The reality is that everyone has had, will have, or currently has a Bad Boss. It is one of the easiest topics to find common ground on and can be heard all through the Happy Hour watering hole after a work day is over.

Bad Bosses can show up in many different forms: the one who asks you to work on the weekends (a la Bill Lumbergh from Office Space), the most self-centered person you know who does no work (a la Michael Scott from The Office), or even the weird power-hungry one (like Miranda Priestly from The Devil Wears Prada).

I’ve had Bad Bosses I’ve been grateful for because of all the things I learned not to do. I’ve had Bad Bosses that induce a sort of PTSD-like trauma response when I think about them. I’ve also had Spectacularly Bad Bosses who were downright emotionally abusive and required an intervention to convince me to leave my job.

Not all bosses are bad. In fact, many are good, and almost all are good people who just don’t know that they’re bad. Bosses are often subject to all sorts of weird authority and power issues. Even the best boss can fall easily because they commit the One Fatal Error that they didn’t know was the Thing you were waiting for them to do.

Here, I want to examine some of the Bad Bosses I encounter in my work as an Organizational Development Consultant and not only tell you how they could avoid being a bad boss, but how you can deal with your Bad Boss when they are being Bad.

While every Bad Boss needs some correction in their action, no one should be publicly shamed. All my examples of Bad Bosses and their employees are drawn from real life but are composites of several people or instances.

Janelle is a mid-level project manager for a medium size tech company. She has worked there for almost a decade, slowly rising through the ranks to larger, more complicated jobs. Her job now as Project Director is to take the specifications a customer needs and spit out something as close as possible within the confines of what the organization can produce.

Her boss, Lisa, is the VP of Engineering and has worked for the company for over a decade. She hired Janelle out of the Operations department when she had a sudden onslaught of small- and medium-sized customers that she couldn’t manage along with all the large customers. The company had just opened up its purview to include these customers and, unlike the slow trickle they thought they would get, after a year it was clear they needed their own manager since Lisa couldn’t divide her time to give everything enough attention.

Lisa and Janelle actually have a great working relationship. Janelle is wildly competent so she can be almost entirely self-sufficient. She occasionally has to check in with Lisa about resources or timelines, but it’s a rare occurance that Janelle can’t figure out how to make a situation work well.

One day Janelle and Lisa sit down with the rest of the executive leadership of the company. Eleven people in total in the room, all of whom are excited about the next year of growth and opportunity for the company. Specifically, Janelle’s department is expanding even more and even faster and the company is in a place where they will be slightly more selective with the size of contract they take on. Rather than taking all small- and medium-sized clients, they are going to institute a minimum threshold for the size of contract they will take on and look for customers they can build recurring relationships with over the one-and-done experience they have with the smaller contracts.

This group had come together to do some specific strategic planning about their new messaging and how to deal with inquiries from customers who don’t fit the new desired profile. The meeting was highly productive, ending with specific criteria everyone agreed on and a procedure for handling new customers. At the end of the meeting, the conversation veered to a particularly problematic customer under Janelle’s purview who would have been eliminated if they had been vetted with this new criteria. The group was venting about their frustrations when Lisa piped up.

“If I had known they were going to yield such a small profit and use so many resources, I would’ve have allowed them to sign a contract. It’s too bad I never heard about what they were seeking,” she said looking at Janelle.

Janelle made a small smile and replied, “Well…I did. We had a conversation about what the scope of their needs were.”

Lisa looked back without blinking, “No we didn’t. I was never told.”

“Yeah, it was in your office about six months ago.” Janelle was becoming upset, but managing to keep her composure.

“No. That can’t possibly be true. I wouldn’t have allowed it.” Lisa was now sitting back in her chair, her hands brushing away the words Janelle was saying.

The rest of group looked on stunned, but it was unclear if the stunned silence was because of Lisa’s inability to track her conversations, or the possibility that Janelle was lying to cover up the situation.

The CEO called the meeting over and said that this wouldn’t be a problem in the future with the new criteria. They all left for the rest of their day’s activities. Janelle went back to her desk and tried to get back to work. Lisa clearly was. Janelle could see her in her office on the phone. Janelle could’ve sworn she’d had that conversation, but Lisa seemed so sure about not receiving the information. She spent the next few months on edge as she waited for the problem customer to be given their deliverable and she wouldn’t have to think about this again.


√ Janelle works as a Project Director in a medium-sized tech company
√ Lisa is her boss, the VP of Engineering
√ Janelle was put in charge of all contracts below a certain size so Lisa could focus on the larger ones
√ There is a small contract customer who is turning out to require more resources than initially anticipated
√ Lisa claims Janelle never told her about the customer otherwise she wouldn’t have let them sign a contract
√ Janelle thinks she remembers having a conversation about them and Lisa giving the green light to the project


What the boss should have done: Bosses, never deny your worker a second time. Do not be Peter to their Jesus. Like Jesus, they are trying to tell you something important, namely that there is a communication gap going on and you need to investigate.

In this instance, Lisa’s best bet would’ve been to touch base with Janelle after the meeting, privately. Having this conversation in front of the larger leadership group just ends up with one of them looking bad. Here, Lisas of the world, I’ll write you a script:

“Ok. It sounds like we may have a little communication gap here. Let’s touch base after the meeting to check in about how to work around it.”

See there? No one was made wrong, you stated the facts and made a plan to act on it. This is what good management looks like.

Once in the private meeting, ask your Janelle for specifics about the date and time of the meeting and other content you may have covered. If she can’t come up with it, now is the time to teach your direct report about documenting conversations.

If it turns out you were wrong, apologize and make a plan to avoid it in the future. Here, Lisa and Janelle may have had this gap because Janelle is so self-sufficient she doesn’t need a ton of supervision, so Lisa largely doesn’t give extra attention to Janelle’s work. A regular check-in with someone with this level of responsibility is a way of circumventing this. A quick 15 minutes at the end of the week for a status update takes care of this.

And if you don’t think you have 15 minutes a week for a status update from your Janelles, then you aren’t really doing your job as a manager. As a manager, your product is your people, so make time to create and hone your product.

What the worker should have done: Janelles of the world, here is where your flawless system of documentation comes in handy. If you don’t have one, this is where keeping notes on meeting agendas, minutes, and action items will save you. Not only is it a way to track down what you have to do for any given project, but in the times when someone doesn’t remember something, you can gently point them in the direction of either a publicly kept document, an email, or your notes from that date about that topic. If Janelle had cited the date, time, and topics of the meeting, Lisa couldn’t really chide her for not being forthcoming about something that she had documented so meticulously. Contrary to pop culture, most people don’t concoct meeting notes to cover up lies. It seems more like Lisa just might have had a lot on her plate and didn’t pay attention.

If you find yourself defending yourself against your boss in front of a larger group, here’s a script for you:

“Ok. It sounds like I’m missing something. Can we touch base after the meeting?”

It is in your best interest to make your boss look good.

Accept (some) fault here and then immediately follow up with action. If it turns out you were right, graciously offer to come up with a way to make it so your tasks and progress are more easily accessible to your boss.

If you were wrong, apologize and ask for the help you need. If you have too much on your plate, ask for an assistant or assistance. If you simply don’t have the right tool for tracking information, ask for it, like Evernote, Basecamp, a bunch of Moleskins, or something else. Ask for time to check in at a relatively soon date (2-3 weeks) to get some “coaching” from your boss on your new system.

And if your boss sucks and gloats about your mistake, don’t rise. Vent with a friend after work, and then TRACK YO SHIT.