On the Clock

The Subtle Ways to Rebuff Your Boss

Bosses are the biggest source of workplace stress. Here’s how to rein in the won’t-take-no-for-an-answer type.

About a year into her marketing job, Jenny had reached her breaking point. Her boss was pulling her in too many directions: no matter how big the request from a client, no matter how tight the deadline, he would agree to it and drop the work on her desk with an unspoken “Figure it out.” Jenny was stuck in an endless web of half-baked projects and timelines, forcing her to ignore the work she was supposed to be doing for her core clients. And though she tried to talk to her boss about it, she never seemed to get through.

In this hyperconnected, 24/7 business environment, Jenny’s scenario is quite common. In fact, nearly two-thirds of professionals say their stress levels at work are higher than they were five years ago, with bosses being their number one stressor, according to a survey by Korn Ferry.

If you only point out problems, it doesn’t matter how right you are—your odds of making a change happen are low, and you’re most likely just going to get on your boss’s nerves.

But talking to a difficult boss isn’t easy, especially when generational differences are involved. While millennials will make up more than 75% of the workforce by 2025, they're still the youngest workers in the office, and the way they communicate critical feedback may not work well with a boss who is 20 years older. For managers like Jenny’s, who climbed through the ranks in an old-school hierarchical workplace, being a yes-man or yes-woman was just called being an employee. Saying “I can’t do this” was virtually unheard of. Yet even with the staunchest bosses, there are ways to approach the conversation without coming off as accusatory, resistant, or the dreaded millennial stereotype—entitled. Here’s how to do it.

Take a page from the improv world.

A little wordplay can open doors with a manager whose style is “my way or the highway.” These people can’t handle the word “no,” so try the phrase “yes and” instead, suggests Joyel Crawford of Crawford Leadership Strategies. This phrase is valuable because it builds off of what someone just said while allowing you to take the conversation in a direction of your choosing. So for example, if your boss gives you a research project and suggests you go about it in some roundabout way, you might say, “Yes, and I’d love to see if there’s a way we can get that information from a more direct source, like the team next door.” Add the benefits of going that route and include any data that backs you up. Remember that controlling bosses often just want to be heard, and their behavior is often driven by insecurity, so it’s your job to “check in regularly until they trust that you’ve got things handled,” Crawford says.

Ask them to help you prioritize.

When a boss has a habit of dumping work on you, sometimes it’s because they don’t have a clear understanding of how much other work you’re handling. This is quite common in many organizations today that are matrixed, meaning employees are part of multiple teams and answer to many managers. So make it their business to help you prioritize; when they give you something new, ask them when they need it by and remind them of what else is on your plate. Because your boss is likely also busy, you can say things like, “I know you’re busy, but I’d love your help on this one thing, and I can take care of the rest.”

When you do want to challenge something, question in an inquisitive way, not a resistant one. For example, instead of saying, “Do we really have to do this project right now? We don’t even have all of the information,” you can say, “Would it be possible to get more information on this before we take it on? I’m happy to help, but I just want to make sure we’re staying on top of our other deadlines.”

Show up with solutions.

If you only point out problems, it doesn’t matter how right you are—your odds of making a change happen are low, and you’re most likely just going to get on your boss’s nerves. Instead, make sure your boss knows that you’re bringing the issue up because you want to meet or exceed expectations. Then frame your case for a solution. “Share recommendations on how to move forward, and include a few options for a manager who likes to be part of the decision-making process,” says Marquitta Cherry, a Korn Ferry Advance career coach.

Don’t have the conversation in the heat of the moment.

Lashing out at your boss might feel good in the moment, but it’s probably not the most professional route. In a conversation that’s making you emotional, it’s totally fair to call a time-out. Say something like, “I would love to continue discussing this, but after we both have some time to think about it,” says Hallie Crawford, an Atlanta-based career coach. Resume the conversation later when you’re better able to listen and express yourself logically instead of emotionally.

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