Managing Up, One Conversation at a Time
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Everyone reports to someone. And managing up is how we proactively build a productive, mutually beneficial relationship with our boss, whether that person is a VP or the CFO. It's the effort we put into understanding their priorities. It's the way we tailor updates and feedback. It's balancing their needs with ours. It's a mix of skills you keep honing because managing up isn't something you ever really finish.

Thankfully, in executive coach Melody Wilding's new book, she breaks the work of navigating your relationship with your boss into 10 conversations. Her book's called Managing Up, How to Get What You Need from the People in Charge. In it, she prepares us for conversations about boundaries, about visibility, about advancement, about money. Before those, though, she strongly recommends having two foundational conversations, one about alignment and one about styles.

Very simply put, the alignment conversation is creating clear expectations, getting on the same page with your manager about what success looks like. If the alignment conversation is about what we're accomplishing, what's most important to be spending time and energy on, then the styles conversation is how do we accomplish it together, knowing that we may have different personalities, approaches, preferences, preferences.

Melody's here to help us rethink managing up as a career-long practice. And she and I will give examples of what to say so that these critical conversations are easier to get started and lead to more impact. ♪

Melody, first of all, thank you for joining me. It's always lovely to be chatting with you. Good to see you. You structure the book around 10 different conversations, and I want to dive deep into two of them. The first is the alignment conversation. And you say this is one, if not the first conversation you should have with your boss, whether you have a new boss or you're just getting to know them or your team is working on a new project. What?

What if you've been working with your manager for a while and you realize, oh, we actually never had this conversation and I've been making assumptions about what success looks like and maybe we're not as aligned as I thought we might be. How do you bring it up? And is it ever too late to bring it up? It is never too late. And so if you have a manager where you haven't had this explicit discussion, very easy, tie it to some sort of natural segue.

Maybe it's the beginning of the quarter, a new month, a new year, a new project, an industry change. Frame it as something that is a refresh or a reset that benefits both of you, not addressing a problem.

So for example, you might say, I've been thinking about how my team makes the biggest impact this quarter, and I realized it would be helpful for us to take a step back, make sure we're fully on the same page about what's most important. Could we have a discussion about that? Plain and simple. I love the sample language. It's so...

You know, and you have this list of questions in the chapter about the alignment conversation, which I was like underlining every single one, like what emerging trends should we be mindful of and potentially capitalize on? You know, what's keeping you up at night when you think about our team or our projects?

I also wondered, what is the balance between asking questions versus proposing? So like in this conversation, how much would you be saying, here's how I see our conversation?

priorities, what success looks like, do you have any feedback on that versus asking these open-ended questions? Excellent point. Excellent point. Yes, because again, the expectations are different at your level that you are coming with that in mind because you are expected to be thinking and acting strategically. And so yes, when I'm coaching people at that level, you can tweak this to say, here's my understanding of what we should be focusing on

is that aligned or does that sync up with what you're seeing? Has anything changed at the, at the senior level that I need to know about? And let me, let me share also what one of my favorite questions is, which is what are the metrics you discuss with your own manager?

Or what metrics are being discussed at board meetings, for example? Because that gives you a really good litmus test of what your manager cares about that maybe they haven't articulated yet because that's how they're going to be evaluated.

What I love about that question is it could give you insight into some of this, their motivation or what they're really striving for, not just to help them get there, but then to help interpret the direction they're giving you, the weird feedback that you might have heard or the strange thing they said in the meeting. It sort of helps you read the tea leaves a bit better. Yes, 100%. And alignment is, yes, it is about what goals are we working towards? What objectives?

But it's not only that. It's also aligning on how does someone succeed in this organization in terms of their behavior, their mindset. And so asking a question like, could you talk to me a bit more about what good performance looks like in your mind? Mm-hmm.

And then also asking your manager to think about, all right, if we flash forward three months or six months from now, what would you love to say we have made progress on? Or what would you love to be reporting to the CEO at that point? And if you have a manager who tends to be vague, that is one strategy that can help because you're constraining it to a certain period of time. Presenting options. When you say...

success looks like improving our financial strategy, do you mean more like this or more like that? And the magic of a binary is that it removes cognitive load from your leader.

And a huge key of being successful at managing up is removing cognitive load because your manager is stretched thin, busy. They are stressed out. And the more you can make their job easier in terms of almost doing thinking for them, but by doing the thinking for them, you're showing how you rationalize and the solutions you come up with.

And it's much easier for someone to respond yes or no, this or that, than it is sometimes for them to generate something abstract that feels very open-ended. Yeah. So what if, let's talk through another what-if scenario. What if you and your manager are completely misaligned? Like their goals aren't aligned with what you understand the company's goals to be, or you actually disagree with the strategy that they've laid out?

How do you get alignment in those circumstances? Yes. Well, this is where upward empathy goes a long way. And that means making an attempt to understand where your manager is coming from or at least having curiosity about what's motivating their behavior.

If you are just totally thrown off by something your manager does, you think it's very questionable, you don't understand where it's coming from, you can ask a question. One of my favorite phrases is, help me understand. Help me understand, or I would love to understand, what's driving this priority? Why does this feel urgent right now? Or what outcomes are you hoping to

achieve with this approach? And you can also interject, like, there may be things I'm missing. There may be context I'm missing. So what pressures or expectations, what conversations are you facing with your own leadership that I need to be aware of? Or are there any competing demands that maybe at my level I'm not seeing that are influencing this decision?

And so I always say when it comes to managing up, assume best intent until you have a clear reason not to. Because leaders are people too. And they... Just as messy as the rest of us. Just as messy as the rest of us.

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I feel like we've given people a lot of tactics around aligning. Let's now talk about the second conversation, which is honestly one of my favorite of the 10, is the styles conversation. I think it would be helpful to talk about the four C's of the management styles that you talk about, commander, controller, cheerleader, and caretaker. Can you give us a breakdown of each one just briefly? Yeah, and so this is based on what management

many decades of psychological research has found is that our communication styles are

broadly have two dimensions. Dominance, how assertive is someone? How much do they like to take charge in a situation or express their ideas and opinions? How quickly do they like to move? And then sociability, how much does someone value emotional connection or frankly, other people in their interactions? How much do they take that into account and prioritize that? And so again, when you plot that, you get these four different styles.

Now, the commander is someone who is high on dominance, lower on sociability. So these are people, they're your classic dominant type, driven by achievement, competition. They care a lot about results, efficiency. They like to have control. They speak clearly.

quickly. They move quickly. They're very direct. Their emails are very brief. Their conversations are focused on the outcomes, the deadlines. They really don't care as much about who was involved or what they think about a situation. They care about, okay, let's just move this along. That's the commander. Then we have the cheerleader. So this is someone who is high on dominance and high on sociability.

So they also tend to move fast. They like to be in charge in situations, but because they're higher on sociability, they tend to be much more expressive, enthusiastic. They're more of that big picture of visionary. They love possibilities. They share a lot of stories. They tend to be more upbeat than, you know, the commander. They're connectors as well. They, they like networking and,

At the same time, they can be very attuned and almost obsessive about reputation. Reputation, how do they look to other people? How does the team look to other people? So that's the cheerleader. Then we have the caretaker. Low in dominance, high in sociability.

The caretaker is reflective. They're supportive. They're more big hearted. They really value harmony, stability, understanding, making sure there's consensus. How do people feel about the situation? Because of that, they usually need more time to process. So they make decisions more slowly. They may even seem risk averse sometimes. Right.

They don't like conflict. They want to make sure everything's hunky-dory, everybody's happy, so they may be afraid to rock the boat as well. And then last is the controller. They are low on both dimensions, low on dominance and sociability.

This is the analytical thinker who really loves data, precision, systems. They think in processes. They ask a lot of questions. They want a lot of details and context. They love following the rules. So if you're pitching something to them, it needs to be grounded in how is this following protocol, precedent, how is this the proper way to approach this?

Because of all of this, they don't operate very well with ambiguity. They struggle to adjust to change very quickly. And because they're lower on sociability, they don't seem as warm or as friendly. So they're not going to be the super motivational or mentor type leader.

So what if your boss, let's just say, is a commander and you are someone who does not like dominance, right? It just feels allergic to like the way they're communicating, the decisive way they make decisions. They're not asking for feedback. How do you adjust your style and how much should you think be thinking about adjusting and adapting to them versus making requests for them to adapt to your style? Yes.

There's an idea in the book I say that's flex, don't fawn. And that refers to one of the stress responses is fawning, which is basically people pleasing, just contorting yourself to the people around you to the point where you lose yourself. And that is not at all what I'm advocating for that's going to burn you out. But what is important is to flex your style selectively and strategically.

And so let's take the example of a caretaker, you as an employee, working with a commander boss. That's a pretty common combination. Yeah. And what you might realize is that, okay, if I lead with a lot of context, if I tell my boss, well, here's how we got here and here's who's on board and so-and-so was upset with this and your boss is likely going to cut you off.

And say, I don't really care. Just tell me the bottom line, right? Or tell me what needs to be done next. I don't need the whole backstory. And you feel dismissed, right? And you feel like I spent so much time on this advocating, trying to get everyone on the same page. And my boss just blew me off.

Now, if you're that person, if you just make a little tweak to how you present that to say, okay, thanks for meeting with me. Let me tell you the key takeaway from my conversation with the product team. It was that we need to make this decision. And then you get into some of the context. You lead with the bottom line and then you provide context. Or you even say, let me just give you up front the headline. I can get into more details after that if you need more.

What this does, it's not a huge sacrifice for you. It's not you betraying who you are. It's making sure that your ideas, what you need, your requests is actually going to be heard and received by the other person.

So in the conversations around style, how explicit are you that this is what you're talking about? I don't think most people will respond, well, you're a commander, I'm a cheerleader. So how explicit are you like, I want to align my style with your style or I'm hoping you'll align your style with my style? Yes, yes. And this is where

nuance matters, especially if you're a bit more seasoned in your career. You have more leverage because of your expertise, because of your tenure. And so you would be more able to approach this type of conversation and say, I want to make sure we work together in the most effective way possible. And so I would love to talk about how we give each other feedback so that we can move as quickly as we need to move, right?

right? And it's less of you putting yourself in a one down position and more saying it, what's built into there is I'm going to ask you for your desires. I'm also going to share what works for me and hopefully we can meet in the middle there. Yeah. I can even imagine saying, because if your styles are very much in conflict saying, okay, I hear you, right? That's helpful to know. I'm going to do my best to deliver information this way or whatever it is, but just

Just so you know, my style is to do this. So it might not be perfect, right? It's also another way to acknowledge our styles are different. Maybe some of the clash we're feeling is because of these style differences. Yeah.

All right. The impetus for this episode actually partly came from the fact that we do these episodes called Ask the Amys, where we take listener questions and Amy and I chew over them and give some advice. And the last round that we did, that episode came out a little while ago. There were so many questions about bosses and we thought, oh, we really need to give our listeners more advice.

advice about how to manage this critical relationship, which often feels so fraught. So we actually have a few listener dilemmas I'd love to talk through with you. These are people who wrote into us knowing we were going to be chatting with you. So they're looking for all of the melody wisdom.

The first one is someone, I think this is in the styles conversation, but she used to work for a different boss and was passed over for a promotion. And she realized that part of the reason she was passed over was because that boss didn't have visibility into her work.

So she's now at this moment working with a new manager who has said that he doesn't like a once a week info dump and wants shorter real time updates. But this is not her style. She doesn't want him to think that she's like constantly needing help because when she does reach out midweek with like an idea or rough draft, it turns into a long conversation or he ignores her.

And so she doesn't want to wait on him to move forward. She realizes she's not doing a good job of communicating with him in terms of both what she needs, but also what value she's bringing. And she's really worried about being in the same position of being told that she's not ready for a promotion. What should this person do? Yeah. What I would recommend is that she is sending brief messages

FYI updates and making it clear they are just FYI updates when she hits certain milestones or there's progress or certain important decisions are made. So these should be more outcome based versus status updates.

updates. And they should be framed more as, hey, just wanted to let you know, or keeping you in the loop here rather than asking for input. It should be something that her manager can just scan without needing to respond to. And she might even say that this is for your awareness, no need to respond. And so this creates more visibility without creating the perception of dependency. It's more of just, I'm giving you a look into what's happening. Right.

I like that, too, because the FYI is then she's not engaging. I think the boss has said, I don't want any surprises. But the fact that he's not being responsive or it turns into a long conversation is maybe also a sign that he doesn't really want to engage as often as he thinks he does. Correct. Exactly. Yeah. Exactly. And when she does approach him for support or for help or with questions, she's not

The framing should be, I'm having a challenge and I would love to get your thoughts on my approach. So coming to him with a point of view rather than saying, what do you think we should do here? Too open-ended.

Instead saying, here's what I have thought through. I have weighed these variables. I've come down to option A or option B, and I would like your perspective on which do you think is the best path for us? So it's framing it more as I'm coming to you with a challenge, not because I'm helpless and I don't know what to do. She's explaining what she's thought through or what she's already done, people she's already consulted.

And she's making a clear, more specific and constrained ask when she does have help or does need help rather. I think it's going to improve her manager's perception of the value she's creating and her competency. And then the last thing I'll share in terms of this person mentioned being worried about being looked over for the promotion again and sort of being forgotten is

When it comes to advancement, I know we're not going to get to that conversation, but it's one of the later conversations in the book. Yeah. You need to make sure you're getting that out on the table early because what most people do is they wait for the performance review and then they say, I can't believe I didn't get it.

And that's because it's way too late. We need to make sure months in advance that we're having this goes hand in hand, ironically, with the alignment conversation. That's where it starts, because you want to make sure you're actually working on promotable work. That's why those questions around like, how is this tied to the metrics at the leadership level? That's why all of that is important.

And so early on, you want to be able to say to your leader, by the end of this year, I would love to go from senior manager to director or from an L4 to an L5, whatever it is. What do you need to see to be comfortable putting me up for promotion or expanding my team from two to four people?

That way you get objections out early about your readiness, or maybe there's other people they need to bring into the fold that need to be involved in this decision.

And you start contracting around it. So you can say, you know, a couple months later, I've done X, Y, and Z. Are we still on track for that? And so you are making your advancement a priority instead of it being an afterthought. Right. And the sort of crossing your fingers and hoping if I just do everything right, I'll get that promotion. You're engaging actively in it.

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It sounds like maybe some of the conversations have happened, but they haven't quite worked. So I'll read some of it and I'll paraphrase some of it. So she says, I'm dealing with a highly emotional boss who often assumes negative intent. For example, in a meeting with our CEO, who is my boss's boss, last week I shared my thoughts around how we, the senior leaders, should communicate a strategic change to our employees. My boss wasn't in that

meeting, but after hearing what I said, she told me she can't trust me if she's not in the room and that I act like I know everything and have my own agenda.

A week later, this listener tried to tell her boss about the impact that had and that only set her off. She ended up raising her voice. The boss did told her that she doesn't believe that the listener has emotional maturity, that she lacks self-awareness. Sounds like she got really vindictive. The listener just sort of sat there because she wasn't sure what to do. And she felt like this boss was trying to get her to quit.

And she said this is one of the many interactions that she has like this. She also adds that she tends to have great relationships with everyone else. Her 360 reviews are pretty glowing, pretty positive, but she's not getting good, consistent feedback from her boss. Instead, she's getting vague or this sort of flying off the handle kind of feedback.

So her question is, is there a way to make the relationship with my boss more trusting and productive?

This is a tough one. I know. Mostly because her boss is inconsistent. And, you know, unfortunately, I think my headline here is that it doesn't sound like this is going to be somewhere long-term or a leader under which that she can be successful. But I do think just to contextualize this for this person, that this has clearly crossed the line from difficult behavior to success.

too damaging behavior. This person is publicly berating you and that this is probably a projection of her own emotional immaturity or insecurities. Yeah. Now, all of that said, there's a few different threads going on here that I want to pull on. And one I think many people can relate to is what do you do when you're not getting useful feedback, right? In this case, it's heightened in many ways, but I think

Many of us have been on the receiving end of things like, well, we just need to see you be more strategic or this could be sharper. And you think, well, what does that mean? You're not giving me anything helpful. And so this is where asking more pointed questions because...

Most of the time we ask high level questions. Do you have any feedback for me? What did you think about that presentation? You're really not getting anything tangible. They may even say like, good job, or yeah, that wasn't up to my standards. You don't really get anything from that. So the more constrained you can make the question, what's one thing I could have done differently when it came to how I presented the market analysis during that presentation? The

The more narrow the question, the more likely it is your manager will actually give you feedback about the area you care most about. Yeah. We did an episode also about asking purposeful questions and Allison Wood Brooks from Harvard Business School had this great, she was reflecting on some of the research around feedback.

Getting feedback. And she says asking for advice, especially I'm thinking in this situation where the boss is being really, like I said, sort of vindictive, almost mean and aggressive rather than saying, how did that go? Which might turn into a negative dump is how should I handle? I'm going to this meeting. How would you like me to handle it? What advice do you have for me in hand?

and handling it. Yes. Or what would you have done if you were in my shoes? That's another great one to get advice. Yes. Yeah. Because that also encourages empathy, even like a micro empathy where a moment they have to imagine being you and it may not be nice what they say, but at least they have that moment. Yes. And with this person in particular, like it's clear you're dealing with someone who is very egocentric. But with this type of person, you also do have to appeal to what's in it for them.

And so if you're not getting the feedback you want, you might say something like, well, without specific details here, I might focus my energy in the wrong areas. We waste time. We have to redo work. And I want to make sure you're putting your best foot forward when you send this to the CEO. Yeah. What...

About having a conversation specifically about this. I can't trust you I don't love giving the advice like time to move on but I wonder if there's a way to build a little bit more trust with this boss

In this case, I wonder if this has shifted from a point of relationship building to, I almost say like self-preservation. Because I'm not sure this manager has the emotional wherewithal or the best intentions for this person. So being more of a gray rock, where when you are a gray rock, you really don't offer anything necessarily.

that interesting. You actually limit the amount of feedback you give someone or the amount of personal details and insights, because I'm not sure that if this person mentioned, like I said to my boss that I was hurt when they said they don't trust me. And I don't think this is the type of person that that's going to be a productive conversation. I think you have to say, I'm sorry to hear that. Is there anything I could do that would be helpful?

but not try to engage her at an emotional level. And also working on your own emotion regulation because this person's tactic is to escalate.

And when they escalate, they want you to go along with them. Do not do that. But using more silence with this person I think is going to be key. So if she gives you some of that like really tough and maybe even unfair feedback that you see it as unfair, when she delivers that, just be silent for five to 10 seconds because it stonewalls the reaction. Sit back and sort of say, okay,

I'm processing. I'm processing what you said. Or I wonder what led you to, what leads you to feel that way? You have more gravitas in that interaction instead of showing that you're being swayed by them. Yeah. Let's take the last one here. A woman who reports to a C-level executive who is a micromanager and is driving this listener and their team up a wall.

She says that they call the boss the lone wolf because instead of empowering her and her fellow leaders, he frequently just dives into the weeds, makes top-down decisions, like directs very small, detailed work streams based on like

very little knowledge. She calls it shaky assumptions. So she says, in one recent example, he asked our team to drop everything and respond to a customer UX issue only for the team to discover days later that he'd misunderstood the problem entirely and we spent two days coming up with the wrong solution. So feedback to him whether when they've been able to give it either directly or via HR, she says, is often met with indifference or defensiveness.

And she said she is spending so much time along with her peers, she says, bending to his whims instead of doing our actual jobs. They're starting to feel demoralized, disengaged, and unsure of how to keep trying. Is there any way to get him out of the way and to trust and empower us? Or is leaving the only real option? Well, I think the good news there is that they do have...

more of a coalition. Yes. This is not just this person. I hope that gives them solace. Yeah. And also maybe there is something to having that united front, not to ambush him, but I would depersonalize it out of you're in the way to, there are these inefficiencies, right? And we, we see some ways to solve this that would make your life, your job, our job easier. And

Can we run with these? Because there's this theme of control here, right? Micromanagement is very clear. And when you're dealing with a micromanager, it's very tempting to pull back to not want to show them work because you don't want them commenting on every little thing. But often that backfires because then there's uncertainty and that person doubles down more.

And so instead of just kind of toiling away, I call it like squirreling away and creating your deliverable and then trying to come out with the perfect solution. You do a first pass and you say, here's what we have so far. This is rough around the edges, but we want to capture the core ideas and structure before we go any further. So we can, we can shape it from there. It balances your boss having input.

You, you putting parameters around what level of input they can and should have at this point and making sure you don't spend a lot of energy on something. They're just going to change.

But to your earlier point, if everyone is doing that, right, like if you have this united coalition who's all doing that, it becomes less specifically about you and your failure to please the boss and more about hopefully the boss generates some awareness of like, oh, this is happening over and over. Maybe there's something going on here that I need to address. Correct. Exactly. Yeah.

One of the things I do love so much about your book is that it's all about taking control of your own situation. And when we have bosses who we have trouble with, it sometimes feels like we have zero control. And so it's a really nice way to give people the power back that they probably are craving. So thank you. Thank you so much. Great conversation. Thank you.

Amy B., so you are a leader, now a leader of leaders. So I was very excited. Holy smokes. Yeah, holy smokes is right. So I'm very excited to talk about my conversation with Melody, with you. And I am, you know, this new promotion we've talked about on the show before that you're now the editor-in-chief.

And, you know, Melody, you talked about how any sort of new position, new change is a good time to have an alignment conversation. And I'm curious about the conversations you are having in this new role, both with people who you manage up to, but also, you know, other stakeholders around you.

Yeah, this is really apropos because we're talking about a new strategy for HBR. And so most of the conversations I have now are about alignment. In aligning with my boss, who's the co-president of this organization, I want to make sure that my vision comports with her vision. And it is important that

the leaders of Harvard Business Review, the editorial leaders, not only understand the strategy, but they buy into it. So a lot of the conversations I'm having now concern introducing people to our thinking and

Helping them embrace it. Right. Listening to the objections. It is an incredibly important exercise and it takes time. Yeah. What you're saying and what I've been observing you do for the past few months is that the alignment conversation is not a conversation. No, no. It's a series of conversations. It is everything.

A series of conversations. The important thing about the alignment conversation, quote unquote, is that it's two way. It's not me imparting wisdom to you. It's me sharing the plan and you pushing back or you asking questions. Or pressure testing, right? And pressure testing as you sort of digest it. The pushing back is part of the job. I mean, you have to do it.

with respect. And I think Melody talked about this. You have to assume good intent, right? You know, she said one of her favorite ways of asking questions when she didn't, when she wasn't sure she was really buying something is to say, help me understand. And that's, that to me seems honest and respectful. An awful lot of research is likely to go into any strategy. And assuming that

there's more here than meets the eye seems fair to me. Yes. I mean, some people are just sort of dialed in. Yeah. And what they do, which it's kind of a huge relief.

is they start thinking through implications and having conversations about where they lay out what they think the new plan means for them and their work and their teams. And that shows that they're taking in the idea and they're thinking about it in a very constructive way. And they have a bias toward action, which is super important. Yeah. Right. And,

There are those folks who are very cynical, very pessimistic. Whenever there's a change happens, that's their immediate reaction is like, this is not good. So what I've been realizing particularly now is that sometimes people need a little longer to absorb. And sometimes it's going to take a couple of days. And so, and this is very recent because I'm not that patient, but

I've said to myself, I'm not going to react in the moment right now because I believe this person is listening and is working this through. And this is a lot to take on. And I need to give this person some time and space and come back. Because as you said, it's not one conversation. ♪♪♪

For more advice on managing up, check out the resources we've linked to in our show notes. Women at Work's editorial and production team is Amanda Kersey, Maureen Hoke, Tina Topey-Mack, Hannah Bates, Rob Eckhart, and Ian Fox. Robin Moore composed our theme music.

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