When and How to Stand Up to Your Boss

November 10, 2017

Advice here on when and how to stand up to your boss.

Hopefully, you never have to use the advice in this article. Hopefully, the bosses you have are compassionate and self-aware enough where you can work with them without having major issues.

Unfortunately, as we all know, that’s not reality. Most of us will have a bad boss or two in our lifetimes. And, if the behavior gets extreme enough, you’ll be put into a situation where you have to stand up to them.

That’s not a fun situation to be in. But, by approaching it the right way, you can often curb their behavior. And that can make your life much better.

In his LinkedIn Learning course Dealing with a Difficult Boss, Instructor Todd Dewett broke down the two main issues here: when to stand up to your boss and how to handle that conversation. Let’s take them one by one.

(A big caveat: Extreme behavior like harassment of any kind should always be reported immediately to HR. This article covers less extreme, more common behavior, like a micromanaging boss or a boss who doesn’t collaborate well.)

When to stand up to your boss

No work relationship is perfect, and that’s particularly true for a boss-employee relationship. Your first reaction should be to look within: by changing your own behavior or the way you react to your boss’s behavior, can you fix the situation, without having to stand up to them?

But, there are times you absolutely should stand up to your boss. To determine when that is, Dewett suggests asking yourself these four questions:

    1. How long will you be working for this person?

Is this a temporary job for either you or your boss? Or, are you actively looking for something else?

If you are only going to be around for a short period of time, it’s not worth standing up to your boss. But, if this person is potentially going to be your boss for years, it makes more sense to say something.

    2. What is your relative power compared to your boss?

Are you a new hire, and have a boss who has been at the company for years and has a great reputation within the company? Your relative power to that boss is very low. Conversely, if you’ve been at the company for some time and established yourself, and the boss is newer, you have a lot of relative power.

The more relative power you have compared to your boss, the less risk there is in speaking up.  

    3. Is this behavior just directed at you, are or other people affected as well?

Does everyone else seem to like the boss, and they are only giving you a hard time? Or is your whole team fed up with the boss?

Generally speaking, the more people who are annoyed by the behavior, the less risk there is to bring it up.

    4. What’s the cost of doing nothing?

The biggest question of all. Is the boss’s behavior curbing your development as an employee? Or, are they making life so miserable for you, you are dreading coming to work each day? And is there no way around it?

There is a risk to standing up to your boss and you can only do it so many times. So, you want to pick your spots.

How to stand up to your boss

Let’s say your boss's actions are bad, universal, you have some clout within the organization and the boss will be your boss for some time. It’s time to stand up for yourself.

This is the tricky part. Dewett said it comes down to nailing these three things:

    1. Pick the right time to have the conversation.

You should stand up to your boss in a one-on-one meeting with them – not in front of others. Ideally, you should schedule this meeting during a relative down time in the office, when the boss isn’t dealing with some kind of crisis, Dewett said.

Also, you should schedule the meeting with them directly, as opposed to going through an executive assistant, Dewett said. If you don’t feel comfortable doing that, you probably shouldn’t have the meeting.

If you schedule this meeting by asking them in person, you need to be ready have the conversation on the spot, Dewett said. Be prepared for that.

    2. Be observational and specific, not accusatory and general.

In the meeting, it’s essential to frame the complaint the right way. And that means being observational and specific, as opposed to accusatory and general.

Dewett gave the example of a micromanaging boss. You wouldn't tell your boss they always are hovering over you, he said. Instead, be specific: tell them they checked in with you on the Johnson account eight times last week, and if there’s anything specific they’d like to discuss.

    3. Use a light, positive tone.

Building off the last point, keep it light. Don’t tell your boss their micromanagement bothers you to no end and you hate it, for example. Instead, just ask them why they check in so much, and if there’s anything you could do to address it.  

That’s it. Most of the time, just raising awareness to an issue will cause the boss to address it on their own.

What if that doesn’t work?

Let’s say you do talk with your boss using the following advice and they don’t change. What do you do then?

Dewett said directly asking them to stop a behavior is risky. Instead, he suggests documenting the behavior and going to HR, and letting them guide the next steps.

The bigger point? Smart organizations have some form of feedback mechanism, both via HR and through employee surveys, that help bosses identify their weak spots. This creates a system where employees can trust the organization to fix these issues, instead of them having to stand up for themselves.

But, unfortunately, not all organizations have such frameworks. That leaves it up to employees to stand up for themselves. If you are in that situation, following the advice above is your best bet for reaching a good outcome.  

Is your manager driving you crazy? Learn what to do in Todd Dewett’s LinkedIn Learning course, Dealing with a Difficult Boss.