Career Transitions

DAN MCGINN: Welcome to Dear HBR: from Harvard Business Review. I’m Dan McGinn.

ALISON BEARD: And I’m Alison Beard. Work can be frustrating, but it doesn’t have to be. The truth is that we don’t have to let the tension, conflicts and misunderstandings get us down. We can do something about them.

DAN MCGINN: That’s where Dear HBR: comes in. We take your questions about workplace dilemma’s and with the help of experts and insights from academic research, we help you move forward.

ALISON BEARD: Today we’re talking about career transitions. And here to talk through your questions about that is Whitney Johnson. She’s the author of Disrupt Yourself: Putting the Power of Disruptive Innovation to Work. Whitney, thanks so much for being on the show.

WHITNEY JOHNSON: Thank you for having me, Alison.

ALISON BEARD: So, I know that you have, ad a lot of transitions in your own career. Tell us a little bit about you.

WHITNEY JOHNSON: Oh, yes indeed I have. So, here I am, I’m working on Wall Street. It’s 2005. I’m at the top of my game. I’m making a lot of money. I’m institutional investor ranked and I go into my boss and I say to her, “I’m going to leave.” And she said, “Are you out of your mind? Like this is the best job ever. Why would leave this?”

And I decided to become an entrepreneur, eventually cofounded an investment firm, where we were investing in disruptive stocks, both early-stage and publicly-traded securities.

DAN MCGINN:  Whitney, what’s the biggest misconception about career transitions?

WHITNEY JOHNSON: I think the biggest misconception is that when we look back on it, it looks very, very linear and yet, the reality is you go up and then you step back. And then you go up and then you step back. And you go up and you step back. And I think it’s rare that when we’re making a transition that we’re able to just go from step to step to step. Almost always there’s a step back in order to slingshot forward.

ALISON BEARD: Dan, you want to take it away?

DAN MCGINN: I’ll take it. Dear HBR: I’m a female dentist and I worked hard to get where I am. The hours are good and my parents are proud, but I’m not happy. It’s not what I imagined. And maybe I chose it for the wrong reasons. I yearn for a career without the Monday blues. Leadership is my jam. I love managing people, honing and sharing new vision, problem solving, strategizing. As a dentist in a corporate setting with quotas, there’s a little bit of that, but it’s mostly surgical skills. People say they change careers all the time, but any doctor or lawyer will tell you, after you spend a better part of a decade and a half million dollars getting your license, you do not change. If I could go back I would listen to my passions and what I hope to accomplish with my life. My heart is in leadership and nonprofit management. What can I do?

ALISON BEARD: Whitney, this sounds like a lot like your situation.

WHITNEY JOHNSON: Yeah. It’s hard isn’t it when you, I do feel bad for her because here she is, she’s at the top of her learning curve. She’s on this peak and she probably has a lot of people looking at her and saying, you’ve got everything. You’ve got stature, you’ve got financial security and you’re saying you’re not happy. And she probably feels bad when she says she’s not happy, so she’s in this place of being stuck. And I think that that’s really hard.

ALISON BEARD: It’s funny because if she’s in the medical profession why can’t she seize leadership and management opportunities there? In the medical field there’s great respect for people who play both of those roles. So, I wanted her to think to herself, why can’t I do both at the same time?

WHITNEY JOHNSON: Right, it’s not an either or.

ALISON BEARD: Exactly and so, I think that would be my first question for her.

WHITNEY JOHNSON: Yeah, and it’s such an interesting question, is why do we get into this either or paradigm right? I’m either a dentist or I’m running a nonprofit. Why can’t you do both? I’m thinking about Doctor Jim Kim who’s the president of the World Bank, same thing. He’s a physician. He did Partners in Health and now he’s running the World Bank. And so, this woman has a really interesting opportunity where she could be a dentist moving into a nonprofit or as a manager so then being a dentist becomes her distinctive strength, or she can bring her managerial skills toward the practice of dentistry. And so, the question becomes which does she want to do? It sound to me like her heart is longing to be in a nonprofit managerial role in which case she would bring the dentistry aspect of it as her distinctive strength. One of the first questions I would ask her is, she knows it’s time to do something new and she hasn’t yet. If you haven’t made the jump, why haven’t you done it yet?

DAN MCGINN: I think the issue of some costs is really important here. In the United States not only does medical school or dental school cost a whole lot, but most people have to borrow very heavily. So, they come out not with just this emotional idea that I invested 10 years, but in many cases with hundreds of thousands of dollars in payments to make.

ALISON BEARD: I think that’s not a dentist. I have friends who are dentists and I go to the dentist, but my perception is that dentistry, it’s a profession that isn’t just about the money. It’s very much about work life balance and all of those things and maybe that’s what’s holding her back too.

DAN MCGINN: When you google quitting dentistry, all the top hits are about how to renew your passion for the field. How to recommit to the practice. The idea is, nobody really quits dentistry. They’re unhappy, but they try to find a way to make themselves happy.

WHITNEY JOHNSON: That’s so fascinating because people quit being a lawyer all the time, right? Daily. And so, that’s fascinating that when you’re a dentist people don’t.

ALISON BEARD: What if this woman just decided she hates being a dentist. She wants completely out of dentistry because she doesn’t like looking at other people’s mouths all day. And how does she then Whitney, reposition herself to go work for a nonprofit or some other organization that has nothing to do with the degree that she’s earned?

WHITNEY JOHNSON: I think when we’re tired of something or we’re burnt out, I know for me for example, when I first left Wall Street in 2005, I was burnt out. And so, I wanted nothing to do with Wall Street. I wanted to write a children’s book. And I wanted to start a television show. And so, I think when we get burnt out, there’s this tendency, we kind of go into fantasy land. I want to go do with this, and this and this and it’s completely divorced from anything that we’ve ever done. And so, I would really encourage her strongly, even if she’s burnt out to say to herself, there was a piece of me that at one point in time felt it was important to do this. It’s valuable. I have learned this and this and this and this and this, and it’s important that I own that and bring that to bear in whatever I want to do next. And so, what I would encourage her to do is try to sort out, be like, is she burnt out or does she truly hate it? And then in the process start to look at OK, what are all the nonprofits out there that could benefit from someone with my expertise? So that she’s going to an organization that would be so grateful and happy to have someone who knows something about the medical profession, who is a doctor and then can also get as a kicker, the fact that she’s really good at managing people. And so, that is where I would start, is look for nonprofits in the medical field as a starting point.

DAN MCGINN: One of the pieces of wisdom about career choices that I’ve always liked is from James Citrin who’s a big recruiter at Spencer Stuart. He uses a concept called the Career Triangle. He has at one end of the triangle is job satisfaction. At another is money and at a third is lifestyle. And his big point is you can never have all three at once. If you want more of one you’re going to have less of another. So, clearly she’s making a lot of money as a dentist, she needs to recognize that she can get something that’s more satisfying, but it may mean a hit to her lifestyle and it will almost certainly mean a hit to her financially.

ALISON BEARD: Particularly if she chooses to work for a nonprofit.

DAN MCGINN: Even more so.

WHITNEY JOHNSON: Right. So, she’s got to have a plan. So, it may not be that she’s at the top of this curve and wee, she bungee jumps off and is going to start this new thing. She’s got to have a plan for, OK, next five years or five years from now I want to go do this. How much money am I saving so I have some type of cushion that will allow me to move into this new field? Because again, fantasy land, it’s easy to think about all the things that we’ll get, forgetting that there’s a lot of things that we’re giving up in the process of making that shift.

ALISON BEARD: Yeah, Herminia Ibarra wrote a book awhile back on career transitions and the thing that really stuck with me and the advice that I think is really relevant to this letter writer is this idea of experimenting, small steps. She can’t just tomorrow quit her job as a dentist because she has no idea what that life is going to be like if it is really something that she wants to do. If she’s going to be happy. If the finances can hold up and so, I would advise her to just embrace a sort of long period of transition where she takes on a few unpaid gigs to see whether this thing that she suspects she loves and is going to really make her happy and ignite her passion, truly will do all those things.

WHITNEY JOHNSON: Agreed.

DAN MCGINN: I’d go even further with that. I wonder if she cut back on her dentistry hours, but didn’t try to get completely out of the field, if she just had something that was really positive in her life, even if it was a hobby working with these nonprofits. I wonder if it’s not that she’s running away from dentistry, but once she sort of fills this hole in her satisfaction and her job satisfaction, whether working as a dentist to pay the bills, but her avocation becomes something else. Whether that might be a long term, sustainable mix that she doesn’t need to ditch her dental career altogether. She can make it a smaller piece of her life and put more of her energy and her passion into something else.

ALISON BEARD: Is there a danger in doing that though Whitney? I mean, you in your life made very clean breaks and did you end up being more successful because you took that approach?

WHITNEY JOHNSON: You’d have to ask my husband if he thinks it was a good idea. I think there have been times where, as I reflect on what I’ve done, I think there have been times when I was a bit of a daredevil. I’m probably a bit foolhardy like when I just left Wall Street without a plan. Would like to advise myself to have a plan and so I think for her, for this letter writer, it depends a little bit on how done she is with dentistry, but I think if you can take that approach, where you’ve got this side hustle and allow that side hustle over time to become your main hustle, certainly is the most prudent approach.

ALISON BEARD: And if you could go back would you have done it that way?

WHITNEY JOHNSON: I would have. I would have.

ALISON BEARD: Yeah. What’s interesting about your story is that you circled back to finance.

WHITNEY JOHNSON: Exactly. Exactly. And so, that’s the thing is yes, she did dentistry because it would make her parents proud, but she still did it and so there’s something to be gleaned from that and so, I think whatever she does going forward, a willingness to own and appreciate that is important.

ALISON BEARD: I do wonder for her because she really seems to think that management is what she wants and the way to go, should she go to business school? Dan, you have an MBA.

DAN MCGINN: Lots of people in her situation who are career changers do think about an MBA and one of the things that an MBA is really good at is giving people that second chance to start over again. In her case, she’s already spent so much time and so much money on schooling, I’d be tempted to find a little bit more of a direct route.

ALISON BEARD: Yeah. Especially because she’s intending to sort of go into nonprofit management, not sort of some high flying consultancy career post her MBA. At the same time if she could transition to a company that sponsors people into MBA programs because they want doctor’s to be a management track, I think that might be something she should explore too.

WHITNEY JOHNSON: I like that idea.

ALISON BEARD: So, what is our advice to this woman?

DAN MCGINN: So, first we think that she really needs to explore whether she’s just burnt out and needs a break from dentistry, or she just really hates it and needs to get out of the field altogether. She needs to think about her distinctive strengths and what she can leverage to get into that kind of leadership job. Try to find a place where dentistry is going to be an asset. Something that is at least adjacent to dentistry rather than starting out in some sort of random nonprofit. And she needs to have a plan here. She should not bungee jump out of this job. She needs to think about the financial consequences of moving away from a field where she’s invested a lot and she may have some debt and some payments that go along with that. So, have a plan, try to leverage it and try to think about whether there’s a transition with side gigs or staying a little bit in dentistry, but pursuing something else on the side.

DAN MCGINN: Onto the next letter.

ALISON BEARD: Dear HBR: I’m having a hard time reentering the professional workforce after more than a decade without fulltime work. I’ve done a few interviews and keep getting the sense that the employers were expecting to bring in a 30 of 40 year old. Instead, when I walk in they see a 57 year old with a big gap in employment. It can be like employing mom. And mothering is the main reason I quit my job over a decade ago. I’ve raised two children. One man who interviewed me twisted his wedding ring throughout. Another asked me about my attitude to gay people. Was I being compared with their mothers? Do they see me as old fashioned or am I the one who’s out of date? Being rejected for these jobs has made me feel like a failure. Getting work used to be really easy. And it’s not like I haven’t been doing anything for the past decade. I completed a diploma in environmental science. I’ve helped run the local women’s center and I’m the managing partner of the small farm and breeding operation our family has where I live in New Zealand. I’m interested in a public sector job or business planning in the agriculture or environmentally area and in using technology to support these fields. But in those interviews I felt like all that experience and success didn’t count because I’d taken so much time off from traditional work. I have a high standard of achievement and I felt judged to be less capable than I am. What should I do?

WHITNEY JOHNSON: Oh yeah. So frustrating, right, to have all this experience, all this experience and to have it not be valued. It’s just got to be tremendously frustrating. So, I guess the first step is to make sure her skills are where they need to be and make sure she’s talking about them in a way that is beneficial or makes sense or translates to what the people are looking for.

ALISON:  Yeah, I focused on the story that she’s telling, the narrative. This gap that they might see in her resume is not at all a gap. She was incredibly busy during this time doing things that are very relevant to the field that she wants to go into. If her interviewers aren’t getting that she probably needs to work a little bit on her storytelling because she has a great story to tell.

DAN MCGINN: Yeah, she describes herself as not having had a fulltime job for the last 10 years, but then you get into her story and she was completing a degree, she was the managing partner of her family business. Those are both significant fulltime kind of endeavors.

ALISON BEARD: Not to mention raising two children which is also a fulltime job. I mean —

DAN MCGINN: Right. She’s undervaluing what she brings.

ALISON BEARD: Yeah. Just to take a step back though, her apprehension and her perception is probably reality.  You know, we’ve published really interesting research recently showing that stay at home parents with exactly the same skills and experience on their resumes as people who have been laid off, are as half as likely to get a job interview. 73 percent of women who want to return to work are able to do so which means that a significant percentage aren’t and only 40 percent of that original 73 percent got regular fulltime jobs. So, this is a serious problem that she’s facing. Whitney, your husband took time off to raise children didn’t he?

WHITNEY JOHNSON: Yeah. My husband 12 years ago now, he’s a biochemist so he’s a PhD and when our oldest child graduated from high school, and my husband was ready to go back to work, he was having a dickens of a time finding a job. And what’s interesting is that it’s hard for women to on-ramp. It’s like an order of magnitude harder for men. He did end up on-ramping. He’s now a professor in central Virginia. He got this job because of his network. So, whenever there’s a gap and I think this is especially true for men and certainly true for women, is that people think there’s something wrong. Something wrong with you. And so, when you have a network that can help vouch for you and close that gap and say, here’s this person’s credentials. Here’s what they’ve been doing. Here’s what I’ve seen them do. Here’s what I know they know how to do and by the way, they are a great person to work with. That network becomes even more important. So, I think one of the pieces of advice that I would give to her is it sounds like some of the interviews she’s doing are kind of cold call interviews and that’s going to really lower the probability that she’s going to be able to move into what she wants to do because she clearly has skills. And so, if she can package that and then light up her network, it’s going to make her move back into the paid workforce a bit smoother.

ALISON BEARD: She did have sort of a cohort and her university where she studied for her degree. She has professors there. Surely she’s dealt with people in government and people in business as part of the family farm. I think also thinking more expansively about what that network could be. We’ve also published some interesting research on dormant ties and the idea that you can get back in touch with people who you worked with 15 years ago and update them on your life and your new ambitions. And it works. It doesn’t work all the time, but it can be effective in helping you get to that next step.

DAN MCGINN: Part of what I read in her letter is that she is almost fighting a two front war here in the sense that she’s got this gap on her resume, but she’s also 57. So, she’s, part of it seems like her question is, is it just my ten-year gap or could it just be straight out ageism that she’s dealing with? Is there anything she can do on the age front?

ALISON BEARD: Are you suggesting that she dress younger, get plastic surgery?

DAN MCGINN: I’m not suggesting anything. I’m just asking the question.

ALISON BEARD: Sorry, I was teasing you. [LAUGHTER]

DAN MCGINN: So for instance, technology is considered an industry that’s extremely hard, not just for people at 57, but for people in their 40’s. Some places are going to be more amenable to someone in their 50’s and some places might be less amenable and I wonder if she might be able to find the places that are more amenable.

WHITNEY JOHNSON: You Dan, I think just moved to this sort of emotional side of this and whenever I hire someone or you hire someone, we’re hiring them to do a functional job which is what we’ve been addressing. But we also hire them to do an emotional job for us. We tend to like to hire people who look just like us. If they don’t look just like us we like a shinier version of ourselves and so, when you’re hiring someone and they potentially look like your mother, then that becomes a bit more complicated. I would encourage her to say, OK. If I am playing this mum role, or mom role as I would say, she would say mum. You know, in the organization that she’s working in right now today, what role does she play in those organizations, where she’s being effective? So, for example in the family business, or in the Board of Trustees that she’s on, what role is she playing? What does that look like and where she’s able to say, it’s working really well in this particular instance, role that I’m playing that I’m cast in. How does she find a way to replicate that and look for organizations where she can play that same emotional role? I think that’s going to go a long way toward her being able to find an organization that is interesting and challenging and fun for her and where they’re amenable to having her in a type of role that she would play both functionally and emotionally.

ALISON BEARD: Yeah, it seems like she needs to do a little bit more research on the organizations to which she’s applying. She needs to know that they are welcoming of a sort of diverse workforce. There are organizations that have return to work programs and once she does that, it’s targeting the right places for her. I think she’ll be more successful.

WHITNEY JOHNSON: I do too and as you were saying that Alison, I found myself wondering is this what she really wants? Given her varied experience and background, I’m wondering if she potentially is looking at this job because she thinks that’s what she should be doing, she wants to sort of show that she’s still got it. When in fact she might be a lot happier doing something a little bit more entrepreneurial with smaller organizations who can really sort of look at the breadth of her experience and be like, oh my goodness, look at this gut we’ve just got. So, I would encourage her also just to do a little bit more of introspection alongside the other work that she’s doing in terms of making her skills are where they need to be and figuring out what kind of role she would play within in any given organization.

ALISON BEARD: Yeah, I did wonder sort of why is she so desperate to return to fulltime work in a job that she has to go through sort of a standard interview process for. Could she start out by taking on projects or doing consultancy work, prove her work with something more temporary. I think she’s then in a much better position to interview for those jobs, ask for more in those jobs. She doesn’t necessarily need to start at this entry level. I think she’s selling herself short.

WHITNEY JOHNSON: Totally agree. And it might be that she’s not even aware of this because having been out of the workforce for 10 years is sort of temporary, why don’t we date for three months before we decide if we want to get married, wasn’t as much of a thing, so that is great advice Alison, of just saying why don’t I find organizations that I want to work with, suggest that we work together for a three month project, see if we like working together. Given the fact that she sounds like she’s really capable, once she does that she’s probably going to find fulltime employment if she decides she wants it pretty quickly.

ALISON BEARD: Whitney, should this letter writer sort of hide or gloss over the fact that she’s older and a mom or should she be completely upfront about it and sort of make overture of it? I constantly talk about the fact that I’m a working mom.

WHITNEY JOHNSON: You know Alison, that’s a really good question. I think the answer is it depends. For example, if she’s going to do sort of a short term stint where they’re hiring her as a ringer, she’s just going to come in, she’s going to do the job, she’s going to leave, kind of this expert in the field. They don’t care. They don’t want to know about any part of her life. If she’s looking to build a business where it’s a great place for people to work and people can bring and show up with their whole self, then it becomes part of her brand to talk about who she is, whose she’s been, all the different aspects of her life. So, again, it depends on what they need to know about her in order to be more comfortable in hiring her.

DAN MCGINN: So, Alison, what are we telling this woman?

ALISON BEARD: So, I think that one, she should start to feel much more confident about herself. She has spent her time off learning new skills and working in the field where she wants to go. At the same time she needs to make sure that all of her skills are up to date, particularly on the technology. She needs to develop a better narrative that she shares with the people she interviews with. She needs to reach out to her network to find better and more appropriate opportunities and to have people vouch for her. She needs to think more carefully about the organizations that she wants to work with. Pick ones that will value her. And she needs to possibly consider not doing this sort of straight leap back into fulltime work, but think about whether she could work as a consultant on a short term or part time basis to familiarize herself with an organization and really prove her worth before she then lands that fulltime gig.

WHITNEY JOHNSON: Totally agree.

ALISON BEARD: OK, let’s move on to the next question.

DAN MCGINN: Dear HBR: I’m a sign language interpreter and I’ve been with my company for 12 years. It’s been great for me so far. As a divorced father I’ve been focused on giving my kid a stable home. Now he’s heading off to college and I’m ready for a big transition too. I want to move into management. My company has small offices all over the country with a manager in each. I want one of those roles. I’m enthusiastic about what we do and my performance has been spot on for years. But I’m worried about applying. Honestly I don’t have much manager experience. I talked to my boss and her boss and they told me about the priorities and personalities of managers in our business. I’ve done workshops and webinars and I’ve read books about teamwork and customer service. I helped set up our center when it opened and then have helped lead it. I’ve always been someone people go to with questions. I also served on a Board of a local professional association. I organized a team of coworkers to run in a fund raiser. I’ve helped with conference planning, things like that. When I apply for one of these jobs, how can I explain my lack of direct managerial experience? I want to show the interviewers that I’m ready to make that transition.

WHITNEY JOHNSON: I would say that he is at the top of a learning curve and it’s time for him to jump to the bottom of a new learning curve which is a big transition. He’s looking to move into management. He’s potentially looking to move to another state. And the reason this is especially important in terms of it being a transition, is it’s one for him, but it’s also one for the people he works with. The challenge for him is to figure out a way to get buy in for that change. For him to pack a parachute essentially for the various stakeholders. Helping de-risk it so that they say, oh you know what? He’s logical for this. He’s the right choice.

ALISON BEARD: Yeah, I definitely thought that this was more of a transition for him than it would be someone who simply wanted to move up to management because he clearly has plateaued for a long time. And we published some interesting research that talks about when people and particularly men step back from work or step back from advancement, they might be stigmatized or penalized because they haven’t sort of followed that traditional path.

DAN MCGINN: It seems like part of what happened here is his lifestyle decision made him prolong that time and sort of the time for him to be promoted passed him by and now he’s trying to sort of undo that decision.

WHITNEY JOHNSON: Absolutely, and first of all, I think one thing that happens is if you think about this learning curve and you start at the bottom and you move to the top, this cycle in general is going to be at most four to five years and then it’s time to jump to a new learning curve.

And so, one of the things I think you’re potentially hinting at is if you’ve tried to prolong being at the top of a curve for years and years and years and years, there is the potential that we get stale. And so, we stop developing and we stop progressing and even if we’re not stopping developing and progressing there can be the perception that we are.

ALISON BEARD: And so, this man needs to persuade his manager that although he has plateaued for this time, he’s ready.

WHITNEY JOHNSON: Yeah. One of the things it occurs to me that might make sense for him to do is to hire someone to redo his resume for him. Because we all know it’s really hard to see ourselves objectively and we, in fact by definition we can’t. We tend to undervalue who we are and overvalue what we’re not. He’ll start to through that process of self-reflection and guided self-reflection be able to use it as a way to reset how he thinks about himself and in the process of doing that, reset how his various stakeholders from whom he needs buy in to get this promotion, see him and view him and perceive his abilities to be.

DAN MCGINN: Even if he’s never managed people, he’s managed processes, he’s managed projects and in some ways those are harder to do because you don’t have command and authority over the people that you’re working with. So, I don’t think people should discount their lack of formal people management if they’ve been managing a lot of stuff. He also clearly has expertise in the subject of what they’re doing in this office and we published research that shows that if people are given a choice between working for a boss who just has really good people skills or working for a boss who’s deeply competent in the technical stuff, that someone who can actually step in and do the job of the subordinate, people prefer to work for people who are experts. And he’s got that expertise, so I wonder if he’s selling himself a little bit short here.

WHITNEY JOHNSON: I was thinking the same thing. Is he thinking expansively enough? So, I suspect if he were to take all of his various component pieces of his skills and put them all out of a table, sort of like a recipe. You’ve got all these ingredients and you’re like OK, I’ve got these 10 ingredients. I could do this with them. I could do this with them. I could do this with them. I suspect he would find that there are more opportunities than he perceives or to be. If he is absolutely convinced that he wants to stay with his organization, your baby step of OK, how about if I take on a project internally here right where I am and I’m able to show or demonstrate my management skills to step, to being in management. I think that’s a possibility. At the same time, sometimes it’s harder to manage the people that you’ve been managing or you’ve been, to go from being a peer to a boss. So, he might be able to move to another state if he wants to stay with his organization and manage a small project. So, take a step back in order to slingshot forward. Start anew. Be a manager of a project and then, and how people perceive him in the way that he wants to be perceived.

DAN MCGINN: In some ways it’s perfectly suited for somebody like him to step into one of these managerial roles because you have offices all across the country that are really doing the same thing. I was in this situation once. I worked for a company that had offices around the country. They sent me at a very young age to Detroit to run their office and I spent a lot of time in Chicago seeing what the Chicago manager did and when I wasn’t visiting with him I would be calling him. And so, some of what I think he can do is network into the other managers of these offices and create the support network. He’s not running a one off operation. He’s running a replica of all these other organizations. There’s lots of people who have a vested interest in helping him succeed.

WHITNEY JOHNSON: Yeah. It does sound like from what he said, he does have a lot of goodwill inside of the organization. Another thought that I had too is every time someone gives him a compliment inside the organization to write it down. Because people are giving him information all the time about what his genius and his superpowers are and if he can write those compliments down, it will help him in the process of having those conversations across the organization as he’s trying to get buy in for this move into management that he wants to make.

DAN MCGINN: If we were talking to him here, I’d love to know a little bit more about this meeting with his boss and his boss’s boss. He says they told me about the priorities and personalities of the managers. He’s not giving the sense that they were really positive about this or really negative about this and I think typically if somebody thinks somethings a really great idea, you can either see it in their face or they’ll tell you directly, we think this is a really good idea. I think there’s a lot of signals being sent there.

ALISON BEARD: My question was whether his own worry about his lack of experience sort of prevented him from just walking in and saying I really want this. Which is sort of the first thing you need to do. You need to signal your intention, right? I’m not sure that he’s done that yet because he does seem a little bit afraid.

DAN MCGINN: He seems focused on what he lacks instead of what he brings.

ALISON BEARD: Yeah, absolutely and he clearly brings a lot.

DAN MCGINN: What if he applies for this management job in his own company, he doesn’t get it. What’s his next move then?

WHITNEY JOHNSON: That’s such a good question. He will have a lot of information because they will effectively have said to him, this is where you will be and this is, so you’ve got to decide if you’re going to be willing and happy to do this job. To me that is an indication that he is at the top of a curve and it’s information and time for him to truly jump to a new learning curve and reset both for him in a place where he feels fresh and it’s brand new and he’s at the low end of the learning curve, inexperienced and where all his brain will be asking lots of different questions and having that experience of being a novice again, I think there’s tremendous value in that for him and also for the organization that he would be in.

ALISON BEARD: Isn’t that so hard for him to do though as a man who’s probably middle aged. I mean it seems to me like the safer path is for him to stay in this organization that he really likes and feels passionately about and in which there are management opportunities. This sort of greater disruption seems scary at his age.

WHITNEY JOHNSON: It’s not the safest bet. I think it’s still worth his at least considering it and just thinking, do I want to do something different? Because it sounds like he hasn’t even explored that at all. So, I would encourage him to at least ask that question.

ALISON BEARD: Yeah. So, what are we telling this person to do?

DAN MCGINN: We’re telling him to focus not on what he’s lacking in terms of experience and background, but to focus on the real strengths he brings to a management job. We’re telling him to probably redo his resume and redo the way he thinks about what he’s managed. Even if he hasn’t managed people, he’s managed a lot of processes. We’re telling him not to focus only on internal opportunities, but to think a little bit more broadly and expansively about this is an opportunity to disrupt himself. Whether he wants to change companies, he’s got the opportunity here to sort of rethink a lot of things in his life. So, think about his strengths and think about the range of opportunities, not just the one he’s focused on.

ALISON BEARD: Terrific. Well Whitney, thank you so much for working through these questions with us. I hope that we’ve helped the letter writers and you have been a terrific source of advice.

WHITNEY JOHNSON: Thank you.

DAN MCGINN: That’s Whitney Johnson. She’s the author of Disrupt Yourself. Thanks to the listeners who wrote us with their questions. Now we want to know your questions. Send us an email with your workplace challenge and how we can help. The email address is DearHBR@HBR.org.

On our next episode, we’ll be talking about bad bosses. To get that episode automatically, please subscribe!

ALISON BEARD: And if you like the show please give us a five star review.

DAN MCGINN: I’m Dan McGinn.

ALISON BEARD: And I’m Alison Beard. Thanks for listening to Dear HBR:.