How to deal with an annoying boss

Annoying peers are hard enough to deal with. Things get even more complicated when the annoying person is your boss. As with peers, there are several ways that a boss can be annoying. Unfortunately, you have to tread lightly with many (though not all) bosses.

To be clear, the focus here is on annoying bosses, not toxic ones. A boss who is a narcissist, a harasser, or who sows mistrust isn’t just annoying, they’re bad for you and the organization. I’m going discuss four things that may seem petty, but if you start dreading your engagements with your boss (or resenting them for their foibles), it can come back to hurt your working relationship.

The cipher 

Some people are blessed with the ability to communicate clearly. They open their mouths, and full paragraphs of well-formed sentences spill out that illuminate whatever they are talking about. But, as Steve Martin once said, “Some people have a way with words, and others . . . uh . . . not . . . have a way.” 

If your boss is in that latter category, they may ask you to do things, give you feedback, or generally talk about things going on at work that you don’t fully understand. It might be tempting to nod along with them and then try to figure it out later. That avoids an awkward discussion, but it probably causes more problems than it solves.

Instead, develop a routine with your manager to summarize the outcome of meetings/discussions at the end. Tell your boss that this is to help you remember. Then, repeat back the important bits. Your boss will correct anything you get wrong. As an added bonus, this exercise might give your boss additional words and phrases they can use to talk to you about similar things in the future.

The micromanager

A boss who gets into the details of your work is frustrating, because you’d like to be able to complete what you’re doing without constant oversight. There are two common reasons why bosses micromanage.

When someone gets their first supervisory role, they are usually in a transition from front-line work to management. Because their job (up to that point) involved doing something just like what you are doing now, it may be hard for them to let go of the details of the work to focus on what they need to do with their new position. For these bosses, it is often okay to have a gentle conversation in which you ask questions about their new responsibilities and provide a subtle reminder that the front-line work is not part of their day-to-day any longer.

The second typical source of micromanagement is anxiety. When your boss is not confident in their leadership or when they feel threatened by other factors at work, they may clamp down on the people working for them to ensure that nothing goes wrong. While this tactic may make them feel better, it makes everyone else miserable.

There are two things you can do here. First, create a schedule of checking in with your boss every so often. You’d like to get that to once a week if you can, but you may have to start by doing it at the end of a work shift, or every two days, and gradually work your way to once a week. Second, provide a shared document of the status of projects. This record is helpful anyhow, because it can be used when something goes wrong with a project. If your boss has access to the status of key projects, they may be less likely to pester you for those details and add suggestions about how they would approach things.

The forgetter

One of the Big Five personality characteristics is conscientiousness, which reflects the degree to which you focus on details and follow rules. Some bosses are highly conscientious, and they are up on the details of every project. Others are not.

When your boss is not conscientious, they may be great at giving strategic and tactical advice, but they may forget things later. They may miss meetings that don’t make it to their calendar, or forget something they told you they would do later.

A forgetful boss needs more constant reminders than a conscientious one. Follow up meetings with a written summary of key points and any specific information you need from your boss later. Send that summary by email. Even bosses who aren’t that conscientious are likely to check their email and to respond to direct requests on those emails.

If there are particular things you need to get from your boss by a specific date, coordinate with their admin if they have one. Try to ensure that key dates and requests get on their calendar. Often, a forgetful boss is aware that things slip through the cracks, and so they have a system to help them keep from dropping too many balls.

The (long-winded) storyteller

One thing about being the boss is that people feel like they need to listen to you. Some bosses (particularly those who have been in a leadership role for a while) get used to having an audience, and they may use meetings and even hallway conversations as an opportunity to regale you with stories.

A good storyteller keeps it brief and relevant. If your boss is not a great storyteller, then seeing them wind up to tell a long tale can send shivers of dread up your spine. You may have to bear a certain number of these stories—particularly if you’re sitting in the break room. But, you should try to have something scheduled up against meetings you have with your boss so that you have something you need to get to. That way, if your boss does launch into an epic narrative, you have a good reason to excuse yourself and move on. 

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