Why Do I Keep Getting Passed Over for the C-Suite?

MURIEL WILKINS: I’m Muriel Wilkins, and this is Coaching Real Leaders, part of the HBR Presents network. I’m a long-time executive coach who works with highly successful leaders who’ve hit a bump in the road. My job is to help them get over that bump by clarifying their goals and figuring out a way to reach them, so that hopefully they can lead with a little more ease. I typically work with clients over the course of several months, but on this show, we have a one time coaching meeting focusing on specific leadership challenge they’re facing. Today’s guest is someone who we’ll call Randy to protect his confidentiality. He’s achieved a lot in his career and is now at the executive VP level at his company. His aspiration is to make it to the C-suite and he’s been working hard to do so.

RANDY: I’ve tried for many C-level positions. It seems that I always get through to the finals, but I never get the final decision to take on the brass ring or take on that job. And I was just wanting to understand, maybe there are things that I’m doing or saying, or don’t know that led to that. I’ve had just a couple recently that really I thought were just fantastic. They loved my background, loved the interviews, had several interviews over several months and then no opportunity. “Sorry, we’re going to go another way. We think your background’s outstanding. We think you did an outstanding job with your interviews. However, we don’t feel that you will be happy with us.”

MURIEL WILKINS: Randy has faced this situation several times, where he gets close to getting the C-suite role, but then doesn’t. As some who has had a longstanding, successful corporate career, he finds himself questioning what exactly is going wrong. I should also mention that Randy is black, which adds a nuanced layer to his experience.

RANDY: You start to scratch your head and say, “What am I doing wrong? Is it something that I’m doing? Is it something that I need to look at and do a hard look in the mirror and say, ‘Maybe there’s something I can do better.’ I’m all about being better. And I think I can do that. It’s not that I deserve it, I want to prove that I can do it. And I believe I can.

MURIEL WILKINS: Randy is wondering, why not me? When it comes to these CEO roles that he’s running for, will he ever get to the goal? I start by asking him about the secret sauce that he thinks has made him successful so far.

RANDY: I would say the secret sauce is very strong in my knowledge of the industries that I’m in, but more importantly, personality. I would say the experience I’ve had with good listening and developmental skills of my team members has been very successful for myself. I’ve been labeled as a guy that can take what many people in the industries will throw away as employees that have bad reputations in terms of work performance. And based on my skill set, turn them around and they are very successful and they become A players. And I’m very proud of that. And then in the many industries that I’ve been in over the years, I’ve been able to attract many people in my network to continue to work with me, which is also plus.

MURIEL WILKINS: Yeah. And so, I mean, that’s great that you’re able to turn around poor performers to A players. Not a lot of people are able to do that. And what drives you? Like, what gets you going every day in terms of your role?

RANDY: I am goal-oriented. So the goal and the objective of achieving something that is impossible always has been something that has motivated me to achieve and achieve great things. So in all the aspects of the areas I’ve been in, it’s always been in areas where I’m underrated or underestimated. And that to me is a motivator where I always have come out on top and delivered more are than expected.

MURIEL WILKINS: All right. So I’d love to understand what challenges you’re facing right now and why we’re having this conversation. What brings you here today?

RANDY: I tell you, I am trying to get to that next level of C-level in the executive ranks. And it’s been like a glass ceiling for me. I have not been able to achieve that even though I’ve had tremendous success. And I am challenged to know if it’s relative to my age or my race or something there other, because I’ve had roadblocks in both of those where I’ve achieved, I’ve hit all my numbers, I’ve delivered in every aspect that was expected. And, like we just talked about develop the resources, but never the prize. So it’s been a challenge for a number of years.

MURIEL WILKINS: Mm-hmm (affirmative). And is that challenge internal to the organization that you’re in now? Or have you explored external opportunities as well?

RANDY: It’s happened internal, but it’s been more external when I’ve been exploring other external opportunities as well. I’m also exploring opportunities outside of corporate America where maybe it’s time to take the tremendous skill set that I have and do something on my own and explore that. So these pitfalls and roadblocks that I’ve highlighted, I make them lemonade basically, I take them and turn them around and produce something that is my own.

MURIEL WILKINS: And so, I always like to think about what the alternative scenario is, right? So, particularly for those of us who are fixated on the goal, myself included, sometimes it’s helpful to think about, well what happens if the goal doesn’t come to be? Right? And so if you didn’t get the C-suite and this is not to sound pessimistic, again, just curious. If you didn’t get that C-suite position, what would happen?

RANDY: I would probably definitely take another road. I’m at a point in my life where based on young adults in my household with my children, they have opened my eyes to a lot of things that as my age, where I was very quiet upon in terms of my personal thoughts or personal feelings, the generation today is pretty vocal on those things that make them interesting, make them successful, their concerns. And then in my generation, those are things that was never communicated. I don’t think many people even cared, it was more of a suck it up and figure it out and go make it happen. And in many cases I did that.

MURIEL WILKINS: Mm-hmm (affirmative). Okay, got it. So our children often teach us the greatest lessons. Like, what is it that you’re seeing in them in terms of what they’re able to communicate that you felt you did not voice as you went through your own career journey?

RANDY: I would tell you their confidence of being vulnerable, their confidence of their ability to voice their opinion and not look at it as a weakness, but a strength to overcome and become stronger with a community, with others helping along the way. When I grew up, and even in this current state, I’m less inclined because of trust issues. Because I would see those things being used against me more than helping me. And in the environment… Oh, if you’re talking about you’re having a challenge in achieving a goal in an evaluation period, it could be thrown back at you that that challenge was highlighted as a weakness and they use it against you.

RANDY: I’ve seen it happen many times in evaluations of others, or the fact that you don’t feel you have the strength or the capability to complete a goal, but you need help. That can be thrown in your face as well. Even though I think all of us at some point need help to move forward, need help to achieve something, need help to become who you want to be. No one’s [inaudible 00:08:34]. But I think in the world that I’ve been in as a black man, a lot of those things were never offered to me more as they were to my contemporaries. They were offered only as, lack for better word, never stated, but just led to that lack of trust where I would want to keep that to myself, work through that and not seek the help.

MURIEL WILKINS: So I’m getting the sense, Randy, and correct me if I’m wrong, that you really are sort of a pull it up by the bootstraps, as we say, type of guy in terms of how you manage your career.

RANDY: Absolutely.

MURIEL WILKINS: Okay. What I’m also hearing is that the support or hope was not offered, and as a result of it not being offered, you did not feel in a position like you could ask.

RANDY: That’s correct. And I’ve had examples where others, in my purview, had and I saw the consequences.

MURIEL WILKINS: Mm-hmm (affirmative). All right. And those others, were they folks who also were black males or black women? Or were they just in general, peers?

RANDY: Peers of color.

MURIEL WILKINS: Peers of color. Okay. So very specific-

RANDY: Men and women.

MURIEL WILKINS: Mm-hmm (affirmative). Very specific in terms of the experience that you have. And I think that’s important to flush out because that’s the context that we’re operating from, right? It is really about what is your experience as a black man through the corporate ladder versus just generally as an executive, right? That there are certain things you’ve experienced that others might not have. And how do you deal with that?

RANDY: Yeah. I will tell you one thing that challenges our own social biases, and it’s become even more prevalent today working with certain peers and certain companies that they already come into the workplace with, and that has been a noticeable challenge. I’ve always guarded, protected my workforce and abdicate for them in those social biases, but at the same time, I see them in play many times for whatever reason. And I’m a big abdicate to break those.

MURIEL WILKINS: Okay. Got it. So I’d like to fast forward to current where we are today, right? And going back to the original question you had, which is I’m ready for the next level, which is at the C-suite, I’m putting myself forward for those roles, but I’m not getting them. And the question is why. Is it because of your race or age or because of experience or some other factors? Who knows what they are. So I’m wondering, could you share with me some of the experiences you’ve had in terms of getting to that place where you’re putting yourself forward in an opportunity and getting the role, like what happened?

RANDY: Yeah, sure. I’d be glad to. I had an experience outside of my current role right now, senior leader position, went through all of the layers of interviews with all of the executive leadership and then had interviews with board members, because the role would report up through not only the CEO, but also to some of the relative board members. Had those interviews all with flying colors, plus, plus, plus. A, We’d like to have this guy. Come to my last interview, had a video conference. I would tell you at sometimes, and you may get a chuckle, people when they see you, they jump or they recognize, because when we all talk to others without video, we have an impression of what they may look like and sound like. And I don’t think she recognized me for who I was. I think that startled her because it was very noticeable to me. And then she-

MURIEL WILKINS: As a black man?

RANDY: As a black man. Right? And I don’t think that came up in any of the conversations with the other executives, of course. And we proceeded to not really talk about the job, but all the things about, social things relative to being on site, making sure that I understood that the requirements were X and Y, are you sure that you can fulfill these obligations? And I’m like, I’m wondering to myself, obviously you’ve had these conversations. We’ve been going with these interviews over three and a half months. None of this should be new to you.

RANDY: We ended the conversation where I did answer all her questions. And then my next comment back in about a week was, “You’re outstanding. We love your background, but we think you’ll be disruptive to our environment because of all the things that you’ll want to change because of your tremendous skill set. And we’re just not ready for that. And for that reason, we’re going to have to say, you’re not a good fit, but we wish you the best. And if something comes up where we’re ready for that, we’ll give you a call.” That was the gist of that conversation.

MURIEL WILKINS: And so how did that land with you?

RANDY: Well, I wanted to call immediately and find out more, challenging myself to ask so I could get better, understand why they made that choice, and why do they feel that my ability to be a change agent is disruptive, would be disruptive. I never gave any indication I would be disruptive, I never gave an indication that the skill sets that I do and work with every day lead that way. I’m more of a collaborator. I’m more of a team builder. I’m more of making sure the organization social norms and goals are met. I do think out of the box, but I would tell you what, I’m quite considerate in wanting to make sure that I achieve the things within the right parameters of the company. And everything I’d done led to that and blew away the people in that regard. And they made comment to that. So I was just shocked.

MURIEL WILKINS: Mm-hmm (affirmative) Okay. And so did you ask? Did you call and follow up and say, “Hey, I have a couple questions.”

RANDY: I still did.

MURIEL WILKINS: Okay. So I’m like fascinated now, right? Like, and so what happened?

RANDY: Well, you know what? I called, and it’s just the funniest thing and the most frustrating thing, I called the CEO and he said, “I can’t give you an answer other than it’s just not right for us.” And I said, “Well, can you expound on what’s right for you? So I can become a better individual in understanding how I could tell my interviews for the future. What was wrong in what I did?” No answer. So it was really no big answer, right? And that’s been the case in about three, I’ve had three like this, where I am a finalist or I am the finalist and they either go a different way or they say you’re not a good fit.

MURIEL WILKINS: So there’s sort of a pattern or you’re thinking it might be a pattern in terms of what your experience is. So that’s a very logical, up in our head way of thinking about it. And so I want to drop it down a little bit and ask you, what is your gut telling you?

RANDY: Good question. In that respect, my gut was telling me it was definitely social. It wasn’t professional. My gut also told me that there is an internal bias that is there. So maybe it’s smart for me not to be there, because I would be a disruptor, and I would challenge the status quo in that regard because that’s not who we are and not who I am, okay? My gut also told me that, why would I want to work for a company that is not honest, but propagating something that is not fair and truthful? But I didn’t go down that road. I’m too strong for that. But I am very educated and open to logical and constructive criticism. I always have been. But in this case it was very generic and really nothing to say that I had an issue, or if, let’s put it this way, they were not willing to share. So, and in my case, I’m saying, how can I be critical of myself when I didn’t get anything to understand, but I reflect on it? So I think the things I thought that I just shared with you, but internal I’m saying, “Okay, I’m not going to change how I am. I’m not going to change what I look like, but at the same time, maybe I need to look at areas that are more open and receptive to me.”

MURIEL WILKINS: Mm-hmm (affirmative). Okay.

RANDY: As I am.

MURIEL WILKINS: As you are. Exactly. As you are. As you stated, you’re extremely goal-oriented, right?

RANDY: Exactly.

MURIEL WILKINS: So I could imagine that when there’s no explanation as to why you can’t reach the goal, it can make you feel a particular way.

RANDY: Well, you want to look inward. And first of all, always look at those things that are, what you believe. We all have them in our own back mind or our minds as shortcomings, right? Why not? Why wasn’t I successful? If you can pin it on something, it’ll just leave you hanging. I really dislike that a lot, because to say you’re not a good fit for us, there are legitimate reasons they don’t want to say. You know that, we all know that. Many times I’ve had interviews with candidates, I’m very clear on the reasons why we can’t select them or couldn’t select them. Or, “Here are the things that we would recommend that you build your resume on. Here are the things that you should go back and get some training in.” To give some tangible evidence of why is very helpful. When you don’t have that, you start to internalize and look inward, I think. And then in my case, I did. But at the same time, I got to keep moving forward.

MURIEL WILKINS: RANDY is someone who seems to be open to change, to learning more. He’s very goal-oriented. And so it can be very frustrating to get so close to the C-suite that he can touch it, only to be told no with little information. As someone who’s used to constantly working on himself to prove he can meet expectations, this situation leaves RANDY in a conundrum and digging for the why. Is it me that’s the issue? Or is it them? And while trying to understand the why, it’s hopeful in many cases, at times, it can lead to constant back and forth internal debate that leads nowhere. So to help RANDY move forward, I ask him to consider what he could do, even if he doesn’t know the exact answer to his question of why he’s not getting the role. So it’s interesting to me that you said in absence of the why, you internalize it. And so I’d like to think about what your other options are in absence of the why, in terms of how you respond to situations when the why is not clear.

RANDY: I did internalize it. The why is to go beyond myself and start reading more. I start looking at skill set analysis more. I start looking at my personality and my level of communication. I start doing analysis on, I don’t think my skill sets of challenge, but maybe how I communicate, how I answer questions, how I refrain to responses, maybe of some question. Don’t know. But I looked at all those things, I personally said no to all of those things, they weren’t a problem, and then you start evaluating other things, such as the things I talked about, social biases or things like that.

MURIEL WILKINS: Right. I mean, look, here’s the thing, right? There will be situations where there is no clear why. And I think that part of it for you is, as you’re doing right now, seeing that there’s many paths to responding to when there’s no why. It doesn’t always have to be about, there’s a shortcoming in me. Yes, that could be a starting point, and you’ve got to also look at it in the context of everything else, which is the external piece, right? So I think that’s really important because even as you move forward, regardless of what you do, when there is ambiguity as to why something is happening, you can try to get it as much as you can, but you might hit a wall where your endeavor to figure out the why is actually not helpful. And the frustration that you feel is, I just want to pinpoint exactly what directed at. You’re frustrated about filling the blank.

RANDY: When you try out for a role and you have several interviews and you have several candidates that fall to the wayside` and you’re still the last one, all of these things were done. And then you get to this end state that happened. But I’ve had others the same way. So I’m just questioning that.

MURIEL WILKINS: Yeah. So the frustration is about doing everything that you possibly, in your mind, you possibly can do.

RANDY: Correct.

MURIEL WILKINS: And then getting to a place where it feels like the decision is based on something that’s out of your control.

RANDY: Absolutely. Yeah.

MURIEL WILKINS: And so Randy, like over the span of your lifetime, how have you dealt with, and it doesn’t have to be professional. Like, I’m just curious like, how have you dealt with situations where you are not in control?

RANDY: Well, it goes without saying in my background, I’m a religious person. So we pray, of course, I’m very prayerful. But at the same time I, like I said, I look for other opportunities and I keep pushing. So those are things that keep me going. Plus I have a very successful family where we do a lot of things for others. That also is something that’s outside of this world. And let’s be clear, I don’t have a bad role right now as an EVP. I just want more.

MURIEL WILKINS: You want more. And look, there’s nothing wrong with that, right?

RANDY: Yeah. Yeah.

MURIEL WILKINS: As long as it’s for the right reason.

RANDY: Absolutely. Yeah.

MURIEL WILKINS: And you can only know what that reason is, okay? No judgment on my end as to why somebody wants to get to that next level. What’s interesting to me is that you, well, let me back up a little bit. Like, I don’t have a crystal ball to be able to say whether here nor there, why you didn’t get those roles, right? Like, I’m not talking to those people, so I don’t know. But I also know that yeah, does bias exist? Absolutely it exists, right? Now whether that’s the reason or not, I don’t know. I’m not in a position to say, “Hey, here were the skills or the communication factors or all the things that you could possibly work on.” So I’d be a fool to sit here and say, “Oh, well, here are the attributes that I think you’re missing.” What I can do is we can work through how you approach that situation and how you’re thinking about the pattern that you’ve identified in terms of not getting the roles that you put yourself forward with. And then based on that, determine for you, what do you want to do with it? Right? One of the things that’s striking to me is that it sounds like, even up until recently with the interviews that you had, but throughout your career, you have looked for, what do I need to do in order for me, me meaning Randy, to work out for you? You being the organization, the people. So in a way, you’ve adapted yourself to fit whatever the need was, whether it be organizationally, personally, whatever it might be, right? And that has really been your kind of a trademark of being able to succeed and move up the ladder. And I guess my question is, at what point do you start asking what works for me versus what works for you?

RANDY: That’s good. Can you help me a little bit more in terms of when you say me versus you? I kind of blend them together.

MURIEL WILKINS: Yeah. What works for Randy? What works for Randy? Yeah. I mean, so there you go. You said you blend them together, right?

RANDY: Exactly.

MURIEL WILKINS: So before we even dig into that, the fact that you’re blending them together in terms of what works for the other, versus what works for Randy means that you are making your success contingent on the other, rather than grounded in what it is that works for Randy, what works for you. And I’m not saying you have to ignore environment and ignore context. Clearly, you have to do that. Like, you go work for a company, you figure out what’s going to work and you try to make it work. The question is at what cost.

RANDY: Yes.

MURIEL WILKINS: And the cost usually is a cost of self. And so what I’m asking you is you have spent so much of your career figuring out what you need to do to be successful in these other realms, right? By other people’s definitions, what does it mean to be successful for you and what environment works for you? So I’m flipping the question.

RANDY: I know, and I like it. You’re right. I’ve always blended the two to be more of a chameleon instead of adjusting to what I know is right. Now, I’m an abdicate for what is right for me, but more in the context of navigating in the company in which I’m in, versus what’s true to me as a person. And that’s very telling because, and again, age context, I never looked at it that way until kind of the fog has been lifted and I can see a little clearer now. So to your point, yeah. What’s good for me may not be any of these companies, more and more I think about it. And as you and I have talked here, maybe the better thing for me is, is to move on to something where I can be that change agent myself, I can drive the right expectations that I feel are pertinent for me, make sure others that I see are under represented or don’t have that voice have it, and be all those things that are important for me to others, but also keeping myself focused on those things that are important.

MURIEL WILKINS: Mm-hmm (affirmative). Yeah. I mean, look-

RANDY: For me. Yeah.

MURIEL WILKINS: Right. So you reach a point where as talented as a chameleon one can be, there’s some things you can’t chameleonize away. I don’t even think that’s a word, but I’m going to make believe it is, right? Like, you can’t. And so it is what it is. And I think a part of this process is you seeing things clearly for what they are and operating from that place, rather than from a place of what it should be, right?

RANDY: Right.

MURIEL WILKINS: The frustration comes from what it should be. The frustration comes from that. It comes from-

RANDY: Absolutely.

MURIEL WILKINS: Right? It comes from, I should get candid feedback. We should get candid feedback on why we’re not getting the role. There should not be ageism or racism or any types of bias in the hiring process. I should be able to get to that next level based on my track record and that experience, right? And listen, I’m all for, if all those things deem themselves to be true in my lifetime and your lifetime, I will be a happy camper. And we have to see things for what they are today in your situation, and then make choices for you based on the reality of what’s happening. And the reality is you’re not getting those roles. So when we start thinking about it more in the context of, what works for Randy? Specifically, what type of environment or company. I know part of it is you might go on your own, but let’s say it was to go into a company where you’re actually interviewing, what type of company would you be looking for?

RANDY: Well, it’s interesting you brought that up. I’m starting to look at companies that have a social platform, companies that have a vast… The board of directors and the staff is a diverse staff, diverse board, which gives me some indication that they have some of these things that we’re talking about. They are working through and working on, not saying that that’s the case, but at least that’s an indication that they have some openness to a number of different personalities, as well as people.

RANDY: And then I’m looking for companies that have growth and history of growth in the areas that we’ve talked about, that allow that transparency and have no fear factor in that. And then I’ve also reached out to leaders in certain companies, I’ve had deep conversations on to get some better feel for if this is the area I want to work in and I’ve started to apply for some of those areas. Whereas before, I would tell you, I was not as selective. I was selective once the knock came on my door versus me knocking on the door myself. That’s one of the things I’ve turned around as well. So I’m working on my brand, which would be all about me. And I’m working for those companies that I feel will support my brand versus the other way around. So-

MURIEL WILKINS: Versus the other way around. Yeah. Yeah. I mean, look, again, like your superpower has been, up until now, your superpower has been looking at yourself internally and saying, “Where am I missing the mark? And let me get stronger.” Right? And without necessarily looking outwards at the same time and saying, “Well, where’s the company missing the mark?” Right? “And is that a place that I want to be?” So as you said, be as selective with the environment that you’re in, or be as critical of the environment that you’re in as you’re doing your due diligence, as critical as you’re being for yourself when you’re being introspective and reflective and figuring out what you need to do.

RANDY: No, I agree. I think that approach is the better and it supports me doing the homework, doing the research and focusing on those things that I can bring to the table versus what the reverse of that is. So for me, that makes a heck of a lot of sense.

MURIEL WILKINS: Yeah. And look, here’s the thing, I think that what you’re facing is quite frankly choosing to be an outlier. And you don’t have to make that choice, right? You could say, “Hey, you know what? I’m done.” Like, “I’ve reached a certain age, I’m not going to change my skin color, I’m out.” Right? And that’s a choice. That’s a choice. And the choice becomes, if you choose the outlier choice, it really becomes, do you have the wherewithal to really be cultivating your career against what is still the norm? Okay? Do you have the wherewithal? And then the second question becomes, what’s the purpose behind making that choice? So if you think about… I mean, look, we can look at the data. There are not a tremendous amount of black individuals in the C-suite. Doesn’t mean it’s impossible, but I’m sure it’s not an easy path, and it is still an outlier. So for you, if you continue to choose that path, even if it’s in other types of organizations, I want to understand, or I want you to understand really clearly, what is the purpose behind you continuing to pursue that path?

MURIEL WILKINS: Let’s pause here. His whole career, Randy has followed the work twice as hard mantra that so many underrepresented professionals use to prove that they are deserving of the role that they’re in. But that’s not working for him anymore. And now he’s considering opting out of the corporate path altogether and venturing out on his own. Now, whether Randy continues to look for C-suite roles at organizations or decides to take another road, it’s important for him to recognize that it’s a choice he’s making and it’s his choice. And he has to have clarity as to why he’s choosing a certain path. So we pick up the conversation where he reflects on just that.

RANDY: Well, I would tell you this, it is my choice, and I am deserving of those things that I’ve worked so hard for, but I have to earn them just like anyone else. And I choose that because that’s what I want to do. My biggest obstacle is fear, fear of failure. When it’s all on me, that is the biggest concern I have, if you look at something from an entrepreneurial standpoint. So for me, it’s to overcome that, systematically make sure I have countermeasures in place to offset those things that I know of, but understand that it’s okay to not have all the answers.

RANDY: I come from a generation if you didn’t have the answer, stay with a sure thing. And when you stay with a sure thing, there’s things that you may not be sure of and fearful of. And when you go out on your own, that drives into those unsure things that lead to some areas of fear and insecurity that I’ve got to face. And so I think that’s my biggest obstacle. The skills are there, the knowledge is there, the contacts are there, the ability to drive what I need to do I think is there, it’s that what I just mentioned, so.

MURIEL WILKINS: Okay. So fear of failure.

RANDY: Fear of failure. Yeah.

MURIEL WILKINS: Of being out there on your own.

RANDY: Of being out there on my own.

MURIEL WILKINS: And yet when I asked you about, or I ran by you the notion, confirmed the notion that, I think what I said is, “Hey, Randy, you strike me as the type of guy that like your whole career, you were sort of a pull it up by the bootstraps.”

RANDY: Absolutely. Yep.

MURIEL WILKINS: Okay. And where did that get you?

RANDY: I’m bumping my head every day and dealing with things that… I’m very successful, but not to the level I want to be. I want to go beyond where I’m at and I’m not getting there.

MURIEL WILKINS: Yeah. It feels like, because you said you didn’t ask for help, you didn’t get the support, it feels like you have been on your own already.

RANDY: Well, I tell you what, life is interesting. I’m still going down the path, and I don’t want to sound like I’m going in the circle, but I’ve gone down the path of moving in the area of abdicating for me, to your point, and being of, from an old school, never giving up on a sure thing. I just mentioned that too. Taking risk means it’s all on you. So I’m about there mentally.

MURIEL WILKINS: Yeah. But so Randy, I just want to mirror, I’m going to be a little more direct, right? You’re saying that your block is, don’t give up a sure thing, fear of being out there on your own. And what I’m saying is, everything I’ve heard you say about how you have led your career so far, there has not been a sure thing.

RANDY: Absolutely.

MURIEL WILKINS: And you have been out there on your own. So what’s the difference? Why are you fearing something that you’ve already done?

RANDY: I guess the difference is, when you work for a company, you have a paycheck, you have insurance, you have all the things that are the trappings of the things that you need in your day-to-day life, right? When you’re on your own, those things… And to your point, I see your point. They’re still on you, but that has been my roadblock. I was just being transparent and honest. I think I’ve come to a point where those are not as big a concerns as they were. Financially, I think I am at a position where I don’t have to be fearful of those things, but I’m also of the mindset that you should always be mindful of those stakes. So save, save, save, plan, plan, plan, have a nest egg for a contingency, always, has always been my mindset. So even though I hear you and I understand what you’re saying and you’re absolutely correct, in my environment, if I didn’t have the ability to pull myself up and always do that, I wouldn’t be considered a survivor. Okay? So in that case, looking outside of a company which gives you some level of confidence, which is really none, you’re correct. I’m beyond that paradigm. That’s a paradigm in my mind. And it’s finally one that I can face openly and even say that I have that fear because in one, I’m not really open to telling my fears either publicly or my concerns, because it’s also looked at as a form of weakness. If you got to look at it from my point of view, being a black male. So the fact that I’m going to talk openly about that, I’m embracing it and I’m looking for a way to overcome that despite the fact that the history has supported that. If that makes sense, what I’m saying.

MURIEL WILKINS: It makes a ton of sense, right? And I think that… Look the fear, and I’m using quotations, like the fear that you have is not an uncommon one, it’s not an uncommon one. This notion of what is the safe choice? Where do I need security? Which is what I hear you saying is there’s a certain level of security that you have felt you needed. And that security came in the form of compensation and benefits and all the things to make sure that you could survive at the lower levels of Maslow’s hierarchy, right? Okay? Now here’s the thing, as we had advance in leadership and in life, our needs change, at least those who mature recognize that their needs change, right? And if you keep on hanging on to making sure that the things that you needed to be stable 10 years ago are still the things that you sort of equate your success with today or what you need to be stable, those are the actual things that might hold you back instead of propel you forward.

RANDY: That’s correct.

MURIEL WILKINS: And so the question becomes, because I’m not going to… Look, everybody needs some form of stability in their life, right? I’m not an advocate of like, just go buck wild and do whatever you want. But my question is, what are the things, or what are the areas that you actually need some security and stability in today, versus what you felt you have needed all along?

RANDY: Most of them, when you put it that way, I already have. The ones that we talked through, the risk of shelter, the risk of healthcare, the risk, there’s always risk. Something catastrophic could wipe anyone out, as you put it, the lower level of hierarchy. But I mean, at the same time, I don’t feel I have those concerns. Like I said, there’s been plenty of contingencies put aside to secure those things. So as I have matured in this process of this role we’re talking and we’re talking today, I see those as futile reasons that don’t matter anymore, whereas they did at one point. Conversation has a way of opening your eyes if you’re willing to receive. And that’s some of the beauty of this conversation here. And I see that, I think you’re getting me closer to that. And for me, sure, there’s risk, there’s risk on anything you do. But the risks are, I think in my case would be smart, calculated ones, and not like I said, there are going to be some things that I’m unaware of that I would have to plan for or react to, but I do that today. I just have an umbrella that has bigger purse strings, that if you make a mistake, you can offset it, right? But I haven’t done that in my life at all. I’ve not made those kind of mistakes. So I think I’m a sure bet for myself. It’s just getting over that hurdle that you’re a sure bet for yourself.

MURIEL WILKINS: That you’re a sure bet. Exactly. And listen, you’re the only one who can jump that hurdle.

RANDY: Absolutely.

MURIEL WILKINS: And what’s on the other side of that hurdle is what matters most to you. Right?

RANDY: Right.

MURIEL WILKINS: Exactly what you just said, right? Like, what matters to you.

RANDY: And what matters most to me is leaving a legacy, which I’m doing every day in all the things that we’re attributed or associated with in terms of outside of the workplace, but even a more strong legacy for my family in terms of independence, where they don’t have to rely on someone else to validate or substantiate who they are and what they’re all about. And for me, that’s even more important. Let’s talk about that, right? And those are the things that I really ruminate on. So those are more important to me than anything right now. And I think that’s something that’s also in my purview.

MURIEL WILKINS: As we end our coaching conversation, Randy sees that the real question is not about why he can’t get that next C-suite level role, but more about how he can ensure his efforts are putting him closer to his ultimate goal, which is to leave a longstanding legacy. This is a different place than where he started and helps him operate with more agency in making his career choices. When he starts framing his career path from a place of self-defined purpose, rather than solely based on whether he’s accepted by others, he’s able to see more clearly what he can do to move forward and to take action in a way that’s right for him. That’s it for this episode of Coaching Real Leaders. Next time.

Speaker 4:

And so I’m sort of at that point of being sure of myself, right? So how am I living up to this next level? Because what got you here won’t keep you here, right? I have that playing in my head and then trying to figure out how this business, it’s moving so fast.

MURIEL WILKINS: Thanks to my producer, Mary Dooe, music composer, Brian Campbell, and the entire team at HBR. Much gratitude to the leaders who join me in these coaching conversations and to you, our listeners who share in their journeys. If you are dealing with a leadership challenge, I’d love to hear from you and possibly have you on the show. Apply at coachingrealleaders.com, and you can find me on LinkedIn, on Twitter, @MurielMWilkins or on Instagram @CoachMurielWilkins. If you love the show and learn from it, pay it forward, share it with your friends, subscribe, leave a review. From HBR Presents, this is Muriel Wilkins.