them. And I’ll try to answer whatever question they have because I don’t want them to leave the meeting with unanswered questions. And if all we do in the meeting is answer their questions and things they want to talk about, that’s okay.

Vidal Graupera 00:07:08 I think that’s okay. Now, a best practice there is to have a sheet — like, it could be a Google Doc, I find Google Docs very convenient — and you write out things that you want to ask your manager or talk about. So, when the manager says, hey, what do you want to talk about today? You’re like, well here’s a couple things — things that happened during the week, maybe you write them down, some questions you have, some things you want to talk about. So that’s really the first part of the meeting. Second part of the meeting would be, okay, is it okay if I give you some feedback? So, this is where I, as the manager, if there’s something I want to give them feedback about — whether it’s good or bad — I’m going to share with them some feedback confidentially and see how that feedback lands. And thirdly, if there’s time at the one-on-one, we’ll talk about their career, career progression, how they’re doing, how their performance is doing, so that there are no surprises later. Sometimes we don’t get to that in the one-on-one, but I like to touch on that whenever I can so that when we have a performance review discussion in the future, there are no surprises. So, that’s the ideal structure for me. There’s three parts.

Brijesh Ammanath 00:08:26 Right. So, to summarize the three parts, the first section is for answering any questions the direct might have. The second is for manager feedback. And the third one is to talk about career and aspirations.

Vidal Graupera 00:08:38 Correct. I think that is the ideal formula.

Brijesh Ammanath 00:08:40 Right. And how long should a typical one-on-one be scheduled for?

Vidal Graupera 00:08:46 That’s a good question. Typically, I do 30 minutes. Some people have one-hour one-on-ones. I think it depends on what’s going on. Maybe there’s a lot of things, maybe there’s a lot of complicated projects. Maybe this is someone who manages a lot of people, so they’re maybe not even asking just questions for themselves, but questions for their direct reports, or they need advice from their manager. So, I think they go between 30 minutes to an hour, normally. I think you have to, it’s going to depend on what the relationship is and what is the job of your direct report. And so, I think you just gauge it, and you can adjust and say, okay, it looks like we’re always running out of time, so maybe we need to make the one-on-one longer, or we always have time left over so that maybe we can make a little shorter. But I think it should be no less than 30 minutes. Ideally, it should be every week. Now sometimes you can’t do that because of other scheduling constraints. So, you could do every other week, but ideally if you could, it would be every week for 30 minutes minimum.

Brijesh Ammanath 00:09:52 Right. And should there be any ground rules for, in terms of time spent talking by the manager and by the direct? Because it’s easy in such situations where the manager takes over the agenda and talks for majority of the time?

Vidal Graupera 00:10:08 Well, that’s a great point. That is why I always like to start the one-on-one with what is on your mind, what would you like to talk about? So that way I try to clear anything that’s on my direct report’s mind before I start talking. Because yes, I as a manager could probably spend the whole 30 minutes to an hour, either giving them feedback or talking about their career or other things. I’ll say one other thing about the one-on-one — I should have mentioned this earlier — a one-on-one is not a one-on-one status meeting. This is a common mistake that I see. It’s not a meeting just go, hey, what’s going on with this project and why are you late? Or things like that. There are other meetings, standup meetings for example, where you can get status of things. There’s status reports people can send you.

Vidal Graupera 00:11:02 So the intention is not for it to be a one-on-one status meeting. And it’s actually going to be very stressful because I know people, if that’s the thing with their manager, then I know it’s just stressful. Now it’s not to say, I mean I’ll be honest, the relationship that the manager has with their direct report is a work relationship. So, oftentimes we will end up talking about work, and about the project and how do you feel the project is going, and do you need any help with the project, and things like that, which are definitely related to the work that they’re doing. But it is not like a one-on-one status meeting, I would say.

Brijesh Ammanath 00:11:43 Right. And also you mentioned that ideally it should be every week.

Vidal Graupera 00:11:47 Yes.

Brijesh Ammanath 00:11:48 So the question is, is there a point where if you do it more than once a week, does it mean you’re overdoing it?

Vidal Graupera 00:11:56 Well, I don’t really know very many people who do one-on-ones more than once a week. I don’t think that’s very common. I mean, if there was that much stuff to talk about, then you could do it. You could make a longer meeting. I will do one-on-ones twice a week with new hires. So, if you’re a new hire, for the first month or two, I will offer to do one-on-one with you twice a week just to have more touchpoints just to make sure you’re not lost or off track. But then after a month or two and you seem to have settled in, then I will go back to once a week.

Brijesh Ammanath 00:12:34 Right. And also in terms of the audience, I understand the one-on-ones you have with your direct reportees, but what are your thoughts in terms of having one-on-ones with your skip team, that is the team members managed by your directs? If you have the time and bandwidth?

Vidal Graupera 00:12:50 I mean, skip level one-on-ones usually happen much less frequently. Maybe once a month, once a quarter, depending on how many skip levels you have or the person has. I think in those, a lot of it is to check in with people, see how they’re doing, answer questions, maybe give them some more context on things that are going on. It’s not intended to be, again, a status meeting. And it’s not intended to be a like, okay, tell me how your manager is doing. It’s not a thing to like kind of somehow evaluate how the manager is doing. It’s not for that.

Brijesh Ammanath 00:13:32 Okay. From our team member’s perspective, what is the team member looking to get out of the one-on-one?

Vidal Graupera 00:13:39 That’s a great question. So, team member, there’s lots of things a team member can do, right? To get out of it. One, like I said, get any questions answered. People always have questions, right? So, you might have a question on a policy, you might have a question on a project. A great thing to ask is about priorities. There’s always more things to do than there is time in the day. So, a very legitimate question you can ask your manager is, hey, I have this, this, and this to do; what do you think is the priority of them? Right? I think that’s a great thing to get out of a one-on-one. Understand about priorities, understand about how your manager sees the value of the work that you’re doing and the context to get information about how you’re doing on your career and on your performance.

Vidal Graupera 00:14:30 Am I performing to expectations? What can I do better? What can I do to exceed expectations? These are questions that you should be trying to get an answer to in your conversations with your manager so that you kind of know where you are, what you need to do, the importance of your work. You should also try to understand a little bit about your manager if you have time. Like, what do they worry about? What are they thinking about? Is there anything you can do to help them, or to help the team? That’s always a very welcome thing when somebody comes and says, hey, I have this idea that could help the team. What do you think? Or do you need help with a certain thing? Or how can I help you? These are all really good things that a direct report can bring up at a one-on-one and hope to get out of it.

Vidal Graupera 00:15:22 So, I think they’re very important meetings because, as I tell people, your manager is a person who has a lot of influence over your career at the company, over your success. They directly, they rate you, they write your performance review, they do all these things for you, and here is your opportunity in 30 minutes to basically make a good impression on them, right? To make a good impression, to find out how you’re doing, what you can do to do better. This is a huge opportunity that if you are a direct report and go into a meeting and don’t try to get some of these things, I think you’re really missing out. I mean, it’s really bad when someone comes to a one-on-one and I’m like, hey, what do you want to talk about? And they’re like, oh, nothing, nothing. I’m like, really? There’s nothing on your mind? Nothing you want to say, nothing to share, nothing that you want to ask me? I think it’s really a wasted opportunity.

Brijesh Ammanath 00:16:21 Got it. So, carrying on that same thought process, what can a direct do to make her one-on-one more effective?

Vidal Graupera 00:16:30 I would say keep a running document of things you want to talk about. Come prepared to the one-on-one. I usually, when I have a one-on-one with my manager or a skip level one-on-one, I will spend time, I might spend 30 minutes thinking about what do I want to ask, what do I want to say, what do I want to share with them? So, I don’t come into the meeting with nothing ready. So, I think it’s important to prepare, maybe spend some time, think about what you want to share with them. Maybe you have a couple ideas, you have these three ideas, what do you think of them? Which one do you like more? Things like that. I think that’s really the best thing you can do is prepare ahead.

Brijesh Ammanath 00:17:16 Right. And from a manager’s perspective, what are some good questions to ask your directs in one-on-one meetings? And are there any broad categories of topics that they should try to cover in the one-on-one?

Vidal Graupera 00:17:30 Well, as you pointed out in the intro, I actually have a GitHub repo with like many hundreds of one-on-one questions if you run out of things to ask. In the beginning, when I started as a manager, I had trouble coming up with things to ask people. So, there’s questions on all kind of categories you can ask there if you want to look at that list. Things about what do you think we could do better in the team? What do you think about the strategy of the company? Who do you work well with in the team? There’s all kind of questions. Is there anything I can do better to support you as your manager? There’s probably like a couple hundred different questions there. I find that I don’t need that as much now because I’m able to be more in the flow with it, right?

Vidal Graupera 00:18:17 Like, I always start out with this question: what’s on your mind? What would you like to talk about today? And once I build enough rapport and trust with my direct report, usually they’ll open up and there will be things on their mind that they want to talk about. So, we don’t usually run out of things. And then there’s usually something I can give feedback on, and we can always talk about career stuff. So, when you have a better connection and rapport, I think it’s easier. But at the beginning, when you don’t know the person very well, there are lists of questions you can use, things you ask them about their family, where did you grow up? Tell me about your background, what was it like to work at this other company? Why did you get into this field? Like, just a lot of kind of interesting questions you can ask to kind of start the relationship.

Brijesh Ammanath 00:19:16 Right. And I’m assuming over time that relationship builds and you’re more comfortable.

Vidal Graupera 00:19:20 Right. And then you need less scripted questions because you kind of already know some things about them so you can go, oh? Exactly. Exactly.

Brijesh Ammanath 00:19:31 Are there any no-go areas that is questions that ideally or topics that ideally you would not cover in a one-on-one?

Vidal Graupera 00:19:39 Hmm. I’m trying to think. I mean, things that you probably wouldn’t cover, you wouldn’t talk about at work anyway, anything that’s I guess kind of, not safe for work, anything that would be inappropriate. I mean you have to be very sensitive, right? I mean, it’s a work environment, right? So, these are not like your friends that you’re out drinking with. So, I would just keep it very professional, and there’s certain things or jokes or stuff that I might talk with my friends about that I would not do it a one-on-one.

Brijesh Ammanath 00:20:13 Right. I think it’s irrespective of the level of comfort, the thing that you need to remember is that it’s a professional relationship, and you need to keep the context in mind.

Vidal Graupera 00:20:24 Correct. Correct. So, I think that that’d be the biggest thing. But other than that, yeah, I would just talk to them about, whatever and we can still talk about TV shows, we can talk about sports, the weather, there’s a lot of like personal topics but just, kind of keep it professional.

Brijesh Ammanath 00:20:42 You did touch on this briefly when we were talking about the frequency of one-on-ones, but once you’ve got it scheduled, the challenges you have emergencies and fire drills, and if something disrupts your calendar, what’s the preferred approach? Should you cancel the one-on-one or should you reschedule it?

Vidal Graupera 00:21:00 I always try to reschedule it, if possible. So, if something comes up — and that happens a lot, that happens a lot to managers because we live in the realm of meetings. There’s a meeting that comes up, I’ll be like, hey look, I’m sorry something has come up. Is it okay if we move our one-on-one, or I need to reschedule it? Almost always people are okay with that. I actually know a couple managers who are really hardcore, and they actually will decline a meeting if somebody schedules it on top of one of their one-on-ones. Because they don’t even want to move the meeting with the direct report because that kind of sends a message to your direct report that, hey this other thing is more important than you. And they’re like, no, you are the most important thing. So, they won’t even move the meeting, which is very strong.

Vidal Graupera 00:21:50 Like, I’m not so hardcore on that. I do think my direct reports are super important, but if it’s possible to move the meeting by 30 minutes and then still talk with them and talk with someone else, then, if that other meeting can’t be moved, right? I’m assuming a conflict comes up that I don’t have any control over and it’s right at that same time. And me and my direct report do have control over when we do the one-on-one, I will try to move the one-on-one if I can. But I really don’t want to cancel them. Canceling them is really bad. I had a very bad experience earlier in my career where I had a manager who would cancel the one-on-ones, and not only would they cancel them, they would cancel them like right before the meeting. Okay. Like I would be like getting ready to meet my manager.

Vidal Graupera 00:22:34 Okay great, I’m going to meet my manager today at three o’clock and I want to talk to them about this and this, and then it’d be like 2:58 and their assistant would go, like, I’m sorry Vidal, so-and-so’s not available, we have to cancel the meeting this week, and I’d be like, wow, you know? That could happen a few times. But that happened a lot, and it really sent me a message that I was not very important to my manager because they did this. They did it to other people, too. It wasn’t just me, but this was someone who really didn’t value these meetings. So, I would never cancel them like that. I will offer this, though, that sometimes your direct report — for whatever reason, like, maybe they’re not in a good place, they don’t want to talk, something’s up, I don’t know what it is.

Vidal Graupera 00:23:22 So, I’ll let people, if they really, or they’re really stressed out about work, I gotta get stuff done. If they want to cancel the one-on-one themself because they have some reason, I’ll let them do that once. They can do that, maybe once a quarter or once a year. Like, okay, you don’t want to meet today, something’s happening, I don’t know. You sure? Yeah, Vidal, I really, I can’t meet today. Do you want to reschedule? No. I’m like, okay fine. We can skip this week. I’ll give you your 30 minutes back. But I don’t let people do that more than once because if they want to cancel it again, then I’m like, wait a minute, why don’t they want to talk with me? What’s going on? So that, for me, would be a red flag if someone wanted to cancel the one-on-one more than once. But one time, things happen so that’s fine.

Brijesh Ammanath 00:24:19 Yeah, I was just wondering, once you see that cancellation pop up and if that’s the second time that you’ve seen it, how do you approach that scenario? Do you pick up the phone and ask him what’s happening or…?

Vidal Graupera 00:24:31 Absolutely. You’re going to get a Slack message, a phone call, something from me. Because if you cancel it then my first question is, what’s wrong? Like, something’s wrong, like what’s going on? And I’m not even assuming it’s something bad between us, but maybe something’s really bad going on in their life, and I want to know that. And I’m going to give them the benefit of the doubt. But if it’s not, then they just don’t want to talk to me for some reason. Then I start to get really worried. So, I’m definitely going to reach out to them and say wait a minute, what’s going on?

Brijesh Ammanath 00:25:01 Yep, call it. Any scenarios when a one-on-one is not needed with your direct?

Vidal Graupera 00:25:07 I can’t think of one. I think it is the most important meeting that you can have. It’s like a manager’s superpower, a one-on-one meeting. You can get ahead of so many problems as a manager. This is what I’ve learned. I can go to a standup, I can go to a status, I can go to a program review meeting, I can go to a meeting to review an RFC, I can go to a staff meeting, and people will say a lot of things, and I can leave the meeting going, oh okay, this is what’s going on. And then I go into a one-on-one with someone and they go, Vidal, let me tell you da da da da da da. And I go, wow, there’s some stuff going on I didn’t know about, you know? And that can also happen when you’re having a one-on-one with your manager, right? They might tell you stuff that’s not obvious in a bigger meeting is going on. So, I would never skip them. No, I think they’re very important.

Brijesh Ammanath 00:26:05 Right. You talked about how a direct should prepare for the one-to-one. From a similar perspective, how should a line manager prepare for the one-to-one?

Vidal Graupera 00:26:16 Okay, so you should kind of be up to date on what your direct report is doing, right? I mean, you should be attending these meetings or looking at stuff… So, you go into a meeting — and this happened to me in the past, right? To the extent you can, you should try to understand, know kind of already what is the status of their work, right? And what’s going on. And that also prevents the need for this kind of one-on-one status meeting because you kind of know. I take notes, we didn’t talk about this, but I always take notes at one-on-ones, and sometimes I’ll take action items. My direct report asks for something: hey, I need a mentor. That’s a great one: I need a mentor. Can’t find a mentor; I say, okay, I’ll try to find you a mentor, or I have a question about immigration or I have a question, or I need a point of contact in something.

Vidal Graupera 00:27:09 And I’ll say, okay, I’m going to go find the answer to your question or this person. So, I’ll take action items sometimes. And then what I like to do is when I go to the next one-on-one I have an answer for that. So, if at all possible, what I do before the one-on-one is I review the action items that I took if there are any. And so, when I come to the meeting I can be like, hey last time we talked about your need for this thing, and here’s what I found out, or here’s who you should talk to, or here’s the answer to your question. Like, maybe they asked me a question, I don’t know the answer. I’m going to have to look it up, let me get back to you next week. So, I think that’s what managers should be prepared to basically have done their homework because it kind of sends a bad signal, right? If a one-on-one asks you something and then you’re like, yeah, let me look into that. And then you didn’t look into it; that’s not good.

Brijesh Ammanath 00:28:02 Yes. And when you take the notes, do you share those notes with your direct?

Vidal Graupera 00:28:07 I don’t because I have a notebook where I keep all my one-on-one notes all together, so it’s not possible for me to share it because then you’d see the notes for all the other direct reports.

Brijesh Ammanath 00:28:22 So, it’s actually a physical notebook?

Vidal Graupera 00:28:24 I keep a physical notebook where I write them down. And so, I found that is actually very useful. It’s one of the few things that I do that’s on paper anymore. Everything else we do is email and Google docs and things like that. But one of the very few paper things I do is this paper notebook of one-on-one notes.

Brijesh Ammanath 00:28:46 Right. You talked about the three parts that should be covered in a one-on-one. How do you close the one-on-one, or what’s the ideal way to ensure that you come out feeling better than how you went into the one-on-one for the direct?

Vidal Graupera 00:29:04 Well, I mean I oftentimes I’ll close with things like is there anything else on your mind, anything else you’d like to talk about? Again, kind of going back to point one, I don’t want people to leave with unanswered questions or doubts. So that’s one way I’ll usually close them out. I’ll ask people too, sometimes I will ask them, sometimes we’ll get a vibe like when you’re having a one-on-one with someone and it’s not very juicy, right? There’s not a lot of stuff to talk about. They don’t have very many questions, you don’t have a lot of things to give them feedback on. And so, I will ask, sometimes if I find myself in that situation where I feel it maybe wasn’t so valuable, I’ll say like, how is this one-on-one for you? How could I make it more valuable for you? Is there anything we could have done differently?

Vidal Graupera 00:29:51 Because I don’t want it to be a waste of time for them. That would be really bad. But it doesn’t have to take the whole 30 minutes either. Like sometimes it’s perfectly fine if things are going well and there’s not a lot of questions and there’s not a lot of feedback to give. So, you don’t have to use the whole 30 minutes to one hour if you don’t need it. I think that’s bad to kind of drag it out. But yeah, I’ll just kind of check in with them how did it go? What do you think of the one-on-ones, and things like that.

Brijesh Ammanath 00:30:27 Thanks. I think we covered a lot of ground over there. We’ll move into the next section, which is around measurements. And I wanted to understand, if you are a manager, how do you gauge the effectiveness of your one-on-ones?

Vidal Graupera 00:30:41 So, I will judge the effectiveness of them in like, part of it’s like kind of the quality of the conversation that I have with them, right? If I feel that we’re having a good conversation and a good connection, then I think that kind of the immediate goal of the meeting is being met. So, part of it’s kind of subjective, like how do I think the one-on-one is going? Does it seem productive? Are they saying that was really good, thanks for the feedback, thanks for explaining that. Okay, now I understand. If I’m getting signals that is kind of working. But, one way to measure this too is we do, and like almost every company I’ve worked at does this, they do upward manager surveys.

Vidal Graupera 00:31:31 So, there’ll be like these 360 things where all the direct reports on your staff will be asked questions.Like does my manager support me, do I understand how my job ties into the mission of the company? Different questions, right? And if you’re having really good one-on-ones and really good staff meetings and your directs are saying, yeah, my manager supports my career goals, yes my manager’s on my side, yes my manager, blah blah, all these questions about your manager. If you’re scoring high on those, then I would say the one-on-ones are effective because that’s kind of the primary way that people are going to get the feeling that you are helping them on their side trying to clear roadblocks, looking out for them, things like that. So those manager surveys are like an objective measure and then for me more subjective just how is the meeting going, did they seem happy with it? Do they seem engaged in the meeting or are they kind of distant and not really happy with the meeting? That would be the other part.

Brijesh Ammanath 00:32:37 Right? One of the challenges I’ve seen in managers surveys is that if you set a high bar for your team, or if a line manager sets a high bar for the team and really holds the team members to account, you usually notice those managers getting a lower score than some of the other managers who might be reluctant to give that tough message to their team members. How do you differentiate that in these surveys?

Vidal Graupera 00:33:03 Well, I mean it’s not related to one-on-ones, necessarily. I think that people want to do, they want to do challenging work, right? Like usually people, it’s like a game, right? I’m just going to make an analogy to a video game, right? If the video game is too easy then people will be bored and lose interest in the game. So, if you’re a manager and you make the job too easy, right? You have very low expectations, you don’t expect a lot, the game is very easy, people are not going to be very engaged in the game. Okay? I mean maybe there’s some lazy people that would like that, but generally people don’t want that. Normally, people want to learn and grow, and they want interesting stuff. They don’t want to be bored at work, right? So, you can’t make the game too easy. If you make the game impossibly hard, like the video game is so hard that you’re dying all the time in the video game, you can’t make any progress, it’s frustrating, then people are going to be very turned off by the game, right? So, if you’re a manager and you’re putting too much pressure, you’re making it very painful, you’re stressing people out, they’re also not going to be very happy. So, you have to kind of find that space where it’s challenging, interesting, engaging, but not so crazy hard that people are like, I hate this game. Because after a point of time they’re just not going to want to play the game anymore. They’re going to go work somewhere else.

Brijesh Ammanath 00:34:33 Okay, got it. Moving on to the next section, which is around hybrid working. I wanted to understand if there is any difference in the way you conduct one-on-ones with your remote directs. Maybe, even before we get into that question, should you be having one-on-ones with your remote directs?

Vidal Graupera 00:34:49 You should, you should have one-on-ones with everyone on your team. Well, let me talk about that. Okay. I do one-on-ones with all my direct reports, even if they’re contractors. I know that some people treat contractors differently, and you have to treat them differently. But as for one-on-ones, I still have one-on-ones with my contractors, right? Because I need them. I mean, the team needs the work that they’re doing, right? So, since they’re part of that work, I will meet with them. Now I will also have, we didn’t talk about this, we basically talked about one-on-ones with manager direct or, direct to manager. But I’ll have peer one-on-ones. I’ll have peer one-on-ones with other managers, project managers, TPMs, any of these people who are surrounding my team, that we depend on to get our job done, I think you should have a one-on-one with them too. And I will also encourage my direct reports to have one-on-ones with people outside the team. So, now let me go back. I think your question was, was it any difference between hybrid and before hybrid?

Brijesh Ammanath 00:36:02 Yes.

Vidal Graupera 00:36:04 Yeah. So, I think the one difference is that I spend more time in the hybrid world basically checking in how you are — how are your kids? How’s your family? (if you have kids, maybe you don’t have kids) How are your parents? a little more personal stuff. I will try to check in on because, see, when we’re in the office I could just go by your desk and I’d be like, hey, how are you? How was your weekend? Like, I could chit chat more with you, right? There was more chit chat opportunity. I could kind of see how you’re doing. Where we’re totally remote, there’s less opportunity, so I will spend more time in the hybrid case doing that. In person, it wasn’t as necessary because I kind of already knew some of those just by running into you in the hallway.

Brijesh Ammanath 00:36:56 Yeah, and flipping it slightly, are there different challenges if the manager is remote?

Vidal Graupera 00:37:03 I think that not really. I mean it’s manager can manage remote just like the direct can be remote, the manager can be remote. I think the only challenges happen when you have a situation where you have a bunch of people — this would happen before — you have a bunch of people in the office and only one or two people remote, right? So, then they can kind of feel that they’re at a little bit of a disadvantage because they’re not all going to lunch together every day or hanging out in the office. So, it can create a little bit of inequity. But I think in today’s environment, what’s really interesting in Covid, when that hit, everybody had to go home, right? So, it was like a level playing field. So, when it’s a level playing field, I don’t think there’s any problems. So, it’s an unlevel playing field, I think there can be some challenges. So, you have to be a little more intentional about it. But I mean it totally works. I mean there’s people who are fantastic managers who are remote.

Brijesh Ammanath 00:38:03 Right. Excellent. We’ll now move into the next section, which is around the pre-work that I did before this recording and trying to get some ground-level challenges faced by managers as well as directs. And I wanted to see what your thoughts are and any directional opinions that you could give for each of these. The first one that’s from a manager who says that my direct does not open up, he refuses to ask questions. So, how do you get directs to open up in the one-on-one?

Vidal Graupera 00:38:32 I think you have to kind of demonstrate, you have to come from a place that you really, you’re trying to help them. It’s non-threatening. You have to try to create a safe environment, right? Like, if the direct doesn’t trust you, right? If they think that you’re there to interrogate them, right? And the one-on-one is not an interrogation meeting, it’s not a let me see what you’re doing wrong meeting; you have to create a safe space. You have to create this psychological safety. You have to really make it clear to them that I’m here to help you, and what you say here is confidential. That’s another rule of one of ones you’re going to talk about. But everything that says one has to be confidential. You can’t be like sharing it with other people. I mean you have to kind of chip away at it.

Vidal Graupera 00:39:20 But yeah, some people are a lot more reserved; some people really don’t want to open up and it takes time. But I think, as you try to understand them, what are their motivations? What are they interested in? Why are they working here? Why are they on the team? Are they there just for the money? Are they there because they want to get promoted? You try to just find out what their motivations are and talk to those and how you can help them meet their goals. I think you can get them to open up over time, but some personality types can be difficult. I agree.

Brijesh Ammanath 00:39:51 Thanks for that Vidal. Moving on to the next one, and I find this quite interesting. So, this again comes from a manager who is a people manager and she basically says, what do you do if your manager does not remember anything from the previous one-on-one? And she’s given more context. She says that she has fortnightly one-on-ones with her manager. She works in a metrics organization, so her direct land manager is different to a functional manager. In every one-on-one share apprises her direct manager about the initiatives and projects that she and her team are working on, but the manager does not seem to be interested because she has to re-explain the same thing in the next one-on-one. How can she correct this and make it a better relationship?

Vidal Graupera 00:40:32 Okay, what I’ve done in my career when I have this kind of maybe skip-level meetings, I will ask my skip-level manager, what do you want to cover at this one-on-one? Do you want me to update you on these things? Do you want me to bring you suggestions? I’ll try to ask them what do they want? Because it seems like what you’re describing is she’s offering the manager some information, and the manager doesn’t seem interested in it. So clearly, there’s a mismatch there. So, I would go to them and say, we’re having these meetings, and what would you like me to present to you? What would you like out of it? And find out what this person wants because it sounds like they want something else than what she’s providing, and hopefully that will help.

Brijesh Ammanath 00:41:25 Right. So have that conversation with the manager and understand his priorities and try to align the priorities so that the one-on-ones are more aligned to the priorities, I guess.

Vidal Graupera 00:41:37 Yeah, I think that’s well said. It sounds like whatever information she’s sharing isn’t a high priority for that manager because they seem they’re not interested in it, right? So clearly, she’s not on the same page with the priorities. So, I would say like what is important to you? What do you want me to bring or share with you that would be interesting? Or just ask them like what, if you have time, ask your manager what are they working on? Okay, we’ve talked about what I’m working on, but I’m just curious what are you working on? What are the things going on at your level? And maybe if she asked that question and found out maybe that manager’s really stressing about something else and might say aha and this is maybe what I could help with?

Brijesh Ammanath 00:42:22 Yep. It’s a very good solution. The next one is from a team member, and he says that I’m a hands-on technologist with line manager responsibilities. So, he’s a manager with functional responsibilities, as well. So, he says with that, with the weekly one-on-one meetings, I don’t have enough time to focus on the actions that come out of the one-on-one. How do I address this? Should I reduce the frequency of my one-on-ones?

Vidal Graupera 00:42:45 Well, that’s a tough situation because they’re a manager but they also have to code or something, right? They have to do this as well. I mean, it depends how big the team is, right? If the team is very small they’re a manager — like, I had a team once that was very small, right? And also, when I had my startup, which was at the beginning, very small right? Then, yeah I could code and I could also do one-on-ones. But as my team grew, I needed to kind of give up the hands-on coding part. And I think once you get a team that’s like maybe five people or so, four or five people, there’s probably like, it’s kind of hard to keep the coding. So, I don’t know how big is their team, so if their team is very big, then I would say one, can you hand off the coding to other people so you can focus on the manager task?

Vidal Graupera 00:43:37 Now, say you can’t do that because you’re expected to code also — at some companies that’s the expectation — and you have too many direct reports and probably your only choice would be to reduce the one-on-ones to maybe every other week. And I may, that’d probably be okay because if you are coding hands-on in the code base, you probably have lots of other opportunities to talk with your team, right? I think the scenarios that I’m talking about is the manager is not necessarily coding; the manager’s not in all these operational kind of meetings with the team all the time. So, the one-on-one is more useful to build connection, but if you’re actually building along with the team, then you probably already have a good connection and kind of understanding what’s going on. So it’s probably fine to do every other week.

Brijesh Ammanath 00:44:23 Right. The next one is from a new line manager, and she asks how long will it take for the awkwardness to go from one-on-one?

Vidal Graupera 00:44:32 Well, it’s going to depend a lot on the people, right? Everyone is different; some people are very open, some people are not. There’s also cultural things you need to consider. Because in some cultures people deal with people in authority in different ways. You have to be sensitive to that. And so, it can take quite a while. It depends on what is the delta between you and the report, right? Between your cultures, your personality, things like that. It might take quite a while to kind of bridge the gap that you can actually build a connection. Whereas if the person is very similar to you in background, then it’d probably be a lot faster.

Brijesh Ammanath 00:45:16 Okay. Got it. The next one is a tough one. So here the line manager says, my direct has told me that she does not see value in the one-on-one and does not want to do it. How do you deal with this, and how do you deal with no-shows? We have touched briefly on this in our previous conversation when you talked about making it, it’s not an optional meeting, but how do you convince the direct that there is value in the one-on-one?

Vidal Graupera 00:45:45 So yeah, I don’t know this manager, maybe they’re not, we’ve talked about what I think the ideal one-on-one is, right? There’s what do the direct want to talk about? Giving them feedback, talking about their career. I don’t know if they’re following that formula. I think if you follow that formula and you genuinely want to help your direct report, it should be valuable to them. But let’s say you’re offering that and your direct report still says no, I’m not interested, right? And I have had people who, they don’t want to do one-on-one, they’re like, yeah, I’m busy, I have to code, I have to work, I have to do these things, right? I have to explain to them your job is just not to code, right? Software engineering, I have a mentor of mine, and he always says software engineering as a team sport, right?

Vidal Graupera 00:46:30 So, I’m the coach of the team, right? You just can’t play on the field and not talk to the coach. It doesn’t work that way. So, it’s not an optional meeting, I tell them it’s definitely not an optional meeting. I want it to be valuable for you. Here’s how I think it would be valuable for you. But if you don’t think that’s valuable, tell me what do you think would be valuable? What do you want to do at the one-on-one? Do you want to sit and, I don’t know, code? Like, what is it that you want? Because I think everybody comes to a job like, I have direct reports that are interested in all kinds of things, right? Some of them are interested in money, career advancement, bunch of other things, right? They want to learn things.

Vidal Graupera 00:47:08 You need to find out what is this person interested in, right? And say okay, how can I help you get that? So, I would start with that hundred percent like, explain to them it’s like this concept, right? Whenever you want to get somebody to do something right, you have to kind of explain to them what’s in it for them, right? So, I think with this direct report it seems like they don’t get what’s in it for them, right? So, it’s like, hey what this is what’s in it for you? And see what they respond and what is their answer to those questions.

Brijesh Ammanath 00:47:37 Yep. Agreed. The other one is from our individual contributor. So, he says that I have these one-on-ones with my manager. I go through my list and then I ask him, do you have anything for me? And he always says, no

Vidal Graupera 00:47:50

Brijesh Ammanath 00:47:51 What should I do? How do I educate my manager?

Vidal Graupera 00:47:53 Okay, this is very common, okay? This is very common, and it’s not great when you ask your manager do you have any feedback from me and they don’t have any, but here’s how you can get some, okay? Because from a manager perspective, this is actually very hard. This is actually a harder question than it seems because you asked me is there any feedback for me? Then I have to think back: okay, well what happened since the last one-on-one? were there any incidents, anything that was done? It’s actually a hard question because now I have to immediately scan my memory and try to think of something and it’s hard. So, here’s what you should ask your manager. Instead you should say, okay, I gave a presentation last Tuesday to the team on this topic. What did you think of it? How could I have done it better?

Vidal Graupera 00:48:39 I sent out this document last week, did you have a chance to look at it and what do you think? So, make it easier for your manager so they don’t have to scan their memory — if they have trouble, right? And this some managers that can easily do this, but let’s say that this manager clearly can’t think of something. Go back over the past week and pick two or three things that you did, and ask for specific feedback on those items. And then, they should have some feedback. I was like, hey, how is my presentation on the team? So, and then they might say, well I don’t have any feedback on that, or let’s say they still try to dodge the question like, well, it was fine. Okay fine. Then you can say, okay, what should I have done for that presentation to have been amazing?

Vidal Graupera 00:49:22 Okay, this is actually a really good question I learned from someone because someone could say it was okay. Yeah, this thing you did, it was fine, it was okay, but it’s hard to dodge the question, what should I have done to just make it the best presentation you ever saw? Because now how do you not answer? Now you have to think of something, right? That they could have improved, right? What’s the delta, right? What’s the delta between this being fantastic and just okay. And you could ask that question.

Brijesh Ammanath 00:49:53 That’s a very good solution. Thanks, Vidal. The next one is from a manager who says that you usually have good and bad feedback that you need to convey back to your direct. How do you position it? Do you start with the positives and then move on to the negative?

Vidal Graupera 00:50:06 That’s kind of a classic question, right? Do you want me to try the good news or the bad news first? But even before I give feedback I will ask them, can I give you some feedback on some things? And sometimes people don’t want to give feedback. You’d be surprised. They might say I’m not in a place to hear it, or I’m upset or whatever. Like, okay then I can give you the feedback later. So, I’d first start I have some feedback for you, and you could say I have some good, some bad, what would you like to hear first? You could, I mean if they totally don’t care then I would probably give the constructive feedback first and then, so maybe end the meeting on a higher note, give the positive feedback afterwards. What you don’t want to do is like confuse them though. You don’t want to give like some positive feedback and then some negative feedback. Then some other positive, you don’t want to sandwich. Like a negative feedback in between two positives because that can be very confusing. So, I would keep them very separate. Like here’s the constructive feedback and here’s the positive feedback and which order you do it up to you. Or you could ask them, but don’t mix them because then it can be very confusing.

Brijesh Ammanath 00:51:19 Agreed. I’m not a big fan of the sandwich method. The last one, from these questions is around a topic we have already touched, which is around taking notes. Over here, the person says my company has a continuous performance system and the firm encourages conversations to be documented in the system. This however, makes the one-to-one very formal and inhibits honest discussions. Are there any particular scenarios where documentation is recommended, or should we just bypass and not document the one-on-one conversations? I think it also touches on the confidentiality part that you touched on from the one-to-one.

Vidal Graupera 00:52:00 Yeah, that’s interesting. I have not worked at any place where you are required to document the one-on-ones. What I would do if I was in that situation, myself, is okay, you have to document some the one-on-ones, but how much detail do you have to put? Right? You could say — like, I don’t know if this is okay, right? Again, I don’t work there — but okay, we talked about this project and I gave some feedback to them. Right? Do I have to say exactly what the feedback was? Or maybe I could, to keep it more confidential, right? Like I could maybe talk about the outline, but then verbally I could tell them stuff. Or again, I don’t know if it’s acceptable there to have certain things maybe off the record. Like, I might say, all right, let’s just go off the record here for a minute. I’m not going to write this down, but tell me honestly what do you think about whatever so maybe you could have that thing with your direct that you could maybe have a couple things off the record to keep if they’re very sensitive. But again, I don’t know what the policy is; I’ve never encountered such a place where you’d need to document what is discussed in a one-on-one meeting.

Brijesh Ammanath 00:53:12 Yeah. I’m not sure. Yeah. The person seems to be mentioning about performance systems, so maybe it’s not about one-to-ones, but it’s more about documenting the performance. Yeah, you’re right.

Vidal Graupera 00:53:22 Or, if you really want to do that, then again, other don’t have is you can have a separate meeting. Right? You’d have the one-on-one that you document and then you have, I don’t know, some other, if you have a question, I don’t know, just talk about it separately.

Brijesh Ammanath 00:53:35 Excellent. Cool. We’ll move to the last section and we’ve covered a lot of ground over here. So, before we close off, what are some good learning resources for line managers to support them in conducting effective one-on-ones?

Vidal Graupera 00:53:47 Yeah, I learned a lot. I took this class — there’s this company called Manager Tools, and Manager Tools has a course action running one-on-ones and it’s covered in one of their books. There’s a couple books that talk about it. There’s actually a book. I can send you a link from another company about how to have a one-on-one with your manager. They sell like a one-on-one software. I don’t use the software, but I thought the book was interesting that they wrote. It was kind of an e-book to promote their product. Had some best practices. I can drop you some links and then you can put them in the show notes if you want. So, there are some resources on that.

Brijesh Ammanath 00:54:21 Sure. Thanks Vidal that if you can send me the links, I’ll make sure I add it to the show notes. Anything we missed or anything you want to mention?

Vidal Graupera 00:54:30 No, I think this has been really a great discussion. I hope this is helpful to people. I think one-on-ones are super, super important. I did not appreciate them fully at the beginning of my manager career and now I can’t say enough good things about them. So, I’m happy to talk to people. Feel free to reach out to me on LinkedIn or anything if you want to talk more about them.

Brijesh Ammanath 00:54:50 Excellent. Vidal, thank you for coming on the show. It’s been a real pleasure. This is Brijesh Ammanath for Software Engineering Radio. Thank you for listening.

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