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Six Ways to Handle a Difficult Boss

Luca has a bachelor's of science in accounting and finance and years of experience as a tax accountant including management experience

a man and a woman in a conference room sitting across from one another

a man and a woman in a conference room sitting across from one another

We have all been in work situations where we have had to deal with difficult managers. In a perfect world, all our bosses would be looking out for our best interests and have enough time to help us out immediately.

Unfortunately, managers often become busy or aren't conscientious about doing their jobs. Below are six steps you can take to address these situations.

1. Follow up With Your Manager

I know this is counter-intuitive. Technically, your manager is likely the one who should be following up with you. However, this really clicked for me one day as I sat in my mentor's office listing some long-term difficulties with a manager I had. She responded, "Well, sometimes you have to manage your manager." This wasn't the first time I had heard that saying, but I think it was the first time I really got it.

I can send my manager an email asking them to look at something, but the truth is that they are human. They might lack time to be able to look at it. They might lack the memory to remember to look at it. They might even lack the motivation to care to look at it.

The truth is that you need to be the responsible one and follow up with your manager. As a manager who has had my staff follow up on items, I personally am always thankful for reminders, and I have never had someone get upset at me for giving them a gentle reminder of something they owe me.

If you are still nervous that you will be seen as aggressive or impatient, try phrasing your request a little differently. You can ask your manager if they need anything else from you or have any questions before they look at whatever you sent them.

2. Observe Your Manager's Interactions With Others

If gently following up with your manager does not seem to be helping, it may be time to take a little more action. Before immediately escalating the issue, though, it would be good to do a little research.

Note how your boss likes to communicate with you, with their own superiors, and with their peers. Do they prefer email, IM, phone calls, or in-person talks? Perhaps one communication method is better for them than others. If you know that your manager doesn't do well with emails, try to be respectful of this and communicate with them in a way that you know will be effective for them.

Also, pay attention to the style of communication they like to use. Some people are very blunt while others are less so. If your manager communicates bluntly, you may want to work on becoming more direct yourself.

One effective way of researching your boss's preferred communication style would be to discuss it with other people who also work for them. Others who may have more experience or more success can be a great source of information about the best way to handle your boss. Keep in mind that this is not an excuse to gossip and complain about your manager to others in the office though. Gossip is unhelpful, unprofessional, and unkind. Be an excellent employee by working to foster a positive work environment.

3. Take Notes on Any Issues

Make sure you document any difficult situations with your boss early and often. By the time a situation has escalated to the point where you feel it is time to involve a third party, it may be too late to produce any proof of your frustrations and concerns.

By ensuring that communications with your boss are well documented, you can be sure that you will never get into an argument over what actually happened. Even if I am not concerned about my manager's responsiveness, it is a good practice to save emails and messages when possible.

As a side note, if the worst does happen and you are ever forced to defend yourself over a situation, it helps tremendously to have a reputation as an honest, hard-working employee. As a manager, I can often tell how hard my employees are trying and how honest they are with me. If you regularly call in sick when you just want a day off or do half-hearted work on a regular basis, your managers will not be as gracious or willing to side with you when you come to them with any issues you are having.

4. Talk to a Mentor

It is always wise to spend some time and effort trying to improve a difficult work situation before involving a third party. First, because the situation may be easily remedied by yourself. Second, if you do involve someone else you will be able to show them that you have taken the initiative to try to work through things on your own before escalating the issue.

Use wisdom with your specific situation and note that the fourth step sometimes may need to be done after the fifth step instead. Consider the relationship you have with your boss and your comfort level with them before deciding if you should talk with them without prior outside input.

Again, this is not permission to gossip about your manager, to complain about them, or to insult or slander them. Stick to facts and concerns, not to how you feel about the situation.

When speaking to a mentor, you are not asking them to fix the problem for you. You are simply explaining your situation and presenting a few ideas of next steps that you would like to initiate. Talking to a mentor should never be about asking them to do all the work for you.

5. Have a Discussion With Your Manager

This is a very important step. Even if you don't think it will help, at some point you need to sit down with your manager and outline your concerns. Again, stick with the facts of the situation and not with how they make you feel. Instead of saying that you feel like you are not a priority to your manager, maybe you can explain that they tend to answer your questions less than 24 hours before your projects are due which puts you under time constraints that don't allow you to do as careful a job as you would like.

It is important to remain calm and reasonable. You should not be making personal attacks. This should be about the things your manager does, not about your manager, and you should express this with your language. Remain respectful at all times.

Depending on how serious the situation, it might be a good idea to take notes and document this discussion. Even if you are not expecting the situation to escalate, it is always better to be overly cautious when confronting a direct superior.

6. Don't Give up

Do not be discouraged if you don't see immediate change. Progress takes time. It also can sometimes take months to learn to work well with a specific person. You never know what personal circumstances someone may be going through.

I purposely have not added a specific step that says to go over a manager's head. This is because there is no formulaic sequence on when the perfect time would be to do this. Sometimes this may be called for, but you are the one who knows your work situation best. I would highly recommend discussing with a trusted mentor before taking this step.

© 2019 Luca Pacioli

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