The Fine Art of Managing Up
An Article of the Modern Survival Guide
Hi, and welcome to the Modern Survival Guide, a long-running blog that I write to pass on lessons I’ve learned about survival in the modern world. For this article, we’re going to start with a core premise: you have a boss. That applies to most of us, I think, especially if your definition of “boss” is someone that you have to report to, someone who is in charge of your work, or someone that you must keep happy in order to stay in your current position.
How do you deal with this person?
That’s a question that is absolutely central to our individual survival in this world, considering that your boss exerts enormous power over your life. They can make your job harder, or easier. They can raise or lower your stress level. They might be able to force you to work in your free time (or more accurately, convince you that you need to do so), or otherwise affect the quality of your non-working life. They control your money.
Bosses can really be quite pernicious, which is why managing up is such a crucial survival skill. Now, there are a lot of definitions for “managing up” out there. Some people will say that this is a relationship where you and your boss work to make each other better workers. Some people will say that this is a talent whereby you use your boss to make you a better employee. Some people will say that it’s a method of creating the best value for your company by streamlining the boss-worker relationship.
I say those people are all sniveling at the corporate bootlace. To me, “managing up” means one thing, and one thing only: keeping your boss happy with you. This is the number one thing you can do to ensure that you remain gainfully, perhaps even satisfactorily, employed. Bosses retain the people they like, and they remove the people they don’t, and it’s that simple most of the time.¹
Now, coincidentally, keeping your boss happy will also probably result in your working relationship being better, your work in your organization being more appreciated, and possibly even the success of projects or work efforts that might otherwise fail. But folks, this is the Modern Survival Guide. We’re operating on the principle that you’re working to live, and that survival is your game plan first and foremost. I’m not going to worry too much about your organization thriving; I’m more focused on you not getting canned when you might otherwise retain a job.
The rest of this article will be my opinions on what you can do to keep your boss happy — and where, in my opinion, a lot of otherwise good workers go wrong. Let’s dive in.
Managing Up to Keep Your Boss Happy
The first and foremost goal of managing up is to keep your boss happy with you, and consequently more inclined to continue to employ you. There are five strategies that I consider essential to this point, and they are:
- Maintaining connection
- Understanding the boss’s definition of success
- Understanding the boss’s priorities
- Making the boss look good
- Developing trust
We’re going to go from top to bottom, so buckle up and grab a snack. Some of these are strategies that will work regardless of who you are, but some will require art. I can’t teach art; I can only tell you when you’ll need to employ some. The rest is on you to practice. For each of these strategies, I’ll do my best to point out the art part, so that at least you can know what to practice. Here we go.
Maintaining Connection
What the heck is connection? This is simply to say that you and your boss should know one another, and your boss should be used to interacting with you. You should be a known face, and you should have a regular touchpoint with your boss. You should never, ever, let your boss forget who you are or what you’re doing. Maintain that connection, or become Peon #12.
If your manager doesn’t know who you are, that’s bad. They can’t like you if they don’t know who you are; if you’re Peon #12, that’s actually worse than being a bad employee from a certain point of view. If you’re a bad employee you can at least have certainty you’re going to be fired; you can plan for that. Not so with being an unknown face.
Being Peon #12, you live your life under a blade, and you can never be quite sure when it will drop. Because make no mistake, when the layoffs come, the bosses feel much better about firing Peon #12 than they do about firing Jill. Jill has kids, and cracks jokes at the staff meeting, and asks questions. Jill likes dogs. Jill seems keen. We like Jill, even if she struggles sometimes. Nobody gives a shit about Peon #12.
It’s important that your boss knows who you are. That means, more than anything else, that you have to find a way to be present. Don’t get this wrong, I’m not advocating that everyone go into the office (perish the thought) like we’re some pre-COVID barbarians. No, being present means that your presence should be noticed.
I’m not saying you have to brown-nose, and you shouldn’t. I’m not saying you have to be the world’s perfect worker. I’m not saying that you have to be friends with your boss.² None of these things are required. Being present simply means that you are interacting with your boss on a regular basis, in a pleasant fashion, with constructive results. The starting point for this is to simply be present at meetings and events, and say hi to people. Talk. Be more than a face in the crowd. That goes such a long way it’s not even funny. From there, you can adopt a strategy of making yourself known.
That can take a lot of forms, but the easiest one, by far, is to ask your boss questions. Questions are incredibly useful, if used correctly. The correct type of question to ask is a clarifying question. The objective is to find something the boss said that is somewhat ambiguous, or relates to your job, and ask them to explain it in more detail. You can do this in a lot of different settings, and so long as it isn’t a blatantly stupid question you’re going to do one of two things: you’ll stroke your boss’s ego, because everyone likes talking about their ideas, and/or you’ll start convincing your boss that you are a keen team player. Either is good. Both is better.
There are some things that you need to avoid when asking this kind of question, and it is a bit of an art form. The first thing you have to do is avoid asking redundant or stupid questions. There is, in fact, such a thing as a stupid question. It’s a question that demonstrates that you don’t know how to do your job. A redundant question is one that demonstrates you weren’t paying attention. Avoid both of these like your should avoid the plague.
The next thing you have to avoid is being a pest. Don’t keep asking questions, unless you really have to. Find a good question to ask, make sure your boss knows who’s asking it, and then let them get on with the meeting, briefing, or rant. Don’t monopolize their time. Don’t try to take over the meeting. Get in, get out, get noticed.
The correct kind of question is one that identifies a piece of instruction or a part of a plan that was ambiguously phrased, unclear, or simply absent, and raises that up for consideration in a constructive fashion. “Constructive” means that you’re using a respectful tone, you aren’t accusing the boss of anything, and ideally you’re suggesting a productive action with the question. The objective isn’t actually to improve your knowledge, although that should be a happy side effect. The objective is to make your boss think that you’re an interested, active team member.
This is art. Pure and simple. I can’t tell you how to do this, because the strategy is going to change with your situation. But you can practice this. Just listen in at your next employee meeting or briefing and, you know, pay attention. Sooner or later the boss will ask for questions, or say something that you’ll recognize they need to elaborate on. When this happens, just try to imagine what you could ask that would be constructive. Go through that a few times, and then start asking questions.
After a while, your boss will get used to this and, more importantly, start to expect it. They’ll start planning for you to ask questions. They might even solicit you to ask certain questions. They’ll know who you are.
From there, you can start to work on other methods of maintaining connection, such as one-on-one meetings, mentorships, attaining high-visibility assignments, etc. But at a low level, it starts with presence and making sure your boss knows who you are.
Understanding the Boss’s Definition of Success
Now your boss knows who you are. What’s the next step? Well, the next step is to start making yourself one of those people who they like and ideally making yourself someone who is too much trouble to fire. That means making yourself useful. And that means that you have to know what “useful” means to your boss.
Every boss has a definition of success for their work — often several, since most bosses are managing several different things at once. The boss’s job is to turn that definition of success into reality by leading their team along the path to that promised land. Different bosses have different definitions of success, even if the overall objective is the same.
For example, if you’re on an assembly line, your boss’s ideal corporate definition of success is probably something like “churn out the projected volume of products, with the lowest possible defect rate, at the most efficient cost.” But their personal definition of success might simply be “meet quota and don’t get yelled at by upper management,” because that tends to be how people think.
You need to know your boss’s definition of success, and the easiest way to find out is to ask them. It’s usually that simple. While you’re establishing your presence, ask them questions that focus on discovering their definition of success, if they don’t just give it to you, which a good boss should.
This question is a bit of art, and may take a variety of forms, such as:
- “What is the most important objective for this project?”
- “What would meet the customer’s need?”
- “Are there things we should focus on?”
- “What is your biggest concern with this effort?”
- “How can we make this customer happy?”
And so on. You’ll need to tailor this question to your particular situation and your boss’s personality. If they’re very customer-focused, asking from the customer perspective might work better; it they’re very process-focused, asking about process steps might yield the answer. For some bosses, you can probably just ask “What is your definition of success?” and be done with it, but other bosses might take that the wrong way.
Regardless, once your know your boss’s definition of success you can move on to the next point.
Understanding the Boss’s Priorities
A thing to keep in mind here is that, particularly with a boss who is running several projects or who has given you several tasks, knowing their definition of success is only half of the story. That gets you the end-state definition, but that’s a goal, not a process. Understanding their priorities is critical to getting to that goal.
This is crucial, because your boss definitely has an idea about how you “should” go about getting from point A to point B. When they give you a task, they probably have a plan in their head about how you carry it out, and where it should fit into your job. Even if — especially if — that understanding is as simplistic as “It’s Dave’s job to do this as soon as he can,” if you’re Dave it behooves you to figure out more about that task priority so that you can fit it around your other work.
Because here’s the thing, you’ve probably got a lot of tasks on your plate, especially if you work in an office. You almost certainly have an idea about which of those are most important. What happens when your understanding runs foul of your boss’s understanding is that you run the risk of misprioritizing work. That makes your boss unhappy. You can get away with that for a while, if you show willing, but eventually that will land you in your boss’s bad books.
There are a lot of ways to go about figuring out your boss’s priorities, and there’s some art here. A lot of bosses, for example, don’t actually like it when employees ask that they prioritize tasks (these are bad bosses, and you should reconsider working for them, but still). These folks won’t respond well to the simple question “What priority should I give this task?” and will require a more gentle touch. This might require some spin like:
- “Sure thing, I’ll take care of A right after X,” where X is another task. This prompts the boss to consider whether A or X is more important. This is especially useful if both A and X are crucial tasks. Good for impulsive bosses.
- “Can I show you my task list and we can add this in?” This is especially useful if you get a lot of different tasks, and it makes you look good by demonstrating that you’re tracking them all. Good for process-oriented bosses.
- “Sure thing — when does the customer want this?” This is a good tactic if your boss is a throughput lane for customer requests, which is often the case, and makes you look customer-focused while also taking some of the onus off of the boss to make the call. Good for timid or indecisive bosses.
Those are just some examples, and you’ll want to tailor things to your situation, but you should be regularly asking this type of question to make sure that you are doing what your boss thinks you’re doing, when they think you’re doing it.
Making the Boss Look Good
We’re starting to bring things together here. When you have established a connection with your boss, you know their definition of success, and you know their priorities, you can start doing things to make them look good. Making the boss look good makes them like you, if they’re at all good at their jobs (and if they mistreat people who make them look good, you need to leave, so that’s also good information to have).
Depending on your job and your relationship with your boss, this can take a variety of forms, including but not limited to:
- Ensuring that critical tasks that you know they value are completed on time, at good quality.
- Reminding your boss to follow through on critical actions, or reminding them when you have completed critical actions.
- Helping your boss explain complex subjects to customers.
- Helping your boss prepare for meetings with their management.
- Documenting work and action items, and presenting metrics for them to use.
- Clearly communicating status reports.
The art here is figuring out which of these will work for your boss. That may take some trial and error, and then probably some practice to get things right.
Remember, the key point of making your boss look good is to keep in mind that they are constantly telling a story to their management chain. That story is setting expectations, and they look good (or not) based on whether they are able to meet those expectations. They very worst thing you can do to your boss is to give them the wrong information to set the wrong expectations.
This is actually much worse than simply screwing up a task. If you screw up, particularly on something critical, the only way to manage up is to tell your boss immediately so that they can modify their communications. You screwing up can be managed and mitigated in most cases. Not communicating the screwup is how your boss gets taken by surprised on a call with their boss, which is the absolute last thing they want to happen.
Every other part of making the boss look good centers on delivering what they want, when they want, how they want, making sure they know that the task is done, and making sure they know that you did it.³ That lets them communicate accurate messages up the chain. Good bosses absolutely do keep track of who makes them look good and who makes them look bad, and they absolutely do make employment decisions accordingly.
Bad bosses don’t. This is actually a good litmus test for whether you have a good boss or a bad boss. Don’t work for bad bosses if you can help it.
Developing Trust
This is the final piece of the puzzle. Once you have established a connection, understood your boss’s definition of success, established priorities, and made them look good, you start to develop trust.
“Trust” means that the boss has confidence in your ability to do your job without them hovering over your shoulder. “Trust” means that they are confident that the job you do will meet expectations. “Trust” means they aren’t worried because of you. Establishing a relationship where your boss trusts you (note: I didn’t say a damn thing about you trusting your boss) is one of the key things you can do to ensure a less-stressful, more stable work environment.
It’s important to recognize that “trust” doesn’t necessarily mean that your boss is going to give you plum assignments, or even necessarily recognize you publicly with awards or kudos. It simply means that you have established a relationship where they don’t worry much about failure coming from you. You haven’t won anything by establishing trust other than a certain surety that you are not at the top of their list of employees to fire in the morning. Still, from a survival perspective, that’s a pretty good result.
That being said, as a rule bosses do not give plum assignments, awards, or kudos to people that they don’t trust. It is a necessary precondition for your success in your job. If your boss doesn’t trust you, they will sideline you, micromanage you, set you up for some form of job abuse, or simply fire you outright, because they do not want to deal with you. Remember, managing up is about making your boss happy so that your work life is better. If they look at you and their first thought is “I wonder what that idiot is going to do wrong today,” they are not happy. Trust is key.
Common Mistakes
Real quick, let’s look at some ways that people can screw up. I’ve seen most of these happen in my career, as I’ve encountered folks who just didn’t get the program. Don’t be those people. Keep these points in mind:
- Don’t Assume: The worst thing you can do is assume that your definition of success, your priorities, or your goals are the same as your boss’s. This is how you end up doing the wrong work and executing a job fail.
- Don’t Gossip: The second worst thing you can do is run your mouth about your boss to a coworker. It will eventually get back to the boss. Remember folks, the reason treachery is so reviled is that traitors are usually the last people you’d expect. Your coworkers may be your friends, but some of them are also your competition, and some of those people will play dirty.
- Don’t be the Kid in the Back: None of this stuff works if you are the quiet kid in the back of the room, head down, working away. I’m sorry, introverts. Some bosses will recognize hard work, but more will take it for granted or simply not realize you’re working hard. You have to put yourself at least a little bit forward.
- Don’t Lie: There are few more efficient ways to annoy your boss than to give them the wrong impression of reality. If things are going to hell, it’s much better that your boss hears that from you first rather than a disgruntled customer or stakeholder. This is just good practice in any case, as it allows you to anchor the narrative.⁴
- Don’t Forget to Ask for Help: If you don’t know how to complete a task, ask for help. Don’t push on and deliver a poor product as a result. Your boss will be more annoyed than if you’d simply told them you need assistance. Bosses generally know how to manage an ask for assitance, but there’s no helping a poor work product once it’s been delivered.
- Don’t Break the Chain: Don’t break the chain of command. Don’t go over your boss’s head, unless your goal is to get rid of them. Bosses do not like it when people play “mother may I” with different people in the organization, and they really don’t like hearing that their boss heard something related to their work before they did.
- Don’t Hand Problems to Your Boss: Note that this doesn’t mean to lie to your boss, and it’s doesn’t contradict the point about asking for help. What this means is that, if you have the capability of handling an issue, and it isn’t expanding the scope of your work or otherwise involved in a policy decision, don’t task your boss with the work. Another way of saying that would be the admonition to solve problems at the lowest level possible.
In Summary: Managing Up for Success
To wrap things up, “managing up” involves maintaining a connection with your boss, understanding their definition of success, keeping appraised of their priorities, making them look good, and establishing trust. The goal is to set things up so that they like you, they think you do good work, and they trust you to do that work.
This isn’t going to guarantee success at your job. “Success” in a job is a meaningless phrase coming from me anyway; I can’t tell you what “success” looks like for you any more than I can tell you what your favorite food is. That’s a personal thing. But I can pretty much guarantee that “success” doesn’t mean that you’re jobless at the end of the month (unless that’s your decision).
Managing up doesn’t achieve success. But it does enable it. It gets you the placement and information that you need in order to be successful, and hopefully positions you into a spot where your success won’t be truncated by a sudden lack of employment.
¹There are some limited exceptions if your work is so valuable to your organization that they don’t dare fire you, but in that case be warned: any, and I mean any, smart manager is already training your replacement in the name of strategic redundancy.
²Fun fact, there is almost never any such thing as being friends with the boss. There’s a power dynamic there that is inimical to true friendship. In most organizations, there is Labor, and there is Management, and the two operate with different goals. Keep this in mind. Don’t try to be friends with your boss, and be very wary if your boss is trying to be friends with you. Managing up has nothing to do with being friends with your boss.
³A quick note for the sociopaths: do. not. take. credit. for. other. people’s. work. Don’t do it. You can get away with that once or twice, but when it bites you (and it will) you will lose trust with a competent boss. Also, that kind of thing is just begging a coworker to plant a knife in your back, and, you know, it’s morally wrong. Don’t do it.
⁴Anchoring a narrative is just a fancy way of saying that whoever speaks first gets to set the stage in a conversation. If you want your point of view for a failure to be known (and you should), speaking first is the best way to make sure that you don’t get more blame than is your due. You might even be able to explain your actions and come out looking ok. But you have to be the first voice in the room.
