How to Manage: Rising from Middle to Senior Management

AMY BERNSTEIN: You’re listening to Women at Work from Harvard Business Review. I’m Amy Bernstein. No matter how ambitious and talented you are, rising up and out of mid-level management can be slow going for reasons beyond your control, like when the person who’s in the higher-level position you want has been there forever and might stay there forever, or when the company doesn’t have a business need or the budget to upgrade your job title and salary from senior to executive.

When you’re ready to take on more, and especially when you’ve been waiting and trying for what seems like a very long time, the prospect of remaining stuck in the middle indefinitely is suffocating. My three guests have been there. They’ve gotten themselves out of there, and now they’re here to direct, inspire, and reassure you. Two of them are COOs: Megan Bock and Lauren Reyes. Megan rose up through the insurance industry and switched to tech a few years ago.

MEGAN BOCK: I think in early days, I perhaps wasn’t as effective at articulating that I wanted to do more. As more time passed, I got more explicit.

AMY BERNSTEIN: Lauren rose up the ranks at the YMCA.

LAUREN REYES: I joke with my mom all the time that I feel like I’ve been not qualified for every job that I’ve applied for and gotten. And in actuality, I was qualified. I had what it took, but there’s always that self-doubt.

AMY BERNSTEIN: Before becoming executives, their careers had stalled, but they managed to find ways to accelerate them again.

LAUREN REYES: I had no idea prior to walking into that meeting that I was going to say those things.

MEGAN BOCK: When you apply to another organization, they see you for who you are today, and the potential of what you’re willing to sign up for and do.

AMY BERNSTEIN: They’ll recount the conversations, decisions, and networking that jump-started their advancement. Before we hear their stories and advice, let’s start with Cynthia Pong. She used to be a public defender before becoming a coach, and now she advises women of color who are looking to move into positions of senior leadership. Cynthia, let’s start with sort of the basic stuff.


AMY BERNSTEIN: How common is this feeling of being stuck in your career?

CYNTHIA PONG: Oh, it’s extremely common. I feel like I encounter it at all levels, although I will say that there is a particular set of feelings, I think, that come with folks who are in the middle of their career. So they’re mid-career, they’re in middle management, or they’re kind of at a director level, and there is this feeling of both stuckness and also slightly a bit of being lost, not knowing where to go next, not knowing what to do next, that kind of thing.

AMY BERNSTEIN: What is it about that sort of midsection of the career that makes it treacherous?

CYNTHIA PONG: Oh, great word for that, because I do think there are a lot of potential traps that we have to look out for, especially as women. So, first of all, being a middle manager, being in a middle position is tough at baseline. You are often caught in the middle between upper management and what they want, and your direct reports who are looking to you for certain things and have probably a great deal of expectations as well.

So, you both have to lead them and you have to manage up. And oftentimes, on both sides, people want different things, and they also may not be clear about what they want either. So, there’s a lot of miscommunication that can happen. And frankly, often it’s a thankless job, Amy, because you face that ongoing background dissatisfaction from both sides, and that is very frustrating for a lot of women, I find, because there’s nuances in terms of gender there.

AMY BERNSTEIN: So, what are those nuances exactly?

CYNTHIA PONG: Right. So, one of the stereotype biases against us as women is that we are communal, or we are expected to be communal, and to look out for the collective, and to put the team, the mission, the company always ahead of ourselves, and combine that with the fact that there’s often deep conditioning that we’ve been subjected to over our lifetimes to seek or want to promote harmony. So, people-pleasing, if you will. Imagine how frustrating that is, and you’re in a position where inherently, intrinsically, there are going to be people upset at you from both sides, continually.

AMY BERNSTEIN: Right. It’s just very hard to make the twain meet, your bosses and your direct reports, or the teams that you manage. Let’s talk about moving from the vast mid-management level into senior management. What makes that so particularly challenging, especially for women?

CYNTHIA PONG: Right. I would say it comes down to three things. One, the function of it being a numbers game. What I’ve noticed at certain companies, Amy, where they have, for whatever reason, created a lot of middle management roles. So, there’s almost a bloat at that level. So, that’s why you feel it so specifically at the mid-level, because it feels like less of a jump from individual contributor to middle management. And then from there, it really tightens up, and there’s a big jump down in terms of roles at the VP, SVP, et cetera levels.

So, one, the numbers are kind of against us in that sense. Two, there’s a pipeline issue in the sense that sometimes for these very sought-after C-suite roles, there’s somebody who’s been “in line,” quote, unquote, or being groomed for that role for 10 years or something that we didn’t even know about, and there’s absolutely no way we could have made ourself that person, or done anything to advocate harder for ourselves.

The third thing is that the higher you rise up in the organization, the stakes are intrinsically higher. And so, that’s where gender discrimination, other kinds of racism or bias, conscious or unconscious, may result in women, and especially women of color, not getting the benefit of the doubt as much as men. It’s that whole, “You have to have the track record,” versus “We see your potential.”

AMY BERNSTEIN: I also wonder how relationships play into this.

CYNTHIA PONG: Yeah. I am so glad you brought that up, because I think that is something that sometimes as women, as relational and as strong on building relationships as we are, I think we could be a bit more strategic about who we are making ourselves visible to, and that is not always people who are in our same company or organization.

You have to be visible to enough of the right people so that enough of those people will become your sponsors or champions, say your name in rooms that you’re not in, nominate you for awards and stretch opportunities, make key connections for you. Those are the key to advancement, and sometimes we may deprioritize that.

AMY BERNSTEIN: I also think it’s important, particularly for women who don’t ask for what they want, to say that they want the promotion to the VP level, to the C-suite, because you have to let people know that you’re ambitious. But you also need to say, “If I don’t get this…” You don’t have to say it explicitly, but the message can be, “This is important to me, and I’m not going to stick around for 10 more years waiting for it.”



CYNTHIA PONG: That is so powerful. However, there’s many reasons why we may feel that we cannot do that. I think one thing that’s a gendered thing for us as women is we feel extremely accountable to our word. And it’s like, if I say something and I don’t follow through to the tee 100,000%, and early or whatnot – like, the over-delivering – then we may take it very personally. The hyper-self-criticism can kick in. And so, that prevents us from actually even saying certain things out loud, but it’s so key. But that’s why having people you can trust to practice saying out loud to first, then you can practice saying it, hear yourself saying it, then maybe in a few months, you can say it to someone who is a decision-maker.

AMY BERNSTEIN: So, be my coach, let’s say, 20 years ago.


AMY BERNSTEIN: I got a call. In my business, I would have been a senior-ish mid-level manager at that point, and I got a call from a headhunter about an editor-in-chief job, which would have been the high-level job, the one I secretly wanted but would never have had the courage to say out loud. And I responded with fear and insecurity. My first thought was, “Why would they want me?”




AMY BERNSTEIN: And I said, “No, I don’t think so.” And then I lied and said, “I’m really happy here.” And I could feel my heart racing. I could feel myself just kind of… The voices in my head were shouting. What would you have said to me then?

CYNTHIA PONG: Oh, this is a tough one. First, I would have talked about, let’s unpack what’s actually going on with the voices that are screaming in your head. Where are they coming from? Literally, what are they saying? You actually hearing it outside of your head or getting it on paper, whatever is possible, is actually going to change how you feel about it as well. That’s the first set of things. We have to unpack that, and if we don’t… I don’t even care about this one editor-in-chief position, right? There will be others. If we don’t actually unravel this, it’s going to show up again, and it’s going to stymie you again.

AMY BERNSTEIN: Yeah. So, I hear fear when I talk to younger women or other women who are being offered that great leap of a promotion in some form. I often hear what you just described, and to me, it sounds like fear. And what I find myself saying is, when you feel yourself responding with fear, that flight kind of response, what you owe yourself is a little space to think.


AMY BERNSTEIN: And what you say in the moment is, “I need a little time to think about this. Give me 24 hours,” whatever, and then go talk to people you trust.

CYNTHIA PONG: Yes. Just like you said, you can always hit pause. When we feel rushed, that’s when we make the most mistakes. So, do not be complicit in false timelines on yourself. You go right back to the person, to the headhunter, “Thank you so much for your inquiry. I will get back to you.”

AMY BERNSTEIN: That’s really, really useful. So, if you really want to move up at your company, there has to be a role for you to move into, right?

CYNTHIA PONG: Ooh, okay. I love this. Yes. And I feel like the underlying assumption is that the role to move into has to preexist. It has to exist already.

AMY BERNSTEIN: So, okay, is that a bad assumption?

CYNTHIA PONG: Maybe, maybe not. I think there’s always room for opportunity. Why not propose a new role? This is part of that showing initiative and actual leadership, honestly, that I think is important for us to demonstrate and show rather than tell as women. But if we’re like, “Oh, I noticed that there is this gap here, and the company could really benefit from a cross-functional role in X, and the title could be this or that, doesn’t really matter, but the scope would be such and such, and I want to know what you think about that.”

AMY BERNSTEIN: And what you said there was such an important point to make. The company can really benefit.


AMY BERNSTEIN: You’ve got to make the business case. It can’t be all about you.


AMY BERNSTEIN: The company doesn’t exist to make us happy.

CYNTHIA PONG: It doesn’t.

AMY BERNSTEIN: Well, thank you so much, Cynthia. I really wish I had known you all those years ago, but I’m so happy to make your acquaintance and have this conversation with you now.

CYNTHIA PONG: You are most welcome. It’s been such a delight.

AMY BERNSTEIN: And now to those two COOs I mentioned earlier, Megan Bock of Federato, which is a company that uses machine learning to assess risk, and Lauren Reyes of the YMCA of Greater Boston. Megan and Lauren, did you feel stuck before you made it to upper management? Describe what that was like. Lauren, why don’t you go first?

LAUREN REYES: Sure. Yeah. So, I’ve had the privilege of working in one organization the majority of my professional career, but definitely didn’t feel as though I was always valued and appreciated as much as I felt I should have been in certain spots.

So, I can definitely recall in particular a couple of times. One was when I had been in some place for almost 10 years, and I think it was them seeing me always as the person I came into the organization as and not as the person I felt I had grown into, realizing that it didn’t matter what I did. They thought I was great, but there were some folks that were always going to see me as that young 20-something-year-old who started with the organization, and I decided that I needed to go in order to be seen as something better than that.

AMY BERNSTEIN: Yeah. What about you, Megan?

MEGAN BOCK: I absolutely felt stuck in that sort of middle management-type role. You’re responsible for keeping your team motivated, keeping them trained, keeping them rowing in the right direction. I was very attuned to making sure that I did a really good job, that I understood what all of the expectations were, and was doing all of that and more.

I found myself in a couple of different situations, being a middle manager, leading a team of individuals, but having the senior role above me open. So, I was essentially doing both. And so, threw my name in the hat to say, “Hey, I’m doing a lot of this role now and would like the opportunity to take on that title, take on that responsibility.” And I was passed over for that promotion, was told that they needed to hire someone from the outside who had done the role before, had a proven track record.

And that’s the kind of thing that actually gets me really frustrated, because how am I going to get experience doing the role if you’re required to have experience doing the role before you’ll have an opportunity to do the role? Right? So, it’s a little bit of a catch-22.


MEGAN BOCK: The guy they brought in was, in fact, not super expert, didn’t bring additional value, and I now had to train him on how we did things around here, and was continuing to do a lot of his work that he was now delegating to me. Now, that was the impetus that led me to leaving that company and taking on a new role elsewhere. But that expectation that you have the experience has been a notable theme, and the hard part is, you don’t have the experience until you have an opportunity to have the experience.

AMY BERNSTEIN: Yeah. Well, as you said, a total catch-22. Lauren, what about you? Did you reach out to senior management and say, “I want a promotion. I want a senior role”?

LAUREN REYES: Yeah. So, I will say, I know I’m fortunate in the organization I work for. The culture is a little bit more “kumbaya” than I think in some for-profit spaces, or even in some other nonprofit spaces. And so, I am fortunate that I felt like from the most part… When I started, I had supervisors who really cared about my development and my growth, and that they really poured into me. But what I was finding was that it was still going to be on their time frame and not on my time frame. And I know lots of times, we give so much flak to the younger generation because they’re like, “I want to come out and I want to be a CEO on day one of my employment,” and we realize that that can’t happen, right?


LAUREN REYES: And so, I really took some time to think about, “Is this what I’m doing? Am I expecting something more than what I should expect at this stage of my career?” I always came into spaces for the most part being the youngest person of my peers. And I think when you’re also the youngest person and then one of the few females in the space, I think that can also be something. And then I have typically been, in a lot of my career, the only person of color in that space as well.

And so, it’s like this multitude of things that I’m walking in and trying to really evaluate, and make sure that I’m not feeling something that’s not really there or making excuses of something that I’ve just made up. And so, I did have conversations with my supervisor to say, “This is what I want to do. I’m ready for more, and this is why.” I felt like it was very important for me to come with the examples of how I had proven myself and the examples of how I had done the things they asked me, and exceeded those things, and taken on additional projects.

And in this particular instance, when I felt stuck, I was proposing to make a transition to shift from an operational role to a leadership development role. And I felt that I had done a lot of things that proven why I had the experience in that field, why I would be a good fit for that position. And when I was having those conversations with them, they said, “Oh, yes. You have done these things. We agree. This is great. We’re really interested in seeing you in this role.”

And then nothing really happened with it. And I followed up, and I said, “I am just checking in to see what the status of this is.” And they said, “Oh, we’re still having some decisions and conversations about what this role might look like,” because it was going to be a new role in the organization. And then it was only after they found out that a YMCA from a different state was recruiting me to come work for them. And it was only then that they said, “Oh, well, maybe we need to think about this role, and if it’s something that you’d really be good for.” And so, that was frustrating in a lot of ways, because I felt like it shouldn’t take you being concerned that I’m leaving for you to see my value.

AMY BERNSTEIN: So, you’ve talked a little bit about this evaluation process. You kind of size yourself up. You size the organization up. Lauren, talk us through how that worked for you, “Am I ready for this?” How did you go about answering that question for yourself?

LAUREN REYES: Yeah. It’s interesting, because in my role now every day, even in my role as COO, I ask myself all the time, “Am I ready for this?” I don’t know. But definitely, I think when I started my career, I would have thought that I was ready for everything and had all the skills I needed. And yes, I can learn, but I’m already pretty good. And I think, obviously, as you’re confronted with different challenges every single day, you realize, “Oh, there are a lot of things that I still have left to learn.”

And I went through a development program where the whole goal was really focused on helping people go from a program-level role to become an executive director. And in that, part of it was self-evaluation. You did a lot of self-assessments. And at the end of it, you get this report that was really robust, and the feedback that you get is all feedback that you’ve… It’s a self-assessment. Nobody else put in on this but you, and a lot of the things that came out of there were really eye-opening for me.

AMY BERNSTEIN: Like what? Give us some examples.

LAUREN REYES: Oh, the one that jumps out the most, because I argued about it, even though I self-assessed, I did a self-assessment, was, it said, “Lauren has little regard for people’s health and personal well-being.” I shared this with my friend, and I said, “What are they talking about? I feel like I’m a fairly caring person.” And she said, “Oh, no.” And she rattled off pretty quickly three examples.


LAUREN REYES: This was in a pre-pandemic world, so I’ll preface that, but it was somebody… And the example she gave was, I had a staff person call me one day and said, “Hey, I have a sore throat. I’m not going to be able to come to work today.” And I said, “Okay, fine.” But I was upset. I was annoyed. I rolled my eyes. I mean, the person was on the phone, so they didn’t see me, but I said, “A sore throat? Oh, come on. Come into the office.”

And it was some of those instances that once I had time to reflect upon how I evaluated myself, how people were viewing me, and I said, “There’s nobody else that is causing this issue except me. There’s no one else that’s telling people who are sick, ‘Oh, you should just come into the office.’” And even though I didn’t say those words to them, that was the attitude that I had. So, obviously, that came across in any kind of conversations I was having with them about if they needed additional time or if they weren’t able to maybe meet assignment deadlines because they weren’t feeling well. And then there was another one about how I would get really excited about the beginning of a project, but I would really lose interest partway through, and then sometimes not complete it with the same enthusiasm that I had started the project. And I was like, “Man, that is 100% true.”

And I think what it allowed me to do, though, is also better evaluate what roles I should be in. Do I need to be in that role where I am the doer doing it every day, or am I better in a strategic role where I’m having that conversation and generating ideas to then pass on the actual day-to-day, in-the-detail work to somebody else?

But it’s very interesting when you have to hold the mirror up to yourself and recognize, “These are skill gaps that I have,” or “These are emotional intelligence gaps that I have,” and “How do I take control about going and fixing that rather than kind of using it as an excuse for why I’m not getting the roles I want or why I’m not excelling in the ways that I wish I was?”

AMY BERNSTEIN: Yeah. So, Megan, how about you? Was there a process where you sort of evaluated yourself to figure out whether you were ready for that big leap into senior management? What did that look like?

MEGAN BOCK: So, I joke about this, because if you don’t laugh about things, you might otherwise cry. But the year I turned 40, I was a senior vice president in a large insurance organization, and that happened to be the year that I, number one, got divorced; number two, left my job; and number three, did some real soul-searching on what it was that I wanted to do going forward. And so, less about the feeling-stuck-in-a-middle-management kind of role and wanting to break through to that next level, more around… Just being at the next level isn’t necessarily enough. Right? There’s still an element of, are you passionate about the things that you are doing on a day-to-day basis? Do you get motivated to show up to work in the morning and actually coach people or set strategy, or ensure execution is happening? And the answer for me was no. The role that I was in, even though it was a senior leadership role, and I felt like, “Okay. This is where I thought I wanted to go,” it wasn’t filling me up in all those ways. And as you just heard, there were other ways in which I felt stuck. There’s just a lot of integration and work that goes on because work isn’t the only thing that impacts our lives. There’s a whole lot there.

AMY BERNSTEIN: Yeah. I want to ask two questions of both of you. One of them is, was there a trigger that sort of set you on this path into senior leadership where you said, “You know what? Enough. I’ve been doing the job. I’m not getting the promotion,” or in your case, Lauren, “I’ve got all of the technical skills. I’m working on the soft skills. I’ve had it”? Is there a moment where you just said, “I’ve had it”? Lauren, I’ll ask you first.

LAUREN REYES: Yeah. So, in the original example I gave, there was probably not that definitive moment. In a later time period, I definitely had that moment. I was in a situation where they promoted somebody who was my peer to become my supervisor. And when I asked about why that decision had been made, they said, “Oh, we felt that you needed some more wins.”

AMY BERNSTEIN: What does that mean?

LAUREN REYES: Right. Right. What does that mean? They couldn’t really articulate it well. And what I then did was, I said, “Well, this is what I see. This is what I see that other individual has accomplished, and this is what I see I have accomplished.” And it was nothing against this individual at all. We were just serving different communities. The community that individual was serving was an affluent community, where there were boundless resources.

And so, people had money and they came, and they did, and they partaked, and revenue was great. The communities that I was serving were not that way. We were having to do a lot more with a lot less. And so, I said, you know, “let me explain to you the wins that I feel that I’ve had, and this person has those too, but they’re different. And if you were to put that individual in my situation, I don’t think they would’ve been as successful because they don’t understand how to work within the finite resources that we had available.” But I realized in that moment that I wasn’t going to change their opinion on that. And so, at that moment, I actually said to… I still sometimes don’t know what possessed me to say this, but we had our leadership transition. And so, it was the COO at the time that I was sitting with. It was the first time I’d ever met him, and we’re having this conversation. I’m explaining to him that I was frustrated that they’d promoted one of my peers without even a conversation prior to about what that was going to look like, and I said, “It’s clear to me that you all don’t see my value here. And I know my value, so I’m going to go someplace that will appreciate me.” And so, I told him, I said, “I’ll be gone by the summertime.”


LAUREN REYES: And he kind of just gave me this look as if to say, “Oh my gosh, what did I just step into?”


LAUREN REYES: Because he was new, and he was making decisions under the guidance of people who had been there longer than him. And so, I think in that moment, he started to think, Did we make the right decision? And I don’t know Lauren, but is it worth losing her? I’m not sure. And so, he just said, “I’m really sorry to hear that. I really hope that we can do something to change your mind.” He’s like, “I don’t really know you well, but I’ve heard good things about you, and I hope that you will stay with us.” And I did not.

AMY BERNSTEIN: Yeah. Yup. Yup. Well, okay, so now I want to hear your story of being fed up, Megan. Tell us.

MEGAN BOCK: I had a similar experience. I wouldn’t say there was a switch flip for me, but I had the opportunity. I’d been promoted a few different times, but still at that middle manager level. And I had a lot of exposure to executive leadership, and I had a multitude of opportunities where I was building skills, where I was running projects, driving impact, and had expressed my desire to grow my career, take on that senior-level role, and was sort of rebuffed. Right? You’re in that succession planning. It’s a promo within two to five years, and I’m thinking to myself, “Okay. You’re trying to say the things that are going to make me feel okay, but two to five years? That’s a lot.”

AMY BERNSTEIN: Whoever stood up and cheered at, “Let’s talk about this in two to five years.”

MEGAN BOCK: Right. Right.


MEGAN BOCK: And at the same time, I was witnessing the way those executive leaders ran their businesses, showed up, set strategy, made big decisions that had real impacts on the organization, on the people who I had led at various points, who I interacted with on a day-to-day basis, and I was just feeling like, “Oh, I can do it better than that.” I have a way of actually driving forward the values that our company says we hold, and pulling that through into strategy and execution and leadership, and wanted my chance to prove that out.

AMY BERNSTEIN: Good. Well, so one of the things I noticed as I look at both of your career paths is that you were both willing to take risks to get to the level you wanted to reach. So, Megan, you moved from one insurance company to another. You did a tour of duty as a consultant, right?

MEGAN BOCK: Absolutely.

AMY BERNSTEIN: You also hired an executive coach. You knew something needed to change for you, and you were going to make it change in order to achieve this level you wanted. Talk us through that whole line of thinking, that process.

MEGAN BOCK: Yeah. There’s a couple of points that you just called out, and they sort of build on each other. I’ve talked through that frustration and feeling of stuckness as a middle manager. And given all the experiences I had had, I realized, You know what? It may be a risk, but it’s worth taking it to apply for and become a senior-level leader in another organization, because the company where you’re working has their own best interests in mind. Right? It’s not personal. It’s business, but they’re used to me in the role that I’m in where I’m making a good impact. And so, there’s a deterrent. There’s a downside to promoting me on.

When you work in another organization or apply to another organization, they see you for who you are today. They see you for the accomplishments that you’re able to articulate, and the potential of what you’re willing to sign up for and do. And so, that was a bit of a risk, but paid off in my case, and that’s how I made that shift to senior-level leadership. The sort of next shift that you describe is hanging up my hat on the insurance industry.

My entire career, nearly 20 years was spent in that one industry, in that one trajectory. And now I want to do something different, and I’ve got to figure out, A, what it is; B, how to do it; and C, gather the courage that’s needed to do it. So, having an executive coach really helped me to do that, gave me some frameworks to kind of map it out, understand what’s the stuff that I actually love to do, and what might that translate into.

AMY BERNSTEIN: And so, when you hired that executive coach, did you hire that coach with the idea that he or she would help you get to this promotion?

MEGAN BOCK: That specific coach was aimed at helping me find a career pivot that is going to be more fulfilling. It wasn’t with the end in mind of where I am now, but I will say, doing that work, being open to that risk, and having the courage to try new things is very much what has led me to the COO role I have today at a technology company that is serving the insurance industry, and it’s a nice full circle for me. But there’s no end in sight, right? I am still learning, still growing, have a different but also incredible executive coach now.

AMY BERNSTEIN: Great. So, Lauren, you kind of pushed yourself out the door, but talk about… You know, you actually relocated first for a VP job in Tampa, then a COO job back in Boston. How did that willingness to take the leap factor into your career path?

LAUREN REYES: Yeah. So, I knew very early on when I started at the YMCA that I love the organization, and I love the work that it did, not just in my local community, but across the globe. And I felt strongly that I would probably not leave the Y. They also have a great retirement plan, so I was like, This is probably the place where I’m going to be for the long term. And fortunate enough that I made a lot of good connections over the years with people from across the country working for the Y. And I knew that I was passionate about serving people and helping to contribute to positive change in the world, but I didn’t necessarily always see that exact thing replicated at the Y where I was. But I knew that it existed at YMCAs out there, and whatever version that looked like for the next evolution of Lauren and who I was. And so, when I got into these spaces where I was feeling stuck, where I was feeling like, “This space is no longer aligning or serving me,” it was comforting in a way to know that I could have change but still also have familiarity.

And so, I could seek change in a new role, in a new location, but with an organization that I knew, and content that I felt really comfortable I could do well. And so, I was fortunate that I had a really good support system. I was married at the time, and he was very supportive of me following my path and where I wanted to be. I have kids that very much look at a new city as a new adventure, and that’s not always the case. And so, a lot of the reasons, I think, people are afraid to relocate didn’t exist for me. A lot of people say, “Oh, my kids would be devastated,” or “My partner maybe wouldn’t be supportive,” or all of the different reasons. And thankfully, a lot of those people were very supportive in my life and made it very easy for me to really look at the opportunity and say, “Is this a good opportunity for me, for us? Can I go to a place where I feel like I can really help contribute and make things better? And does it keep me on what I felt as my journey and my path?”

And I say that because I was in a program years ago, and they brought up the idea of career mapping, and they said, “Where is it that you want to be when you retire? And what age are you going to be when you retire? And then what you need to do is then work backwards, and then I’ll tell you how many different career moves you have left between now and when you want to retire.” And that was really helpful for me, because it allowed me to see… Because of that great retirement plan, I planned on retiring early. And so, I said, “Okay. I don’t have a ton of moves left to make necessarily, and I want to make sure that each one counts and gets me closer to where I want to be.”

I think sometimes when we do things without intention, we end up following and chasing shiny objects, or things that maybe sound like a really good idea, but really aren’t putting you any closer to where you ultimately want to be. And so, having that career map done, it was easier for me to look at the opportunities and say, “Is this really something that’s just good for right now, or does it really help get me closer to where I ultimately want to be?”

AMY BERNSTEIN: Well, your story really resonates with me, that self-reflection, but also that honesty, that really astringent honesty that you don’t have that many career moves left. So, that sobers you up real fast. But then also the courage, both of you, Lauren and Megan… it took guts to make those moves. You were willing to take the leap with the idea that, “You know what? It might not work, but I’m not happy right now, so I need to do something.”

So, you are taking responsibility for yourself, and that really resonates for me. It’s how I got to Harvard Business Review, was realizing… I mean, I don’t know if I said I was stuck when I was thinking about it, but I sure had to own what part of it was my responsibility, and then I had to really put myself out there and try for something I wasn’t sure I was going to get. It represented a huge step-up for me. And moving across the country, the prospect of moving from San Francisco to Boston, was somehow less daunting to me than the prospect of finding out that, you know what? I actually didn’t deserve the job – the fear of rejection. That was almost harder for me to deal with. So, that’s what I mean I put myself out there. I sort of dared myself to handle that, and man, am I glad I did. But that fear of rejection is part of what kept me stuck in place for too many years. Does that resonate for either of you?

LAUREN REYES: Yes. I joke with my mom all the time that I feel like I’ve been probably not qualified for every job that I’ve applied for and gotten, so there’s always that fear. And in actuality, I was qualified. I had what it took, but there’s always that part of you, that self-doubt, that just says, “This is not for me,” or “I’m not good enough,” or “This is not my opportunity.” And I think it definitely makes sense that we have that little inner voice that tells us all these different things, and we sometimes just have to knock it out and say, “No, I’ve got this.”

MEGAN BOCK: One thing I just want to add. And agree, having the courage to take the risk is absolutely a factor. I also think that the so-called risk is blown up to feel bigger than perhaps it really is. And hear me out for a moment. It’s like, as I’m thinking about moving companies so that I could take on a promoted position, the risk is, I don’t get that job, and then I stay where I am, and there’s really no impact, or the risk is, I do get that job, and I hate it.

Well, what’s the outcome? It’s not that I end up penniless and incapable of caring for myself, right? It’s like, okay, well, then you find a new job, or you go back to the old company. I share that only to say, I know I have felt ingrained in me that these kinds of things are very risky, but that’s my inner critic, the one that’s telling me, “Oh, well, you may not be successful at doing this.” But if you actually step back and you look at the data, it’s like, “Oh, this isn’t that big of a risk.” And so, it is one that I’m willing to lean into, because the upside potential here is absolutely worth it.

AMY BERNSTEIN: And the downside, the certain downside is staying where you are.

MEGAN BOCK: Exactly. Exactly. And recognize that not everybody has the same set of circumstances, and the risk could be different to others. But I do think that there is a bit of like… It’s our evolution. We have a negativity bias. We think that it is more risky than it is. And if you look at it, it could actually be a much easier swing to take.

AMY BERNSTEIN: And particularly, if your goal is to get the promotion you believe you deserve, to reach a level that you feel that you have earned, there is way more downside to not taking the leap. I have another question for you. So, Cynthia talked about the importance of making yourself visible to influential people outside your organization. Megan, did you think about that as you were thinking about your next big move when you didn’t get the job you wanted?

MEGAN BOCK: That is an awareness and something that I have gotten much more intentional about as years have gone on, probably not something I was doing terribly effectively in those earlier stages or when I was in that middle management position, and I think probably falsely believed that essentially the fastest equation to get me from where I was into a senior leadership role was to do a better job at the specific role mandate that I already had.

And I took that to mean, Okay, spend all my time and energy focusing on doing as best a job as I possibly can on every single one of my accountabilities, when what might have been true is that point that Cynthia brought up, which is, I poured plenty of extra hours and energy into an area of diminishing returns, – making sure that every “i” was dotted and every “t” was crossed on every single attribute of my job description versus redeploying that energy, some of those hours, to being visible, creating relationships, and perhaps creating coaches or mentors or sponsors outside of the organization.

So I didn’t do that at the time, but I think it’s very relevant, because that is a big part of what I did when I was leaving the industry, creating a consulting organization, and then in that consulting organization, getting to know all types of other leaders of other businesses, and exploring the ways in which relationships there could actually create more opportunities to do different and more fun things.

AMY BERNSTEIN: Yeah. That’s one thing that surprised me as I moved up through various organizations, was how important it was to develop an external reputation, and how much more important it got as you moved higher and higher. How does that sound to you, Lauren?

LAUREN REYES: Yes. Networking, I think, is key, and it is a big part of how I’m in the seat that I am in today. So, while I’ve spent most of my career with the YMCA, I’ve been in four different YMCAs. So, each one is operating like its own separate company. And I was very intentional about developing relationships with people that were in different YMCAs, in different roles, in different parts of the country, and having connections to them allowed me to be chosen to serve on national groups and project teams, planning committees for different conferences that gave me a different level of connectedness to the overall organization, but also exposure to different people.

And so, this opportunity, this role that I’m in right now, when it came up, the CEO here was new to the YMCA. He hadn’t had any experience with the organization, but he did make phone calls to different leaders around the Y movement to ask for possible suggestions of people he should talk to for this role. And my name came up from several different people, and that is because I did step out of my own location to ensure that I was building those relationships. And so, it’s definitely been key to me, even though I’ve been with the YMCA for most of the time.

AMY BERNSTEIN: Mm-hmm. It’s very strategic of you. So, I want to ask for you both to give advice to our listener, Maggie, who wrote to us about feeling stuck in her current middle management role. So, let me describe the situation. Maggie’s worked for her company for 19 years. She was promoted to manager about eight years ago. And over the last year, she’s applied for a number of senior management roles, and has been vocal about wanting to be promoted. But so far, nothing has panned out.

She’s actively seeking career mentorship from leaders within and outside her department, and has completed leadership courses that she’s been nominated to attend. And while she’s described her leadership style as more quiet and that she prefers to lead from behind, as she puts it, she can be more authoritative when she needs to be. Despite her efforts to be seen as a leader, she’s having a hard time getting other leaders to see her leadership potential.

While her performance reviews are excellent, and the feedback is essentially to, “Keep doing what you’re doing,” she’s been told indirectly that she’s not ready for senior management, that her career role suits her because she’s good at it and that she’s too nice. Her mentors have suggested that to help her case, to support her case, she should start offering her opinion on things that she’s not an expert in to help leaders see her as a source of insight on more than just her narrow areas of expertise. So, what do you guys think of that advice?

LAUREN REYES: I would not do that personally. People can sense when you don’t know, and I think sometimes it’s more dangerous to offer advice on something that you really have no knowledge of rather than just to be honest and say, “You know what? I don’t know.” I mean, honestly, in this case, I feel as though her organization has shown her time and time again what they think of her and how they value her. And I think they do value her, but they value her in the role that she’s in, and they don’t see her value beyond that.

And so, I would say for her, “are you okay with that?” Because they’ve shown you very consistently that that’s what they think and that that’s what they’re going to continue to do. And the frustration of not having any valid feedback essentially about how she can improve, I think for me, that just says they’re probably not invested in seeing her get promoted or have a future beyond the role that she’s currently in.

AMY BERNSTEIN: Mm-hmm. Anything to add, Megan?

MEGAN BOCK: I completely agree with Lauren. Eight years in a current role with stellar feedback, but zero support or direction towards developing into that next role? The message is pretty clear. I guess I would also encourage her not to take it personally, to really separate that out. Her employer does not get to decide her inherent value. Right? She is deciding her inherent value. And in fact, the data says she’s adding incredible value in the role that she’s in. And if she’d like to take on new challenges, then it probably is time to look for other places where there might be more opportunity to add value immediately in that sort of higher-level way.

AMY BERNSTEIN: So, do you think there’s any way for her to change the perception of her potential within the organization? What do you think, Lauren?

LAUREN REYES: This is probably a personality test between how somebody would choose to go about this. For me, I would look at it and say, “I don’t want to be in an organization where after 19 years, I still have to fight for you to see the potential in me.” So, for me, I would say, “It’s no longer worth my energy and effort. I’m going to just go on to other places.”

AMY BERNSTEIN: Do you agree, Megan?

MEGAN BOCK: The one extra thing that sort of occurs to me is, how can she maybe try another tactic that would be beneficial to her in addition to giving yet another opportunity to this organization? I don’t disagree that they’ve essentially made clear who it is they are, but there could be a way where Maggie could have some additional fun and build some additional skills, which, if we go back to needing to have the experience before you have the opportunity to have the experience, could fill some of those gaps for her, to the extent that there are opportunities to do work that is independently motivated, that is self-guided, which would be identifying a problem that exists or an opportunity that needs to be filled.

That could be something for her to do some project work, really vet that out. Create a plan. Create a framework. Get people involved. Mobilize teams to sort of fill that need, and have some fun while she’s doing it. It’s an opportunity to potentially engage some other leaders than her direct chain that’s been giving her kind of meh feedback, could be an opportunity to create a sponsorship-type relationship.

And either way, if she finds a niche or a problem statement or a gap that makes her excited to do some extra work, to create solutions, that could be a way to build some skills, build some relationships, and give it another shot to see, “Okay. I’m fulfilling what you would expect of senior leadership,” which is not executing existing strategies and guidance, but instead identifying challenges, solving them, mobilizing the team to do work, and use that as a platform on which to talk about her further development.

AMY BERNSTEIN: Well, the only thing I would add to what you’ve both said is that this is exactly the time to start working on reputation building. Get out there. Go to conferences. Post on LinkedIn, and don’t weigh in on topics you don’t know anything about. That’s not going to get you anywhere. But do project your value, your knowledge, your experience out into the world, and see what it says back to you.

MEGAN BOCK: Yeah, absolutely.

AMY BERNSTEIN: So, this has been great. I so appreciate the candor and your willingness to share your stories. Thank you both, Megan and Lauren.

MEGAN BOCK: Absolutely. Happy to do it.

LAUREN REYES: Thank you.

AMY BERNSTEIN: If Megan sounds familiar, that’s because she first appeared on Women at Work in our Essentials episode about executive presence. In that one, you’ll learn how to improve your own influence and impact, keep a virtual audience engaged, and grow while staying true to yourself. This is the final episode of season two of How to Manage. I hope you got something out of it. I hope you got a lot out of it, actually.

Send me your feedback by emailing Women at Work’s editorial and production team is Amanda Kersey, Maureen Hoch, Tina Tobey Mack, Rob Eckhardt, Erica Truxler, Ian Fox, and Hannah Bates, who’s producing this season. Robin Moore composed our theme music. I’m Amy Bernstein. You’ll hear from me and Amy Gallo in the fall when we’re back with more episodes.

In the meantime, subscribe to the Women at Work newsletter by going to, and listen to the other HBR podcasts that are there to help you manage yourself, your team, and your organization. Find them at, or search HBR in Apple Podcasts, Spotify, or whatever app you’re using right now.

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