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Career advice

Working with your manager

For when you'd like the person you report to to know what you're doing, tell you where you stand, and be on your side.

What to understand about working with your manager

Your manager is the person at work with the most say over your days, and usually the one with the least time to watch them. They tend to have a boss of their own, goals they're judged on, and several other people to think about, so what they know about your work is mostly what reaches them: what you tell them, what others mention, what goes wrong loudly. Much of what feels like being overlooked or misjudged starts there. It's less often a verdict than a picture built from scraps.

That leaves more room than it looks like. You can find out what they're trying to get done this year and say how your work fits into it. You can tell them what you need, which sounds obvious and is surprisingly rarely said out loud. You can ask how they like to hear things, hard things especially. None of this is flattery. It's two people with different views of the same work comparing notes, and the first move is usually open to either of you.

The hard part is that it isn't an even relationship, and not every manager is good at the job. Some are stretched thin, some were promoted for being good at something else, and a few are unkind. You can make it easier for a decent manager to help you. You can't turn a poor one into a good one, and trying harder at a relationship only you are working on wears people down. Sometimes the honest finding, after a fair try, is that the answer is a different team or a different job.

What people often get wrong about their manager

  • You might think“My manager can see how much I'm doing. If it mattered to them, I'd have heard about it by now.”
    More oftenMost managers catch only a small part of anyone's week, and usually the part that went wrong or the part somebody told them about. Work that goes smoothly is often the quietest work there is. A few plain lines from you, sent regularly, tend to be the main way a good week gets noticed at all.One thing to try: Send a three-line weekly update →
  • You might think“If I haven't heard anything, I must be doing fine.”
    More oftenQuiet can mean fine. It can also mean busy, conflict-shy, or saving it for review season. Saying a hard thing unprompted is uncomfortable for most people, managers included, so a small, specific invitation often gets you what silence was holding back.One thing to try: Ask your manager for one thing to change →
  • You might think“Some people just click with their boss. We don't, and that isn't something you can fix.”
    More oftenSometimes two people really are a poor match. More often, what feels like chemistry is a handful of habits nobody has named: one of you thinks out loud and the other wants it in writing, one likes plenty of warning and the other decides in the hallway. Those are easier to talk about than whether you like each other, and they tend to shift once they've been said.One thing to try: Notice where your styles differ →

Things to do when you or your manager is new

“I don't know this person yet, and they don't know me.”

The first few weeks are when questions cost the least. Nobody expects you to know how they like to work yet, so you can simply ask, and tell them the same about you.

Things to do when you're not sure you're working on the right things

“I'm busy all week, and I couldn't tell you whether it's the work they care about.”

Priorities move quietly, and the person who moved them often forgets to mention it. These are ways to check where you're pointed and keep your manager current without waiting to be asked.

Dealing with something else at work?

Things to do when you need something and haven't asked

“They must be able to see I'm drowning. Why hasn't anything changed?”

A manager can only help with what they've heard about. A plain ask, with a reason and a size, gives them something to say yes to. If the answer is no, it gives you a no you can ask about.

Things to do when you have something to say they may not want to hear

“Maybe I can sort this out myself before it has to become a conversation.”

Waiting until it's fixed, or until you're certain, is a kind instinct that tends to backfire. Whether it's a slipping date or a decision you think is wrong, early and a little rough is easier to work with than late and polished.

Things to do when things between you have gone wrong

“I dread our meetings, and I've started reading something into every message.”

Start with the cheapest explanation and work up. Some rough patches turn out to be a bad first month, or a story nobody checked. Some don't, and it helps to know which kind you're in before you decide anything big.

  1. Step 1: Check the story you're telling yourselfMost of the sting is in the part nobody actually said10 minutes
  2. Step 2: Prepare for a hard meeting in five minutesFour short lines that take the dread out of the first minute5 minutes
  3. Step 3: Ask to start over after a rough startName the bad start out loud and give you both a second first impression10 minutes
  4. Step 4: Try to fix it before you leaveOne honest conversation before one hard decision20 minutes
  5. Step 5: My boss is a jerk to meWhen it's only you they're harsh with, waiting it out rarely helps · Podcast episode · Ask a Manager34 minutes

What working with your manager depends on

  • How many people they manage

    A manager with a handful of reports can notice things on their own. One with a large team mostly knows what they're told, so more of the keeping-in-touch falls to you.

  • Company size

    In a small company your manager may be the owner, and can say yes on the spot. In a large one they are often carrying your request to someone else, and it helps to hand them a case they can repeat.

  • Remote or in person

    Sharing an office gives a manager a hundred small glimpses of your work for free. Working apart, those glimpses mostly have to be written or said on purpose, and tone is easier to misread.

  • Whether they've done your job

    A manager who came up through your kind of work may have strong opinions on how it's done. One who didn't tends to leave the how to you, and needs more help judging how hard something was.

  • How long you've worked together

    Early on, almost everything is worth saying out loud. After a few good years much of it runs on trust, and if it's running well there may be nothing here you need to fix.

How working with a manager changes through your career

  1. Starting out

    Your manager is often your main window into how the place works, and it can feel like every question costs you something. It rarely does. Asking what good looks like, and repeating back what you've been asked to do, tends to be read as care.

  2. A few years in

    You know the job, so the conversations can move from how to do the work to which work is worth doing. This is often when people first say what they'd like more of, and find out their manager had been guessing.

  3. Senior

    You're closer to a partner than a pupil. You may know more than your manager about your area, and part of the job becomes telling them what you see coming, with a recommendation, and disagreeing in a way they can use.

  4. Later on

    Your manager may be younger than you, or someone you once trained, and you may manage people yourself. Pride can get in the way on both sides. The same questions still apply: what are they trying to get done, and what do you each need from the other?

Manager terms worth knowing

One-on-one (1:1)
A regular private meeting between you and your manager. In principle it's your time, for whatever you most need to talk about.
Managing up
Making it easy for your manager to know what you're doing, what you need and what's coming. Done well it looks like good communication, not charm.
Skip-level
Your manager's manager, or a meeting with them. Normal in many companies, and usually best mentioned to your manager first.
Direct report
Someone who reports straight to a given manager. You are one of your manager's direct reports.
Escalate
Take a decision or a problem to someone with more authority because it can't be settled where it is. It lands better when the people involved agree to do it together.
Disagree and commit
Say plainly that you'd have chosen differently, then put real effort into the decision that was made.
Dotted line
A second, looser reporting relationship: someone who directs part of your work without being your formal manager.

When you have more time

Questions people ask about working with their manager

My manager keeps cancelling our one-on-ones. What should I do?

It's more often about their calendar than about you, though it still costs you. You might offer a shorter slot or a different day, and in the meantime send the few things you'd have raised in a form they can answer quickly. If it goes on for months, it's fair to say plainly that you miss the time and ask what would make it easier to keep.

Make it answerable in one reply →

My manager checks on everything I do. How do I get more room?

Close checking often comes from not knowing where things stand, or from having been surprised before, more than from doubt about you. Getting ahead of the question helps: say when they'll hear from you next, then do it. After a stretch of that, asking directly for more room on one piece of work is a much easier conversation.

Say when they'll hear back →

Is it all right to talk to my manager's manager?

In many places a conversation with your manager's manager is ordinary, and telling your own manager beforehand keeps it that way. Taking a disagreement over their head is a different thing. It tends to go best when you say you'd like to raise it higher and invite them to come with you.

Escalate together when it matters →

A reorganization just gave me a manager I didn't choose. Where do I start?

They're probably as short on context as you are, and may be meeting a lot of new people at once. One good early conversation about what they've been asked to do, and what you've been working on, tends to settle more than weeks of watching for signs.

Stay steady through a reorg →

Should I tell my manager I'm thinking about leaving?

It depends on the manager and the company, and it's reasonable to be careful. Saying what would make you want to stay is usually safe and often useful. Saying that you're actively looking carries more risk, and many people choose to keep that to themselves until they have something firm.

Set ground rules for a quiet job search →

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