The Conversations You Should Be Having with Your Manager

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Welcome to the HBR Idea Cast from Harvard Business Review. You want to advance in your career, from getting things done as an individual contributor to showing you can build and motivate a team to demonstrating ROI and results. You're most often doing that within an organization, a management system, an organizational culture, and a power structure that you don't often fully understand, appreciate, or even see sometimes. How to succeed within such a system, what many people call managing

is a skill that you can learn and develop with experience. And that effort pays off, not just in opportunities and rewards, but also just in your satisfaction in your work day-to-day. Today's guest is here to help you stop seeing yourself as a victim of workplace. And start moving. productive way. Melody Wilding is an executive coach. Her new book is Managing Up, How to Get What You Melody. Thanks for having me. What do you consider managing up, like how do you define it?

I think very simply, managing up is navigating your relationships with people that have more positional power than you. primarily that's going to be your boss, your direct supervisor, but it has to extend beyond that because we are working in environments where you may have a project lead, you want to make sure you're building a relationship with your skip level. So work is more complex now. You may have many different bosses.

And the way we think about managing up has changed over the last ten, twenty years. It's no longer just sucking up or ingratiating yourself to your manager. It's more so positioning yourself as a thought partner or a trusted advisor to them. No matter what way you slice it, you are going to be dealing with politics at one level or another. That is just human nature. It is how human systems work.

And so you can be smart and navigate that with integrity and with thoughtful strategy and building trust, or you can opt out of it and you do that at your own peril. Why do you think people have such a hard time with it? I mean you're you're an executive coach, you've had these conversations with with clients, you surveyed thousands of workers for this book. What's kind of the common thread there?

I think first and foremost, we're dropped into our careers and we are taught the technical aspects of excelling at our job, but no one really ever gives us the psychological aspects Playbook. And so much of work is being able to navigate human behavior. understanding what motivates people. How do you get buy-in? How do you persuade them to go along with your idea? Or how do you avoid someone getting defensive if you need to push back?

That's really the crux of what we do every day, but we're not equipped with that knowledge. or those tools. And I think many of us we come from upbringings or cultures where you are told to stay in your place, don't rock the boat, respect and defer to authority. And so we think that managing up is

it it's not our place to do that. That that that would be stepping out of line. Who am I to tell my manager what to do? Or why should I have to do my manager's job for them? Shouldn't they just be a better leader? It's a little bit of a both and that yes, leaders have a responsibility to be better, to improve, right? And so do the systems around us that we work in. And at the same time, you don't want to wait for that to happen.

So you've identified ten common types of conversations that often arise with one's manager, you know, regardless of what level you're at. And I'd like to ask you about some of them.

Starting with the alignment conversation, what's what's the goal of that conversation? The alignment conversation, it's the first conversation because it's also the most foundational. And the alignment conversation is really understanding what are the priorities, what does success look like. In this role in this team. So you make sure you are working on the highest value, most meaningful, and promotable work.

because there's nothing worse than toiling away on something. You bring it to your manager and they say, this isn't what we wanted, or we've already moved in a different direction. And so the alignment conversation is about making sure you are on the same page, you are rowing in the same direction as your leadership. Where do people Yeah. Stumble here. We gloss over this conversation. We think that we have alignment.

But really, we spend so much of our day in the weeds, responding to the minutiae, that we rarely zoom out and have a higher level understanding of what. what pressures our leader is under, what is keeping them up at night. That's really key because only then can you make sure you are working on the right things. You are prioritizing your time correctly.

The other thing I see is that if you've been working with a leader for a while or you've had the same manager for a while, you may think, how am I going to bring this up? This feels very awkward. But it's never too late to have this conversation. And actually, again, the higher you rise in your career, the more important and frequent this conversation often has to become because it shows

you're operating at a more strategic level. You're thinking about the bigger picture. And usually things are changing very quickly. You need to make sure you have closer, tighter alignment than you may in other situations. Some people are fearful of having this conversation because they don't know how to bring it up without it sounding forced or contrite. Yeah, or like they don't know what they're doing. Right.

Yes, I don't I don't want to reveal or give create a perception that I don't know what my job is here. I think even sneakier is that we may not want to have this conversation and then realize we're not focused on the right thing. and we have to make some tough decisions or we have to advocate for ourselves to get onto a different project, which can open a can of worms around a whole new area that we need to focus on and

Sometimes it's easier just to stay the course, do what you're doing every day. That's easier in the short term, but in the long term can have consequences. You also recommend that as part of this alignment that you meet with your skip level boss, right? Your boss's boss. Yes, managing up has to extend beyond your boss. You want to make sure you have the bigger picture.

Right. And your skip level operates at a higher level than your manager. So they are in different conversations. They may have information or line of sight that your manager doesn't have that can inform what you're doing day to day. Also from a career growth standpoint, you want to make sure that person knows who you are. They know your name. They know the types of things that you work on, because your advancement in the organization, even project assignments,

may involve and typically will involve other people besides your manager. Meeting with your skip level can be a little tricky because you don't want your boss to feel like you're going around them, you're cutting them out. There's also organizational culture here. In some organizations, some of the people I work with. Skip level conversations are baked into the culture. There's an expectation that you will meet with your manager's manager.

somewhat frequently. Whereas in other cultures that that isn't as common. First you you have to understand what sort of environment am I operating in. But if you feel like your manager may assume you're going around them. There's a there's a few ways to approach this.

So first of all, when you make the request for a skip level, make sure your manager understands why are you asking for this. You can say my intention is not to go around you. I want to make sure that I'm understanding from a higher level. what they're seeing, what is most important, so that I can take that back to the rest of the team and make sure we're we're focusing on the right things. So explaining the why and contextualizing it.

But also if if it would even feel better, you c instead of asking to meet with your skip level alone or separately, you could say, Do you think your manager would be willing to sit in on one of our one-on-ones? Where I would be able to hear from both of you about this. Or maybe you ask that that person can come to one of your staff meetings, for example. So there's ways to do it that feel a little less threatening.

And does this kind of help you avoid those situations where I don't know, all of a sudden your boss is fired or let go and you realize, whoa, they weren't even on the same page with their manager or this project that we're working on is actually not in alignment with what the organization's looking for right now. Is that unpleasant realization that people sometimes have when their boss that they get along with great, you know, suddenly disappears.

That's exactly what happened to me, is I got along great with my boss at the time, but it came as a shock to me. I was very suddenly laid off. And when I looked back on it, it was because I was working on something that My manager and I were aligned on, but the project was not in alignment with the strategic direction of the organization. And so when time came for cuts, I was the easiest candidate to let go of. And so yes, it's it is also

important for you to have that connection because change can happen at any time. I have a lot of clients now who their organizations are going through one, two, sometimes even three reorgs in a year. A lot can change and you want to make sure you have relationships at different levels to see that through. Let's be honest, most HR platforms aren't exactly a joy to use.

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So I wanna talk about, you know, management styles, understanding what your manager's, you know, leadership style is. That often is at the root sometimes of personality clashes between you and your supervisor. I like to say that often what we perceive as difficult behavior comes down to a difference in style. there is truly toxic, damaging behavior. But most of the time our frustrations, our annoyances, If we decoded and understood other people's styles, a lot of that would go away.

Yeah, play decoder for me. You're Yes. Um if uh I don't know, if I complain my boss is a micromanager. What may be happening is that you're working for someone that has higher dominance. Right. When we talk about communication styles, generally speaking, there's two dimensions to it: dominance and sociability. Dominance is how much control does someone like to assert in a situation? How quickly do they move?

And then we have sociability. How much do they care about personal relationships, connections with other people? And you could be high and low on either You map those, you get four different broad communication styles. Now, understanding that, when you understand someone may have a higher drive for control and certainty in a situation.

It doesn't mean you have to like that or accept it, but you can put it into context more to understand that this person's tendencies are not necessarily a reflection of they don't trust me. It's more of a reflection that they have a high drive for a lot of detail. They want to be in the weeds of this. And so maybe I can make some selective strategic adaptations. I can overshare. I can give them a dashboard that they can pop into at any time so they can get the data that they need.

And you eliminate so much frustration for yourself because once you do that, the person may loosen the reins and may feel more comfortable because you're meeting what their needs are. You also mentioned in the book a story I liked about somebody who basically had a conflict because they they had lots of ideas, right? They came into those meetings and they wanted to like blue sky and

share some of the things that they were thinking and wondering about and they basically had a boss who was I don't know what Daniel Goleman would consider a pace setting boss, right? Somebody who's just like driving ahead and trying to get everybody to follow and keep up with them. And there was just a ton of conflict there between those two and that got ironed out once this employee sort of understood the style of the manager and and and and adapted to it.

Go ahead. Yeah, that's what I would call in in the vernacular I use in the book, the pace setter type is more of what I would call a commander, someone who's high on dominance, low on sociability. And so that person is very results outcome oriented, no nonsense, moves quickly, tends to communicate very concisely, which to some people may be perceived as rude, versus someone who is a cheerleader. A cheerleader is still high on dominance, so they like to move quickly, but

They tend to be more blue sky, big picture, visionary type. They're high on sociability, so they tend to be more people oriented, enthusiastic, they like telling stories. And again, that can lead to misunderstandings between the two because the commander can see

you know, some of that vision boarding as just a waste of time. But if as a cheerleader you are saying, actually this is going to help us move faster in the end, because if we have a sound strategy, we can make better decisions, we'll get better results. So it's all about that translation piece.

So let's talk about having a conversation about boundaries, um, because that can also jive here with personality clashes. And for some people You know, they wanna get away from just I gotta please the boss, I gotta please the boss and continually finding themselves unhappy doing that. That's not the kind of managing up that you're you're advocating for here. How do you see this conversation playing out?

Yeah, the boundaries conversation is about walking that fine line between being a team player without becoming a pushover. In the workplace, no is not a complete sentence. We're often told that, and it may be true in many other areas of life. I mean you hear people talk about it a lot recently. Sounds like you're cautioning against that a little bit.

I'm cautioning to set boundaries in a tactful, diplomatic way, because we do need to set boundaries. I have seen so many situations where when someone just says yes chronically, That backfires, of course, in the form of burnout for them, but you also create this perception that you don't know how to push back, which When you go up for promotion, they may say, well, how could we possibly give you more responsibility if you're already stretched thin?

or we don't really see you know how to negotiate in terms of workload, and that's really something that's required at this next level. Wow, that's that's harsh. Yeah. Yes. So diplomatic boundaries, let's put it that way. The way you you straddle that line, there's there's a few tactics. One of them is to ask questions first. Seems deceptively simple, but most of us, when yet another task is dumped on our plate, we either just roll over and say, sure, yeah, I'll figure it out.

Or we snap back because we're s already so overloaded. We reactively say, How could you put one more thing on my plate? I can't believe this. I can't get this done. And so asking questions allows you to buy yourself some time to calm down, to collect yourself, but also get more details about what the request is. Because on the surface,

You may not know everything. And once you ask, okay, can you tell me more about the urgency here? Or who else will this be visible to, do you see this becoming a ongoing request or is this a one-time thing? when you ask those questions, you not only get a better understanding of is this something I can, want to, need to, say yes or no to You

Also, make it a piece of information that allows you to latch on and say, actually, what you're describing really sits with the operations team. And so I can pass this over to them because it's going to be more efficient to do it that way. And it subtly puts the ball back in the other person's court to to justify why are they asking you for this? At what time? Or at this time.

You know, if you say, what made me come to mind for this request in particular, then that person has to sort of explain their rationale.

Well I want to ask about taking ownership of things because you talked about how promotable work is really important to do. you want to, you know, be able to lay claim to some of that and and take ownership, but we're also in much more collaborative, less hierarchical organizations now in many ways. And so It's kind of a tricky balance to take ownership without stepping on toes. How do you recommend people approach this conversation with their manager? The ownership conversation is

Best approached in an incremental way. When ownership really puts people on the defensive is when we come in very strong and we think we know best or we make sweeping changes. And that's where people feel a little taken back or like you didn't listen to our needs. They just feel railroaded. And so when it comes to going beyond your job description,

You have to do what's called pre suading. So we've all heard of persuasion, but one of the the top psychologists who has studied this for decades, Robert Cialdini, has this idea of pre suasion. which is how can you plant a seed in people's head that this sort of change is needed? Basically, how do you get incremental buy-in for this idea?

And that may involve asking people questions about, hey, I'd love to hear how uh it's going with that product or project management process. How is that working out for you? Are you hitting any barriers there? your bread crumbing objections or challenges they may have that you can then solve later, for example. That matters and so does presenting a path forward.

Because yes, it's one thing to identify a problem. You also want to make sure you make it easy for the people around you to say yes or no to your proposal. That is a core tenet of managing up is how can you remove Cognitive overhead for the people around you. That may mean creating a couple of sample slides that they can present to. the senior leadership team on this idea or uh maybe a template email they can send around.

Or even if you're just a at the beginning of proposing this idea, you may bring them sort of three ready-made options to say this is what I've considered or the factors I've weighed. My recommendation would be we go with option A, but I I would love to hear what you think. Which of these would be the best way to go? Do you find that most people make mistakes by going too far in in taking ownership or don't take enough ownership that they don't go far enough?

Yes, I would say it's that one. That most people play it too safe and will think, Well, it's not my place. It's not my place to solve that problem. Someone's probably thought of that or had a better idea for that, and that we we are not bold enough to step up.

That kind of gets to the you know, visibility conversation, getting recognized for what you do or what you accomplish. That can vary a lot by workplace, that can vary a lot by boss. How do you bring that up with your manager? We all have to operate in workplaces where we have to share credit, right? No, nobody wants to look like a a credit hoarder.

one tactic to straddle that line is called we then me. And this is great. This is a structure you can use in your one on ones with your manager when you're Talking with an executive when you're presenting in a meeting, you first share, here was the group's effort, and then here was my individual effort. And so you may say something like, It was really wonderful to see how the team pulled together to really get all of that over the finish line.

Rebecca did an amazing job with the analysis and Bobby really was a key player in making sure that the client was on board. I really enjoyed working on the product side, making sure we had everything buttoned up there. That really balances that, making sure that you're giving credit where credit is due, but you're also making sure that your piece is not lost in there.

No, we've been talking a lot about maybe call it soft power, right? That we're we're talking about getting influence, about getting assigned better work, we're talking about getting credit. But there are certain things that, you know, we would like to see from bosses that are you know, more concrete, more tangibly associated with career development, even though those other things, you know, play into that. And that's earning raises and promotions.

There's a lot out there and we've got a lot of episodes about this too, but how would your advice for that differ from, you know, what people have maybe already heard or know, how to how to advocate for yourself or getting a raise or getting a promotion? There's two things that I I have observed where my clients double the most. The first of those is that they don't start early enough.

Many of us fall into the performance review paradox, which is we await that all-important conversation and we think we're going to get the raise at that time or going to be assigned to that new role and then The conversation comes and goes and nothing happens. And we feel overlooked. When in actuality, we needed to start six months ago talking about that.

And so I am always recommending that if you have a goal, like let's say you approach your manager and you say, by the end of this year, I would love to expand my team from two to four people. What would you need to see in order to feel comfortable doing that? Or what would have to happen to make sure we have the budget? And so that way you are getting your ambitions out on the table early. It's not going to be an afterthought. You can surface objections from your manager early so you hear

We need to see you improve in these couple of key areas. And that helps you contract. So that as the year goes on, let's say Once a quarter, you can follow up. You can have a dedicated one-on-one where you are talking about, okay, last time we talked about this. I've done X. Are we still on track for that title change by the end of the year? Has anything changed? Does anybody else need to be involved?

And so it's making sure that the goalpost does not keep moving on you and that it's a priority because you're treating it that way. So that's the first thing. The second thing, specifically when it comes to compensation. is we talk a lot about asking for what you're worth, which is important. You deserve to get compensated for what you bring to the table. But how you make that business case is critical. And what I see is that people focus way too much on what they've already done.

and not enough on the value they can continue bringing to the table if they're compensated to do that. Well that's interesting. It's almost like uh thinking of yourself as a stock, like here's my future value because you've already been paid for what you've already done.

That's a great way to think about it. Yes, exactly. And so when you are making a case for bigger compensation, Yes, you do have to talk about your past accomplishments, very important, but you also have to say, all right, if I'm promoted and compensated at the VP level, here's what else I would be able to undertake. or what I would be able to launch. So paint that future because your manager has to go make a case to their leadership and prove how is there ROI in this for us?

Melanie, this has been really helpful. Thanks so much for sharing this practical advice and I know that you've helped a lot of people see a wider path forward. So thank you. Thank you. That's Melody Wilding. Her new book is Managing up. And whether you're managing up or down or just managing yourself, we can help. There are more than 1,000 episodes of Idea Cast, and HBR has more podcasts.

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