How To Talk To Your Boss And Fix Your Job

It’s all too easy to spend long stretches simmering at your desk instead of having a straight-ahead talk with your boss. Here are a few strategies to help you start the conversation.

How To Talk To Your Boss And Fix Your Job


It’s easy to talk about your job with lots of people, except your boss. 

We talk to our employer differently than almost anybody else, and for some very good reasons–reasons that keep groceries coming and careers advancing. Even when the problem itself seems obvious, talking to a boss about it makes it seem complex. Here are a few strategies we’ve gathered from experts on managerial and corporate relations.

What follows are a few common questions, phrased the way they might sound in your head, but which you should not actually say or write.

“You ask me questions, make little observations, and distract me eight hours each day, unless you take lunch. I need time to actually, you know, work.”

This is a common issue, especially with newly minted bosses, says Lynn Taylor, the author of Tame Your Terrible Office Tyrant. Two of the chapters in the book are about this very issue–one is about “endless questioning,” the other “neediness.” It might seem like nervous butt-covering, but there’s usually an undercurrent of asserting new authority. “The theme is, ‘You work for me, therefore I can ask you questions at any time,’” Taylor says.

Newer bosses tend not to trust the people they’re bugging regularly. The solution, Taylor suggests, comes in controlling the over-sharing you’ll have to do to get their trust. Email or message when you’re starting new phases of projects, and set up a schedule of letting your boss know where you’re at. Set up meetings to answer a few different questions, where you’ll have documents and answers on hand. Do everything you can to let your boss know that you’ll let them know where you’re at in your work, and their scattergun questioning should subside.


“It’s not unlike dealing with a toddler,” says Taylor. “You need to be a beacon of calm, and not let them create stop-the-presses situations.”  

“You change our ‘focus’ every week and turn on a dime whenever you get a new opinion. Don’t they pay you to make decisions?”

In this economic climate, indecisive managers are likely to be even more indecisive, says Katherine Crowley, a psychologist and cofounder of the workplace consultancy K Squared Enterprises and coauthor of Working For You Isn’t Working For Me. “We call this person the ‘rule changer,’” she says. The trouble is that most organized, smart people will try to pin this person down, “but that’s going to lead to more frustration when they change again.”

“You have to keep checking in, but you’ll get better at reading your boss as you do that more consistently,” says executive coach Kathi Elster, the other half of K Squared. “And they’ll get better at making decisions, as they know their employees are following them.”

“Another coping tactic is to bring statistics to support the decision you want them to make,” Crowley says. “But when they side with you, don’t rush to take credit, or act surprised, sarcastically or otherwise.”

Elster concurs: “It’s always a good strategy to let your boss take credit for making a decision, even if you pushed it. Allow them to look affirmative to their higher-ups, and you’ll benefit.”


“I feel like the unique work I do isn’t really noticed because other people here are simply louder–or because you’re taking credit.”

Taylor suggests that documentation and quick response are key if you believe some credit-stealing goes beyond accidental. It starts, most often, when there’s a “Muddy territorial problem that often happens on projects.” If you write down what you’re doing and when, and what you’re in charge of on the project, and report it to your boss on a regular basis, it’s harder for someone to snatch up your better efforts.

The same goes for bosses who like to subsume their workers’ ideas and ingenuity. Meet with or write to your boss on a regular basis, and go out of your way to pin down exactly which parts of the job you’re responsible for. If you have to confront them about a slight, always start and end on a positive note, Taylor says (which one former boss of this author called the “compliment-criticism-compliment sandwich”).

In any office situation where you feel a conflict coming, stick to what Taylor calls the CALM method–Communication, Anticipation, Levity, and “Managing up.” (Taylor explained the method in more detail for the Gainsville Times.)

“I honestly can’t fit this extra duty on my plate right now. Seriously.”

Whether it’s someone’s former duty, or a new task that you know is bigger than your boss realizes (”How about being in charge of our social media?”), the key, according to the K Squared consultants, is carving out a piece and tackling at least that.


“I think you should be able to say that you’re eager about this project, and that you can take a piece of it, but not all of it,” Elster says. “Say that if you can get your other work done faster, you might be able to take more.”

“Or say that you’d be happy to be teamed up with someone else to tackle this,” Crowley said.

“You could say that you see a way to work it into your schedule in two weeks … if that sticks, then you have some time to assess what the job really means, and report back,” Elster says.

“I just can’t talk to you, period.”

All the consultants quoted here emphasized the importance of knowing yourself, and testing that knowledge. Use your best means of communication when it really matters, whether that’s an email, a one-on-one meeting, or having presentation-quality materials ready to make your case. But it’s just as important to know how you generally relate to authority.

Elster and Crowley offered up a sample chapter from Working for You Isn’t Working for Me that quizzes the reader on the “baggage” they carry from previous bosses. If you’re generally intimidated by speaking for yourself and making your case, getting public speaking training, such as offered by Toastmasters International, can help. And Taylor suggests that taking a step back to assess what your boss needs to succeed, and working in your spare moments to fill in the gaps, is a big part of “managing up.”


But no strategy or self-awareness can help you if your boss has an entirely different view on what’s important.

“If you can’t deliver for your boss, and you can’t enjoy your job while doing so, and nothing you do makes you look good, you have to decide if this is really a job you can do at all,” Taylor says. “That’s a hard decision to make.”

For more advice on how to improve your work life, read these articles:

[Thumbnail and Image Provided by Shutterstock]