How to deal with a difficult boss

difficult boss 500x400-1Dealing with a difficult boss is something almost all of us have to do at one point or another in our careers. However, with a proper game plan in place, the situation can be made slightly less difficult to manage. There are countless ways a boss can be hard to work with, but we’ve taken some of the top recurring themes and looked at ways to manage and mitigate them.

In this article, we cover:

  • Helpful tips for dealing with a difficult boss
  • When to stay and when to quit
  • The traits of a toxic boss

Learn The Traits Of A Toxic Boss

The best place to start when dealing with a difficult boss is to determine what exactly makes them difficult to manage. From there, it’s easier to determine how to address it. Let’s take a look at some common situations.


A bossy bully brings every employee back to feeling like they’re in elementary school again. Bullies make for a bad boss.

It’s important that you talk to your HR department if you have a problem that can’t be resolved with a difficult boss. You never know, maybe leadership will terminate an employee based on their rough management style—stranger things have happened. Don’t feel bad about getting your boss fired if they use verbal abuse as a management technique.

Tough Talks D


Some ‘bosses’ or managers will isolate your work and funnel it into their repertoire to impress higher-ups into thinking they are responsible for a great new improvement (or something to that effect). In a sense, yes, a manager does in fact deserve credit for things going well in the workplace, but that doesn’t mean that they have to hide an outstanding employees’ work in an effort to stay on top.

It truly can be a dog-eat-dog world out there. While it may not play out well to undermine your boss on the stop, be sure to speak up when appropriate to get the credit you deserve for putting in extra hard work.

Burned out bosses

There’s always that leader who just seems to be over it all and doesn’t seem to care about anything. These types of bosses can be difficult because maybe they won’t want to help you, or maybe they’ll make a process slower or difficult just because they aren’t willing to be an upbeat personality.

Spark your boss’s motivation by inspiring them with hard work and great ideas. An enthusiastic employee can encourage a boss to perform better, or at least to put in the effort on the projects you’re working on.


It’s extremely frustrating to have someone peering over your shoulder 24/7 trying to tell you what to do. Micromanaging bosses who plan your every minute in the workplace aren’t as toxic as other difficult bosses, but they do tend to stress employees out and lower morale.

Overly political/opinionated Bosses

More often than not, people generally flock towards trades and work that coincide with their character and belief system. However sometimes you may find the contrary, or they may have strong opinions about unrelated topics.

Political, religious, and other controversial topics are generally inappropriate in the workplace. However, many people feel comfortable sharing these opinions — and often do. When it’s your boss, it’s even more uncomfortable. However, remember that this type of behavior is generally inappropriate and it is perfectly acceptable to state that you prefer not to talk about certain topics.


Some bosses are powderkegs just waiting to explode. Stress levels over workload or pressure in one’s personal life can lead to catastrophic meltdowns for some people in charge.

Let’s just say that hotheads shouldn’t ever be the boss, but things don’t always happen how you expect they should.

Break down the problem you have with your boss

To better understand a difficult situation, you’ve got to define the reason why you are having a hard time with a particular boss.

Pick apart the reasons why this boss feels difficult to you. Look at the situation upside down, sideways, and backward. Also, look inwards towards yourself. Many people aren’t self-aware enough to realize that their actions may also be contributing to the problem.

How to deal with a difficult boss

Once you’ve identified some of the reasons your boss may be “difficult,” you can move on to finding ways to address it. These will vary for everyone, after all, each person and situation is different. However, there are a wide variety of tools you can use to alleviate a bad situation. Consider which options best fit your situation and give a few a try.

Set boundaries

Professional relationships

Creating professional relationships helps keep work at work. Yes, it’s good to get to know each other in the workplace, but keeping a good distance outside of the workplace generally helps the operation run smoother.

It’s like putting two beta fish in the same cup; too much time spent together in work relationships can end up in arguments and other problems. Our advice is to keep your work separate from your personal life as much as possible.

Finding an even work-life balance might be the thing that helps mend your relationship with a boss. It’s good to be friends with your boss, but let them do their own thing when you’re not at work unless it’s a travel event or something similar.

Don’t let other people micromanage your time

Your time is valuable, and, even at work, it’s yours. You should, by all means, take responsibility for your own time. Block out sections of your calendar to work on projects and make it clear when you’re “in the office” vs on lunch or on a break.

Additionally, life isn’t all work, although sometimes it seems that way. You have the right to take vacations and other time off from work. Plan in advance and track things on the calendar to ensure others are aware of when you won’t be around.

Reverse the situation

Handle a difficult situation by evaluating it from their point of view. Be productively critical. Not in a negative way, of course, but changing things up in the equation helps your brain understand and process circumstances like a difficult boss. What might they be thinking from their perspective? Could your actions be interpreted the wrong way?

Find common ground

So there’s no way around it, unless you’re able to change positions — you have to deal with a difficult boss. You can start by finding some common ground because no one enjoys clashing the whole day. If you feel uncomfortable about a difficult situation with your boss, there’s a good chance they would like to see it resolved too.

You can start by looking for things that both you and your boss like. Two people can be completely different, but we’re all humans, so there are always things that make them the same. This could be as simple as a favorite vacation spot. However, you could also look for more work-related overlap — perhaps you both have a similar method of organization. Starting from a place with at least some common ground can help you better navigate areas of disagreement.

Be Sympathetic

Don’t forget that your difficult boss is a person too. You might not think that someone who tells you what to do all day has feelings, but they do, and you should be aware of that.

In fact, you should try to study your boss’s every move. Find out what might be their warm spot, if you understand where they’re coming from you might be able to work with them better. It doesn’t necessarily mean you should give them a free pass on bad behavior, but context is valuable in understanding their actions.

Stay one step ahead of your boss

Look for jobs that need to be done and help identify things in advance to take the load off. The more of an asset you are, the better your relations with your supervisor will likely be.

You will reduce your boss’ stress levels if you are always on the lookout for something to do. For some bosses, having to constantly give direction makes them stressed. Generally, a supervisor wants their employees to be busy, but they may not have time to give you frequent direction. By looking for things that need to be done, you’ll show initiative and address existing problems. Does everything seem to be all buttoned up? You could try cleaning the work area or enhancing it by adding things that will make the work easier or more pleasant.

Remember, people who are higher up in companies have more redundancy in their day-to-day routine, so they will appreciate an employee who livens up their workplace.

However, staying ahead doesn’t just come down to tasks. If you can anticipate your boss’ emotions pertaining to certain work events, you can try to craft the situation to result in the best possible outcome. By doing so, you may be able to stop problematic situations before they happen. There’s no shame in wanting to make your boss happy, and you should even try to look on the bright side with grumpy bosses and try to find ways to improve their day.

For example, if you know your boss is going into a difficult conversation with their manager, then immediately after may not be the best time to talk to them about other issues. Instead, try to leave some time for them to cool off. Even better, try to handle issues that come up on your own — they might appreciate a lighter load and a few headaches averted.

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Don’t play your bosses game

The classic manipulative boss has the ability to rule people’s lives, and that’s not what work is about. Work is about getting the job done and living your life at the same time. If they seem to be partaking in such behavior, then don’t play games with your boss.

Try to understand what motivates them and let that drive your actions. If they’re very numbers-oriented, then refer to numbers in conversation. Stick to the work, and approach it in a way that they’ll appreciate. Other bosses may want to look good in front of upper management or other departments, so keep that in mind and perhaps avoid questioning them in a large group setting.

Request/Give Performance Review

Performance reviews help put things into numbers. There are always bosses who expect more than is produced but often in an irrational manner. Some bosses don’t actually realize the productivity output because they don’t take the time to go over the numbers, or they might not realize how great an employee is doing compared to others because of neglect from the situation.

Requesting monthly performance reviews is an effective way to put things into the light when it comes to how you’re doing at work, and a difficult boss might become less challenging when they find out you’re excelling in your trade.

You could also give your boss a performance review. In this capitalist world, there are some situations where you could actually review your boss and have it be successful. Why not, right? If you can leave a Google review for 5 stars a business you like, then why can’t you do the same with your boss?

You could even request your HR department to issue a survey for all workers to fill out that requires their opinions about the boss and how well they’re doing their job.

Schedule A Meeting With Your Boss

Weekly or monthly check-ins sometimes play a huge role in the success between a boss and an employee. Maybe the boss isn’t really that difficult after all, and all you needed was to set them aside on a scheduled period to make sure you get what you need out of them.

Say No To Low Numbers

It’s extremely important to be stubborn with your boss when it comes to your pay. You need to know how much your services are worth, and don’t back down until you get the money you need. Some companies may pay employees less than they could, simply because nobody asks for a raise.

Don’t nod your head in agreement the next time your boss tries to reason with you that they can’t pay you a certain number. Sometimes they may not be able to give you the raise you want, but you definitely won’t get it if you don’t try.

Don’t Gossip About Your Boss To Other Coworkers

A big no-no is saying things about your boss to coworkers that could end up relaying them the information. Talking about co-workers behind their backs isn’t good practice either, but if your boss catches wind that you’re talking bad about them then you risk being terminated from your job.

Don’t get fired. The best way for you to keep your good reputation is by keeping all your bridges standing, so make an effort to protest in silence or to your boss’s face when things at work get stressful.

Talk To Human Resources

Human resources is your guide for creating a good working relationship with your boss. You deserve the best work environment in the place you work, and most times human resources is there to help you solve problems so that you don’t have to confront your boss alone. If you haven’t been able to address an issue yourself, or don’t feel comfortable trying, then this is the next step.

Know When To Leave A Bad Situation

While unfortunate, sometimes a toxic boss needs to be left behind for a better situation. Life is way too short, and there are so many jobs out there. Chances are, if you leave your current job, then you are bound to find another opportunity that is better for you. Generally, this shouldn’t be your go-to option, however, if you’ve attempted to address the issue and haven’t had any luck, then it’s likely the best next step.

Sites like LinkedIn, Zip Recruiter, Indeed, etc… are all great options for finding a better job.

Don’t Burn Bridges With Bosses

You should only cut ties with a manager or owner if they have done something completely awful. You never know what is around the corner in the professional world. Your boss could move to a different company with better opportunities and have a position open for you. Additionally, you never know when you might need a reference down the road.

Be A Boss

Taking control of your own situation is the best way to deal with a boss. Sure, almost everyone has someone who is ‘higher up’ or ‘richer’ than them, but it’s important to realize that we are all bosses of ourselves. Ultimately, they may be your boss in the workplace, but no person has more value than another when it comes to the real world. Know your value and feel comfortable standing up for yourself.