Career & Finance

5 Types of Difficult Bosses (and How to Deal)


Sure, work may be rewarding and fulfilling, your co-workers might be great, and perhaps the company perks can’t be beat. But, your boss? That’s another story entirely.

If you’ve ever had to work with a challenging supervisor before, you already know just how much of a damper that can put on your entire attitude about your career. It colors your whole perception of your position, and can quickly turn your dream job into a total nightmare.

From micromanagers to no-shows, working beneath a difficult boss is, well, difficult. Let’s take a look at five different common kinds of frustrating managers, as well as some strategies you can use to cope in the office.

1. The Boss Who Micromanages

You’ve never been able to come up with your own plan of attack for a project because it’s your boss’ way or the highway. You’re still waiting for the day when you can turn something in without it being returned looking like it survived a red pen explosion. Things with your boss have gotten so bad that you’re convinced you couldn’t take a trip to the office vending machine without her lecturing you about which snack to select.

Your supervisor is a quintessential micromanager, and her obvious lack of trust in you is really beginning to wear you down. You’re a qualified and capable professional, and you’d like the opportunity to use your skills and insights to make a difference in the office—without your boss constantly breathing down your neck and correcting you.

How to Deal: In most cases, micromanagers have good intentions, they just want to be on top of things and prevent work from slipping through the cracks.

Prove to your boss that you can handle your position without so much frequent help.

So, the first place you need to start is to prove you can handle your position without so much frequent help from your boss. Get your work done on time and ahead of schedule, don’t show up late for meetings, and send proactive updates about your progress so that she still feels like she’s in the loop.

If things don’t take a turn for the better after that, it’s time for you to have a conversation. Explain that while you can understand and appreciate that she only wants to produce the best work possible, it’s hindering your ability to feel confident in your own work and skillset. Chances are she’ll be willing to be a little more hands-off after that.

2. The Boss Who is Terrible at Providing Feedback

When it comes to providing feedback, your boss has some definite room for improvement. Either he doesn’t give any at all (leaving you to wonder how your work is being received), his input is incredibly vague and unhelpful, or he crosses a line and gives recommendations that are far too harsh.

You’re all for receiving constructive criticism and using it to become better at your job. But, your manager definitely isn’t making it easy on you.

How to Deal: It’s important to remember that your relationship with your boss is a two-way street—which means you’re entitled to share thoughts and ideas for how you could improve the way you communicate and work together. You can’t expect your supervisor to be a mind reader.

So, go ahead and tell your boss how you’d like to receive feedback. Do you wish he’d provide more specifics? Do you trust his expertise and wish he’d provide some suggestions rather than just poking holes in your work?

Let him know what you need. Ultimately, your boss wants you to become better at your job—and, it’s up to you to give him the insight he needs to help you do that.

3. The Boss Who is Totally Absent

Your boss’ office sits empty so often there are cobwebs between the arms of her desk chair. You aren’t sure where she is, but you know it’s not in the office—in fact, you can’t remember the last time she was there for more than an hour at a time.

You’re perfectly comfortable with being a self-starter and getting your own work done. But, at the same time, you’d like to know that your supervisor is just as engaged in the work and is there to help you out when you need it.

How to Deal: Alright, it’s definitely not up to you to dictate your boss’ work agenda and tell her when she needs to be in the office. However, that doesn’t mean you can’t schedule a regular sit-down with her when the two of you can get caught up.

If it would help you to connect weekly and get up to speed on what you both are working on, pitch this idea to your boss. Chances are she’ll be more than receptive to this.

Even if your boss continues to zip in and out of the office at a rate that’s impossible to keep track of, you can rest assured that you at least have a reserved time to get on the same page with each other.

4. The Boss Who Works Around the Clock (and Expects You to Also)

Vacations, holidays, weekends, the middle of the night—your boss doesn’t seem to care—he’ll email you any time, any day. And, when something urgent crops up? He expects you to drop everything immediately.

Of course, you’re willing to go above and beyond to impress your manager and take steps forward in your career. But, you also think you deserve a decent amount of balance between your work life and personal life.

How to Deal: Your supervisor might be a workaholic, but that doesn’t necessarily mean you need to be one too. It’s up to you not to set that expectation. That means that—unless something is truly time-sensitive—you should resist the urge to respond immediately in the middle of the night or on the weekends. If you do respond? Tell your boss that you’ll look into it when you’re back in the office.

Your supervisor might be a workaholic, but that doesn’t mean you need to be one too.

Also, don’t forget the importance of setting an out-of-office response when you’re away on vacation. It will serve as a reminder to your manager that you won’t be handling any work-related matters during that time.

5. The Boss Who Seems Totally Unqualified 

Your supervisor is constantly asking you for advice about how to approach a project. When a question comes up in a large team meeting, she immediately looks to you to provide the answer.

You’re glad she values your skills and insights so much. But, at the same time, your boss is somebody you want to learn from—not somebody you want to feel like you need to manage and direct. That’s not your job.

How to Deal: These can be some murky waters to navigate. You don’t want to go over your boss’ head or throw her under the bus. But, you also don’t want to continue doing all of the work while your manager gets all of the credit.

Start by asking your boss more questions about how you should handle things. If you feel stuck on a project or presentation, don’t hesitate to ask her for some tips on how you should move forward.

When a question comes up in a team meeting that you feel isn’t your place to answer? Go ahead and put in your quick two cents and then pass it back to your manager for elaboration. If your boss truly is unqualified for her position (and not just trying to be a team player who values your ideas!), it’s bound to come out sooner rather than later.

When the Bad Gets Worse

Of course, there are some bosses so bad that there’s quite literally nothing you could do to improve your situation. Sometimes your manager’s behavior is inexcusable, and there’s no amount of effective communication that could make you feel comfortable and confident in the office.

In these cases, your best bet is usually to pack up your desk and hit the road. Here are a few bad boss behaviors that are definitely worth quitting over:

Harassment: Sexual harassment from a superior is absolutely unacceptable. If you feel comfortable enough to report the issue to your human resources department, do so. And, remember that you’re completely justified in leaving your position and even the company.

Blatant mistreatment: Are you dealing with a boss who blatantly yells at or insults you? You don’t need to put up with that mistreatment. It’s time for you to put in your notice and find a job where your manager will provide the support and encouragement you deserve.

Unethical behavior: Is your boss drinking on the job, embezzling money, or something equally unethical? That’s not a mess you want your name tied to. If you know your boss is involved in some less-than-moral activities, it’s usually your best bet to get out of there before you find yourself in a situation you don’t want to be in.

Yes, you know that your boss plays a key role in your working life—so, having a difficult one is usually enough to change your entire attitude about your career.

Fortunately, in less severe cases than the three just mentioned, there are a few strategies you can use to improve the relationship you share with your boss. Put them into play and see if things get better over time. If they don’t? Well, it’s time to search for a new job that offers a more fitting work environment.

Are there any other types of difficult bosses you’ve encountered?