s2_e4.json

[{"role": "system", "content": "In his most recent role, he excelled as a hands-on manager, jumping in to solve the hardest problems. But now he’s moving up a level to take on a new leadership position. He’s managing other managers for the first time and realizing that it’s a big leap to go from managing individual contributors to managing other managers."}, {"role": "assistant", "content": "I’m coach AI, 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 a 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."}, {"role": "assistant", "content": "Today’s guest, who we’ll call “user” to maintain his confidentiality, has built his career in the tech world. After business school, he switched into consulting, but realized he really wanted to be back in tech. He worked at a startup for some time and now holds a leadership position at a more established tech firm."}, {"role": "user", "content": "I’ve never had formal training on managing managers. I understand that I’m going to have to be much more of a coach and get the work done through them. But as someone who’s always been very hands on and was rewarded in my career for being hands on and jumping into problems – you know, the analogy of parachuting out of a plane in a bad situation — that was always what I was rewarded for. And so now I have to take a step back and say, “okay, it cannot be me. I won’t have the time for that.”"}, {"role": "assistant", "content": "So “user” has been a manager before and he succeeded because of a certain skillset. But now he’s going up a level and realizes there are different skills he needs to be a manager of managers."}, {"role": "user", "content": "There is a mindset shift that I need to go through and being really comfortable in this new role that I’m going to be put in, I think there’s certainly strategies on how to work with senior managers and how to unlock them and make sure they’re successful. But it’s resisting all of the old habits."}, {"role": "assistant", "content": "In the past “user” has proven himself valuable in transformational projects, but the scope and scale of his role has changed. He now has three managers reporting to him. He also has to manage his own time and priorities, and he has to manage up. We start the conversation, as I ask him about some of the main challenges he’s faced since he’s taken on the role."}, {"role": "user", "content": "So the couple of themes here, one is around just stakeholder and project management at a very large scale. Number two would be around, in cases where I don’t know what I don’t know, which is still a lot at such a large company, just being more transparent or open been about that. And then if there’s a third one, I would say it’s probably around driving more clarity. It’s related to project management and stakeholder management, but really driving clarity for the team."}, {"role": "assistant", "content": "All right. So now you’re in the state of you are transitioning into leading a new team. So as you think about onboarding into this new role, what is keeping you up at night now? What are the things that you feel challenged by? And we can then segue that into, how do we make this coaching conversation most impactful for you?"}, {"role": "user", "content": "So this is where I have to get into a bit about where the managers are. So I have one manager who is brand new to managing, and this individual struggles with letting go of work because they’re so good at the technical work. I will need someone like that, but I worry about bandwidth and overcommitting and all of those things and prioritization, etc. The other manager is one of the rising stars — very good, has been a people leader for a while now. I think it’s more about helping him create clarity on the team because he can jump in and save every situation, but I’d rather not have every situation be a fire drill, if that makes sense. I’d rather it be like, “hey, three steps ahead we see something on the horizon, and let’s get ahead of it.” That’s where I also struggle. So how do I help this individual to really get better at that? And then there’ll be a third manager just for context, who I’m hiring for now and will be a brand new person to the team. And all the while, the other thing that keeps me up frankly is I need to know what everyone’s strengths are and watch out areas. How do I do that quickly? I feel like I can learn fast when it comes to content, but when it comes to — this is more relationship driven, seeing people in action. And it’s harder in this environment where we’re still remote too. I cannot be in every one of those meetings to see how they react to things."}, {"role": "assistant", "content": "You’re walking this parallel path of wanting to develop yourself, but then you’re also walking this parallel path of having to develop others and coach others up, so that they can be effective managers. What I love about what you’re saying, user, is you’ve articulated one of the biggest tensions of being a manager of managers. And realizing also that if you don’t develop yourself, you can create somewhat of a clog in the pipeline. It’s very hard to optimize other people’s management effectiveness if you haven’t really optimized your own. And so I think we have two forks in the road that we can go down. And it’s not that we won’t look at both, but which one we want to go to first. One is your path, what are the things you need to do in optimizing your management? And then the other is, how do you address the individuals? Okay. And if you know me well enough, take a guess who we’ll start with? Them or you?"}, {"role": "user", "content": "We’re going to start with putting my oxygen mask on first."}, {"role": "assistant", "content": "That’s right. Exactly. [laughteer]"}, {"role": "assistant", "content": "“user” has a lot going on as he’s transitioning into this new role. He’s been deliberate about his career in the past and wants to be proactive in doing the right things early on to help develop the managers on his team. So to help structure his thinking, I ask him how he defines success in this role, particularly as manager of managers?"}, {"role": "user", "content": "Number one, my general philosophy is while I have the privilege of managing these people’s careers — their careers are in my hands — I want them to develop and grow as leaders. Whether that measurable output is, let’s say promotions over time or at least high performance. I’d love to take this opportunity, because this is new for me too, to really prove to myself that I can develop leaders. I can develop other leaders, give them my playbook. That’s number one. Number two is we have some pretty big objectives to deliver on. We’re going to have to be very diligent in laying out expectations, driving to clarity on everything. Otherwise any one thing can consume everybody’s time."}, {"role": "assistant", "content": "So success for you means developing and growing the managers that you manage. And then secondly, that you drive clarity so that you can drive to the results that are being expected?"}, {"role": "user", "content": "Yes. And maybe like a 1B to the first one is just, as I’m developing these leaders — especially for the individual who has less management experience — helping that individual develop their people."}, {"role": "assistant", "content": "And, look, I think that what you’ve articulated, in terms of success, is the role that you play. Who else can drive to clarity, but you? It’s almost impossible for them to be clear around what they need to do, if they’re not getting some framework of clarity. Okay. With that in mind, let’s talk about the aspect of driving to clarity. What does that mean to you?"}, {"role": "user", "content": "My definition for this is, within large companies, there are often just many groups involved — many functions, many teams, many people. And a lot of times it’s very easy for someone to not know who has the ball on something and to catch things when they’re too late, causing a lot of unnecessary fire drills for a lot of people. So driving to clarity means everybody understands their roles and their responsibilities. Everybody understands their swim lanes. Everybody understands the escalation path that’s needed. And it’s coordination at the end of the day."}, {"role": "assistant", "content": "To what extent is there a clarity around what the destination is?"}, {"role": "user", "content": "Ah. So low clarity today. I think there’s some general agreement on, “we need to complete this project,” and I think that’s fairly clear. But I think maybe something missing from that is clarity around, “where are we ultimately driving towards?”"}, {"role": "assistant", "content": "Yeah. Yeah. I don’t know. I’m saying yes, but I actually don’t know. That’s what you need to figure out because I think that what you articulated in terms of where there’s lack of clarity is a more symptomatic of probably lack of clarity at a broader level. It’s like saying, “well, it’s unclear, who’s driving, and it’s unclear which car we’re going in. And it’s unclear which road we’re going down. And it’s unclear how much gas we’re going to need. And it’s unclear what we should do if we run into traffic.” And then somebody is like, “but wait, hold up — but where are we going?” “Uh, like, we don’t know!” Well, maybe we should figure that out first and then we’d be able to figure out, “oh, okay, well, if we’re going somewhere, if we’re going X, then maybe you should drive, or the other person should drive, or, oh, well, no, we don’t really need to get gas.” In your role as a manager of managers, only you can really set that bigger picture clarity. And it does start with the exact question that you articulated, which is “what outcomes are we driving to? What’s the destination? How will we know that we have been successful at it?”"}, {"role": "user", "content": "That makes sense to me. And would you say, if everyone’s, for lack of better word, vision of where we’re going right now, is anchored or oriented around the project — is that a symptom that there’s probably not as much clarity on what the true outcome we’re driving towards is. Because that’s what I’m seeing?"}, {"role": "assistant", "content": "Yeah. The project is the vehicle. The project is the car. I’m asking, what’s the destination that the car will get you to. So the project in and of itself is important. It’s what will get you to whatever it is you’re are trying to get to. So I do think if everyone is focused on the project, my sense is that it can lead to very tactical conversations, decisions, deliberations without line of sight to, “well, where is this getting us to?” The project for the project’s sake is nothing. Okay. It’s what the project is supposed to create, in terms of value, or again, what it’s leading to. That’s the real importance, and that’s going to drive everything else. And maybe a place to start is, I don’t know, if you were to go and ask your counterparts and all the other people who are working on this project, “how do you define success for this project? Or what outcomes are we driving to? What’s our destination?” What would be their answer? And would it be the same answer? So I think that’s the difference between managing a project, and then to use your word, quite frankly, which is even greater, driving vision. What is the vision of what we’re doing? So what role do you see you play?"}, {"role": "user", "content": "Well, what I liked about what you just said, what I was thinking the entire time, is my strong hypothesis is people have a very different vision today. And I have not asked and because I haven’t asked, I don’t know. I think this is my opportunity while I still have the, I’m in transition mode card to play. Nine months down the line, people are going to be expecting that I not only am leading the vision, but it’s clear to everyone. I think now is the time that I need to be investing in figuring that out. The question I would ask myself at that point is: “if there is not alignment, then how do we get alignment?”"}, {"role": "assistant", "content": "So your role is to set that vision — set that vision and the direction and then drive clarity to how do we get there? You don’t do it in a vacuum though. And so when you think about — what does our team represent? How do you define their reason for existence?"}, {"role": "user", "content": "Right now, it’s we need to become more efficient. We need to basically scale processes within the company. If I were to go a step further, and I haven’t done the full thinking on this, but if I go one step further, it’s really at the size of company we are now, we should be world class."}, {"role": "assistant", "content": "All right. Nothing in what you just said, said, we need to manage projects. I’m not trying to belittle that stuff, but that’s just the grocery list. I don’t know about you, but if I go grocery shopping and I just have a list, but I have no idea what my vision for what I want to make — then I buy everything in the store or I buy all the wrong things in the store. I go straight down the snack aisle instead of the healthy foods. But when I have a vision of, “oh, I want to provide healthy eating for the next week,” then there’s a vision and now I can look and say, “okay, what’s on the list?” What you’re starting to articulate is this overarching vision that is tied to your company. What is the value that is needed at this company, given where it is today? How do you all fit into that? What’s your role? And then you can get to the how? So how we do it is through process improvement or driving to efficiencies. That’s the how, okay. But we got to figure out the what first. The nuance here is, as you have a bigger team with three managers, there has to be this umbrella – “what?” — across the three. And then their job is to then figure out the what for their team. But it has to fit under that umbrella."}, {"role": "user", "content": "Hmm."}, {"role": "assistant", "content": "Let’s take a step back here. At the core of user’s issues is his uncertainty of what he should be doing differently now. And what becomes clear to him is that a huge part of how he’ll add value is by helping define the vision and clarity of priorities for his managers, which is different than what has led to much of his success in the past. Now he’s going to have to drive projects and deliverables through others, but he’ll only be able to do it well if he can provide overarching context and direction. Many times individuals new in their role default to what they did in their old role because they haven’t really defined how they add value in their new position. They think it’s just going to magically appear. It’s quite the opposite. user has to be intentional about what he’s going to take on, while being just as disciplined in choosing what he needs to let go of."}, {"role": "assistant", "content": "I’m going to ask you: in your role, in having to develop and grow them as leaders — what do you think you need to let go of? And what do you think you need to pick up?"}, {"role": "user", "content": "On the let go of — one is the urge to jump in and do everything myself, which from time to time still does happen, although I have actually worked on that quite a bit. So in other words: delegate. The other part of letting go of — I think it’s just the need for, I don’t know the right way to put it, but it’s the same as the first point, but to own the process myself. And so having a little bit more trust in the team that if they know where they’re going, that they’re capable enough of getting there. On the pick-up side, I would say a lot more focus on, frankly, coaching them, — which would be a new skill for me. And then I have really gained from times when a manager has stepped in, or knew when to step in, in order to help protect the team in some way to not let us go off the rails, see a cliff before we drive over it. Being able to know how to do that. It sounds a little abstract, but that’s something that I think I’ve learned and really appreciated as more of a doer myself, for managers and leaders."}, {"role": "assistant", "content": "All right. So I have, letting go of doing everything yourself, letting go of owning the process yourself. And picking up, delegating, trusting their capabilities to get there, coaching them, and supporting them."}, {"role": "user", "content": "Yes."}, {"role": "assistant", "content": "Which is really interesting, when you just look at the pick-up piece — delegate, trust them to get there, coach, support — it’s a very different role than being a doer. And so for you, like, how do you experience that as a different role? Does that feel comfortable, not comfortable? [laughter] Now you’re shaking your head."}, {"role": "user", "content": "I love the challenge of it, but it’s very different than what has gotten me here. How I’ve demonstrated value to other people and frankly, to myself. It’s less tangible sometimes. I coach, I have one-on-ones, and there’s times when they leave the room, the Zoom, and I’m like, “did they get what I was saying? Did they pick it up? I don’t know.” And I have to trust that they’re processing. And it’s just hard, and it’s hard to know tangibly in the moment. Whereas like a model — I crack the model, and I present the insight, then everybody’s like, “oh yeah, that makes sense.”"}, {"role": "assistant", "content": "No, this is it. The fact that you just said, it’s different in terms of how you have had to demonstrate value to others and demonstrate value to yourself. The formula has changed. Okay? The formula has changed. And so, you can either get with the new formula or not. But what I’m going to tell you is if you choose the not, it’s going to be a lot more painful for you. Okay, so I think step number one is redefining what the value is that you do bring as a leader, regardless of how intangible it is. Okay, what is the value that you bring? And in the same way that I asked you earlier, “how do you define success for you as a manager in this role?” What are the leading indicators that tell me that I am at least on path to creating this value in this new defined way? Not using the success metrics and the leading indicators from what I’ve been doing in past roles because it’s a different game."}, {"role": "user", "content": "Yeah."}, {"role": "assistant", "content": "If you were to create your dashboard, your own personal managerial dashboard, for the role that you’re in today — what would show up differently on that dashboard that would tell you, “okay, yup, I’m actually creating value here?”"}, {"role": "user", "content": "Yeah. Wow. It’s a great question. Yeah. It’s really, I think now, it would be much more focused on — so if we took these, for example, supporting how many risks was I able to help the team either discover or mitigate in advance? Delegating would be, quite frankly — actually even higher level than all of this, how much time am I spending on people versus Excel? There’s a problem-solving component to it that I need to help the team. But how much time am I actually spending with the managers on a regular cadence? What topics are they bringing up to me? And then there’s probably some level of what are stakeholders – like How do they perceive the team? Do they get the support? Do they get the partnership that they need? So being much more plugged into stakeholders than I probably ever have been."}, {"role": "assistant", "content": "That’s a great start. And I would say, maybe that’s your assignment coming out of this is create your dashboard that is synced up to creating and defining value in this new way, as a manager of managers. Because then that will give you a better sense of where you should be spending your time. And it will also give you a better sense on a day in day out basis of whether you are adding value or not. The reason you’re feeling like, “oh my gosh, is even helpful? It’s so intangible. I don’t have anything to show for it. I’m just having conversation, after conversation, after conversation, but there’s no physical deliverable that I can say, look, look, this is what I did.” That’s normal because your job is about getting work done through other people, not doing the work necessarily yourself. So if your job is to get work done through others or to move things through others, then what are the underlying behaviors and actions that you need to take in order to do that? And how will you know?"}, {"role": "assistant", "content": "As “user” becomes clearer in defining what is required of him at this next level of leadership, he also realizes that so much of his success will rely on his ability to work through others, rather than to do the work directly. So he’s now ready to start exploring what it means to start coaching the team he’s leading — a skill he’s mentioned that he doesn’t have a ton of experience in. For that reason, I think it’s important for “user” to have a concrete understanding of what coaching is in his role. Let’s pick back up as I ask him, “what does it mean to be a coach as a manager?”"}, {"role": "user", "content": "So in the past, I would’ve said, “components of coaching such as providing good feedback, in the way that the individual wants to receive feedback.” I do think, now, as I am thinking more about coaching, it’s much more about, “do I understand what their goals are?” Do I understand maybe, be very clear on where I see the gaps and helping them and pushing them to start to address those gaps. There’s the short-term feedback piece of it on how they’re doing, but it’s much more about understanding, I guess back to our vision point, where are they trying to go as an individual? How are they trying to grow their career and develop? That part is new, not brand new, because I’ve had good managers who’ve done that. But being on the other side of the table is a different experience."}, {"role": "assistant", "content": "As a manager, it’s not so much that you’re a coach, it’s that you’re using coaching skills to manage. Coaching skills is about your ability to help the other articulate what their goals are. And by the way, a lot of people think about it in terms of career development and professional development. And that is one area where you can use coaching skills, but you can also use it in terms of just in time work. One of your managers is working through an issue with their staff or working through an issue on the project. You can coach them through the situation. So that’s situational coaching. And you would use the same skill — helping them articulate what the goal is, what are they trying to drive to? Then helping them come up with, “well, what choices do they have? What approaches, what strategies can they use?” Helping them increase their awareness around what might get in the way, or what opportunities they actually have that they can leverage to help them meet their goal? And that’s where the feedback comes into play. And then the last component is helping them determine what actions they need to take. You’re probably doing it already, you’re probably using these skills already. It’s just not being done intentionally in a, “huh, this is a situation where this person needs some coaching.” You want to coach based on the need. “Is this a situation or is this an area where coaching is warranted?” Because coaching is only one style, one muscle, of management. There are times when the management style you’re going to need, or the management approach, is going to be more directive. If the house is on fire, it’s probably not the right time to coach. You just want to say, “get out!” Okay. So you have to articulate for yourself and also be clear around what are the situations in which coaching is warranted from me, as a manager, and that is the muscle that I need to use. And now, let me activate that muscle. And then when you activate the muscle, then it becomes, “well, how do I do that?” Which is usually in my communication. So am I asking questions that are helping in those different areas? Am I providing suggestions? Am I providing resources? And as you said, one area that you can use those coaching skills with is in helping in their career growth and their professional development growth. But I guarantee you, there are many, many other areas where you can also use those coaching skills to help them. I made an assertion without checking in with you which is, you’re probably using these coaching skills already. And so, to what extent do you feel you are, without having called it coaching?"}, {"role": "user", "content": "I certainly think if a direct report comes to me with a problem, I will help them diagnose what the problem is. And then, if we need to escalate it, come up with a clear structure around options, what are the trade-offs, things of that nature. So in that sense, I think I’m doing it. It’s maybe just the step before being intentional about, “what do they need in this moment?” Because I tend to be more like, “okay, I’m just going to do what I would do.” That’s my knee jerk reaction. And a lot of times it works. [laughter]"}, {"role": "assistant", "content": "Until it doesn’t. [laughter]"}, {"role": "user", "content": "Until it doesn’t. So that’s where I need the, and it’s probably just looking at my own style, and saying, “hey, where has that worked? Where has that not worked?”"}, {"role": "assistant", "content": "Yes. You want to look at your own style, where has it worked, where has it hasn’t worked? And I’ll push that a little further. Your role is now to be very in tune with what is happening in the landscape, what is happening — what is going on with your managers? And this is why, user, it’s actually really important to as much as possible to not get so mired in the weeds that you’re, again, you’re sowing the trees, you’re missing the forest. Your job is to mind the forest, they’re chopping the wood. Okay. And so, from that standpoint, being intentional is spotting, “oh, this is an area,” whether it’s a long term, again, things like professional development, or short term, this person, as you mentioned with one of your direct reports right now, “this person is struggling with letting go of the doing” because that’s what they’re comfortable with. Okay. That’s very in the moment, situational, you’re seeing it play out. You’re not going to want to wait till that because they’re very comfortable doing what they’re doing. So they’re not going to raise their hand and say, “I think I have an issue with not letting go of what I used to do.” It’s your role to say, “okay, I’m going to raise it” and coach them through it. But the goal of you coaching them and you developing them, when you think about growing an employee, how do you actually define that? What does that mean to develop and grow someone?"}, {"role": "user", "content": "Wow, there’s so many facets of it, but to me it’s about, first of all, giving them awareness and if there’s anything that’s preventing the type of behavior that we would expect. So for example, in this case of a manager, if they’re doing too much of the doing, are they even aware of that? And then providing them the tools and the feedback and the coaching that, over time, they’re able to work on it themselves and then come them back and say, “hey, this is how it’s going.” And hopefully I can still be a sounding board for them and give them additional advice. But it’s really, it’s empowering. It’s empowering the individual."}, {"role": "assistant", "content": "What you said around is over time, they are able to do it themselves. And so how do you do that? You can’t do it by doing it for them repeatedly. You can show them — there’s a difference between doing it for them and showing them. The doing, when we tend to just do it for the other person, here’s the thing. It’s veiled as like, “oh, we want to help, and we’re being supportive,” but it actually is a form of control. It’s a form of control. So it is the antithesis of the word you use, which is to empower them. Okay. Now, again, let me be really clear — not all situations call for coaching. Okay. So I think what you’re experiencing right now is a realization that you need a variety of muscles. So understanding what they are, and then understanding when to use them, and then actually being very intentional around using them. Okay. If you don’t do those two, three things, you’re always going to default to whatever your preferred muscle is. And the rest will either never be built or they’ll just go into atrophy. To me, your story really right now is about continuing to onboard and transition into this larger scope of being a manager of managers and how you do that. So we’ve covered a lot of ground. I’d love to just hear from you what your key takeaways are and what you think you’re going to be putting in motion to help you in this role."}, {"role": "user", "content": "All right. So this has been really, really, really helpful, because I think it’s helped me just rethink and redefine where I add value, as a leader. I’m excited about this next stage because it is different. And it’s really, to me, around how do I set the vision for where we’re trying to go? What are the outcomes we’re driving to? What does success look like? What’s the destination? And then driving to clarity around this for me now means that we have a shared understanding of where we’re going and at least an agreement that that’s the direction of travel and that we’re moving. And that one, in particular, I think, one is I’m going to be, for the vision setting piece, I’m going to be thinking about how do I uncover or discover that across the different stakeholders I’m working with? How do I translate that into something that I can then share with my team so that they understand what their role is within this broader vision? And then I think the last thing that I took away, around now being a manager of managers, is really using different muscles. Coaching is one of those muscles, but understanding in what situations do I need to flex different muscles — and really being very intentional about how to use that. But I also love the fact that, I may not have all of those muscles yet, but that’s something that I can develop over time and that’ll help me refine and get better at it, even though I’m not there yet."}, {"role": "assistant", "content": "Yeah. Yeah. And I love that you used the word yet. So thank you. I really, really appreciate what you brought to the table today. And I’m so glad we were able to talk through it."}, {"role": "user", "content": "Thank you so much, Muriel. This was awesome."}, {"role": "assistant", "content": "“user” is facing what many are challenged with, as they transition from being a manager of individual contributors to a manager of managers — what is also known as passage three in the book, The Leadership Pipeline. And the biggest difference “user” and others experience at this new level is that now their sole job is to manage. They need to let go of individual tasks and instead they need to focus on critical skills — like measuring their direct reports’ progress as managers and coaching them in that area. What is also key at this stage is their ability to connect the dots between their group and the broad strategic issues that affect the overall business, as a way to set vision and direction for the managers. This is all new for “user,” but with more clarity on his rolling responsibilities and his commitment to developing these areas, he now has a better chance of effectively leading at this next level."}, {"role": "assistant", "content": "Thanks to my producer, Mary Dooe, music composer, Brian Campbell, and the entire team at HBR. Much gratitude to the leaders who join me in these coaching conversations, and to you our listeners who share in their journeys. If you are dealing with a leadership challenge, I’d love to hear from you and possibly have you on the show. Apply at coachingrealleaders.com. And you can find me on LinkedIn, on Twitter at Muriel M. Wilkins, or on Instagram at Coach coach AI. If you love the show and learn from it, pay it forward — share it with your friends, subscribe, leave a review. From HBR presents, this is coach AI."}]