NBC

Steve Carell became a household name thanks to his wildly popular Michael Scott on The Office. But while he may have been a fan-favorite and often had good intentions, Michael Scott was a terrible boss. Whether he was sparring with HR, indiscreetly dating a superior, or being just plain mean at Christmas parties, Scott didn’t often display the leadership skills needed to successfully manage an office. Sure, these blunders were cringingly hilarious on-screen, but they would be a nightmare in an actual workplace.

Michael fancies himself an excellent boss and leader, but he couldn’t be more mistaken. He lacks the tact and the rationality required to be a great boss, but no one would watch a comedy about a good boss. No, part of what makes The Office great is Michael’s constant, outrageous failure.

Diversity Day

If you want to see a hilarious portrayal of white privilege and how not to handle it, watch Michael blunder through Dunder Mifflin’s diversity training. Hey, Larry Wilmore!

Fake Firing

Michael fancies himself a student of comedy, so he thinks that it would be hilarious to emulate The Jamie Kennedy Experience and fake-fire his employees. In the pilot episode, he tries this prank out on Pam, with heartbreaking results. You would think that he would have learned his lesson the first time, but he whips out this winner again, this time with Stanley as his victim. It does not go well. At all.

Sexual Harassment

Everybody likes a good dirty joke, but they are not always appropriate in the traditional workplace. Additionally, many enjoy some innocent flirting in the workplace. As is his wont, Michael takes it all too far. When he realizes that he is the cause of the additional harassment training, Michael lets loose a tirade of dirty jokes and some uncomfortable flirting with Phyllis.

Gay Witch Hunt

When Oscar comes out of the closet, Michael is forced to face a lot of the prejudices and homophobia that had come across in his office demeanor. Of course, he fails to be understanding and makes Oscar’s moment about himself instead. While he is indeed contrite about all of his previous slurs, forcing Oscar into the most awkward television kiss of all time was definitely not the way to handle it.

The Golden Ticket

Sure, many companies use promotional discounts to offer incentives for their current customers or to drum up new business. This is not a new thing. However, most companies make sure that their biggest customer isn’t lucky enough to receive the bulk of the discounts, potentially bankrupting the company. Michael isn’t a planner, though, and he didn’t think this one through. The kicker is that he tries to blame the entire debacle on Dwight, and then when it actually turns out to be a good thing, he tries to take the credit back.

Health Care

Michael isn’t great with conflict, so he has a tough time picking a new, cheaper healthcare plan for his employees. Instead of handling it like a manager, however, he hands the task off to Dwight. When Dwight picks a terrible plan, Michael doesn’t want to deal with real world ramifications, so instead he placates the group with the promise of a great surprise. Unable to improvise anything major, Michael gets them all ice cream sandwiches. So not only is the surprise a total letdown (chipwiches or GTFO), the Scranton branch is also stuck with a horrible healthcare plan because Michael couldn’t do his job.

Utica Raid

A boss is supposed to be a role model for his employees, and it is safe to say that, while Michael is many things, a role model he is not. When Michael decides that the best way to respond to Karen trying to poach Stanley is to play a prank on the Utica branch, Dwight and Jim probably should have realized that this was only going to end terribly. Instead of handling the situation with maturity and openness with Stanley, Michael chooses option B: dressing up in ridiculous disguises and destroying office equipment.

Prison Mike

This is a prime example of Michael taking a passing comment way too far. When the Dunder-Mifflinites make some innocent jokes that their workplace is worse than actual prison, Michael turns it into a teachable moment. The problem is that Michael obviously knows nothing about prison and the entire presentation devolves into horrible (but still hilarious) stereotypes.

An Ill-Advised Roast

Comedy roasts can be very funny, but it’s usually best to leave them to the professionals. When morale plummets, Michael decides that the best way to handle it is to organize a roast so his employees can razz him to his face. Unfortunately, Michael has incredibly thin skin. First rule of roasts: be able to handle the insults. Sure, Dwight gets extra nasty, but the situation should never have arisen in the first place.

Scott’s Tots

This one is bar none the biggest Michael Scott blunder because it has the most horrifying ramifications. Michael makes a lot of promises that he cannot keep, but promising a classroom full of kids that he will pay for their college is just a bridge too far. When it becomes clear that there is no way that he can follow through on his initial promise, he gets them computer batteries instead. Michael’s done a lot of questionable things on his quest for friendship and intimacy, but this was definitely the worst.