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When Your Star Employee Leaves


HANNAH BATES: HBR on Leadership, case studies and conversations with the world’s top business and management experts, hand-selected to help you unlock the best in those around you.

If you’ve invested in someone you manage, it’s natural to feel hurt when that person tells you they’re leaving, especially if they’re a strong contributor.

The classic management advice is: Don’t take it personally. Be professional. But it’s important to acknowledge your feelings and work through them — for yourself and with your team.

Today we bring you a conversation about how to cope with the shock, sadness, and stress of losing a star employee with the help of two HBR editorial leaders – Maureen Hoch and Nicole Smith – and Women at Work listeners themselves, who share their experiences losing team members.

In this episode, you’ll learn what to tell your boss and the rest of your team when someone leaves.  You’ll also learn how to manage your emotions in the moment, and then how to revisit your feelings later to process them.

This episode originally aired on Women at Work in October 2021 – in the midst of what was known as the “Great Resignation.” You’ll hear it mentioned in the episode, but the conversation has implications for leading through difficult staffing transitions that are relevant at any time. I think you’ll enjoy it. Here it is. 

AMY GALLO: I am feeling for my friends who manage teams right now because this phenomenon of the Great Resignation is hitting them really hard.

EMILY CAULFIELD: What are you hearing from them?

AMY GALLO: I hear a lot of stories about dreading the “Can I talk to you for a moment?” Or getting the invite from a beloved direct report that it’s unclear why exactly they’re setting up a meeting. And the sleepless nights of, how do I make sure I don’t lose anyone else on my team?

Amy Bernstein: I have to tell you nothing strikes fear in my heart like the email the subject line of which is “Got a sec?” I mean, that —

EMILY CAULFIELD: It never takes a sec.

AMY BERNSTEIN: I always want to say — yeah — I just want to say no.

AMY GALLO: Yes. No, I don’t.

AMY BERNSTEIN: All managers have gone through this, and we know how we’re supposed to respond, and it’s genuine. You want what’s best for anyone on your team. You want them to be happy. You know that no employment situation is forever. But even though you know all of that intellectually, it still hurts. It still strikes home.

EMILY CAULFIELD: I didn’t realize how personally managers take it, which is so sad for all my past managers who I’ve been like, bye.

AMY GALLO: You’re listening to Women at Work from Harvard Business Review. I’m Amy Gallo.

AMY BERNSTEIN: I’m Amy Bernstein.

EMILY CAULFIELD: And I’m Emily Caulfield. Every time I see a manager calm and collected after somebody on their team quits, I wonder, what are they actually thinking and feeling? Well, we’re about to find out.

AMY BERNSTEIN: You’re going to hear from several managers, me included, about how we deal when someone leaves our team.

AMY GALLO: We’re starting with two women who opened up to me about their experiences of losing multiple employees.

AMY GALLO: The first woman works in city government in the U.S. Typically she manages a team of seven or eight; but in 2020, two team members left within a couple months of each other. She’d actually been expecting the resignations. Both had been with the city for a long time and had let her know many months prior that they were searching for new jobs.

WOMAN 1: But it was the next three that were not expected.

AMY GALLO: Those happened in quick succession within a month.

WOMAN 1: Those conversations were hard to swallow. It’s an emotional rollercoaster because at first it was part of the job: people will leave; this is part of being a manager. But then it started being like, OK, this is exhausting. I’ve just learned to be quiet and listen, take it all in, ask what their next opportunity is, and let myself breathe in that space and not react in front of them; because I definitely react, but it’s not good to do that in front of them. And I usually touch base with my boss and say, “hey, this person’s leaving, here are the facts, and this is what I want to do moving forward.” Or, “do you have another idea?” Kind of game plan it out.

AMY GALLO: The resignation that hurt the most was the employee who left for a lower-paying but also lower-stress job.

WOMAN 1: Our workload and our capacity has just been overwhelming, so it was really a cry for help that she can’t sustain in this position any longer. That really got to me emotionally just because we have these monthly one-on-ones, and to not recognize the signs that she was struggling or suffering even and that I thought we were decent friends and still not recognizing that.

AMY GALLO: Yeah. Did it make you wonder what other people on your team were feeling that you weren’t seeing?

WOMAN 1: Definitely. Covid has created this hybrid or remote work for us and I’m a pretty good read on people — I usually know what’s up — and that kind of social awareness has disappeared with Covid.

We’ve been doing a lot more in-person work now, so it’s definitely bringing it back to a better place, but yeah, definitely. I think there’s a lot of that question and what does everyone else think. Especially because by that time that those three left we had hired new people. So, they’re coming in a month to three months into an organization saying, what am I getting myself into? Is there something wrong with this place? I’m like no I promise but maybe it is I don’t know.

AMY GALLO: She’s in it for the long haul, but that doesn’t mean she wants the working conditions to stay the way they are. And fortunately, all those resignations, she said, led senior management to offer more support in making the workload more sustainable. They paused some projects and changed the budget mid-year to add a few new positions.

WOMAN 1: For me, emotionally, I broke down for that because I recognized that they recognized how much we were struggling.

AMY GALLO: She’s also making changes to the things that she can control.

WOMAN 1: If we only expect people to stay two years, then we need to be more efficient with our onboarding. I need to spend way more time with people so I can understand their weaknesses or what they do or don’t understand. For me to feel better about, did I do enough? When someone does eventually leave because that will still happen, but did I put enough time in to onboard this person? Did I spend enough time to truly understand what makes them tick to make sure that they’re getting all of the resources that they need to feel successful in the job?

AMY BERNSTEIN: There’s that feeling when someone quits because the work is too much and the pressure is too much. When you realize, yeah, it’s been too much for all of us, and if this person can quit, why do I have to put up with this myself? I’m also totally stressed out.

EMILY CAULFIELD: And once all your staff quits, then your extra-overworked. Managers are going to be the most burnt out people of us all after this great resignation.

AMY GALLO: I think that’s exactly right, Emily. And that’s actually what we heard from the second person I spoke to was how overwhelming the workload was when she lost so many members of her team.

WOMAN 2: It started around about March of this year, which in the UK, that’s when we’d been in a few months of quite heavy lockdown, and you could see that people were really coming to the end of their tethers.

AMY GALLO: To give us context, how many people do you manage and how many people quit?

WOMAN 2: I have a direct team of six people of which at one point four had left the business. That was a really considerable impact on my life.

AMY GALLO: Yeah. Were you expecting the four who quit to do so?

WOMAN 2: Nope. Definitely not.

AMY GALLO: Yeah. What was your initial reaction?

WOMAN 2: It was a mix. There was some disappointment. Disappointment that they were going, a bit of disappointment that I hadn’t created an environment that was great for them to stay. But also, if I’m honest, a little panic of like, what am I going to do now? We have clients, I work in a service firm. We have to provide what we’ve said we will for clients, and that essentially meant me picking up a lot of things directly. Quite a lot of early mornings, late evenings, weekend working, giving up time, digging in and just doing things.

AMY GALLO: Yeah. It sounds exhausting.

WOMAN 2: Yes.

AMY GALLO: Take us back to perhaps the most painful of the departures. How did you react when they told you they were leaving and what were you feeling inside at that moment?

WOMAN 2: I would actually say it was the first. It almost felt like a bit of a cascade following that, but it was that first one that I think really triggered things. So, I’m a believer that when you are surrounded by your team, lot of the time you get a sense of when people aren’t happy. You get a sense of when they may be off doing an interview. And when everyone is virtual, you do not get that. So, ,when they had the conversation with me, which was obviously over a video call, it was a shock. I wasn’t expecting it from this person. This was somebody that I was very invested in, very invested in their future, where they’d come from, where I thought they could go to, and I didn’t expect it. And you have to maintain that face of like, okay, well, that’s really sad. Can we do anything to keep you? And my gosh, this is disappointing. Internally you’re like, when did this happen? When were you doing this? How did I not pick this up? Why didn’t I know about this? Why didn’t you talk to me? In retrospect, why not ask a few of those questions? In a slightly less impassioned way, but yeah. There was a big contrast between how I felt I had to behave and then how I felt I had to then go and talk to other people in the business about this, versus what I actually thought, which was like, oh, this is dreadful and I think this is going to trigger some other things happening off the back of this, and that’s where we were.

AMY GALLO: Describe the contrast a little bit more, because you were saying you were expected to behave in one way and you actually felt a completely different way. Tell us a little bit more about that contrast.

WOMAN 2: I think as a manager, you really have to show that you are supportive of people’s decisions even when that decision is I’m not going to work here anymore. And that’s what I was trying to convey. Like, okay, I understand this. But to be fair, I didn’t understand it. I didn’t actually understand quite why they had quit and why we couldn’t give them what they were actually looking for. And I think it was a really, very, very different feeling internally versus externally. And then, because you’re not in an office and you can’t go and grab a couple of people and talk about it, it then almost sort of compounded as in, why did this happen and what could we have done? And that’s pretty tough, as well.

AMY GALLO: Yeah. If you weren’t behaving the way you thought you were supposed to, what would you have said in that moment?

WOMAN 2: I think I would’ve been more like, you’re really a star employee within the team. I really like what you’re doing. I really think you have a massive opportunity to move forward. There’s this and this and this. Can we just have a conversation over a glass of wine or something, and tell me more about why you are doing this? Just as a person, not as your manager.

AMY GALLO: What would’ve been the harm of doing that?

WOMAN 2: In hindsight, none. It would’ve actually been great. I think that’s a great learning, which is that you would’ve done that in an office environment. You would’ve been like, come on, right? We’re going to go out at least for a coffee now and have this chat and you cannot do that. I do think that’s been another downside of being just on calls for the last 18 months, is that you cannot as easily break through some of these barriers and emotions.

AMY GALLO: Yeah. It almost sounds like you’re saying that having to have these conversations virtually means you end up being less human.

WOMAN 2: I think you can be. Yes. And I think that it’s partly that work has become a little bit more robotic in some ways. It is very much now like, I have half an hour here and half an hour there. And this call, and then this call. And to then recall, or just remember that this is your team, this is people that you work with, to really bring out that human side, not just like, get through the next thing and get through the next thing.

AMY GALLO: Right. The two survivors on your team?

WOMAN 2: Yes.

AMY GALLO: I’m sorry to use that word, but I think it’s apt.

WOMAN 2: No, it’s great.

AMY GALLO: How did they feel? How did you manage their emotion about everything that was happening?

WOMAN 2: Spending more time actually trying to be a bit more human, trying to talk about things other than, great, this meeting is tomorrow, have you done the deck? And the other thing I did was actually start to admit that I was feeling very stressed and that I was feeling that I’d really had to take on a lot and do the jobs of three to four people, and that I actually couldn’t do that anymore. So I actually slowly started to delegate more things and actually get people involved in more things and have them realize how much was going on and how many things were actually behind the scenes that they didn’t know about. And that’s been very helpful all around.

AMY GALLO: Were there other people at work, your boss, the remaining people on your team, who you’ve talked to over the past, it sounds like, almost six months now about how you felt about these employees quitting and being so understaffed?

WOMAN 2: Yes. And to be clear, my boss has been absolutely fantastic. I just got slightly stuck in that piece around sometimes, it takes more time to hand things over than it does to just do it yourself, and I got very stuck in the, just do it myself. If I just do it myself, I can do it quickly. I can get it done. But I actually had a huge amount of support from my boss, and she very much was like, look, what can I take on? Or, phone me if you need to chat. I didn’t really take her up on that, and I would, going forward. I would actually have more conversations that were just, I need to download this or, hey, I have five competing priorities. Can you just let me talk them through and help me prioritize them? For example. So taking away some of this feeling that I have to make every decision, that’s what I would do differently. Not feel that I have to make every single decision.

AMY GALLO: Right. Right. I imagine you are counting the days until you have a full team again.

WOMAN 2: Yes. So, over the next couple of weeks, help is coming. I have people joining the team, which is really fantastic. I’m very excited. We have a lot of things in place to sort of make them feel welcome and supported. I just feel so much lighter. I feel like, ah, it’s going to be a really nice end to the year.

EMILY CAULFIELD: I’m really happy to hear that things are going a lot better for her now, and that things are looking up with her new employees.

AMY GALLO: Yeah. It does sound like relief is on the way for her. Both my conversations with these women, I still had a lot of questions coming out of them. How do you handle the guilt you feel when good employees leave? How can you anticipate if and when people might leave, and how to handle your boss’s reaction? It sounded like the second woman in London I spoke to had a supportive boss, but what if you’re afraid your boss is going to be mad, or going to blame you? I’m not a manager.

EMILY CAULFIELD: Neither am I.

AMY GALLO: But Amy B, you are. So, Emily and I are going to step aside and let you talk with two other managers at HBR, Maureen Hoch and Nicole Smith.

EMILY CAULFIELD: The three of you collectively have a lot of experience managing people, and I imagine you all have some experience with people leaving.

AMY BERNSTEIN: Yes. Yes, we do. Maureen’s the editor of HBR.org and Nicole, who goes by Nicki, is HBR’s editorial audience director. Thanks to you, both for being here.

MAUREEN HOCH: Glad to be here.

NICOLE SMITH: I’m so glad you invited me to this conversation.

AMY BERNSTEIN: Nikki, let me start with you. You know, we all listened to the manager who is based in London. What stuck out to you from that?

NICOLE SMITH: I think her interview was honest and transparent in her shock, in not knowing completely what to say and then having to gather herself, and so many of us are like that. We try to compose ourselves, but the truth is that we’re human. We’re managers, but we’re human. And so, we feel it when other people that we’ve built bonds with and soul ties to and spend day in and day out, leave us, and the only human reaction is to be shocked, is to self-reflect, maybe even some self-doubt.

AMY BERNSTEIN: And that self-reflection for me, at least, often involves asking myself, well, how much of this was about me and how much of it really wasn’t?

NICOLE SMITH: How many times have we heard that phrase, that people don’t quit jobs, they quit bosses? We’ve almost been socialized to think about this and to believe this. And whether it’s true or not, it’s almost a go-to. What did I do to encourage for you to feel like you don’t want to be here anymore? And the truth of the matter is, there’s a myriad of reasons that people could choose to move on from their current job, from their current organization. At the end of the day, you always wonder, was I a part of that decision?

MAUREEN HOCH: I agree. It’s really hard to separate out the personal from the professional, even if you know. I’ve done this myself. I’ve tried to step back and think about when I’ve left jobs in the past. It was because I was making my own decision. I wanted to do something different. I wanted to do something new. I certainly didn’t think of it like, I’m leaving because of my boss in those situations. But when you’re on the other side of that table, and if there’s somebody who you’ve really invested in and you feel strongly about, and you’ve done what you can to make that job great for them, it’s really hard to be like, okay, well, this is just a business decision and there’s no personal connection here that matters. And I think as I’ve progressed in my own career, I’ve had to realize…I’ve had to remind myself that this is a job, and it’s not always about you. It’s not always personal.

NICOLE SMITH: I heard a phrase a couple years ago that really stuck with me in that, you can’t put a changed person back into an unchanged environment. So, if I’m responsible for changing that person, for developing that person, for growing that person, I also have to be mature enough and broad thinking enough to recognize that person is now changed, and,that means that environment may not suit that changed person anymore. And that soothes me when I think about the person coming and saying, I’m moving forward, I’m moving on.

AMY BERNSTEIN: So, there was an idea that came up, both in the story from the person who leads in the private sector in London, and the woman who is based here in the U.S. and is in a government role, which is that it was very hard for them to pick up signals, particularly now since we’re not all together. We don’t see each other, we can’t observe each other. How did that hit your ears, Maureen?

MAUREEN HOCH: It’s something I’ve been reflecting on a lot lately. The ability to really listen to what someone’s telling you, it is hard in the best of times, and it’s even more I think just complicated in our hybrid world. Because it’s harder to get a read on people sometimes when you’re talking through a screen. I think that is still something that requires time and patience and attention on your part as a manager. So, I have tried to prioritize that. I think I always have, but especially through the time that we’ve been working at home. And I have quite a few direct reports, so it’s something that takes up a lot of my time. But no, I really felt like the ability to communicate and stay connected was going to be critical to my ability to manage people.

NICOLE SMITH: So, Maureen, you said part of it is listening. How do you become a good listener? How do you know that you’re doing that well?

MAUREEN HOCH: I think to be a better listener requires asking good questions. I think that’s part of being a good leader, is not always trying to come in with the answer or the solution to everything, but asking people good questions and not trick questions or questions to get them to be like, so have you’ve been on any interviews lately? It’s not that, but it’s more trying to really probe not just how they’re doing what their work, because they could be doing a great at their work, but it’s more like, how are they feeling about where they are in their career? What do they want to do? How are they thinking about the next three to five years? Are you taking the time to ask them those questions or are you focused on the work you’re trying to get through that day?

AMY BERNSTEIN: So, one of the things that eventually occurs to you, if someone on your team tells you that they’re leaving, is you got to tell your boss. And for me, there’s always a moment where I wonder, is this going to somehow bruise my reputation? Have you ever thought about that, Nikki? Do you think about that?

NICOLE SMITH: Well, I have selfishly thought about that. The succinct answer is yes. Anyone who I work for knows my employees equally as well as me, and I’m usually giving updates to my manager. So, by that time I’m hoping that I feel comfortable to say this person quit. This person said, this is why they’re quitting. And maybe even beforehand, when I’ve talked to my manager, we’ve walked through that, maybe we’ve detected that, maybe we’ve tried to do something ahead of time to prevent that. So, usually I don’t think it’s a surprise by that point, because my manager and I have had that conversation. I will say if someone needs to be on alert and he or she knows that by that point. And keeping that openness has helped make that conversation a lot easier. It’s also opened the door for my manager to talk to my employee and see if they can have them open up in a way. Maybe they don’t want to open up to me because I am their direct manager. So, it’s usually a little bit more collaborative by the time I’ve gotten to tell my manager, this person’s quitting.

AMY BERNSTEIN: How about in situations when you didn’t see it coming? Where you were blindsided and now you’re going to have to blindside your manager, your boss?

MAUREEN HOCH: I’ve had to do that. I remember there was one time I had to call my boss, and I think he was technically on vacation, I remember he was driving somewhere. And I said, “I’m sorry but I have to tell you some bad news.” I almost wondered if I should tell him to pull off the side of the road, but I didn’t need to do that. But I was so fortunate. I’ve been so fortunate in these situations I’ve been through where my manager has been totally like, we knew this person was a risk. We knew that this is something that might happen, and immediately pivots to, okay, what do we do from here?

AMY BERNSTEIN: I’ve been on the receiving end of that phone call. Not your phone call. I have to say that my first response, my first instinct was to take care of the person who was calling me, because I knew how painful a call that was. And then, how do we take care of the team? Because one thing I worry about a lot when someone leaves is the fabric of the team left behind. How do you guys think about that?

MAUREEN HOCH: I think you need to manage, ideally with the person who’s decided to exit, how they want to communicate to people on the team. And hopefully, if they’re telling you, they haven’t already told also their 10 closest friends, you know what I mean? Hopefully you’re one of the first people to get the news so that you can understand, are there people they want to tell themselves? And then I think with the team, you want to be a leader in that moment and you want everyone to feel confident like, yes, this is a change, but we’re going to see it through. I’m the driver’s seat. We’re going to get through this. But on the other hand, you don’t want to act like this is no big deal. It’s like saying, hey, I know this is hard, but let’s think about where we go from here. I think especially when the news is fresh… I think once people have some time to digest the news, then you can move forward. When that news is fresh is the hardest line to walk as a manager. I don’t know Nikki, how have you handled that?

NICOLE SMITH: Honestly, first of all I think people have told their 10 closest friends that they’re quitting.

MAUREEN HOCH: You’re probably right.

NICOLE SMITH: I think that if you are open and honest and conversational and not overly corporate, quite frankly. Not overly structured in expressing how you feel, I think people get it, that people decide to move on. It’s not necessarily a reflection of the culture or the boss or something like that.

MAUREEN HOCH: One thing I’ve always believed in is really recognizing someone’s contributions and acknowledging that in front of your team, is so important. Even if you’re feeling very blindsided, upset, discouraged. If you show that to the team and you don’t recognize and thank that person for all the ways that they’ve made a difference, that’s going to hit your team wrong. At that point, you need to put a little bit of whatever your personal feelings are aside and recognize that person for all they’ve done and celebrate them a little bit as much as you can.

AMY BERNSTEIN: And also, you want the person leaving to feel good about their time here, and to feel proud and to feel appreciated. And you want everyone else on the team to know that people are valued, no matter what. Nikki, Maureen, thank you so much for joining me.

NICOLE SMITH: Thanks for having me.

MAUREEN HOCH: Pleasure to be here.

HANNAH BATES: You just heard Maureen Hoch, editor of HBR.org, and Nicole Smith, HBR’s editorial audience director – in conversation with Amy Bernstein, Amy Gallo, and Emily Caulfield on Women at Work.

We’ll be back next Wednesday with another hand-picked conversation about leadership from the Harvard Business Review. If you found this episode helpful, share it with your friends and colleagues, and follow our show on Apple Podcasts, Spotify, or wherever you get your podcasts. While you’re there, be sure to leave us a review.

When you’re ready for more podcasts, articles, case studies, books, and videos with the world’s top business and management experts, you’ll find it all at HBR.org.

This episode was produced by Amanda Kersey, Anne Saini. and me, Hannah Bates. Ian Fox is our editor. Music by Coma Media. Special thanks to Elainy Mata, Maureen Hoch, Erica Truxler, Ramsey Khabbaz, Nicole Smith, Anne Bartholomew, and you – our listener. See you next week.



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