The Boss Show

Workplace wisdom with heart and humor

April 17, 2016

The Worst Bosses in Film

Who does your boss remind you of the most — Steve Carell as a totally useless Regional Manager in “The Office”? Meryl Streep’s tyrannical character in “The Devil Wears Prada”? or maybe Darth Vader? To illustrate art imitating life, blogger Abbie Reedy wrote a post on “The Worst Bosses in Film” and then adapted its audio clips special for The Boss Show.

View Transcript

Speaker 1: It’s a Northwest lifestyle weekend on KOMO News. Now, a show for anyone who is or has a boss. This is The Boss Show with Jim Hessler and Steve Motenko.


Steve: This is The Boss Show. I’m Steve Motenko. I’m the psychology guy. I’m a leadership coach in the Puget Sound area and I do both one-on-one coaching and leadership workshops with my friend across the table.


Jim: I’m Jim Hessler. I’m the business guy. I’m the founder of Path Forward Leadership Development. I’m the author, along with Steve, of the book Land On Your Feet, Not On Your Face. This is the show for anyone who is or has a boss.


Steve: Hopefully, that’s you or maybe someone you care about.


Jim: It’s most people.


Steve: It is most people, but it’s not us.


Jim: That’s true.


Steve: It’s 0% of the assembled multitude.


Jim: In a sense, we both have bosses. We are our own boss. There’s a relationship there in the same sense that there might be a relationship with another person.


Steve: That would be a great thing to talk about.


Jim: It would be.


Steve: We’re not talking about it today on The Boss Show.


Jim: No.


Steve: Today on The Boss Show, a look at some of the worst bosses in film as compiled by blogger Abby Reedy, and how they might be simply exaggerated versions of your own boss or even – horrors! — you as a boss. That’s coming up, but first a listener comment from our listener Alison. We always change first names. I don’t know why we’re calling her Alison.


Jim: You just like the name.


Steve: I like the name Alison. I had a crush on an Alison in college.


Jim: Remember the Russians, or the Russians are coming?


Steve: No.


Jim: Alison Palmer. I remember that cute little blonde girl that the Russian guy was hitting on. Alison Palmer.


Steve: Yeah, the girl I had a crush on in college was a cute little blonde girl.


Jim: Yeah.


Steve: We digress.


Jim: Yes.


Steve: Alison writes, “I was listening to the show and I really liked it. However, the first question that was asked didn’t really get an answer.” She’s referring to another listener comment. The comment she’s referring to was a woman who said that her boss is an idiot and a moron and she’s got all the wrong motivations.


Jim: There were flames coming out of that message.


Steve: Yes, there were. What should she do? Alison goes on to write, “Yes, she should’ve toned down her language,” which is what we suggested, “And yes, she should empathize with her boss, but I know what it’s like to work for a terrible person. What is your advice in that situation, if you’re working for a terrible person?” Which is a great segue into the worst bosses in film that we’ll be treating later in the show, but what comes up for you Jim, first thing?


Jim: Not everybody can do this, but you get another job. For gosh sakes, what’s it worth for your life on this planet to have to put up with that for too long. If you’re not looking for another job, maybe you should start so you feel at least a little more empowered. Second of all, it’s a “to be” or “not to be” question. How much of your life are you going to waste putting up with this? You can either challenge it and challenge the person to be a better person, which maybe they’ve never been challenged that way before, or leave and go do something else.


Steve: Yeah.


Jim: I don’t see any other option other than despair.


Steve: What comes up for me is that it depends on what kind of terrible they are. Terrible people come in lots of different colors and stripes and flavors.


Jim: That’s a good point. If it’s incompetence it’s one thing. If it’s just sheer nastiness and immaturity, that’s something else.


Steve: Lack of trustworthiness. What does terrible mean? How you approach it will depend on what their particular brand of terribleness is.


Jim: Yes.


Steve: Jim and I are always suggesting to our clients that we don’t have honest enough conversations. We’re also always working with our clients on how to have those honest conversations. Can you refer to specific behaviors that are not blanket labels or judgments when you’re talking to your boss? Is there a possibility that’ll make a difference? Can you focus on outcomes that you want together and how your boss is not helping to further those outcomes for you in the way those specific behaviors are playing out? There are a lot of possibilities and I know some of you are listening and saying, “My boss is not going to listen to any of those, is not going to be open to any feedback,” in which case, we’re back to Jim’s advice, which is weigh the balance. What is the balance sheet between the fulfillment you get from your work and the suffering you’re undergoing?


Jim: Is it a redeemable person and is it a redeemable relationship? If neither of those things are possible, then you need to either live in some sort of state of grace about the circumstances you’re in or go change your circumstances.


Steve: Yeah.


Jim: It’s as simple as that.


Steve: Yeah. You can do both at the same time.


Jim: Yes.


Steve: Try to affect change while also looking for other venues to apply your talents to. The worst bosses in film when we come back. You’re listening to The Boss Show.


Speaker 1: It’s a Northwest lifestyle weekend on KOMO News. The Boss Show continues.


Jim: Hi, I’m Jim Hessler. I’m the business guy.


Steve: And I’m Steve Motenko. I’m the psychology guy. Today on the show we’re going to have some fun. We’re going to play a number of excerpts from horrible bosses depicted in film.


Jim: Of which there are many.


Steve: Of which there are many. It’s almost a cultural icon.


Jim: Mm-hmm (affirmative).


Steve: In Hollywood, and they’re not all in the film Horrible Bosses, but one of them is. The reason we’re doing this is I came across a blog post by a blogger named Abby Reedy a while ago who outlined a number of very popular movies and how horrible bosses were depicted in them. She also, although she can’t be on the show with us today for, I want to say contractual issue reasons. I can’t explain anything more than that. She worked with us to put together some audio clips from some of these movies. The take I want to take on this, Jim, is we will be listening to caricatures but all of these characters have grains of truth in them.


Jim: As most caricatures do.


Steve: Right.


Jim: That’s why they’re caricatures.


Steve: I’m going to ask you as the business guy, the guy with the long career in organizations, to see what these excerpts prompt in you in terms of your own memories of working for bad bosses or being a bad boss yourself, which everyone I talked to who ever worked for you said you were.


Jim: It was a miserable experience.


Steve: Yeah.


Jim: Yes.


Steve: Which is why you’re consulting.


Jim: Yes, exactly.


Steve: All right. The first one. This is, as Abby Reedy says, the I own you boss. This is the boss who, work life balance, you got to be kidding. You sell your soul to the company and you’re available 24/7 to do anything that I want as your boss. The classic example is Miranda Priestly in the movie The Devil Wears Prada.


Jim: What a perfect last name for that character.


Steve: Really. What you’re going to hear is a compilation of little mini-clips from the movie with Meryl Streep kind of abusing her assistant in various ways. The noises you hear in the middle are her dumping her belongings time after time on her assistant’s desk. This is Meryl Streep from The Devil Wears Prada.


Meryl Streep: I need 10 or 15 skirts from Calvin Klein.


Anne Hathaway: What kind of skirts do you need?


Meryl Streep: Please bore someone else with your questions.


  Where is that piece of paper I had in my hand yesterday morning? The girls need new surfboards or boogie boards or something for spring break. Get me that little table that I like at that store on Madison. Get us a reservation for dinner tonight at that place [inaudible 00:07:56].


  I don’t understand why it’s so difficult to confirm appointments.


Anne Hathaway: I know, I’m so sorry Miranda. I actually did confirm last night.


Meryl Streep: Tales of your incompetence do not interest me.


Steve: “The tales of your incompetence do not interest me.” It seems to me there are one of two things going on and maybe both. Either this is the classic monumental narcissist, or this is a person who has sold her own soul to the company, that she believes that the company and her representation of it is all that matters in life.


Jim: We can always look at these things from two perspectives. There might be some terrified little child inside of this person who’s terribly insecure and is taking out their insecurities on the world around them.


Steve: I thought I was the psychologist.


Jim: I know, but when I see people acting like this, I always think of that first. For some reason I always think there’s just something really screwed up about this person’s life that she has to treat people this way.


Steve: That in all probability started in childhood. Completely agree.


Jim: Yeah. The other question that always shows up for me in a situation like this is, “Who has or has not stood up to this person in the past?” People who behave this way have almost always gotten away with it for a long period of time in their career and they just repeat their history because they’re surrounded by people that accommodate them. That’s what I think of. Who’s going to stand up and say, “Hey you lousy you know what. Go get your own darn skirts.” I’m really cleaning up my language for this.


Steve: I see how much of a challenge it is for you.


Jim: Yes, you hear me pausing.


Steve: Well done.


Jim: I’m choosing my words.


Steve: This is terrestrial radio, after all.


Jim: Yes.


Steve: In addition to being podcast. They attract people to them that have similar levels of ambition or also similarly dedicated to the industry.


Jim: Or are similarly screwed up themselves, that they have to be treated that way by another human being.


Steve: Right.


Jim: Somehow their victim stance maybe shows up in that way.


Steve: Yeah. The cycle kind of self-perpetuates over time.


Jim: Yes.


Steve: When we come back from the break, we’ll be listening to a clip that you will probably recognize of the unforgiving perfectionist. You’re listening to The Boss Show.


Speaker 1: Now back to Jim Hessler and Steve Motenko. This is The Boss Show on COMO News.


Jim: I am Jim Hessler and I am the business guy.


Steve: I’m Steve Motenko and I’m the psychology guy and we’re talking today about worst bosses in film. Played a clip before the break from The Devil Wears Prada, a classic Meryl Streep character Miranda Priestly.


Jim: Which we should point out in the end, she did stand up to her.


Steve: I don’t even remember. I never remember movies.


Jim: Yeah, at the end of the movie, the character that Anne Hathaway played just simply walked away from the relationship. There was redemption at the end for the abused person in this relationship.


Steve: I love redemption.


Jim: Yeah.


Steve: Will there be redemption for the next one? The next kind of boss that blogger Abby Reedy referred to in her post on the worst bosses in film is the unforgiving perfectionist. This is a boss who rules only through fear and through threats and intimidation. There’s no, unlike Miranda Priestly, there’s no carrot attached to the boot of intimidation. This is another classic film clip from The Empire Strikes Back. The sound that you hear toward the end of this clip is Darth Vader’s lieutenant choking under the grasp of his invisible hand around his throat.


Vader: The Rebels are alerted to our presence.  Admiral Ozzel came out of light-speed too close to the system.


Veer: He felt surprised was wiser …


Vader: He is as clumsy as he is stupid.


Ozzel: Lord Vader. The fleet has moved out of light-speed and we’re preparing to …


Vader: You have failed me for the last time, Admiral.


Steve: I’ve always wanted to say that to an employee. “You have failed me for the last time.”


Jim: Again, these are caricatures. These are so far over the time, but I wouldn’t be surprised if that line has been used by bosses. I’ve never heard it.


Steve: Have you ever worked for a boss anywhere near as abusive, as intimidating, as either of these last two.


Jim: You and I had an interesting conversation about that during the break. I have not really … I’ve worked for some bad bosses, but nobody ever behaved this way towards me. Either I’ve been lucky or the other theory is people know better than to treat me that way.


Steve: You have said that people are intimidated by you sometimes.


Jim: Yeah. I have a feeling that I haven’t seen that in part because people see me as a person not to be trifled with in that sense.


Steve: Have you worked with bosses that have abused other people around you even if they haven’t abused you?


Jim: Yes. Yeah. I’ve observed enough of that to be disturbed by that. It’s clearly just somebody’s ego’s out of control, somebody who lacks self-awareness. Somebody who’s angry. Somebody who’s frustrated. Who know what’s going on in that person’s life?


Steve: But it’s dysfunction.


Jim: Again, we found out at the end of Star Wars that there was some pretty big stuff going on in Darth Vader’s life, didn’t we? I mean really, think about the story.


Steve: “I am your father.”


Jim: Yeah, right. Underlying all of this bad behavior, we always have to remember that there’s a reason. That doesn’t mean that we excuse it, but it means that we’re compassionate towards the abuser to some degree.


Steve: That’s really hard to do.


Jim: Yeah.


Steve: It’s really hard to be compassionate towards someone who’s abusing you.


Jim: Especially if … Of course, compassion only goes so far. You have to protect yourself first and you have to get out of a bad situation. Darth Vader’s a mentally ill person. He’s just evil and in his case, it was impossible to stand up to him.


Steve: Yeah.


Jim: He was just too powerful.


Steve: That invisible hand around your throat gets them every time.


Jim: Yes. Yes.


Steve: When we come back, the next of our worst bosses in film, the boss who has no business being the boss. We’ll play a clip from the film Horrible Bosses. You’re listening to The Boss Show.


Speaker 1: COMO News. The Boss Show is back on a northwest lifestyle weekend. Here’s Jim Hessler and Steve Motenko.


Steve: Thanks for staying with us on The Boss Show. I’m Steve Motenko. I’m the psychology guy. Your turn Jim.


Jim: Sorry, we’re jumping on each other’s lines there. I’m Jim Hessler. I’m the business guy. We are on Facebook. We are on the Twitter. We have a listener line, 206-973-7377. Drop us a message in there or email us at We’ve been able to use more and more listener input in recent months because we’re getting more of it and we really appreciate it. We’d love to hear from you.


Steve: Love to hear what you’d like us to talk about on the show as well as what you think about the things that we are talking about on the show. Today we’re talking on the show about the worst bosses in film. This next one is the boss who has no business being the boss. This is a clip from a movie you’ll definitely remember and a clip that you may remember as well. This is Colin Farrell playing a guy who has inherited a company. He’s inherited from, I believe, his father, the founder. Colin Farrell’s character, on the other hand, has no managerial skills, no real interest, no knowledge of the industry, no natural abilities as a leader, and yet he’s the boss. This is Colin Farrell in Horrible Bosses.


Speaker 9: Your dad made the choice to dispose of our chemical waste responsibly. In order to do that, you’ve got to spend a little bit more money.


Colin Farrell: Guess what? I’m your boss.


  I don’t care about this company. This is just an ATM to me.


Speaker 9: What do you mean by trim the fat?


Colin Farrell: I want you to fire the fat people.


  I’m in charge now.


Jim: I have had this boss. This is actually one I can relate to.


Steve: Tell us about him or her.


Jim: Well, yeah, I don’t even want to give any indication that anybody would know who I’m talking about.


Steve: Maybe you can change your name to protect the guilty.


Jim: This is an amalgam of several people. Let’s just say it that way. This entitled second or third or fourth generation boss is in many ways the worst kind to have to deal with because they don’t know what they don’t know. They’ve been told all throughout their whole life that they’re going to own this business someday.


Steve: They didn’t have to work to get …


Jim: They didn’t have to earn it. They haven’t earned the trust or respect of the people they work with. I’ve even seen second or third generation people who really had great intentions, who worked really hard and still weren’t able to overcome this idea that they were there just because of their last name. Again, here’s my compassionate side showing up. I find that’s pretty tragic to find people in that situation. This guy that just inherited the business, that’s a nightmare.


Steve: You’ve done a lot of work with family businesses in your time.


Jim: Yes. Mm-hmm (affirmative). Some of them are terrific. Some of them, this isn’t a problem at all. I always recommend that the person go work somewhere else for a while and then come back to the business. I find that’s what works best. You shouldn’t spend your entire career with your parents’ business.


Steve: Mm-hmm (affirmative). It’s limiting to your own growth and your own development. The Peter Principle comes to mind. It’s kind of an uber, an ultimate example. The Peter Principle, being promoted to your place of incompetence.


Jim: Yeah, and I’ve seen businesses, and one comes to mind right now where the inheritor of the business is a much better boss than their parent was. I can think of one very notable example. A guy that’s a pretty good friend of mine, and he just has taken the business in places his father never could’ve taken the business. He’s a much more humane and caring person, I think, in a lot of respects than his father was. It can work the other way as well, but it’s the sense of entitlement. “I’m the boss because somebody made me the boss and if you don’t like it, you can go piss up a rope,” or whatever.


Steve: Yeah. Is there a way to guard against it happening?


Jim: I think that, again, I keep coming back to this theme. You’ve got to stand up to people like this. You’ve got to say, “No, that’s wrong. I won’t do that. I can’t do that. That would be immoral. That would be incorrect.” If you have fear of losing your job and you’re in a tenuous position financially, maybe you can’t do that. This person isn’t going to change their behavior until people stand up to them.


Steve: Right. If they haven’t worked their way up, if they don’t own the company through sweat equity, but rather through just birthright …


Jim: They need people who stand up to them. They need people who mentor them. They need people who are tough with them, because sometimes their parents aren’t. Sometimes the parents have a really hard time holding their kids accountable for anything.


Steve: After the break, the passive aggressive boss. One of the most classic clips in horrible boss history when we come back. You’re listening to The Boss Show.


Speaker 1: It’s a northwest lifestyle weekend on COMO News. The Boss Show continues.


Jim: Hi, I’m Jim Hessler. I’m the business guy.


Steve: I’m Steve Motenko. I’m the psychology guy. You’re listening to an episode of The Boss Show that’s treating the worst bosses in film. This next one has become a cultural icon. This is from the movie Office Space.


Bill: Hello Peter. What’s happening? So, Peter, what’s happening? Hello Peter, what’s happening? We have sort of a problem here. Did you see the memo about this? Um, I’m going to need you to go ahead and come in tomorrow. Oh, oh, and I almost forgot, uh, I’m also going to need you to go ahead and come in on Sunday. If you could be here around nine, that would be great. If you could just get to that as soon as possible, that would be terrific. If you could just go ahead and make sure you do that from now on, that would be great. And, uh, I’ll go ahead and make sure you get another copy of that memo.


Steve: That was Bill Lumbergh in the movie Office Space. Even if you’ve never seen the movie, you have heard some of those phrases.


Jim: Absolutely.


Steve: He’s the ultimate manipulator. The ultimate passive aggressive boss. He avoids direct communication at all costs. He sneaks behind people’s back. He hides behind his positional authority. He hides behind company policy, and he acts like everything’s fine and he’s everybody’s best friend when he so clearly isn’t.


Jim: Well, passive aggressive is the perfect terminology for this. This is a guy that never comes right out and says what he’s thinking. He says, “Well, we’re going to need you to work on Sunday,” or what have you. He should’ve won an award for this role. It’s so iconic.


Steve: Yeah.


Jim: He did such a great job. The movie just speaks to so many people who feel powerless, who feel disrespected. I think when somebody’s passive aggressive with you like that, there’s a feeling like they’ve got an agenda. They’re trying to get something out of you in a very kind of insidious way.


Steve: They don’t have the cajones to put that agenda on the table.


Jim: To ask for it. Exactly.


Steve: They work it behind the scenes.


Jim: Yeah. It just feels awful.


Steve: Yeah. As you said earlier, it’s a matter of insecurity. This next one is also a very insecure boss, but as opposed to being passive aggressive, this guy is just passive. This is Steve Carell’s character in the American version of the TV show The Office.


Michael Scott: I guess the, uh, the atmosphere that I’ve created here is that I am a friend first and a boss second.


Dwight: People sometimes take advantage, because it’s so relaxed.


  Can you reprimand him please?


Creed: How do you know it was me?


Dwight: It’s always you. Are you going to discipline him or not?


Michael Scott: Oh, discipline. Kinky!


Jim: He had a toadie. Right?


Steve: Right.


Jim: The Rainn Wilson character was a toadie who would tell him anything he wanted to hear. That makes bosses worse too.


Steve: Yeah. This is a guy, if you are completely conflict avoidant, if you’re more focused on being liked than on doing what’s in the best interest of the company, then maybe you shouldn’t be a boss. It reminds me of what I often say to our workshop cohorts, Jim, which is most leadership development programs talk about how to be a leader and we don’t start there. We start with the if.


Jim: The choice.


Steve: Some of us are not cut out to be leaders, like Steve Carell’s cut out to be a great character in a TV show.


Jim: Yes. You’re listening to The Boss Show.


Speaker 1: Now back to Jim Hessler and Steve Motenko. This is The Boss Show on COMO News.


Jim: I’m Jim. I’m the business guy.


Steve: I’m Steve. I’m the psychology guy. We owe a big debt of gratitude to our friend Abby Reedy, who’s a blogger who put together the clips for her blog post The Worst Bosses in Film and also edited the audio for us. Thanks, big shout out, thanks to Abby. The last one we want to play is the arrogant know-it-all boss played in this case by Alec Baldwin in the movie Glengarry Glen Ross.


Alec Baldwin: I can go out there tonight. The materials you got make myself $15,000. Tonight. In two hours. Can you? You drove a Hyundai to get here tonight. I drove an $80,000 BMW. That’s my name.


Steve: I love it.


Jim: I love it. A Hyundai. Hi-yo, I owned a Hyundai. Wait a minute. Does that make me a loser?


Steve: He’s talking to you. Yes it does. Don’t you forget it. The Boss Show is produced by Boss Media Productions and our sound engineer today is Kevin Doderall.


Jim: If you missed any of the show, you can get it in its entirety at and that’s where you can also go to subscribe to the podcast version or contact us for any reason at all.


Steve: You can also chat with us on Facebook and Twitter. You can send us an email at


Jim: Thank you for listening.


Steve: And don’t forget rule number six.



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