How Do I Become an Intrapreneur?

MURIEL WILKINS: HBR presents. I’m Muriel 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. Today’s guest is someone we’ll call Charles to protect his confidentiality. He’s been a project manager at a real estate development company for around five years after spending time in finance and in the public sector and after getting his MBA. Charles has started thinking about the ways he can develop his niche at the company and move forward in his career in part by focusing on a small but growing part of the business.

CHARLES: I really began to think of it as an entrepreneurial role. I started to really do some research around that and think of myself… Even though I don’t have a separate P&L for this business, I wanted to start thinking like that and start putting myself into that mindset. And part of what I’m navigating right now and in need of some further guidance on, is making that mental switch and also this sort of career adjustment that’s perhaps pushing the envelope a little bit relative to where I am in my career now.

MURIEL WILKINS: Charles is thinking about the ways that his personal goals can align with the goals of the company. Even when there isn’t a formal path to getting there, he’s thinking about how he can be more entrepreneurial.

CHARLES: I would like to really be running this business unit. I, for a long time and perhaps to some degree still, have kind of entrepreneurial ambitions and if the right opportunity presented itself for me to go out on my own, I certainly would strongly consider that. But I’ve also realized that there’s a path that could be equally for fulfilling where I do that within the context of a larger organization. But I know that to accomplish that I’m going to need to kind of create that role for myself. It doesn’t exist today, it’s not like there’s someone else in that job that I can eventually replace it. It’s a whole new job description, if you will, and so kind of crafting the job I want and then moving myself into it is kind of what I’m seeking to do in a way.

MURIEL WILKINS: Charles came to coaching looking to specifically figure out how to carve out this other path. Let’s dive into the conversation now as I ask him more about why he wants to take his career in this direction instead of staying on the track he’s on.

CHARLES: Absent any deliberate effort on my part, I could just follow that track and be here thirty years from today doing the same kind of job but in a different way. And I realized that that’s not what I want to do. I want more than that, I want to have a business development aspect to my job, I want to really have some ownership. I eventually want to have sort of people working under me that I can mentor and coach and grow into a real organization within the organization, if you will. So, in order to do that, I have to kind of create that role. You know, I was promoted a little while ago, but in this capacity I’m still viewed largely on paper and by certain folks in the organization as an execution person, right?

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

CHARLES: Not as a business leader. It’s not an officer role like a vice president role would be. So, part of it is overcoming the mindset hurdle of others to see me as someone who’s already starting down this path of being a business leader within the company and not just a individual contributor execution person. So, that’s part of the obstacle is getting others to see me in that way and to embrace my vision for what my future looks like and how that could dovetail with what’s in the company’s best interest.

MURIEL WILKINS: Mm-hmm (affirmative). Okay. Understood. So why don’t we start with that?

CHARLES: Mm-hmm (affirmative).

MURIEL WILKINS: Because of the two questions that you surfaced are very much connected with each other. One is, what’s the mindset and habit that you need to shift to in order to be an effective entrepreneur? And the other is, how do you change the mindset and habitual way that people perceive you so that they view you as an entrepreneur? Right? So, we’re sort of like chicken and egg.

CHARLES: It is as a very much just kind of hand in hand parallel path thing going on and too much progress in one area starts to kind of run up against not enough progress in the other area.

MURIEL WILKINS: In what way?

CHARLES: Well, if I really push on the changing my habits and I’m trying to shift kind of how I spend my time every day, I can only go so far with that before someone says, “Yeah, but your current job is X and you got to still do that.” So, to move them along that path, I have to get them to begin to see me as, “Oh, no, he should be spending his time on this business development stuff, for example, because that is part of the role he’s increasingly playing.” So, I kind of view these things as moving in lockstep. As I evolve, I need to make sure others are evolving as well in how they perceive me.

MURIEL WILKINS: Yeah. So, I mean, in essence you’re straddling the two variables that I sometimes chat about, which is you’re straddling knocking out of the park your current performance in your day job while demonstrating your future potential in what you aspire to be. Right?

CHARLES: Yes.

MURIEL WILKINS: And here’s the good and bad news. The good news is you have an opportunity to do that, right?

CHARLES: Yeah.

MURIEL WILKINS: Like you have a field where you can play both. The bad news is you’ve got to play both for a while and you’ve got a parallel path on them. Like it’s you almost want to think about them as two businesses; one that you are already solidified and you’re maintaining it which is your current performance, the things that you are currently responsible for, while you have the side hustle, you know?

CHARLES: Yeah.

MURIEL WILKINS: This other business that you’re building and you’re kind of in the stage of building the business case for it. Right? Not quite sure how people are going to respond. So, from the sense of one rubs up against the other, I guess I’m going to offer to you how can you think about them as an and rather than one versus the other.

CHARLES: Yeah, that is a great point and I think it is what I have been doing as this has evolved. I want to be clear that my boss, for example, and some of the others in the region are supportive of kind of the direction I’m trying to take things, and I think they do see this pathway for me as being a legitimate and relevant kind of path for the company. So, I don’t want to make it sound like I’m pushing everybody uphill against their will. There’s definitely support there, but it is an and. It’s both doing the current job at an exceptional level and I’m increasingly working on how do I do that more efficiently? Is there ways to delegate? Is their “fat to be trimmed” there that can make room for the side hustle to grow? That’s been and it is an ongoing effort. And then the side hustle – I realize I have to demonstrate value in that side hustle in order for it to be able to grow. Right? That only if I show the time that I’m spending on that is creating value, okay, well, then you can do more of that. And so for a period of time, I’ve got to juggle both and do both and I have no illusions about that. I think I want to kind of begin with the end in mind here and think about in two or three years when I’m hopefully at the point of letting the side hustle take over, if you will, that I’ve done everything that I can and need to do to make sure that happens.

MURIEL WILKINS: Yeah. No, absolutely. So, what you’re looking at is kind of a gradual shift in proportion in terms of the energy and focus and time that you spend on the day job versus the side hustle, right? So-

CHARLES: Right.

MURIEL WILKINS: … you have a certain amount of time and energy to spend on anything and the question is where do you focus it?

CHARLES: Yeah.

MURIEL WILKINS: So, if I’m hearing you, it sounds like you have the support internally, so that’s not the rub, but it sounds like the rub is in how you allocate yourself so that you can still do the current job effectively, but give attention to the growing business and be in an entrepreneur there so that by the time it’s full scale and there’s actually a business that you can run.

CHARLES: So, I think that is the area that I struggle with the most, because while I can intellectually acknowledge that what got me here won’t get you there as my old boss used to say, it’s one thing to say that, it’s another thing to let go of the things that have made you successful and some, perhaps, a perfectionist in some ways. And let go of some of those things so that you can make that room.

MURIEL WILKINS: So, what are the things that you feel like you need to let go of in your current role?

CHARLES: I would say more and more delegation is something that I need to continue to work on. My first inclination when there’s something to be done is to think, how am I going to get this done? How many extra hours is this going to take? And I probably should be at least in parallel, if not in the first place asking, does this need to be done, period? And then if so, who should do it? Like who’s the right person? Maybe I’m not the right person. The delegation piece and kind of letting go of the control kind of delegate both the task and the authority behind that, you know?

MURIEL WILKINS: Mm-hmm (affirmative).

CHARLES: And not kind of keeping my fingers in it to much-

MURIEL WILKINS: Right. Right. Right.

CHARLES: … which is really hard sometimes. I think that’s definitely one of the things I need to work on. And then I think the other thing which I sort of alluded to, I’ve never really developed a good dial for, quality is not the right word, but the effort dial. I either do things at a ten or I don’t do them, right? I don’t really have a one through nine, and that’s fine when you’re a student, that’s fine when you’re an individual contributor with kind of a manageable kind of load. But I think increasingly I’ve got to develop more shades of that effort in order to… because not every task deserves an A, right?

MURIEL WILKINS: It sure doesn’t.

CHARLES: And once some tasks, a C effort is perfect. And guess what? You’re not going to get any credit for doing more than that. So, anything you do above a C is kind of wasted, and it’s hard to admit that as the person doing the work, but it’s kind of like this task doesn’t need more than that.

MURIEL WILKINS: I mean, Charles, the answer lives within you, right? Like you literally just came up with your own for framework, I’m not even sure why I’m here coaching you. You’re coaching yourself. Because in essence, if the goal is to create more space so that you can then allocate that energy, that time, that focus to building the business, right?

CHARLES: Mm-hmm (affirmative).

MURIEL WILKINS: So, the question becomes, how do I create space? I think what you’ve articulated is really a two step process. The first is delegating. So, shifting from I do the work to who else can do the work if it needs to be done. And then the second is if I do the work, meaning if Charles does the work, what does doing the work look like? Right?

CHARLES: Right, right.

MURIEL WILKINS: Does it always need to be full throttle on ten? Okay?

CHARLES: Yeah. Yeah.

MURIEL WILKINS: The question is, can you have the discipline to go through that process?

CHARLES: Yes.

MURIEL WILKINS: Okay?

CHARLES: Yes.

MURIEL WILKINS: And one of the things that you might want to consider is before you even start doing that for tasks that are going to come your way, that you can start by actually doing an inventory of what’s currently on your plate.

CHARLES: Hmm, interesting.

MURIEL WILKINS: So if you were to post our conversation, look at your to-do list, or even do an inventory of over the past month, if you could roll the tape back and ask yourself those same questions, A, should I be the one doing it? Should it be done? A, should it be done?

CHARLES: Yeah, that’s the most brutal.

MURIEL WILKINS: B, should I be the one doing it right? Should it be done? You know, kind of going through those questions because what that will come up is, well, what do you need to know to actually answer those questions? So, when you think about should something be done, what do you base that on? How do you even make that decision?

CHARLES: I think the answer to that has and continues to evolve for me. In the past, I might have said, well, it needs to be done because it’s pertinent to a project success or it’s something my superior is asking me to do, or it’s going to have a direct kind of impact on my performance review and perception. Right? And all of those things probably are still valid, but perhaps are shrinking in their relative proportion to questions like is this going to move the needle on this business I’m creating? Is this going to drive revenue or an outcome that’s going to lead to revenue versus is this just moving pieces around the board and not really getting anywhere? Maybe there’s, like I said, some brutal honesty that needs to happen with myself to say, “This might feel good to be doing this and it feels like you’re making progress, but it’s not really moving the needle and maybe you need to let it go, because you enjoy doing it, maybe you like doing it in the past, but it’s no longer serving the broader objective.

MURIEL WILKINS: That’s absolutely right. And here’s the thing it’s very hard to make that distinction if you don’t have clarity around what the broader objective is. Right?

CHARLES: Yeah, mm-hmm (affirmative).

MURIEL WILKINS: So just because something has become in the it’s-something-nice-to-do category as you put, it doesn’t mean it’s moving the needle. But it used to move the needle, and so what’s the difference? The difference is in the goal, what is it moving the needle towards? Right? What is the destination? And so I think a big piece of this and probably why you’re experiencing some tension here is that the Uber objectives have changed, but your focus and your habits and your mindset as you put it have not completely shifted over. Right?

CHARLES: Right.

MURIEL WILKINS: And in a way they need to play in both sandboxes. So, when it comes to delegating and starting with that decision point of is this something that needs to be done? The way to filter through that is make sure that you have clarity around what the overlying objectives are, and determine based on those objectives, does this fall in the path?

CHARLES: Right? The question I had was sort of… You know, as you’re trying to think through what that broader objective is, in some ways it feels like that broader objective is becoming less about me directly in a way in the sense of I’m not doing this thing because there’s a direct line between completion of this task and my own sort of performance. The line has become kind of more squiggly and it’s sort of like this task, this thing, this subject is going to drive revenue and grow the business. I benefit from that growing business, therefore, this benefits me. It’s almost like introducing kind of another level or layer that I’m realizing I need to be thinking through kind of that lens versus the old lens of more of the individual contributor. You know, this is my little fiefdom, I just need to manage this to kind of more broadly thinking there’s a business to be grown here and it’s going to take time and there’s lots of steps involved and there’s going to be a winding path. Eventually it will all… The success that I have personally in my career is directly linked to that, it’s just maybe not as straight a line as it used to be in a way.

MURIEL WILKINS: Yeah. I mean, what you’re articulating is you’re scaling up because before, the goals were sort of a direct line to what you can impact as an individual, and now you’re seeing it as there’s a bigger goal, right? It’s at the business level, so you’re leveling up. It’s no different than being, for lack of a better metaphor, a bachelor and all you have to think about is yourself. Right?

CHARLES: Right.

MURIEL WILKINS: And then all of a sudden you got the partner and the kids and it’s like, “Ooh, now I got to think of the family.” Right?

CHARLES: Yeah. Yeah.

MURIEL WILKINS: But a lot of people say, “Yeah, but don’t lose sight of yourself as well.” So it’s an – and so, in this particular situation, you’re moving from bachelor to the family in terms of you’ve now got to think about something bigger than yourself while not losing sight of the things that are responsible for taking care of you – i.e. your current position.

CHARLES: Yeah. That’s a really interesting, I think, relevant way to think about it and perhaps resonates only because I do have a small child now and sort of learning to respect new constraints and limitations that I have, that are definitely uncomfortable, right?

MURIEL WILKINS: Mm-hmm (affirmative).

CHARLES: For someone who sort of didn’t always have to make those considerations, so it’s a really interesting kind of analogy to think about a kid, and you’ve got to nurture it and grow it and make room for it and have a vision for what it will become. And it’s never going to stop growing and evolving so you have to keep up with it-

MURIEL WILKINS: That’s right.

CHARLES: … but you also, I think, make a great point. You can’t lose sight of yourself and in this professional context, it’s the job at hand that is still what I do on paper.

MURIEL WILKINS: Which will also evolve.

CHARLES: Yeah. Right. Exactly.

MURIEL WILKINS: Let’s take a pause here. Charles has already spent a lot of time thinking about what to do next and as I mentioned to him, he’s really coaching himself. But as he thought about the constraints that he faces, the example of what it can be like to have a new child really struck a chord with him that helped him see his situation in a new light. Just like having a newborn required him to change his considerations when he became a parent, he’ll need to shift how he manages himself as he moves to being more entrepreneurial. I wanted to dig a little bit deeper here to see how he approaches his current constraints and to ask him how he decides where to spend his time and energy. Let’s jump back in as he responds.

CHARLES: Usually my first step and my first thought is to try to just be more efficient like we were saying earlier, right?

MURIEL WILKINS: Mm-hmm (affirmative).

CHARLES: The ultimate answer and the one that I’m coming to terms with is being more selective about what you agree to do in the first place and being much more… just being really choosy, I guess, and really recognizing that you’ve got to say no to a lot more than you used to keep the things that really matter. And as you said earlier, that requires having clarity on what really matters and that’s a process in and of itself, I think. But you efficiency is only going to take you so far I think, and then you have to say, okay, prioritization and really trimming out the things that aren’t moving the needle. Whether as a parent or as a professional, trimming those things out I think is ultimately what has to happen and that’s, I think, a lot of where the challenge is but where the opportunity lies also.

MURIEL WILKINS: That’s right. Because as cliche as it sounds, I love it. I love this cliche, but when you say no to something, you’re saying yes to something else.

CHARLES: Yeah.

MURIEL WILKINS: Right?

CHARLES: Yeah.

MURIEL WILKINS: So, the question is what are you saying yes to? And your disposition tends to be to start with, “Okay, how can I make this more efficient?” And then you’re saying, “But maybe I should be shifting to no, let me think about how I can be more selective and move into prioritization.” That shift is a shift between being reactive to being proactive. When you’re saying, “Okay, what’s on my plate, how can I be more efficient?” It’s I’m reacting to what’s in front of me and trying to triage. Right? Versus, “Oh, let me think about what is the highest and best use of my time for what this current job needs, as well as what that side hustle, that building business needs.” Let me be very clear around what I have to offer, what it needs, and then find that intersection of what is the highest and best use of my energy and my focus and my time, and use that as the filter for deciding where you put your time and energy and focus, at least 80% of it, right?

CHARLES: Yeah.

MURIEL WILKINS: There’s always going to be that 20% that-

CHARLES: Right, doing the laundry.

MURIEL WILKINS: Exactly. You were reading my mind, Charles.

CHARLES: You still got to do the laundry.

MURIEL WILKINS: Doing the laundry. Still got to do it.

CHARLES: Nobody gets away with that one.

MURIEL WILKINS: I mean, I try to delegate it, I don’t get very far. So when you start thinking about it from that standpoint, the question of what is the highest and best use of Char… And this is a real estate term so I know you get it.

CHARLES: Yeah.

MURIEL WILKINS: Right?

CHARLES: No, I do.

MURIEL WILKINS: What is the highest best use of Charles as it relates to these two areas that you are responsible for? How do you think about it?

CHARLES: Yeah, and as you were walking me through that, the thing that really came to my mind and this relates to your previous comment about having clarity on the vision or the goal as being a necessary kind of prerequisite. And I was reminded of when I was in my MBA program, I went to school, I was a little bit of an older student relative to my peers and I had a laser focus. Like I went there, I’m here to get an MBA in corporate finance and real estate. I have zero FOMO, I do not have a single FOMO bone in my body, and I’m just going to say no to virtually everything that doesn’t align with that objective of adding this real estate skillset and then getting a job in this field. I was pretty brutal, I mean, to the point where one might argue I took it too far and didn’t do enough kind of fun exploratory things. But I was really, really clear; this is what I’m here to do, and I’m making this investment in myself. I’m not going to dillydally with other things that aren’t directly aligned with that. I don’t know why I didn’t think of this till this conversation, but I can’t remember another time in my life when I’ve had that much clarity that was really then followed through with actual action and behavior change and really saying no to things that don’t align. And not being ashamed to do that, not feeling mixed feelings of about, “Oh, I’m letting this person down, or what are they going to think of me because I’m telling them no about this?” I was unapologetic.

MURIEL WILKINS: Unapologetic, yeah.

CHARLES: And I need to take a page out of that book, I think, here. Really get that clarity on both the side hustle and the current role and then just be unapologetic about these are the things that I’m pursuing until somebody tells me otherwise, that counts.

MURIEL WILKINS: Right, and I think there at the core of it lies your definition of the mindset of an entrepreneur, right? It starts with, I mean, I don’t think you’ll find this in the NBA books of the unapologetic that you’ll see it termed as conviction and purpose and passion, but we’re going to call it unapologetic, okay?

CHARLES: Yeah. I’m with you.

MURIEL WILKINS: Laser focused. Right? So, my question to you is what will it take for you to get that level of clarity now in this current context?

CHARLES: So I think it is going to need to start with some reflection on what are those goals in both areas, because I think maybe they’ve kind of changed a little bit in recent times and I haven’t fully taken that on board. So getting that clarity first because that conviction, that unapologetic nature, I think comes best when you have that clarity. Like my propensity while someone asks me to help with X, Y, or Z, you want to please people, you want to be liked in the workplace, you want to be reliable and you want to be the person who always has a solution or, you know? That’s historically been my sort of self-defining feature, and not that I want to be a complete jerk, but there’s room in there to move in that direction of being a little bit more assertive, borderline prickly to just be clear on that. And then you’re like, “Let me point you in a different direction.” It’s not like just “no go away” but it’s finding the right tools and words to redirect those incoming things.

MURIEL WILKINS: Great. So in that, the reason why the clarity of goals grounded in the business is important for you. It’s because without that you won’t have a good reason to delegate or to say no and not be who you habitually have been which is to do everything, right? And my guess is that just saying no for the sake of saying no is not a good enough reason for you.

CHARLES: Right.

MURIEL WILKINS: In essence it’s creating boundaries, putting a stake in the ground, so that you can create some boundaries and those boundaries lead 80% of the way. We don’t want it to have so much rigidity that you lose sight of things, but how you make sure that you maintain some flexibility is that you’ve revisited time to time. This question of highs and best use and clarity of goal is not a one and done. I’d say particularly now as you’re building this thing and you’re looking to shift your focus from one to the other, you should be revisiting it every couple of months.

CHARLES: Yeah, that’s a great point, and having that regularity is definitely not something I’ve been intentional about.

MURIEL WILKINS: Which segues nicely into the other question you had, which is how do I create harness the mindset of an entrepreneur. So, when you think about what’s the mindset that you need to shift to, how do you define the mindset of an entrepreneur?

CHARLES: I certainly think a big part of it is what we were talking about earlier, having that clear focus, the conviction, the unapologetic nature of that. I think having a mindset that’s flexible and creative around how things get done, that sort of plays into the delegation a little bit but I think it maybe is broader than that of just having an outcomes-oriented mindset versus like an inputs-oriented mindset, right? Putting three hours or thirty hours into this is irrelevant, what’s relevant is does, the outcome match what’s needed? I guess proactive would be another key piece of it; to your earlier point. There’s a lot that comes at you every day and not all of it really deserves your attention or your effort, and you have to sort through that but you kind of need to do so more proactively rather than just being in the midst of the river kind of having the water push past you.

MURIEL WILKINS: Yeah. Yeah, absolutely. So, if you were to think about a theme to the mindset that you’ve had to date before you became an entrepreneur, what would be the theme or the title to that soundtrack?

CHARLES: Hmm. That’s a really good question. I mean the word that comes to mind first is kind of intensity. It would definitely be kind of a heavy metal soundtrack that’s just kind of constant and sort of not nuanced in any way. And there’s a there’s level of just pushing, pushing, pushing constantly, and maybe not having as much of a rudder, right? It’s all kind of forward thrust and not as much kind of guidance. And I feel like that’s been fine, that’s got me here, but I realize that what’s needed going forward is much more nuance and kind of guidance around where do you focus that thrust?

MURIEL WILKINS: So what would be the theme and soundtrack to your entrepreneur music?

CHARLES: I mean, I feel like it would be, like I said, equally intense. Intensity wasn’t really the distinguishing thing, but it’s almost like a really… I’m trying to think of like a very intense classical music piece like Flight of the Valkyries or something where it’s very… There’s a lot of precision and nuance and clarity built into every note, but it’s equally voluminous and kind of filling of the room, you know?

MURIEL WILKINS: Mm-hmm (affirmative).

CHARLES: Similarly, I’m not expecting or seeking for my professional life to be any less driven or hectic or demanding. To the contrary, I know it’s going to continue to be, but it’s about being demanding in the right areas in the right ways.

MURIEL WILKINS: So, what I hear in commonality between the two themes is the activity part doesn’t go away, the execution part doesn’t go away.

CHARLES: Right.

MURIEL WILKINS: Right? But one which is the former as an individual contributor’s activity that falls within directive potentially, but there’s a lot of activity with a lot of intensity and it’s a lot of doing. And what I’m hearing in terms of an entrepreneur in terms of what you’re saying; yeah, there’s a lot of activity but it’s aligned with certain outcomes or certain goals, which is really interesting because I heard… I don’t know who said this. You’ll have to excuse me, my memory is horrible when it comes to remembering names. But I heard somebody once describe or I read somebody describe entrepreneurs as dreamers who do; dreamers who do, and I love that because it basically synthesizes exactly what you said. It’s the and. It’s the and between the vision and the goal and the clarity of that goal and the execution, the things that need to make it happen and that’s what an entrepreneur and an entrepreneur do. Right?

CHARLES: Right. Right. Yeah, a hundred percent and I’m going to revise my previous statement about the soundtrack because I realize that was missing something. I think that the entrepreneurial soundtrack is probably more like John Coltrane. There’s a huge amount of technical proficiency that underlies it, but it’s very creative and free flowing and entrepreneurial, everything that an entrepreneur or entrepreneur needs to be. And it has a melody and there’s a clear consistency to the music and it always resolves it itself where it is going, but the path there is totally improvised, right? And that’s kind of how I see that as is coming sort of together in my mind is as a former saxophonist, I should have thought of that initially.

MURIEL WILKINS: So, my son is a saxophonist so-

CHARLES: There you go. That’s nice.

MURIEL WILKINS: … a current saxophonist is thriving, so I can totally relate.

CHARLES: Awesome.

MURIEL WILKINS: So, I want you to carry that, right? I want to carry these soundtracks because that’s something that you can feel.

CHARLES: Yeah.

MURIEL WILKINS: When you were talking about the heavy metal, I could feel it. Right?

CHARLES: Yeah.

MURIEL WILKINS: I could feel being in a heavy metal environment. I could feel it inside, I feel it in even the way you were describing it, and I could feel a shift in the way you presented yourself and your energy when you talked about it being more of a John Coltrane soundtrack. And that’s something you feel. So, I want you to use this element of soundtrack just as a signal for you as to when you’re operating more in one mindset versus the other.

CHARLES: Yeah. That’s right.

MURIEL WILKINS: And using that as the flag of what shift do I need to make, whether it’s one to the other, because right now you’re straddling.

CHARLES: Right. Right.

MURIEL WILKINS: So, it’ll give you a sense of when you need to shift gears.

CHARLES: A hundred percent. No, I feel like that literally changing the soundtrack, because I do listen to a lot of heavier music in the car these days. That’s more been my mode of operating and I was sitting here thinking when was the last time I listened to John Coltrane or any of the other Charlie Parker the saxophonist that I used to really enjoy listening to when I was playing actively. It’s been a long time, but that resonates very, very strongly. And I think you’re right, the question is like, okay, how do I decide which CD to put in the changer? Right? Is today a heavy metal day or is today more of a jazz day and figuring that out and navigating that. You said something earlier in the conversation that I think I do want to kind of come back to here around the discipline. Following the discipline, rehabituating to this notion of, okay, when something new comes down the pike, the algorithm I’m going to put it through has to change. The steps that I’m taking as I’m thinking through what to do with this thing has to be different. And we’re representing that in this music here, it’s not just… It used to be throw it on the pile and keep plugging and full blast, right? Full volume. And now it’s more of, okay, I need to work it in a more nuanced way. There’s a few notes in my solo that I’m going to add as a result of this, but I’m not changing the whole structure of the song and maybe I’m not even incorporating it at all. Maybe it’s just something that needs to pass me by,

MURIEL WILKINS: By now, Charles has a very clear idea of the steps he needs to take to get on the path he wants. To steadily shift from always doing everything in the mode of an individual contributor to learning to decide what is most vital for him to spend his time on. I wanted to work through some real examples with him to make sure he didn’t just get it conceptually, but could actually apply it after our coaching meeting,

CHARLES: Thinking of a very sort of tangible nuts and bolts example of this, in the past, when I’ve received outreach from other vendors or contractors or architects who reach out to me and say, “Hey, I’ve heard about this new project you’ve got and whatever, we’d love to come talk to you about what we do.” They’re trying to generate new business on their end, and historically more on often than not, I was engaging in those conversations or at least entertaining them and maybe giving people a half an hour of my time mainly to grow my network and to grow my exposure. More recently, I have started to put, for lack of a better word, a script together of a very nice way of saying, “I can’t do that and here’s why.” And importantly, and this is really the critical little nuance, not leaving the door open and in a very professional, nice way I need to kind of move that incoming aside. Right? That’s kind of an obvious example and one a low hanging fruit that I’ve already self-identified. It definitely feels like it’s something that’s going to just require a lot of practice and intentional effort. That’s kind of why I like the idea you said earlier about start by looking backward, things that have already happened and do an inventory. Like, yes, you’ve already done this thing or it’s already entered your to-do list, but how did you do? It’s like score yourself from the past and where could or should I have done differently, that to me feels like that would be an easier way to kind of get in the water because when you’re just dealing with the stuff coming at you in the midst of the day, you’re in sort of live fire environment, it’s really hard to add new frameworks to that, right?

MURIEL WILKINS: Yeah.

CHARLES: You’re just trying to stay, and I’m totally mixing my metaphors here. You’re just trying to stay afloat right and not get swept away. That’s a really difficult time to be introducing new untested things. At least for me, I would not trust myself to step out, and I’m going to try this new thing and it’s unproven and so it could totally blow up in my face and I could lose time and it could be… It feels very risky to do that when it’s in the midst of everything.

MURIEL WILKINS: So, I think what you’re basically saying is clean out your closet before you go shopping, right?

CHARLES: Yeah.

MURIEL WILKINS: Meaning it’s the same framework. You know, do I need it? Should I wear it? Do I give it away? Do I throw it away? But let’s look at your closet first and clean that up, and it’s practice for over laying those decisions that you need to make. And then the next step is then you go shopping you say, “Okay, I see everything in store, how do I make a decision around what I pick based on this framework that I have?” So by looking at what you’ve done over the past couple of weeks, it is practice. It’s the mental practice of running through those questions, how do you make those decisions, recognizing that you might identify opportunities right there on the spot that creates some space for you moving forward. One of the areas that I encourage people to start is even just look… I don’t know how you do your calendar, but let’s assume it’s Outlook. It’s even just to look at the meetings that you’ve had for the past four weeks. Do a retrospective just on meetings alone.

CHARLES: Yep. Yep.

MURIEL WILKINS: And putting those disciplined questions to those meetings, and then in hindsight saying, “Huh, which ones did I really, we need to be at?” Right?

CHARLES: Mm-hmm (affirmative).

MURIEL WILKINS: Which ones could I have delegated? Which ones did we even need to have?

CHARLES: That is excellent and I think what that could also do for me is create a builtin progress tracking mechanism in the sense of if I look back at February and do that analysis and categorize everything, did I need to do this? If no, it goes in that bucket and break it down as you’re describing. And then when I look back at March, did I improve? Right? Did I do better at eliminating? Are there fewer things on the calendar that shouldn’t have been there? Are there things that were delegated or? And give me an opportunity to kind of provide that guidance to myself over time so that over the next couple of months, I’m hopefully making real meaningful progress on that transition.

MURIEL WILKINS: I think that your habits currently are very steeped in action orientation. Yeah. And the shift, the mindset shift that you’re making in order to accomplish your intrapreneur goals and to mind the role that you’re in now, is to think, decide, and then act. So it’s the think and decide that need to be integrated into your process. All right?

CHARLES: Yeah.

MURIEL WILKINS: So, from that standpoint, you said that there’s a couple of habits that you think now you’re going to put in play. What would those habits be? What are the ones that you think just as a summary that you think you’re going to be focused on?

CHARLES: I think the first one, the macro one that comes to mind is just introducing a pause, getting more comfortable with pausing. As someone who’s very action-oriented and kind of go, go, go all the time, introducing the pause I would say is the first step and then what do I fill that pause with? Adjusting the framework from just being how is this going to get done to does it need to be done? Who should do it? And then if it does, what’s the appropriate amount of effort that should go into this? I think the third habit that comes to mind is regularly reevaluating the goals. Every few months kind of stepping back up to that macro level and saying, “Okay, are the overlaying objectives and goals and vision that I’ve set that through which I’m filtering all of these things on a day-to-day basis, have those shifted at all?” All of those fit under this notion of introducing the pause, whether it’s a pause before saying yes, whether it’s a once a quarter pausing to think about the vision. That’s kind of to me like the macro-mantra of the conversation is kind of introduce a pause.

MURIEL WILKINS: You know, when we entered the conversation, we talked about straddling both your current job and the side hustle, and that notion hasn’t gone away. Right?

CHARLES: Yeah.

MURIEL WILKINS: Like you still need to the straddle, I think it’s how you do it.

CHARLES: Yeah, absolutely. Absolutely. It’s a needing to do it and doing it effectively and I think we’ve talked about a lot of good strategies for how to do that, so thank you.

MURIEL WILKINS: All right. Terrific. No, thank you. Thank you. Best of luck. When Charles came into the coaching conversation, he had an idea of where he wanted to be career wise, but not a clear sense of how to get there. In putting some of the strategies we discussed in place, Charles will be creating a bridge between the career vision he has and the execution to make that vision a reality. By creating alignment between his actions and his goals, he has a much better chance of attaining the career he desires. And by doing so, he can now consider himself among those who are not just dreamers and not just doers, but rather they are the dreamers who do. That’s it for this episode. Next time on coaching real leaders.

SPEAKER 3: It’s kind of that aha – like, this is my capability, this is my capacity, this is a product of how I was raised. It is not my team’s and nor should I expect them to meet the standard I set for myself, which means I need to hold them accountable sooner and it’s uncomfortable for me, because I’m in a people role, there’s a piece about being liked.

MURIEL WILKINS: Thanks to my producer Mary Dooe, sound editor Nick Crnko, music composer Brian Campbell, my assistant Emily Sopha, 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’d like to dive deeper into these coaching sessions, join me and the rest of the Coaching Real Leaders Community for live episode discussions at coachingrealleaderscommunity.com. And if you’re dealing with a leadership challenge of your own, I’d love to hear from you and possibly have you on the show. Apply at coachingrealleaders.com. You can also find me on LinkedIn, on Twitter @MurielMWilkins or on Instagram @CoachMurielWilkins. And of course, if you love the show and learn from it, pay it forward, share it with your friends, subscribe and leave a review wherever you get your podcast. From HBR Presents, I’m Muriel Wilkins. Until next time, be well.