transcript of “how to say no to your boss”

Alison: My mail at the Ask a Manager website is full of letters from people who are really unhappy about something their boss is asking of them, but aren’t sure if they can push back – or, very commonly, are pretty sure they can’t push back, because they’re internalized the idea that you’re never supposed to say no to your boss.

Their thinking is that part of the deal when you have a job is that you’re supposed to just put up with whatever is asked of you – or that if you push back, you’ll look like a prima donna or difficult, or not a team player, or any of the other weird words that we tag people with.

But the reality is, in many cases you absolutely can push back or say no to something your boss is asking of you.

It’s just the weird power dynamics of work that are making you think you can’t. But really, you can. You just have to do it judiciously, not every day, but you can do it. And on today’s show, I want to talk about exactly how to do it, and go through some examples of times where you might want to, and we’ll talk about exactly how to do it – what to say and what tone to use.

The first thing to know about pushing back with your boss is that saying no to your boss doesn’t have to be a really aggressive or hostile thing. In the vast majority of cases, it’s not going to be “No, I refuse to do that.” It’s about approaching the conversation in a collaborative way – there’s a problem and you’re hoping the two of you, you and your boss, can solve it together.

So that means you’re going to say things like “We’d originally agreed to X, and that was important to me. Is there a way we can make that work?” or “Hmmm, I’m concerned about Y if we go that route,” or “I don’t have time to do Y this week but I could do X” or “I have a lot of concerns about X. Could we talk about whether there might be other options?”

So you see, it’s not “no.” It’s politely, collaboratively conveying “Hmmm, I’m not as on board with this as you might have hoped or expected. What can we do instead?”

And if your manager is decent manager, she’s going to want to hear this when you’re feeling that way. She might not be delighted about it, but good managers don’t want good employees to be miserable, and they want to know when they’re risking that, and they want the chance to figure out if there’s a different approach that both of you can live with.

Now to be clear, they don’t want to hear that every day! And also to be clear, the answer won’t always be “yes, we can change it.” But when you feel strongly about something, you can and should speak up.

Plus, sometimes you need to speak up when you disagree with something because the reason you disagree is that you have information that your manager doesn’t have. This is something that people frequently don’t realize! Like, maybe your boss telling you to do X and you think the client will hate X – and the reason you think that is that you’ve been in meetings with the client where they’ve said that they would hate X, and your boss hasn’t. In a case like that, you have a professional obligation there to speak up and tell share the information that you have and that she doesn’t have and that would change her perspective if she did.

Another way I see this come up all the time is about workload. So often, people who are overworked think, “Well, my boss must know how high my workload is, she’s the one assigning me all this after all, and if she keeps piling things on me, she must just not care, and she expects me to get this all done.” When in reality, sometimes that’s true but sometimes your boss has no idea how overloaded you are! She’s probably not paying nearly as much attention to your workload as you are. She’s counting on you to speak up if it becomes a problem, and when you don’t say anything, she has no way of knowing. I can’t tell you how often I’ve seen this dynamic play out – with the employee becoming more and more frustrated, and demoralized and burned out, while the manager has no idea and would step in and help fix the workload problem if she knew.

Not always, of course. Sometimes you get a manager who really doesn’t care. But enough times, your boss would want to know, and so you should speak up. That can be anything from a big sit-down conversation about your workload overall, or it can be a simple, “hey, to make sure you know, it’ll going to make me two days to do it this way, but if we do X instead, it would just take a few hours.”

So – not adversarial. Collaborative, working together, problem-solving.

Okay, that’s the overall framework I want you to have in your head as we talk about this. Let’s go through some specific examples so you can see what it sounds like in a variety of situations.

I dug into past Ask a Manager letters to find some examples of times when people did need to say no to their manager, so that we’d have some concrete scenarios to talk about. I once had a letter from someone who had been in their job for a while but got a new manager, and the new manager kept asking them to do things that were really not their job – and where there were specific reasons for why it wasn’t their job and someone else was supposed to do those things. The person writing to me didn’t know if the new boss was giving them these assignments because he was new and he didn’t realize what the system had been, or if he was now changing things and specifically making it this person’s responsibility. And they were trying to figure out how to raise it without sounding like they were just flatly refusing to do it.

So in a situation like that, you could say, “I wanted to check with you — you’ve asked me to do some projects recently like X and Y. I was of course happy to help out in a pinch, but because it’s come up a few times, I wanted to let you know that historically that type of work has been done by the X department. The reason that people in my job aren’t supposed to do that work is ___. I figured you didn’t have that context yet and that I should fill you in.” So you’re approaching this like “oh, here’s this useful thing that you’d probably appreciate knowing.” You’re not dancing around it or acting hesitant to say it. It’s just “oh! Here’s this piece of info you probably don’t have.”

And then if the boss pushes back anyway, you could say, “I’m of course willing to try that out if you want to change that. But I want to make sure you know it would be a pretty significant change to my role, which would concern me because of ___. Before we make the change, could I tell you a bit more about why we ended up dividing things this way?”

But let’s change the situation a little and say your boss is asking you to do something that you really, really don’t want to take on. If you’re a good employee who’s generally helpful and accommodating, there’s room for you to speak up about this! If you’re not a good employee or you have a track record of pushing back on everything, then no. But let’s assume you’re in good standing. And let’s say the thing your boss is asking you to do is … let’s say heavy travel. And you don’t want to do heavy travel, and maybe you even took this job in part because it didn’t involve heavy travel. So you could say, “You’ve been asking me lately to do more traveling. I get why it would be useful to have another person on the team who can travel, but I want to be honest — I really dislike heavy traveling and I actually changed into this field to get away from doing it. I hadn’t realized it would be a part of my role here. Is it something that you’re committed to having the person in my job do or is there any flexibility?”

In other words, just be straightforward. You’re not going at it as the adversary to your boss, and you’re also not dancing around it and hoping they pick up on hints. You’re just laying it out.

The key to talking about this without being insubordinate is that you’re not saying you won’t do it. You’re just giving your boss relevant context that she may not have … some of which might be that it would significantly change your job satisfaction, which any good manager will want the chance to factor into their thinking, even if they ultimately decide to make the change anyway.

So: “To be honest, I took this role in part because it didn’t involve X” or “To be up-front, it’s not a change I’d be thrilled about because of ____” or so forth.

Of course, whether and when to do this depends on things like how reasonable or unreasonable the request being made of you is, how much your employer values you, and how much goodwill you’ve built up. And you do need to do it judiciously; if you’re pushing back on every request, you’re quickly going to run through the political capital you need.

And of course, ultimately your manager does have the ability to say, “Sorry, this is the job now. Take it or leave it.” If that happens, you need to decide if you’re willing to stay in the job, knowing that these are the conditions you’d need to accept. But much more often than people realize, there will be room to push back or renegotiate.

So let’s say you’re in a situation where you’re being asked to take on something that you just don’t have time to fit in with the rest of your workload. A decent manager is going to want to hear that you’re concerned about it, so you should speak up! It’s possible that when you talk it through, you’ll discover that the deadline isn’t as firm as it originally seemed, or your boss will be more open to pushing it back once she hears it’s causing problems. You might find that it’s fine to use shortcuts that you had assumed wouldn’t be okay, or that it’s really just one particular piece of the project that has to be ready on time. Who knows, maybe none of that will be true, but it’s worth having the conversation.

The best way to approach it is to explain what you can do and offer some options for how to proceed. For example, you could say, “I can have an outline and most of a draft ready to go by Thursday. I probably wouldn’t have it completely polished until Monday. Would that work?” Or, “To get this done by Thursday, I’d need to push everything else back, which means that I wouldn’t finish up X and Y until next week. Would that be okay?”

A lot of times, that’s going to solve the problem. Sometimes managers give deadlines that sound reasonable to them, but they’re very open to modifying them when you explain what’s needed and why. But what if your manager tells you that no, you need to stick to the original deadline with no modifications and can’t push any of the other work back? If you really don’t believe you can meet that deadline, sometimes it can make sense to say something like: “I hear you on how important it is to get it done by then. I’ll do everything I can to make it happen, but I want to be transparent with you that I’m concerned that factors X and Y mean that it’s going to take longer. Let me really push on it over the next day and then update you once we see where we are.”

So with that kind of language you’re showing that you get it, you’re taking it seriously, but you also don’t want to promise something misleading, and you’re going to see what you can do and update her when you have a better idea.

Okay, let’s do one that I hear from about people a lot – being expected to use your personal cell phone for work. Some people are fine with this, because they don’t want to carry a work phone and a personal phone. But there are a lot of good reasons not to use your personal phone for work, especially if your company makes you install an app which will allow them to remotely wipe your phone when you leave their employment – that’s not just wiping their data from it, it can mean wiping all your data from your phone. So if you’re using your personal cell for work, make sure you’re reading what you’re agreeing to really carefully – and if you’re not sure about the remote wipe, ask your IT people.

Anyway, if your employer suggests that you use your personal phone as your main work phone, you just be very matter-of-fact: “Oh, I’d rather not use my own phone — can I use a company-provided one instead?” And if that doesn’t work, then, “I’m not comfortable with the stipulations that are attached to this, like the remote wipe. What do I need to do to get a company phone instead?”

Okay, how about a situation where you’re being asked to do something unreasonable. Let’s say you’re being asked to work around the clock day after day. Sometimes you can just use a very simple statement that you just aren’t going to do something the exact way it’s been requested. So you might say, “I can’t work 12-hour days every day this week. But I’ll be able to do A, B, and C this week, but not D and E. Let me know if you want me to prioritize those differently.” So just matter-of-fact with that one, and see what happens.

Or how about a situation where your boss is asking you to do personal favors for her – things that really aren’t your job or anyone’s job, like running personal errands or even loaning her clothes? I say that because I’ve actually had a fair number of letters over the years about varieties of this situation. I once had someone whose boss was asking her to write his papers for a class he was taking on his own time! And I had a letter from someone whose boss would ask her employees to do really personal favors, like driving her to the dentist or borrowing those shoes – stuff you might ask a close friend, but which isn’t appropriate for a manager to ask employees.

With something like that, where someone is so oblivious to boundaries, sometimes the best thing to do is to just always have reasons why you’re not available for the thing. Like, “oh, sorry, I’m just about to get on a conference call” or “no, sorry, I’ve got plans at lunch so I can’t drive you.”

But you can also address it more big-picture, if you’re up for that. You could say something like, “I don’t know if you realize that you often ask us for pretty personal favors, like borrowing clothes or driving you places. Because you’re the boss, there’s pressure to say yes that wouldn’t be there if you weren’t the boss. And that’s a tough situation to be in, especially when it would conflict with something work-related. I figure you didn’t realize how often it was happening, so I wanted to mention it to you.” That can be a tough one to pull off. You won’t always be comfortable doing it, depending on the dynamic with your boss, but some relationships are going to allow for it.

Or with that boss who wanted an employee to write a paper for his class, you could say: “Hmmm, I don’t really feel right doing work for a class outside of the office, especially when I’ve got my hands full with X.” If your boss then offers to relieve you of X so you have more time for his paper, you could say, “I’m sorry, I really don’t feel right about doing that.”

Let’s do another weird one! I had a letter a while back from someone who worked remotely but had to travel to the company headquarters once a month. The company was trying to reduce expenses, and so instead of putting her up in a hotel while she was there, they were having her sleep in the office on an air mattress! She felt awkward about it for all the obvious reasons, but that’s not even why she was writing in! She wrote in because for her upcoming trip, someone else was going to be staying in the office, and so they were going to have her stay in the CEO’s apartment while he stayed in some other property he owned. And this wasn’t even the first time they had her do this – they’d made her do it one time before, and he would come by in the morning each day she was there to get ready for work. So, super uncomfortable, not something you should expect when you’re traveling for business. So let’s say you’re that bizarre situation. Sometimes it’s almost harder to figure out how to say no in a situation like this, because it’s so weird – and the fact that they’re asking you to do it like it’s no big deal tells you that they aren’t playing by the same rule book as the rest of us, which can make it harder to know how to approach it. But you can be straightforward and assertive. In this situation, you’d say, “I understand we’re trying to save money, but I’m not well rested when I sleep in the office. I’d like to start booking an economy-priced hotel instead.” And when they proposed the CEO’s apartment thing, you could say, “Actually, I’d prefer not to stay in his house. Last time he kept needing to come by to pick up his things and get ready, which wasn’t conducive to having a comfortable, private place to stay. So I want to book an economy hotel instead, and I’ll keep the price as low as I can.” So just politely assertive – this won’t work for me, I hear your concerns, so let’s do this other thing instead.

I get a ton of letters from people about something their workplace is doing that’s likely illegal. They’re often wondering what their next move should be … and because most people don’t know what to do if their employer is violating their legal rights at work, they often either threaten legal action too quickly or don’t speak up at all because they’re not sure what to say.

First, before anything, you want to make sure that your employer really is breaking the law. People sometimes assume that the law entitles them to things that aren’t actually enshrined in law, particularly in the U.S., such as fair treatment, paid vacation days, or a warning before being fired. So first make sure that you really are facing a legal violation.

If you are, sometimes people think the first step must be to talk to a lawyer and file a lawsuit. But much of the time that won’t be necessary. It might be, but jumping straight there can really poison your work environment when you don’t need to. To be clear, it’s of course prerogative to talk to a lawyer and pursue legal action at any point if you want to, but often you can get what you want in a low-key way.

Instead, a better first step is often to just talk to your employer. A lot of times they genuinely don’t realize what they’re doing is illegal – which I know sounds ridiculous, but it’s is often true, especially with smaller employers – and often they’ll back down when you point that out. But even if you don’t think that’s the situation – even if you’re pretty sure they’re well aware of the law and just don’t care about following it – it can be helpful to approach the conversation as if you assume they don’t know, and you’re helpfully bringing it to their attention – and that you’re assuming that of course they’d want to know if they were breaking the law. Approaching it that way will usually get you a better outcome than making it clear that you think your managers are flagrant law-breakers right from the start. And when I say “better outcome,” that means not only the legal problem stops, but also that you preserve reasonably good relations with your employer. You won’t always be able to do that – but when you can, it’s usually in your best interest to. To be clear, I am not suggesting that you tolerate illegal behavior in order to maintain good relationships. I’m saying that you can often get both things – the illegal behavior stopped and preserving the relationship. Not always. But enough of the time that it usually makes sense to try. And then if that doesn’t work, you can always escalate if it’s needed

So, let’s take a really common example. In the U.S., all jobs are classified as either exempt from overtime, or non-exempt from overtime. If you’re classified as non-exempt, meaning that you’re supposed to be paid overtime – and that’s not up to your employer, it’s based on the type of work you do – then you must receive overtime pay when you work more than 40 hours in a week. But a ton of people who should get overtime pay don’t. Let’s say that’s you, and your company expects you to work overtime without extra pay. You could say something like, “We’re actually required by federal law to pay overtime to people in my job category. I can work the overtime if you want me to, but the company is required to pay for it. I wanted to make sure you knew that so that we don’t get in trouble.”

Or, let’s say you’re religious and your boss is requiring you to work on a religious holiday when plenty of non-religious employees are available to cover that shift. You could say, “That’s actually a religious holiday for me. Because I know we’re required by federal law to accommodate religious practices, could we schedule someone else for that day instead of me?”

Note that the tone here is collaborative. It’s not adversarial. And that is important. Instead of saying “you’re breaking the law,” you’re saying “we could get in trouble for this.” That’s because the tone you want is that you’re looking out for the company’s best interest, not making a legal threat. It’s the same tone you’d use if you were advising your boss on some legal problem totally unconnected to you. There’s no overt threat of legal action. It’s just, “Oh, we could get in trouble for this.”

The reason for doing it that way is that your goal here is not just to assert your legal rights but also to keep a good relationship. It is far less likely to happen if you wield the law like a weapon. Fair or not, the reality is that few relationships are unaffected when you start making legal threats. You still have the option of taking legal action if you need to, but you’re more likely to get a good outcome by starting out this way.

This came up on the Ask a Manager website recently, and someone asked about the right tone to use, and a commenter said something that I thought was perfect. They said, “I think in situations like this it helps to imagine a situation where you would genuinely have the emotion that you want to convey and then mimic that tone. Like if I were in a parking garage with my friend who wasn’t allowed to park there and they wanted to leave the car in an illegal spot, my ‘I’m worried we could get in trouble!’ would be very sincere.”

And that’s exactly right! That’s the tone. It says “I’m looking out for everyone here,” not “I’m going to take you to court.” At least that’s where you start. You might need to escalate. But you start there.

Now, what if you talk to your employer and you point out the law, but nothing changes? At that point, you have a decision to make about how far you want to push the issue. One thing you can to do to explore your options at that point is to just talk with a lawyer. That doesn’t bind you to taking legal action – it’s just getting more information. And sometimes a lawyer can do things that aren’t bringing a lawsuit but still get the problem solved – like they can advise you to present things a certain way, or they can write a letter on your behalf, or so forth. And they can talk through the options with you and the upsides and downsides of each.

But it most cases, it makes sense for your first step to be a straightforward conversation, and that might be all you need.

Okay! Those were a lot of examples, and hopefully it helped to hear them out loud.

And if you’ve found this kind of sample language useful, you might really like the Ask a Manager book because it’s filled with sample language for all sorts of situations at work, including things like pushing back with your boss. If you want to check it out, it’s called Ask a Manager: How to Navigate Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work. And you can order it on Amazon or anywhere books are sold.

Before we wrap up, I have an announcement about the show: Next week’s episode is going to be the final episode. I have really loved doing the show, but I’ve realized I need to make room for other things – other work, but things like seeing my husband occasionally and sleeping. So I’m taking my own advice that I give to people who are overworked and I’m cutting some things back. I’ll take a bit more about the decision on next week’s episode, which will also feature a bunch of Q&A with callers as well.

Okay, that’s it for today. Thanks for listening, and I’ll be back one more time next week.