How Do I Stay on the Fast Track to the Next Level of Leadership?

MURIEL WILKINS: I am Muriel Wilkins, and this is Coaching Real Leaders, part of the HBR Podcast 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 Rachel to protect her confidentiality. She’s been at her company for a while and has moved quickly up the ladder.

RACHEL: My growth path has been very steep. I started as an individual contributor, moved very quickly into managing a small team, and now I manage a larger team and I manage managers. So, I constantly find myself thrust in these new spaces and I’m playing catch-up in terms of, I move into a role probably before I was a little bit ready, and so I feel like I’m in the role while I’m figuring out what that role is and what you were supposed to do at that level. I tend to feel less like I’m catching up and more comfortable when I have conviction around my priorities and my approach. Every once in a while, I will get to a point where I know where I can add value.

MURIEL WILKINS: While Rachel hasn’t always felt like her footing was steady in new roles, she does feel like there’s been some data to show that she’s done a good job so far. She’s gotten direct team feedback and the aforementioned promotions, including most recently to be a manager of managers. She attributes much of her advancement to her ability to work well with others.

RACHEL: I had done a relatively good job with my smaller team and I had been at the company at that point for a number of years, and so I knew the company and I think I had built a pretty strong network of people internally. And for my type of role that’s important. The relationships is sort of our currency. I don’t have authority over these other functions that I work with. And so, I think because I had done well with my team, I had a history at the company and the relationships. They were willing to give me that chance.

MURIEL WILKINS: Now Rachel wants to make sure she’s positioning herself in the right way to continue to show her value and to adapt with the organization. While she managed to climb the ladder previously, she wants to make sure she’s being strategic going forward. Let’s start the coaching conversation as I ask how the role is going a few years in and where she thinks her pain points might lie.

RACHEL: Part of the problem is I can’t even write a problem statement at this point. I feel very scattered. I feel very reactive to my environment. And the thing I am thinking a lot about is both for where the company is and for myself. It very much feels like as a company what got us from A to B won’t get us to B to C. It very much feels like a transitional scaling growth phase for the company and for myself. What got me where I am is not what’s going to get me to the next level, and I feel like the stars could align again for me to continue to add value and expand my influence and grow to the next role. I don’t know that I’m positioning myself well for that opportunity, and so I’m worried if I’m not a part of that B to C, someone else will come take everyone from B to C and I’ll sort of be relegated to, “You were the A to B person and you did great at A two B and we appreciate you for that, but now these other things are happening.” So, I feel like there’s so much opportunity in front of me and just given what’s going on with the company and the kind of role that I’m in, there’s so much opportunity sort of sitting right in front of me and I could grab it, but it’s hazy and I don’t know how to do that and I don’t know how to take advantage of that or not let it pass me by. And then in the meantime, there’s all these Slacks and emails and meetings that are creating a lot of noise and distraction, and I’m having a really hard time figuring out what is my biggest challenge right now? What should I be focused on? What is that opportunity? How do I take advantage of the opportunity?

MURIEL WILKINS: And just playing it back, just to make sure I understand. You feel like you’ve been able to operate at a certain level, play the sport almost like I’ve been playing, I don’t know, pick a sport.

RACHEL: We can do baseball.

MURIEL WILKINS: Baseball. I know nothing about baseball, but okay. You’ve been playing local baseball and now you’re like, “But I think I can play at the regional level or maybe even at the national level, but not quite clear what that even looks like and I don’t even know what I’m supposed to do to prepare myself to play at that level. And so, I’m concerned that because of that, I’m just going to stay stuck playing in the local town team.” Did I get that right?

RACHEL: Exactly. And it’s not like right now there is an open role on that national team. There’s not a role that I’m trying to move into. There’s no specific role out there. So, it’s not like, Oh, they’re going to be recruiting for the national team next week and I want to be ready. It’s very much, I just want to be ready no matter what. I don’t know when or if that opportunity is going to be there, but I would like to position myself so that if it does and the stars line again, it’s not something that’s just happening to me because of these other circumstances. It’s because I’ve prepared and I’m ready.

MURIEL WILKINS: So going back to sort of the baseball analogy, it’s like, Hey, I don’t know if there’s going to be a spot that opens up on the regional team, but I want to be ready so that if a spot opens up, they can look at me and select me. Yes, understood. I think. And so, why do you want to play at the regional level?

RACHEL: A couple of things. My goal in my head for my career for a while has been I would love to be a COO someday. I don’t even know if I could tell you exactly what a COO does, but just that, How do people work? How efficient are we? So, I would love to get to a very senior level in my career. Right now, I sort of constantly feel like I’m in a learning space, which is what I love. And so, if the company is going from B to C, I really want to be front and center and a part of that. So, I’m seeing it all up close and able to learn what does it look like when this happens and when you’re scaling in this way? Because I want to be able to learn from that and have that experience and be able to take that wherever, if I go somewhere next or just apply it where I am. So, I feel like the kinds of problems either I’m experiencing or the company’s experiencing are the kinds of problems that I like to solve and I’m interested in and I want to know what that’s like. I want to be a part of that transformation.

MURIEL WILKINS: And what’s holding you back from being a part of that transformation?

RACHEL: Just me. It’s honestly just me because I think I’ve gotten a lot of positive signal from our leadership team. Recently, I’ve gotten a lot more exposure working with our executive team, which I never had before. So, I feel like everyone’s kind of leaving the door open for me and they maybe still see some potential and they’re willing to invest in me, but that’s not their job to make sure I get there. But the door’s open and I feel like no one’s telling me I can’t do something or I shouldn’t do something. I think it’s the time where I need to be proactive about what’s needed and can I add value there? So, there’s nothing, hold it, just me figuring out what do I do and how do I do that?

MURIEL WILKINS: And what is getting in the way of you figuring out what do you do?

RACHEL: Partly because there is a lot of noise in my day-to-day. Things feel really urgent and it can be really distracting and it’s hard to carve out the time to sit and focus. I think the other thing that’s keeping me from doing some of this is I’ve been more aware recently that I don’t know that I’m speaking the same language as the senior leaders around me that I’m now interacting a little more with. It’s like there’s this group of senior leaders that have all been playing chess together for a very long time. And there’s politics and there’s biases and there’s their priorities and there’s a lot of things that they’re dealing with that I have no idea about. They’ve all been playing chess together for a very long time and I’m kind of the new person watching on the side and trying to understand those dynamics, but I’m still new in that space and I’m not at the same level as those people. And so, I just feel like I’m speaking a different language sometimes because what I know is probably more tactical than how they’re thinking about things. And I don’t know how to talk about either what’s needed from them or the value that I could bring. Because I see a lot and I feel like there’s a lot happening at the organization and the company and we need to scale and we need to do this and we have all these problems. I feel like I could be a really good bridge with our leaders. They want to understand what’s going on. They don’t always get the real story from people. So, I just don’t know how to figure out where’s the right place to add. Do they even want me to add value there? But I feel like I need to be proactive about something there. So, I don’t know if you can tell. It’s very hard for me to even describe what that’s like and that’s why it just feels like opportunity, but I don’t even… It’s very hard for me to even articulate what that is.

MURIEL WILKINS: And then it makes it easier for, as you put it, the day-to-day noise and distraction to just kind of avoid it.

RACHEL: Exactly. It’s like I don’t know what to do, so I’m not doing anything but great. I have all these things to make me feel important and busy. And then I’m like, “Well, shoot, if I keep doing that, this is going to pass me by whatever this is.”

MURIEL WILKINS: Whatever this is. Exactly. Yes. Whatever this is. And I am just going to be honest with you. I don’t know what this is, because I’m not in your company and part of being proactive is defining what this is and then testing it out. So, let me ask you a quick question. I know you are feeling like you are speaking a different language. Have you gotten any evidence that supports that belief?

RACHEL: A little bit. So, for example, there was one meeting with some of our executive team and I was presenting. And I think I even knew going into that that I don’t think I’m sharing the right information that’s going to enable the decision that needs to happen. But I’m also working with a bunch of other people that have opinions about this and I’m trying to bring the collective voice and the feedback I got after that meeting from one of the executives because I asked for it. He knew how he wanted to see things and what he wanted to see and what I had put together with the team and presented wasn’t giving him what he needed. And we actually were not able to make a decision in that meeting and then things had to be followed up afterwards. So, I have gotten some feedback like that and then in a couple other conversations, just body language and it just feels like what I’m saying isn’t always landing or resonating, but they’re still giving me a shot. It’s like, “I don’t think I quite understand what you’re saying. Let me try to offer something.” And again, no one has told me, “Don’t do this.” No one has stopped talking to me yet. But it’s like, well, how many chances am I going to get to figure this out before they think, Oh, well actually I don’t think she’s that person who can help us do this.

MURIEL WILKINS: So, first of all, I do want to acknowledge your astuteness in sensing that something is not quite on path because that can come from one of two places. It either comes from internally, you’re kind of feeling like something ain’t right, or externally you get the feedback. And I’m a big believer in triangulation. Well, this isn’t really triangulation, dualation, I guess. I don’t know. And that’s why I asked. I hear you in terms of you feeling like you’re not speaking that language, but have you gotten validation that others feel like you’re not speaking the same language? And it seems like at least you have one or two data points where that might be the case, which means we’re dealing with something that’s maybe real rather than the story that we’re telling ourselves and that’s the first place that we want to start. You’ve stated a couple of times, “I don’t know how to speak their language.” If you knew how to speak their language, so it’s the matter of language, would you know what to say? So, for example, if I go to a different country where I know how to speak the language, I might know what I want to say in a restaurant. I might know that I want to say I would like to order the pizza, but I might not know how to say it.

RACHEL: I see.

MURIEL WILKINS: Versus going into a restaurant and being like, “I have no idea what I want or what I want to say, and I don’t know how to say what I don’t know what…” You get what I’m saying, I’m getting myself all mixed up. So, if we decouple the two, you’ve already checked the box on, “I don’t know how to say it.” And I’m just kicking the tire, do you know what you would want to say in those meetings?

RACHEL: That is a really great distinction and a really great question. And I think the answer is no. I don’t even know what I want to say and I don’t know how to say it in a way that’s going to land with them. What I think about in those situations is I really see it as my role and where I add value when I’m bringing transparency to things and a neutral opinion. And so, I know that I want to do that and whatever I’m reporting to this group that I want to have that lens. So, I have some sense of what I think I need to be, but I don’t know that… It’s not always clear to me, “Oh, this is what I want to go say to them. How do I say it?” I think it’s like, “Well, I think there’s definitely things I need to be surfacing, and there’s definitely things they’re going to want to know about and there’s information they’re going to need. And I don’t know how to say that. So, I think I understand the lens I want to bring to it, but I don’t know what that content would even be.”

MURIEL WILKINS: Well, it’s very hard to figure out how to share your perspective if you don’t have a perspective. And I think what I hear you saying is, “I have an intention or an approach on the type of perspective I’d like to share,” which is your lens. So, you said, “I want to be able to provide a neutral transparent perspective on this issue.” And then you’ve jumped from that to, “So how do I share that in a way that’s going to resonate with them and land with them and give them a chance to absorb it?” And in between those two things, there has to be, well, what is your perspective? And you used a word earlier in our conversation and you said, “Well, I never really feel like I’ve caught up, but I did get to a point where I felt comfortable.” And the word you used to describe your level of comfort, of being comfortable, you said, “I had conviction.” And so, I’m curious, what is your level of conviction? Forget the language piece, before you even get in these rooms and in these spaces. I’m curious, what is the level of conviction that you have on these perspectives that you’re trying to bring in a neutral and transparent way?

RACHEL: I would say very low. I have very low conviction. There’s a lot of information. There’s also a lot of voices in the room because part of my role as I’m working very cross-functionally, the way our company is structured is very matrixed. And I feel like because I don’t have conviction in my own perspective, I’m also very easily influenced by the people I’m working with. I can’t believe now we’re getting here because this has been another thought bouncing around in my head is I feel like I haven’t built yet a good judgment about when do I have conviction and feel comfortable about my perspective? And then I really push that to the front of the conversation versus when should I be deferring to these people that are maybe more senior than me and seem to have a lot more conviction than me? And so then, now my conviction is just low going into this situation. And so, I kind of default to, Well, let me neutrally present everyone else’s perspective rather than taking that in and then bringing that forward.

MURIEL WILKINS: So, by you presenting it in a neutral way, it’s almost like you’re preempting the possibility of them for lack of a more gracious, elevated word, poo-pooing all over your idea. And what if you went in with conviction around what you think needs to be done? And again, I don’t know exactly what the content is that you’re focused on, but let’s just play it out, because they’re not here. It’s just me. What if you went in with conviction and a perspective on what needs to be done or the data that you’re presenting and a point of view? What’s the worst case that could happen?

RACHEL: The worst case, I think… There’s two things that come to mind. One is that my perspective or what I’m presenting or bringing to the table causes more confusion and chaos, for lack of a better word. I really want to be bringing clarity progress to the table. And I worry, Okay, if I’m wrong or if I’m off base or if I’m not doing this the right way, it’s going to cause more confusion and be a waste of time. And those meetings are really expensive. So, I think that’s part of it is it’s my job to bring clarity to chaos, not create the chaos. And so, I really worry about that. And I think the other thing is a little bit of what we talked about before. I feel like I’m at the 1000-foot view and I’m working with people that have the 10,000-foot view. So, my perspective that I’m going to bring to that group is going to be missing a lot of factors or what matters to them. Because I did test this one time, I was messaging an executive and I said, “Here’s where I think there is confusion. I think we should just focus on A.” And the response was, “Well actually no, we should focus on B.” Which is fine, at least I knew, and then I can go focus on B. So, my gauge of what I think would be the way forward or my perspective was not lining up with that person’s perspective in that one instance. So, I think that’s what I worry about too. Am I going to cause more chaos if I bring my neutral perspective and is my neutral perspective just going to be so off base from how they’re thinking about things that they’re going to be like, “Okay, yes, this is the A to B person. She’s bringing the A to B perspective and we’re seeing things from a whole other level and talking about them in this whole other language that, yeah, she doesn’t get it.”

MURIEL WILKINS: When our coaching meeting kicked off, Rachel initially had trouble articulating the exact problems she was facing. She knew that she had gotten a lot of great opportunities so far in her career, but wanted to make sure she was making the right moves to continue to advance. The first thing I aimed to sort out was whether there was external evidence that she might not be making the right moves or whether she was the only one who thought so. But she actually had some examples of interactions that made her feel like she might not quite be hitting the nail on the head. And those examples centered around communication and interaction with senior leaders. So, that’s where we dug in, trying to get a better sense of both how and what she wanted to communicate better. There, we hit on something interesting. The idea that she was trying to remain neutral with pieces of information, which actually ran contrary to situations where she did feel like she was adding value. Those times when she took a perspective and had conviction behind that point of view. I was curious to explore with Rachel why she felt the need to back away from her perspective when it came to interactions with senior leadership. So, we went there next.

Now, what difference would it have made if that other person had been a peer or somebody more junior than you, than if it had been a senior executive?

RACHEL: That’s a great question. If it had been a peer, I think I probably would have tried to continue the conversation and, “Okay, we have different perspectives. Let’s hash it out a little more because I want to understand why you have a different perspective. I want you to understand why this is my perspective. I shared the perspective, I can say more about why.” So, I think I would be wanting to engage a little further in that conversation and just hash that out. I think if it was someone more junior than me, I think the same thing. I would really want to understand why that is their perspective and maybe I’m missing something or maybe they’re missing something. Maybe in that case I have more information that they don’t have that’s leading them to have that perspective. I think specifically when it’s executives or people that are more senior than me, my response was like, “Okay, great. Thanks. I’ll just go do that.” Rather than taking that any further.

MURIEL WILKINS: And what holds you back from taking it any further with somebody who’s more senior than you?

RACHEL: I don’t think I have a good answer or reason for that. I think maybe it’s scary, maybe I don’t want to waste that person’s time. Probably those. It’s scary to engage in that conversation further because I don’t know that person well enough to really know how that’s going to go or if they’re willing to engage in that. And I think I worry about wasting their time or taking their time.

MURIEL WILKINS: So, if you were… Let’s just go down both those paths because I kind of want to unravel this a little bit. If you were wasting their time, what do you think would happen? How would you know?

RACHEL: They would either not respond to my message. They could maybe just write it off and say, “Hey, I need you to go figure this out somewhere else.” I don’t know. I feel like that’s where I worry. They would be like, “Okay, if this person doesn’t get it, I have so many other things to do than spend my time unraveling this with this person.”

MURIEL WILKINS: So, they would shut it down, which would basically leave you where you already are?

RACHEL: Yes.

MURIEL WILKINS: Gotcha. And has that happened, by the way?

RACHEL: No, it has not happened. And I think the other thing that I worry about there is they could shut it down and I’m right back where I am, but does their perception of me or my reputation change as a result of that, I think is the worry. So, I would be back where I am in terms of the information that I have to work with, but then I worry they’re forming their perception of me too so they might…

MURIEL WILKINS: But Rachel, guess what? The perception is forming one way or the other.

RACHEL: You’re right.

MURIEL WILKINS:

The perception does not discriminate. It’s always happening.

RACHEL: You’re right. That’s a good point.

MURIEL WILKINS: So, one case is they could say, “Oh my gosh.” Or you could say, “Oh my God, I’m wasting their time.” And they’re like, “Hey, listen, I only have five more minutes and that’s all I can… Okay, great. I got you. I’m off the phone.” The other part is that, what was the other part that was scary to you? One was that you waste their time and the other part what was scary about?

RACHEL: I think it’s because I don’t know them that well, I haven’t worked with them that extensively, so I don’t really know where that conversation’s going to go. And so, it’s scary. I’m talking to someone who is much more senior than me and I don’t know how they operate, what their beliefs are, what they care about at the moment, I have no information. And so, it’s scary to forge into that territory with things I’m trying to bring clarity on and just not really having a sense of how to bring that forward or what’s going to happen once I do.

MURIEL WILKINS: So, because you don’t know them, if you brought it forward, what could happen?

RACHEL: I think it is just the perception thing. I’m either bringing them something that they don’t care about or is not resonating with them, or maybe it’s even annoying them. I think sometimes that has happened where if I’m bringing something… This happened actually with one executive where I brought something forward because I thought we needed some alignment on something and the response was, “Oo, we’ve already talked about this. We’re already aligned.” So that feels bad to me when that happens. Like, “Oh shoot, okay, I didn’t bring the right thing or I shouldn’t have brought that forward. They’re annoyed now that I did.”

MURIEL WILKINS: How do you know they were annoyed?

RACHEL: I think the tone and afterwards that I talked to someone who I do know and understands that space a little bit better, and they said, “Oh yeah, they hate to hear that they’re not aligned with this other person.”

MURIEL WILKINS: Understood. So, there is a part around being careful of holding back so much from engaging with these folks that you then are not seeking to understand what they care about. Because on the one hand, you’re like, “I don’t want to say anything because I don’t really know what they care about.” And on the other hand, you’re saying, “Well, I don’t want to ask the questions because even though it would help me understand what they care about, I don’t want to ask the question so that I can hear what they care about.” And either way, on either side of those, as I said before, a perception is being… You’re sort of left in the same place, you still don’t know what they care about.

RACHEL: I still don’t know.

MURIEL WILKINS: I kind of want to go back to when you said, “I don’t have a good judgment yet. I don’t have judgment on when I feel convicted, when I have a strong perspective. And as a result, when I start hearing all these other perspectives, it makes me even more uncertain.” And that’s like a tree. When it’s windy outside, a tree will be as strong as its roots. What is the foundation of that tree? If the roots are weak, the part that we don’t see, which is analogous to your inner conviction on something. The weaker they are, those roots, the more that tree is going to sway every which way.

RACHEL: That’s definitely how I feel right now. It’s like I don’t feel like I’m rooted in anything, and I’m certainly not rooted in anything I have conviction around. And so, I’m really just being very influenced by everyone around me and it’s confusing. And then I can’t make sense of that. I don’t have a perspective. So, then I’m bringing forward something that I , is just then ultimately not helpful for anyone.

MURIEL WILKINS: And if we continue with sort of that visual, I don’t know, maybe it does exist. I’ve never seen it. I’ve never seen a tree that’s so rigid in its roots where the roots are so strong that when the wind blows, it doesn’t move.

RACHEL: Right. That’s exactly how I feel is when am I being flexible and when am I being rooted in my conviction? And I feel like I’m not doing a good job of making the decisions because the times when I had conviction, I said what I thought, “Okay, someone else had a different perspective.” And then when I don’t bring my perspective, things devolve because there’s no perspective brought to the table. So, I feel like I don’t have the right judgment built up about when am I putting my perspective forward with conviction? When am I letting myself blow in the wind and understand what everyone else is doing and maybe bringing some of that to the table.

MURIEL WILKINS: And have you had moments, maybe not in this role, but in the past where you felt that you were able to do both? That you were able to bring a point of view, conviction and be flexible to what else was going on the room and what stakeholders thought and where stakeholders’ agendas were?

RACHEL: I think I’ve definitely had that before. I think it happens when I have an idea of what my North Star is in that situation, and then I can build everything around that. “Well, if this is the North Star and this is my perspective and this is everything else I’m hearing, I can do my job now and bring all of that together and package it up in service of that. Whatever that is, it could be a meeting goal, a company goal, someone on my teams, a conversation with them. So, I feel like I definitely am able to do that when I know what I’m organizing that information around.

MURIEL WILKINS: And how were you able to figure out your North Star in the past when you did have it?

RACHEL: I think in some cases it felt a little more obvious to me or I had information signal to point in that direction. For example, when I first inherited the broader team, I think it was clear something was not working there. And so, when I inherited the team, I knew exactly that’s the thing I need to go do. I just need to go listen to everyone. I need to go acknowledge the things that have been happening. So, I think I had something to anchor to and I knew that that’s what I had to bring to every conversation I was having with the team that needed to be at the forefront in everything I was doing and hearing and saying. Kind of had to be getting everyone comfortable with, “I hear you, I understand. We’re going to make this better and I’m just listening.” And then I got feedback that people really appreciated that. So, I think I’ve had signal from somewhere whether someone’s telling me something or there’s actual information to point to. That was a very obvious one.

MURIEL WILKINS: But you got that validation after you decided this is it. “This is what I’m going to place my bet on and then I’m going to go out and do it because I believe this is what needs to happen.” And then you got positive affirmation that, “Yeah, we’re so glad you did that.” And in this situation you feel like you have not been able to articulate what that North Star is?

RACHEL: Right.

MURIEL WILKINS: And as a result, what are you expecting back from people?

RACHEL: I don’t know that I am expecting anything back. I think I am expecting myself at this stage to be able to define what that north star is. I should be able to do that, someone at this level should be able to do that. And I feel like I haven’t done it in this context I’ve been in.

MURIEL WILKINS: And have you explored coming up with hypotheses of what that North Star could be and testing it out with others to see if…

RACHEL: I have not, no. I have basically been procrastinating and ignoring it because I don’t know and I don’t know. It’s interesting to think about it as could I come up with hypotheses? Because I think in my head it was like, “There’s got to be the one North Star. It’s there and I just need to figure out what it is or define it myself, and it’s this one thing and it’s right or wrong.” And so, I think it’s helpful now that you’re saying that to think about that as, “Well, I’ve almost even just avoided writing anything down because I’m like, I don’t know what it is. I don’t know what to write down.” But I think thinking about it as hypotheses, what are the various… There could be more than one thing to focus on. And what would even be my initial set of ideas around what that would be? I haven’t even done that step.

MURIEL WILKINS: And understandably so. Sometimes we think if I write it down, it means it’s permanent in the book of life, forever there. If I write it in my… When I was younger, I should say, not when I was small, I had a diary and I would literally… It would just stay empty because I was like, “If I write it down, then it means it’s true and forever there.”

RACHEL: Yes, it feels very permanent. And then I am very much an over thinker and a little bit of a perfectionist. So, if I’m going to write it down, it’s going to be permanent, it’s got to be perfect and it’s got to be the thing. So well, I don’t know yet, so I better not write it down yet.

MURIEL WILKINS: And there’s this beautiful thing called pencils, where we can write any race and then this other beautiful thing called delete on our laptops. And so, there’s a bit of taking it lightly. And I love the fact that you’re thinking about it as a North Star because I don’t know if you’ve ever had that experience, but I have. Where you go out and you look up and, particularly, you’re with other people, which you are too. And you look up and you’re like, “Oh my God, there’s Venus.” And people or you’re like, “Oh, there’s the big Dipper or there’s the Little Dipper.” And people are like, “Where? What?” No, and it takes a while and they’re like, “No, it’s over there. That’s the North Star, or that’s Venus.” You’re like, “No,” and then you debate it and then eventually everybody starts seeing it the same way. And I think that’s kind of what you’re experiencing, except that you’re not pointing out what the North Star is. You’re sort of waiting for it to just magically appear and other people to say, “Oh, we all see it, Rachel, there it is. Go forth.”

RACHEL: 100%. This is a really good analogy for this because I think the other thing I’m doing is because I’m not pointing out where it is, or maybe I can’t even see it, I don’t know. So, I am looking at the people around me, “Okay, this person thinks it’s there, this person thinks it’s there. Okay, well you all… Okay, so I’ll just… Yeah, it’s all those places.”

MURIEL WILKINS: It must be there. It must be somewhere in there.

RACHEL: And I’ll just share what they think because that’s what they’re seeing. And I don’t see it, so I don’t have a way to get everyone aligned. So, I will just share what they all think, which is all very different. And then how can anyone move forward? If I’m just saying, “Well, person A thinks it’s there and person B thinks it’s there and person C thinks it’s there.” Now what do we do? I mean, that’s not helpful.

MURIEL WILKINS: And listen, it’s an and. In no way am I saying or are we saying that, “Hey, whatever you think, Rachel, that’s what it is, and go forth.” Because that would be the rigid tree, right? What we’re saying is I think in the past what’s happened and the inflection point that you are on your leadership path in your career, I think in the past you could create your North Star based on what you heard from others, right? “Oh, that’s what they’re saying. This is how they’re feeling. I can make meaning out of this. That’s going to become my goal and I know what to do to move it forward.” And I think the difference that’s happening a bit of here, which happens to a lot of leaders at this inflection point, the value creation, the value that you bring to the table is not only being able to hear what others have to say, but being able to bring to the table, “Here’s my perspective, here’s my point of view.” And do you take a risk when you do that? Yes, absolutely. But that’s also where the juice is, that’s where the value is. The value is in your Interpretation of what’s happening and being able to say, “I’m going to put a stake in the ground. Here’s what I think the North Star is. Now let’s open it up. What does everybody else think? And let the wind begin. And I’m willing to bend a little bit, I’m willing to bend a lot even, but I’m not going to break.” So, what does that mean in the context in tactical, practical terms? I do believe that step one, before you can start talking about now, how do I language that in a way that resonates? I think you’ve got to come up with these North Stars, and I’m saying North Stars because I think they’re the hypotheticals for now. And you can create a process out of it where you’re not doing it in isolation. “Hey, I’ve been around, I’ve been observing for two years. I know I’m at this level.” You think through things. So, you have been observing the chess game. You haven’t been a bystander, you’re seeing how it’s being played. You must have picked up some things over the past two years around what’s important.

RACHEL: Yes.

MURIEL WILKINS: So, based on what I picked up, here’s what I think is important, or here’s what I hear or observe as being important. Here’s what I think is important. Here’s hypothetically what I think these North Stars can be and why they’re important to me at the level where I sit and also why they’re important to these folks at the level where they sit. And then let me go pick a few senior level people, one on one. “Hey, I’m really trying to articulate the goal here. Here are a couple of options. Here’s what I think it could be. But I want to get your reaction. This isn’t baked. I want to get your reaction.” So, A, tell me if you’ve done that already and B, if not, how it sounds to you.

RACHEL: I have not done that. And it sounds amazing because even as you’re talking through it, there’s three hypotheses in my head, and I think before I didn’t know how to categorize them. So, it was just a lot of thoughts bouncing around in my head. I didn’t know which one was right. So, I’m not writing it down, I’m not committing to it, but thinking about them like hypotheses. I’m like, “Great, there’s probably three or four, at least. I know what they are, they’re bouncing around in my head.” I just didn’t know those were hypotheses I needed to go test. So, I haven’t done that. And I think the thing that stood out to me about what you said when I am having those conversations, which I have not pressure tested my hypotheses that I did not have before. So, the thing that stood out to me when you said that was, “Here’s options. Here’s what I think. What do you think?” Because I think before I was treating that as, “Well, I know I should be bringing my perspective to the table, so I’m going to say it. I think this is the option.” Which then I think puts me in that place of is there perception of me going to change versus if I bring it, “These are options. This is what I think. What do you think?” It’s not, this isn’t baked for me yet. I’m trying to pressure test, engage it. Then that’s a much more open conversation. And then if they don’t agree with my perspective, they’re not viewing that as like, “Wow, this person had a lot of conviction about something that doesn’t align with me. This person has ideas. They’re willing to talk to me about it. I can give my perspective and they can absorb it.” So, I think that last piece of, “What do you think about that this isn’t fully…” I wasn’t doing that. I thought I had to just have my perspective and have conviction and that was the thing I was supposed to be doing.

MURIEL WILKINS: I think that there’s a certain pace to it too. I’m going back to you saying, “I don’t want to waste people’s time and create chaos in the meeting, and I don’t know what these meetings are.” But you do want to be careful of the big reveal at the meetings, meaning you’re waiting for that one shot to say, “And here’s my perspective.” So, there’s a bit of warm up in terms of you’ve been around these senior people enough now. I know some of them are not… You’re not completely known entity to them, but I’m curious around what have you done to identify who are these critical senior stakeholders? Am I spending a bit of time with them outside of these big meetings to understand them and so that I can be in collaboration with them in the way that you just described? So that by the time I get to the big meeting, I’m 80% sure that what I’m sharing has a certain level of alignment?

RACHEL: That’s a great point. And I think I’m not taking advantage of the kinds of conversations you’re saying. Because the couple of times where I asked for feedback about the meeting. That executive was like, “Let’s jump on the phone. I’ll tell you what I thought.” And I think rather than doing that after the meeting, I could have reached out before and just said, “Hey, here’s what I’m seeing. Here’s my perspective of what we should try to be doing. Is that aligned with you? Is that what you’re looking for?” So, I think this is where I feel like they’ve left the door open, they’re willing to so far talk to me about these things in a couple, probably three instances that’s happened, where I’ve actually had their one-on-one time for a number of minutes, but I wasn’t using that time properly or effectively, I guess.

MURIEL WILKINS: So, to what extent have you sat with these stakeholders purely from the perspective of learning what is important to them at that altitude level that they’re at?

RACHEL: Zero. The time that I have spent with them has been about a very specific project and the things happening on that project. Yes, I have spent zero time trying to understand what does it look like to get 10,000 feet, what else is up there? I’m engaging with you at this thing that’s happening here. What else is going on over there at that elevation?

MURIEL WILKINS: And so, there’s no way you can even formulate your own perspective that reflects the context that they’re dealing with, the issues they’re facing, the priorities they have, what’s keeping them up at night, the pain points they’re trying to solve. There’s no way you can solve issues at the 30,000-foot level if you stay at the 10,000-foot level. You’ve got to meet people where they are. And so, what does that require? It requires you to actually go where they are, particularly if they’re not coming to where you are.

RACHEL: Yes, that’s very true. And I think I was always approaching those relationships as, “I need to demonstrate value with this thing that I’m working on, this one thing. I need to demonstrate value and make sure everything’s resonating with them.” But you’re right, without the other information or spending any amount of time, I don’t have any reason to believe they wouldn’t give me that time, if I asked. That’s exactly how I feel, like I’m flying in the dark then. I’m going to take some very uninformed guesses about what I think this might be and then it’s not going to resonate.

MURIEL WILKINS: Before we start putting together concrete action steps for Rachel, I think it’s important to point out a couple of things we’ve discovered so far. As we dug deeper into the interactions that she’d had with senior leaders, we unearthed that she often feels like she isn’t saying the right thing or aligning herself in a way that works for them. This is a common issue when someone heads up the leadership ladder because as much as leadership is about knowing how to manage your team and execute on tasks, it’s also about working with the leaders around you and above you more effectively. In our conversation, Rachel realized that she doesn’t always know where her North Star is, and that changing the way she engaged with senior leaders might actually help point her in the right direction. She can only do that by being less hesitant, by learning to speak the leadership language at her organization and by approaching issues more from their vantage point. And one way to learn about that vantage point is by asking questions. Otherwise, as she says, she’ll be flying around in the dark. Let’s get back into the conversation as we start to think about next steps for Rachel. So, I think part of your assignment is coming up with, “Well, who are the key people?” What they perceive and what they think and what they’re doing matters. So, the critical stakeholders, and let’s not even think about it in terms of a tactical deliverable. This is just you getting context, getting a better appreciation for what they are leading at their altitude. So, you’re going to go up to their altitude. I remember I went on a trip where we had to go up in altitude before we could come back down in order to adapt to the environment and not suffer. And so, in preparation it was, “Well, what do I need to know about that altitude?” Let’s say you’re up there with them. What are the two or three questions that you would want to ask that you think would be helpful to you in not only shaping these North Stars, but also so that when it’s time to communicate them and share them, you can do it in a way that resonates with them?

RACHEL: It’s interesting because there’s questions I want to ask because I’m curious, but what you asked is what questions would be helpful to me? So, I think one of the big ones that I would want to ask is actually pretty simple. How do you view my function and my role? What do you hope to get from our function? You’ve got us involved, but I don’t actually know if they see us as you are the executors or you are the strategic thinkers. I would have to figure out maybe how to say that more concisely, but how do they think about my role? I think some of the other ones would be around, I don’t know exactly what questions this would be, but what does the landscape look like for them? What are the things that are top of mind for them in general outside of the context of this particular project? And what are the things top of mind for them in the context of the project? So, I’d kind of want to understand how this fits into everything else they’re worried about or just prioritizing or thinking about. And the questions I’d like to ask that I don’t know if it would be appropriate to ask would sort of be some question around probing on the dynamics and the relationships between those groups. Because part of what I sense and what I’m trying to navigate is how everyone perceives each other and other teams. But it gets a little bit into just the politics of, is there a question I could ask to better understand how they view these other people in teams and what’s their perspective there? Because occasionally if I pressure test, “Well, I think this person either thinks highly or not so highly of this other person.” I kind of want to know that so that I can tailor things that are going to resonate.

MURIEL WILKINS: So, I hear four different agenda items for you. One is around expectations. So, what do you expect of our function and my role regardless of who were to sit in that role? What do you expect to get from us? What would you consider success in terms of what you get from us? So that’s one. The second is around priorities. So, what are your priorities? What’s top of mind for you? What’s keeping you up at night? Which might be different than priorities, but hopefully they’re the same thing. I think the third is you didn’t name it in this way, but what’s their delta. What’s the difference that they’re trying to make? How do they define [inaudible 00:54:24] Where do they want to be in six months, 12 months, 18 months? So, it’s more the outcome of those priorities. What are they on the hook for? And that in particular is very important because if you can’t connect what you are doing to what they’re on the hook for, it’s very hard to influence.

RACHEL: That’s a great point. I’d want to think about that also and maybe this is part of those conversations in testing this. I have a hypothesis about what they’re on the hook for. I know enough to make some hypotheses or some guesses about what they’re on the hook for, but I’ve never validated that. So, I don’t know if I’m speaking to what matters to them or I’m speaking to what I’m guessing.

MURIEL WILKINS: I think you have a lot of hypothesis validation you need to do. First, you need to put them down on paper, then you need to either go ask or validate. You choose what you want to do. And then I think the fourth element we were kind going down because I just want you to have sort of an agenda going to these meetings is what are the dynamics? And I understand your hesitation around being, do you have a problem with these people? Who are your problem people? We don’t want to do that just yet, but maybe there’s a question around what can you share with me about the dynamics that would help me help you? Is there anything I should be aware of? But a lot of that is going to be the reading between the lines. And as you get to know other people who might have to deal with the same dynamics, just learning from them and being like, “Hey, I’m about to go into these meeting with these two folks, what should I know?”

RACHEL: And I haven’t been seeking that help either. I feel like I’ve just sort of been trying to figure it out myself. So, I do think there’s people I can talk to – “Okay, what do you think the dynamics are?” And again, this is where I will very much the tree analogy in mind. I don’t have to take their view of the dynamics as the rigid thing I have to stick with, but it can inform my own perspective of the dynamic, and then I can actually go validate that with the people directly.

MURIEL WILKINS: And that’s where the discerning… Is that going to send them off or how do I play it? And I couldn’t tell you, I don’t know who these people are. But certainly having that, you said you know who you could ask. You’re new at this, why are you thinking you need to figure it out all on your own?

RACHEL: I think it’s just because things get busy and I’m scattered. So, I just never even took the time to stop and come up with this plan and approach of how to navigate this space. It was just sort of, “I will try random things. I’m sort of paying attention to the responses and the signals, but I’m not really processing or organizing or diagnosing anything.” I just feel like I’ve been putting one step in front of the other and doing stuff, but not in any kind of…

MURIEL WILKINS: And we all get into that. So, you’ve spent some time just throwing stuff against the wall and hoping that a beautiful painting comes up. And now you’re going to step back and say, “But actually what’s the painting I’m actually trying to create? I’ve gotten some inspiration from that, but now I’m going to figure out what’s the painting I’m actually trying to create and what are the conversations I need to have to create that painting and let me go test out if anybody else likes that painting because I want it to sit in the main hall versus in my basement.”

RACHEL: Yes, I do not want to be relegated to the basement. That’s the A to B place that I do not want to be there.

MURIEL WILKINS: So, this is all about racing your game and knowing these tweaks that you need to make and that you’re still in learning mode on being able to operate at this different altitude. So, tell me, because I think you were also very tactical like, “I haven’t taken the time.” So, I want to hear what are the one or two takeaways that you have from this conversation that are going to make a difference in terms of how you spend your time in the very near term?

RACHEL: That’s a great question and I know exactly what it is. I think part of why I haven’t taken the time is because I didn’t know what I was taking the time for. So, I have no issue blocking off time on my calendar, but I didn’t know what I was going to do with that time. So, I think now I have much more concrete things. I know now I can clear the time because I know what I’m going to do with it. And I think the two things that stood out the most to me are one, really articulating my hypotheses for my North Star. I feel like I can’t… I’m not going to be able to make progress in the ways I want to and build the conviction that I want and build my perspective if I don’t have those north stars. I need that to kind of anchor around. Right now, I have no anchor. So, I think writing down those hypotheses, having a perspective about it and then validating with others is a big one. The second one is how I am leveraging my time that these executives and senior leaders are giving me and being more purposeful with those interactions. When am I talking to them? What am I talking to them about? I was not really being purposeful with that. I think I was, again, just letting things happen or sharing what I thought in the moment, thinking that might be helpful. So, I think definitely the star analogy is really working for me. Everyone’s pointing at a different part of the sky. I don’t even know where I’m looking. So that I think really is resonating and it’s going to help me just use that to kind of gauge where I am. Going into this next meeting or this next interaction, where is everyone looking? Do I know where I’m looking? And am I having the conversations to work through those things? Like, “Well, are we all pointing to the same thing?” And if not, then at least I know that and that’s what we can talk about. So that all really resonated, and now I can go carve out the time to really think about that, come up with my questions, figure out when the right time to talk to those folks is going to be. And then I’m in a place of being proactive. When are those conversations going to happen? Is there an opportunity where that’s going to come up in the next couple of weeks or not? And then now I feel like I’m getting prepared rather than just letting things happen around me and react to them.

MURIEL WILKINS: Awesome. So, I’m curious, in one word, how did you feel at the beginning of our conversation and how do you feel now?

RACHEL: At the beginning of the conversation, I felt very scattered. I really didn’t even know exactly what I was going to need to talk about. I just knew I needed something, so I felt very scattered. I think after this conversation, I feel like I have… The word that’s coming to mind is clarity. I don’t have everything figured out yet, but at least I know what I need to figure out, and I have some concrete steps I can take to do that. So, I feel like I have clarity on what I need to do next, and before I really just was going to go into another day of meetings.

MURIEL WILKINS: I get it. You know how I feel? I feel like I’m never going to be able to look up at a starry night again without thinking about Rachel. I’m going to be looking for that North Star and wondering, “Did she find hers?”

RACHEL: “Did she find hers?”

MURIEL WILKINS: Which I’m convinced you will, and you are. So, thank you. Thank you so much.

RACHEL: Thank you so much.

MURIEL WILKINS: When we started the coaching session, Rachel wanted to make sure she was leveling up her leadership and demonstrating that to those more senior at her organization, but she wasn’t really sure where to start. So, we began with gathering examples of what was making her feel that way. From there, we were able to think through specific ways she was approaching communication with senior leaders and maybe where some of her gaps were. What had made her successful previously was when she felt she had stronger conviction. But in some of her more recent interactions with senior leaders, she wasn’t so unwavering. A key for Rachel to better understand the leadership perspective at her company was to ask more questions about expectations, priorities, desired outcomes and dynamics. Understanding those things about her senior leaders will help Rachel get herself to that next level. That’s it for this episode of Coaching Real Leaders. Next time…

NEXT EPISODE’S GUEST: This is the part where I’m just trying to navigate it. I’m content in my… I like my role, I love the people. At the same time, there’s that, Is this it? This is all for me? I can feel there’s more. I’m wanting to take that next step, whether it’s within my organization or outside, and I think I just want to be more secure in what that next step should be.

MURIEL WILKINS: I have a really important ask of you. If you love the coaching conversations on Coaching Real Leaders, it would mean the world to me if you could head over to Apple, Spotify or wherever you listen, to subscribe to the show and leave a five star review. And of course, if you think others would learn from these episodes, please share it with them. If you want more of Coaching Real Leaders, join my community where I host live discussions to unpack every episode and answer your questions. Become a member at CoachingRealLeadersCommunity.com. You can also connect with me on LinkedIn at Muriel Wilkins. Thanks to my producer, Mary Dooe; sound editor, Nick Crnko; music composer, Brian Campbell; my assistant, Emily Sofa; 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. From HBR Podcast Network, I’m Muriel Wilkins. Until next time, be well.