7 Strategies for Dealing With a Difficult Boss

Stressed man in business suit sitting at his desk with his hands crossed in a prayer motion in front of his face.

What happens when you love your job but not your manager? Is it time to quit or should you stick it out? 

First off, take a breath. We’ve got a lot to unpack here. You’re in a bit of a delicate situation, but it’s one that many people have been in before and have successfully navigated unscathed.

It can be hard to find a job you truly love, so chances are, you probably want to stay where you are and work through the issues with your boss. This may be especially true if you’re working in a niche field and it’s hard to find jobs or if you’ve spent a lot of time working your way up the ladder.

Instead of quitting on the spot — which is never a good idea — there are some strategies you can implement to work through any issues you’re experiencing with your boss.

As a human resources (HR) generalist, I’m going to provide you with a few great techniques to navigate your relationship with your boss so you can keep the job you love.

How to Deal With a Difficult Boss [7 Tips]

Before you do anything at all, take a step back and take a moment to reflect on the situation. What’s really going on? What is it about your boss that’s bothering you? Have they done something specifically to upset you? Do you simply not like them as a person? 

Decide if it’s something you need to discuss together because it’s harming your daily work, or if you need to do some work yourself to find common ground with them. Remember, you never have to be best friends with your boss or coworkers. You don’t have to love them, either. But you do need to be able to find some common ground so you can effectively work together.

Before you quit or do something drastic, try out one of these strategies: 

1. Communicate

The first step you should take is to communicate. Does your boss understand you’re upset? Do they know their behavior is causing you to feel a certain way? Typically, when someone’s having a problem and they complain about it — at work, in relationships, in friendships — the first thing they get asked is, “Well, did you say anything about it? Did you tell them?”

Far too often, the person who’s upsetting you has no clue they’re upsetting you. They don’t know they’re doing anything wrong or communicating with you in a way that’s harmful to your work style. Misunderstandings are common; oftentimes, if you simply talk about the issue, it’s easy to work through. 

So, your first step is to talk through what’s bothering you with your boss. You might be worried they don’t have time for you, but a good leader will always make time for their employees. Send them an email and explain you need five minutes of their time. Good leaders are also receptive to feedback.

Don’t come at them with fists raised; immediately yelling at your boss or taking a defensive attitude isn’t the best way to approach an issue.

Instead, keep an open mind and come prepared to take partial ownership of the problem. Discuss what you’re struggling with and speak about how your boss can help you work through it. For instance, if you’re upset because your boss is giving you critical feedback, but it isn’t constructive, try say something like this: 

Lately, I’ve been having trouble with my logo designs. I don’t know how to take them from good to great and I’m struggling when creating a final version to present to the client. It would help me if you could provide specific feedback when it comes to color and font choice. Could you help me with that moving forward? 

In this situation, you take ownership of the problem you’re struggling with and explain how your boss can help you work through it — without directly blaming them for the problem. 

This is a much better strategy than saying: 

You keep giving me terrible feedback and it’s making my job even more difficult than it already is. I’m so stressed and you aren’t helping! What does “make the logo pop” even mean?! I’m sick of this!

Instead of attacking, talk through how you can come to a solution together. 

If your boss has said something to you that’s hurtful or you’d prefer they work with you a certain way, don’t be afraid to talk through it while taking ownership of your feelings. 

For instance, explain how you know your boss isn’t trying to upset you, but certain language may make you feel upset. “When you said this, it really bothered me. Did you mean to upset me?” goes a lot farther than “I know you’re saying this to hurt me.” 

Explain your working style and how you can collaborate together effectively. Be open to suggestions from your boss about how you can work better with them, too. It’s all about collaborating. Come to a solution together. 

2. Wait For Progress

As much as we wish it would, progress simply doesn’t happen overnight. It may take some time for your boss to change and adapt to the strategies you discussed together. 

Give it a little time, even a few weeks, after you’ve spoken to your boss about your complaints. If nothing has changed, it might be time to revisit the conversation (if you feel comfortable) or try another technique.

Boss yelling at staff member face to face.

3. Find Common Ground 

If you find that you don’t particularly like your boss and it’s making it difficult for you to work with them, I advise you to try a technique called “find the like.”

Dig deep to discover what you have in common with your boss and try to connect that way. Spend time discussing your commonalities and what you both enjoy. This will give you a reason to like them and a way to bond with them. When you do this, little grievances you have toward them won’t bother you as much and you’ll start to either enjoy working with them more or you’ll, at the very least, like them enough to not quit. 

4. Get Advice From Your Coworkers

If you’re still working on your relationship with your boss, try talking to your coworkers to get a feel for how your boss operates. They might be able to provide some tips for how to successfully communicate with them in order to have a successful working relationship. 

It’s advisable to talk to a coworker who’s already worked through something like this and is now working well with your boss and seems happy. They’ll be able to provide constructive tips, while a disgruntled employee may not.

There’s a fine line between simply gossiping to gossip and talking through a problem to get constructive feedback, so tiptoe carefully with this technique.

5. Talk to Human Resources

Human resources is a support resource for staff members. They’re there to help you work through issues you may encounter in the workplace. Consult with them — or someone else you trust outside the department — to talk through your problems with your boss. You could even speak to your boss’ supervisor if you don’t feel you have an alternative. 

You can have an off-the-record conversation with HR to discuss problems or personality conflicts. They can help you find strategies to work through the situation or determine if you need to report a specific behavior. Nothing has to go in your file when you’re having an off-record conversation. HR has your best interest in mind and can help counsel you on next steps.

If the company you’re working at doesn’t have an HR department, there should be some sort of resource available to help you navigate workplace issues.

6. Ask for Another Supervisor 

If all else fails but you’re not ready to give up the job you love just yet, see if there’s another manager you can work under instead. This may be a conversation for HR or your boss’ boss. 

Depending on the size of your company and how the department is structured, however, this may not be an option. 

Boss talking calmly to staff member.

7. Pursue Another Internal Position 

There’s the chance you may start to hate your job too because of your relationship with your boss. If you still like the company, find out if you can make an internal switch to a different department. Can you work in a different department led by another manager? 

If you’re worried about navigating this transition — or worse, that your boss may somehow try to retaliate or sabotage your department transfer — talk to HR. Again, they’re a support resource for you and can help you work through your concerns. 

If your job satisfaction is very low, it might be time to start searching for a new job. If you decide to leave your position, make sure you take the time in your interviews to ask about leadership and how you’ll be supported.

Find Career Success

Finding yourself in a situation where you love your job but not your manager can be challenging. However, it's important to remember that quitting should not be your immediate response. Instead, try implementing some techniques to navigate your relationship with your boss and potentially resolve the issues.

Start by reflecting on the situation and identifying what specifically is bothering you about your manager. Determine if it's something you can address directly with them or if you need to find common ground and work through it yourself.

Communication is key. Talk to your boss about your concerns in a calm and constructive manner. Explain what you're struggling with and suggest ways they can support you. Remember to take partial ownership of the problem and seek a collaborative solution.

Ultimately, if your job satisfaction remains low and none of the techniques work, it may be time to start searching for a new job. During your interviews, inquire about the company’s leadership and support structure to ensure a more positive experience in your next role.

Be sure to consider these six questions before putting in your resignation.

At Anderson Trucking Service (ATS), we pride ourselves on having a strong leadership team. We care about our employees, their happiness and their success. As such, we’ve put together a Career Success Center to help employees navigate every aspect of their careers. Check it out for more helpful tips!

Tags: Career Resources

Liz Stone

Written by Liz Stone

Liz is an HR generalist with ATS. She consults daily with employees and managers to work through issues and concerns collaboratively. She not only loves the collaboration aspect of her job, but she loves the ATS culture and team, who make it fun to come to work every day. Before joining the ATS team in 2021, Liz came from a staffing background. She worked with clients from all over Central Minnesota, learning what they need in employees and helping guide them through hiring and retention challenges.

Get the Latest Careers Content Straight to Your Inbox!

We Have a Podcast! Find Us on Your Favorite App.

Apple Podcasts logoSpotify logoGoogle Podcasts logoAmazon Music logoAmazon Music logo

Beyond the Road Podcast logo

Recent Posts

Work With a Transportation Provider You Can Trust

You don't want your freight in just anyone's hands. Find a transportation provider that cares about your safety and your reputation. Learn how ATS can help.

Connect With an Expert