How Do I Transition from a Corporate Role to Entrepreneurship? | Coaching Real Leaders | Podcast

0:01HBR Presents.

0:14I'm Yaria Wilkins, and this is Coaching Real Leaders, part of the HBR Presents Network. I'm a longtime 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 a specific leadership challenge they're facing.

0:48Today's guest is someone we'll call Jane to protect her confidentiality. For the last 10 years or so, she's worked in a corporate environment managing across different lines of business and regions. She and her team were revenue drivers, and she had a reputation for turning around ailing parts of the business. While I certainly have a lot of pride in the revenue and the results that I delivered, I have a ton of pride around the impact that I had as a leader on people. So I had to kind of balance my time between understanding the scenario of the business and start to create a really quick short-term strategy, but also be focused on the people side.

1:33Because as we very well know, if you don't have the people portion correct, you're certainly not going to have the productivity there that you need in order to deliver on the business objectives. That role created the foundation for where she is now in her career. She recently launched her own consulting practice, taking the formula she used internally to now help her clients grow their businesses. But the transition from corporate to entrepreneurship is new for Jane. And I started my own management consulting business hesitantly, I would say. I'm a corporate animal, for lack of a better word, and I truly love being in the corporate environment.

2:12I knew now more than ever, it's going to be so critical that I manage myself, that I lead myself and learn how to not shelve some of those, what I would, what I feel are my superpowers really is the leadership piece. I've completely shifted gears in certain ways and I'm worried that I'm not delivering on a value that I have to bring to them. And I just want to make sure that I'm leading myself to true success. Jane is now building her own business, which can be a pretty daunting shift for a lot of people. She's looking for ways to build influence and be a leader outside of the structured environment she previously succeeded in.

2:57So I started by digging in a little deeper to that success she had in her prior career to really define what she sees as the environment she thrives in. I asked her, what did success mean to her previously?

3:19Certainly there were financial objectives and there were annual operating budgets that we had to hit. My team and I always devised a strategy ensuring that we could go back to the executives. And even though we hit our objective, ensuring that we acted on all of the various strategies and tactics that we had mapped out, that was very important, especially for my teams who oftentimes I found even in large, massive, like multi-billion dollar corporate America organizations, oftentimes they're not fully driven by the strategies. But the people piece was exceptionally important. Empowering people on my team from the youngest members, the most junior members, I should say, so that they could start to earn and gain a very informal leadership experience before they even had anyone reporting to them.

4:20peer-to-peer counsel and support networks were important to me. And then the development of each and every single individual on the team to ensure that they felt that we as an organization, we were investing in them. Okay. So it sounds to me like success when you were internal in the corporate world was being able to meet the business objectives while at the same time developing and leading people. Exactly. All right. So it gives me sort of a, I don't know, I have this picture in my mind of what that land looks like. Yeah, exactly. Almost like a feel for probably what the energy of working in your organization was like.

5:06So what is the mindset that you think you had back then that enabled the actualization of the success that you had envisioned for your organization in terms of being able to drive for results while at the same time developing people? What's the mindset that you had as a leader? Well, there's a mindset and there was also a runway. Just as I'm speaking to you about it, the questions are popping up like, what is different? Why aren't you doing those things? First and foremost, I would say from a business results point of view, I had an infrastructure of the organization where we had annual objectives and long-term objectives that we were trying to hit.

5:48It might be launch a new product line, for example. And so then I could take that larger corporate strategy and then start to define what our accountability would be in driving that. What's absent in the new client-based environment is some of them are operating in the absence of that strategy. And some of them are very entrepreneurial driven. They've had much success leading their organization without a strategy that it'll take some time to help them exercise that muscle to understand that at this stage of the life cycle of their organization, in order for them, because they might've been seeing stagnant growth, in order for them to catapult themselves to the next level, it's going to require planning.

6:44And that's, you know, that's universal. Then I had mentioned the runway in the corporate world, although we oftentimes mostly feel like we have the shortest runway ever, that runway feels that much shorter when you are working with a client with a very finite finite period of time to prove results before they make a decision to say, yay or nay, we should move forward. So on the one hand, what's different for you now, one is there is no sort of overarching structure or architecture or framework that is driving the work that you have to deliver on. Correct. And if there is one that exists, because some clients are different from others, it's a very loose, it's not a formalized plan.

7:38Okay. It's very loosely there and, you know, probably has some holes in it and needs some updating, needs some validation in terms of data, et cetera. Okay. And then there's also this, you know, how much time you have to get them to move. So you've now identified what's different. So how does that make you feel? What's the difference in terms of the impact that it has on you versus the way that you felt in corporate, not having that overarching framework and having a shorter runway? Well, first and foremost, I am definitely hitting the ground running in an influencer role versus a pure leader role.

8:18Because I'm an asset to the executive leadership team, I'm asked to help them possibly rethink their organization. but I'm not being brought in on day one with direct reports and that leadership responsibility. So right out of the gates coming in, I feel as though I do spend, and I do this with any new role that I have. So this isn't necessarily different. I have to spend and invest a good amount of time to build trust within the teams that I'm working with. So there's a lot of listening and a lot of learning and observation. So that's not different. But the difference being is that, you know, through their lens of I'm a consultant, it's a little bit different than, you know, this person is my manager.

9:13I certainly feel as though how I delicately try to influence different people within the client's organization, those individuals are not expecting a leader. Now I have over time with some of the individuals, because I feel as though I roll up my sleeves and I do whatever is required to further, whether it's developing the relationships or mostly to get the job done. It feels to me as you're talking, like something is lacking and I'm trying to understand what is it that's lacking for you? Yeah, that's a great question is probably the leadership piece. In what way? Having a direct responsibility and an accountability to impact the growth and development of other individuals.

10:08I think in a very formalized way that, you know, that's not to say, and I, because I was just mentioning that I, I, I do this in the informal way. It looks different. So it's probably still really very much there, but it's not formalized. So maybe the client won't necessarily be aware of that impact that I'm having. It's hard to measure that. And that's not something necessarily that, you know, those individuals are going to report back to the executives to say, well, this is, you know, this is the impact that I've had. And then there's the, I don't necessarily think there's anything missing. I think it's the mindset.

10:49There's a mindset, maybe shift that needs to happen. And maybe this just naturally happens over time. The more you are out of corporate environment and you are in a consultant role that you become less focused on the, I've got to prove myself. I've got to prove myself. But truth be told, I think I was like that in the corporate environment as well, because every year was a chance to be promoted. Every year was a chance to kind of smash another goal. So maybe that's part of leading myself is reminding myself that it's all the same thing. It's just disguised differently. And the other thing that I definitely had to really have some stern talks with myself about was it's not the number of hours.

11:41Certainly there's a, you know, there's an expectation. If you have clients that expect you to deliver the equivalent of 20 hours of work in a week, you know, even if you're on a retainer base, you're, you're fairly cognizant of that in terms of how you delineate your time, but it's the results that you achieve versus the number of hours that you can, you know, that you're billing for. And I had to remind myself of that oftentimes throughout the last X number of months that, you know, I could bill out 20 plus hours, but if I achieve nothing in those 20 plus hours, that's, you know, that billing process won't last very long with that particular client.

12:24Right. Exactly. So, you know, I think it's really interesting because my sense is you're grasping for what are the measures of success that, you know, a year from now, two years from now, whatever X timeframe you want to use, you can look back on and say, okay, I've done well. I've succeeded. That is 100 % me. 100%. Because I even at the end of the week, I'm trying to create that list to send it out to the client. But I think it's almost more so for myself. Right, right, exactly. And, and, and, you know, you've had that when you're on the corporate side, it was very concrete, right? Like they sort of hand it to you.

13:11They say, Hey, it's January, here's what you've got to do by December, right? And now it's like, nobody's telling you what you have to do. Nobody's telling you what the measure of success is. you have to define it. Okay. And it might be ambiguous for a little bit until you have some repetition to realize, oh, this is how I can measure success for my clients. Okay. So my sense is right now, because you play such a high value on leadership and you're missing that in your role as a management consultant in the way that you've had it before, it makes you feel like, what's going on? Am I succeeding?

13:57And I think one of the things that I would offer you is when you talk about leadership, you know, I remember somebody said to me once, or I may have heard it, I can't recall, but they were like, there's being a parent, and then there's parenting. And the two are very different. Yeah. You can be a parent and not be great at parenting. And you can parent as a verb without necessarily having the title of being a parent. Very true. And I think what you have shifted from when you were in corporate, you had the title of being a leader positionally. And you were also able to lead. So you did both. You were kind of the holy grail.

14:38You were a leader who actually led. Right? Right now, when you're internal to your clients, you don't have the positional title. And I think that's kind of what you're feeling the miss of. Right. Yeah, exactly. They don't see you as the leader. And so I think you need to kind of sit with that, you know, and I'll ask you a sec, like, how does that land with you that they don't see you that way? But that doesn't absolve you from the verb of leading. When I say that to you internally at your clients, they may not necessarily be seeing you as the leader. They're seeing you as the management consultant.

15:22How does that land with you? Well, yeah, it's reality. That's the current reality. And as we're talking through this, just this morning, I identified to, you know, one of the executives, there's an individual on the team that has these types of development needs. So I, you know, not necessarily in this exact moment, part of maybe the accountabilities that I was signed up for. But I definitely, you know, I've been wanting to say something, wanting to highlight something. And I did do that. And it was well received. And I'm almost wondering, as you talk about, you know, the whole like differentiating the title versus the action, the verb, maybe I just have to carve out those moments as they organically come to light.

16:23And maybe in this scenario, it's a little more cushioned around, you know, what we're trying to achieve in this partnership, you know, the productivity, this might be in the way, or, you know, the resources, because I'm often asked to comment on the required resources of the organization. Is there a better organizational design for a certain department? And maybe identifying where it's not a matter of sweeping out certain individuals because they're not performing, but it's going a bit deeper. Were they ever performing? And just using some of those leadership muscles that I would have been flexing before, but trying to keep it again in an organic way.

17:08And I think it's, you know, when I think about... That need, there's almost like a fear that five years from now, I'm called back to corporate, the corporate world. Does that get rusty? Or is it just, you know, I just have to like dust it off a little and it's still there? Because I, for the last 13 years, made a strong commitment that on a weekly basis, I was doing something to elevate myself as a leader. So I don't know if it gets rusty.

17:44You're supposed to say no. Because that's what you want to hear, right? Yeah, exactly. Right.

17:54Jane is up against what a lot of entrepreneurs run into when they can no longer rely on clear cut corporate deliverables and metrics. She's thoughtful and wants to do a good job, but is searching for how to define that and what it means in a different context from her previous career. She can jump right into the tactical with her clients and see what needs to be adjusted in their business, but she's struggling in finding good leadership goals for herself in her own entrepreneurial venture. I'm curious about whether or not she's ready to let go of the structure and familiarity of the corporate environment.

18:26Let's jump back in as I bring this up to her. Yeah, great question. I certainly have my ambition, even though I've veered in a different direction in this current moment, my ambition is C-suite. And C-suite, I feel the most important skill set is that leadership piece. Setting culture, empowering people, that all equates to high level of productivity. I mean, there are other things in that equation for sure. Yeah. So am I, you know, I don't want to read into it. So correct me if I'm completely off here. Am I correct in saying that you having started your own business and become a management consulting is not necessarily the end all, like meaning I'm going to start my business.

19:23This is it. Right. As far as you know, it really is a stepping stone or a bit of a detour and expansion, but still at some point you'd like to be back in the corporate path on your way to the C suite. Correct. OK. Yes. OK. So that makes a difference. That makes a difference because I think in the same way that you mentioned, how do I leverage the skills and the knowledge that I gained when I was on the corporate side? How do I leverage that in terms of serving my clients? I think you have to think really intentionally about how do you use this experience in starting your own consulting business so that you're learning some things and you'll have some skills and knowledge that you'll be able to leverage that prepares you for going back into the corporate side at some point.

20:14Yes, that's right. And I think some of the discomfort you've been feeling is I've started my own business. I'm working with clients and it's kind of like, where's the where's the end? Like you're kind of making this motion where I'm going in circles. But like, where's the end? And is this really it? Very much so. Yeah, that's those thoughts have definitely been popping up for sure. Yeah. OK, so it's good to know that this is in context of this other goal that you have, because then that kind of changes how you approach it. All right. And this piece around, is it going to go rusty? And I said, I don't know, you know, because it depends.

20:56It depends what you do with it. Sure. Right. Sure. I remember when I, I remember when I left my corporate job, right. Corporate. And I had been in like strategy consulting and I moved into coaching and I hung up my shingle and I, you know, it was just me at that point. But I remember always saying, you know what? Worst comes to worst. I can always go back to like being a strategy consultant or go back to corporate because I know how to do this, this and this. And then I remember like a couple of years in, maybe it was on like year five or six, I woke up in the middle of the night and I like woke my husband up and he was like, what is going on?

21:36And I was like, I don't think I can go back. And he said, what? Go back where?

21:44I said, I don't think I, my fallback plan, remember, I could just go back to this. I don't think I can go. And he was like, what are you talking about? I said, I don't, I don't think I can work a spreadsheet the way I used to.

22:01Because I had, I had let it go rusty. But the reason I let it go rusty is that even though that was kind of my little fallback plan. It was a fallback plan out of fear. I didn't really want to go back. So I let it go. But if I really wanted to go back, maybe I should have taken actions there. So what I'm going to ask you is, if your end goal, your Uber goal is to be in the C-suite in a corporate environment, what are the skills and muscles? I'm going to put them in two categories. What are the skills and muscles that you want to maintain and retain and keep fresh that you already have? And what are the ones that you want to grow while you're having this experience in having your own business and working with clients?

22:54The second one, I don't readily have an answer for. The first one, so what's already in my existing wheelhouse? the strategy component, the ability to come into a business, identify very quickly how it's been working, what's led to the current success or lack thereof, what's impeding growth, and what are some of the tactics that can be employed for some quick wins. Well, first off, I always say, I've always said this to my team, no one really truly will follow or jumps on board if you don't have a plan. It's like I'm showing up to a house build and I don't have the blueprints for the house and I'm the architect.

23:49So I'm always rapidly starting to devise that blueprint, but a couple of quick wins really gets people on your side. And having the ability to confidently make bold decisions to chart a new course, it's really hard when an organization or division has been doing something for 10, 20 years. But to boldly say we're going to go in this direction, and I believe these are the results it will achieve. And I feel that that's a requisite in a C-suite role. And of course, it's a template. It can be applied to any business, any division of a company, et cetera, et cetera. And then achieving those results 100%.

24:37What do I need to develop? When I left the corporate world, I was in a fabulous organization. I've been in very big organizations that, you know, very recognizable. I was very proud of that. I was very proud that they believed in me and they developed me and I was able to excel. But I was pigeonholed. So I was even, you know, when I tried to make a leap to the other side of the business, I was always kindly kind of redirected. So learning other parts of, you know, functional parts of the business, I feel is really important. But also making a name for myself and like expanding my own brand to bust out of being known for X, this, you know, this functional expertise.

25:34And that it always be the, you know, my name would be a little more synonymous with, you know, this type of function. So there's a couple of things that I'm hearing from you. All right. When you talked about the things that you can keep, right? Because I kind of see this as like, what do you need to keep? What do you need to pick up? And what do you need to let go of? Right? And I think the let go of part is probably what's going to be a little tricky. But we'll get there. Okay. But the stuff around what do you need to keep? And they're all related, right? Like, what do you need to keep? of the strategy piece, being able to drive to results, being able to lead people towards results and support the agenda of the organization.

26:20You want to be able to keep all of that. What I heard as an undertone is a sense of ownership, a sense of owning how we drive to the results, a sense of owning how you develop the people to get to the results, a sense of owning how do you frame the vision and the strategy in order to meet the overall corporate strategy? And to what extent do you feel you have any ownership when it comes to the work that you're doing for your clients in the way that you did on the corporate side? Well, I definitely feel as though I've shifted to player more so than coach. Because I've had to, I've had to be able to say like, this is something that I have contributed in the last X number of months.

27:13And those have been quite tactical. I mean, I have written a strategy and, but I, I feel that that's a communal document. I took information and data and input from various sources of the organization. And for me, in that particular instance, it matters more to me that it's a communal paper versus, you know, this is, this is mine because then I feel as though I'm trying to take something that I've authored and, you know, kind of like enforce it on people, like as opposed to it, you know, it was a community collaborative effort. Let me ask, when you ask that question, is it because you feel that it's important to me to, to be able to say, I, I, I can put my stamp on that.

28:08Is that why you're asking the question? Um, well, I don't know why I'm asking the question. I just asked the question. I wasn't going anywhere with it. It's just something that I asked. And so I'm going to ask you that. Do you feel a need and without judgment, nobody else's, you know, the clients aren't in the room here, right? No judgment. Does it do something for you? Does it give you more of a sense of confidence or value if you feel like you can point to something and say, that was me? There's a direct line back to what Jane did. Yes. And I don't like admitting that because for the last 15 years, that's exactly the opposite of what I was trying to do.