630: How to Work with a Boss You Don’t Like with Katherine Crowley

Pete Mockaitis
Katherine, thanks so much for joining us here on the How to be Awesome at Your Job podcast.

Katherine Crowley
Hi, it’s so fun to be with you.

Pete Mockaitis
Well, I’m excited to dig into your wisdom. And you also got your own podcast called My Crazy Office. Could you tell us perhaps one of the craziest office stories you ever heard.

Katherine Crowley
Oh, my gosh. Well, actually interesting, one of my most strange experiences was when I was working for a business owner, and she was running two businesses at the same time. And so, my entire workday consisted of finding notes passed under the door of the office that I work in, in her home, and fulfilling whatever the task was that was required, having no idea what the output was, you know, what the outcome of my work was actually creating, and rarely seeing her except once or twice every couple of weeks. So, that was a strange, that’s what we call an absentee boss situation but it was just so strange because I was living in this world where I don’t fully understand what went on.

Pete Mockaitis
Okay. Well, so you have logged a whole host of such boss behaviors, and you’ve got a great title in your book Working for You Isn’t Working for Me: How to Get Ahead When Your Boss Holds You Back. So, tell us, what’s the big idea behind the book?

Katherine Crowley
Well, actually, what’s interesting is that book, Working for You Isn’t Working for Me, came out of the first book we wrote Working for You is Killing Me, which was actually more about peer-to-peer managing up, managing down. And when that book came out, it was a national/international bestseller because it spoke to the pain of so many people. But the one thing that everyone told us, because Kathi Elster and I traveled all over the country giving talks and workshops about how to handle difficult people at work, and every lecture someone would come up and say, “You don’t understand. It’s my boss. That’s different. This person can fire me or demote me.”

And so, we realized that we needed to write a book specifically about dealing with the boss because what we learned was that people don’t quit jobs, they actually quit bosses. So, Working for You Isn’t Working for Me was about coming to terms with, “If you have a difficult boss, how do you manage them rather than waiting for them to manage you?”

Pete Mockaitis
Oh, well, there’s much to dig into here. So, let’s start with your four-step program for dealing with difficult bosses. Can you lay out those four steps and give us some examples of them in action?

Katherine Crowley
Absolutely. And the interesting thing is from the Working for You is Killing Me there’s a four-step of unhooking, and we apply the similar thing to the Working for You Isn’t Working for Me. So, I want to talk about the unhooking process because I think it’s very effective if you can do it. So, the four steps are that you unhook physically, you unhook mentally, you unhook verbally, and you unhook with a business tool. And that means nothing except that the first thing you have to realize is that you’re hooked. So, you know that a boss is getting under your skin if you find that you’re having physical, emotional, mental reactions every time you interact with this person.

And so, if you notice that you get a headache, that your stomach feels tight, that your shoulders hurt, that you have a hard time breathing, that you feel exacerbated after every meeting, you then can establish that you are hooked. Once you established that, then you can start to unhook. And the unhooking physically part, so let’s imagine the favorite tough boss, which is the micromanager, the super controlling, oversees everything you do, and doesn’t let you make any decisions on your own. If you had that kind of a boss, what you could do to unhook physically would be that you might, at the day’s end, work out, or go for a run, or go for a walk. You could splash water on your face, you could go for a drive, you could do something physically that helps you release the toxic energy that you may generate by having to deal with this person day in and day out. So, that’s unhooking physically.

Then, unhooking mentally has to do with kind of talking yourself off the ledge. So, let’s say your – this is very common – micromanaging boss insists that you report on every single thing that you do and everything your team does, and you find that to be just offensive. Unhooking mentally, after you’ve cooled your system down by physically unhooking, would be to ask yourself some important questions, like, “What’s happening here? What are the facts of the situation? What’s their part? What’s my part? And what are my options?”

So, going back to the micromanager, what’s happening? “This person is insisting that I give reports on a daily basis about what everyone is doing and it’s ridiculous.” What are the facts? “My boss is requiring this of me and it’s part of my job.” What’s their part? “So, maybe they’re super controlling. They don’t trust anything we do. It drives me crazy.” That’s the fun question to answer. But then what’s my part? And in this case, it could be that, “My part is that I’m taking their behavior personally, that I’m assuming that this person only doesn’t trust me, and that it’s all about not respecting my work ethic.”

So, then your options are, with a micromanaging boss, you could continue to resent them. That’s always…you’re allowed to do that. You could quit. You could badmouth this person and tell everyone how horrible they are and hope that they quit. Or you could say, “Okay, I’m working with someone who needs control. And so, what would happen if I just followed their requests and see if I can establish trust with this person?” So, that’s where you could get to by mentally unhooking.

Next, unhooking verbally is saying something to move the situation forward. So, with this boss, there’s a high-road and low-road verbal communication. Low-road would be, “I can’t believe we have to write these stupid reports. Don’t you think we can do our jobs?” High-road could be, “I understand that you’re concerned that we’re all on the same page, so let’s try this out and meet in a month and see if it really works as a system.”

And then, unhooking with a business tool is to pick from some kind of thing, whether it’s a procedure, a policy, a document, to complete the transaction. And so, in this case, you could say, you could send a follow-up email and say, “I understand that we’re going to be doing this reporting system for a period of time. I look forward to tracking it and seeing if it really works for you and open to feedback along the way.”

And so, now you’re taking yourself from the hooked part where you’re furious, you can’t stand the person, and you are in a powerful struggle with them, which is usually what happens with bosses that we don’t like, we get in power struggles, to calming your system down, finding viable solutions, and moving the situation forward.

Pete Mockaitis
And so, the business tool piece there, that was just sort of an email or are there different business tools? Tell us what you mean by that.

Katherine Crowley
It in this case it’s an email. So, business tools, what we’d say about those is those are…they’re actually, they’re always with you. They take the emotion out of a situation, because, so often, what happens with bosses and coworkers who drive us crazy is we take them personally, right? So, business tools, anything that clarifies the parameters of your work situation. It could be a job description. It could be company policies. It could be documentation. If someone does something over and over that drives you nuts, usually we just store the instance in our mind and feed a big ball of resentment. What you could do instead is document. That’s a business tool, to write down what happened, to describe the effects that it’s having on your job, to be clear about the costs that may come, that it may cause the company.

So, it’s taking whatever the situation is and looking, “What’s the business tool I can apply here?” whether it’s, let’s say, if someone’s a chronically late person, well, there may be time policies at your workplace that you could apply to the situation rather than feeling insulted by their tardiness.

Pete Mockaitis
Okay. Thank you. Well, so those are the four steps of unhooking there. And you’ve zeroed in on 20 of these behaviors that drive you bonkers. And so, I’d love to get a quick rundown of those if you can give us the cool 30-second version list of all 20. But I’d also, first, actually, I want to hear, you say that often these can even escape detection in the first place. So, can you tell us a little bit about the detect side of things?

Katherine Crowley
Yeah. So, detecting, that’s a very good question. What usually happens is we start to feel irritated. We start to get angry if someone starts to really bother us, and then we get into a whole tailspin, emotional tailspin, about what’s happening. Detecting requires that I look up from my situation, try to figure out “What is going on here?”

So, for example, if there’s a kind of boss that we would call a calculating confidant. And this is a kind of boss that would pull you in and ask you a lot of personal questions and look like they want to get to know all about you, and then use that information against you later on down the road. Of course, when that happens, it feels horrible and like betrayal, and, “How could this person do that?”

But if you actually detect or figure out that, “I’m working with someone for whom this is their style, this is how they operate,” then it gives you just a little distance so that you aren’t just feeling manipulated and poorly treated by this individual. So, does that make sense?

Pete Mockaitis
Understood. So, detected, in so doing you would sort of give a label and some distance, and you say, “Okay, this is not personal. They’re not sticking it to me in particular. This is just sort of how they operate and I hate it.”

Katherine Crowley
Right. Exactly. And if it’s something, like there are bosses who are chronically late. So, if they’re chronically late, to detect and understand that this is, again, this is what they do. It’s probably what they’ve done with every employee that they’ve ever worked with. Then it just gives you a little modicum, I think, of control that, “This is what I’m dealing with, not I’m doing something wrong and it’s driving me crazy.”

Pete Mockaitis
Okay. Well, can you give us the listing of these 20 bad boss behaviors because I’m sure we could talk for hours about them? But I wanna hear just the quick rundown like, “Okay, we got this and this and this,” so folks can recognize it in your telling.

Katherine Crowley
All right. So, I’ll just give you the list and then you can see what you think. First of all, we have categories. So, the first category is called the game players, head game players. And the top of that list is what we call the chronic critic. Then we have the rule changer, the yeller, and the underminer. Next category are the bigshots and the mother superiors. Under that we have “I’m always right,” “You threaten me,” grandiose, and control freak.

Next category is called the line crossers. These are the people who have bad boundaries. So, the first of those is lovestruck, next is the calculating confidant that I mentioned before, the tell-all, the first person who tells you more than you ever wanted to know about their life, and then the liar-liar. Next category is ambivalent leaders, and this is always interesting, I think. The first is the sacred cow, which I’d be happy to describe at greater lengths; the checked-out boss also known as the absentee; the spineless; and the artful bosses, the person you can never find in your hour of need.

Then, finally, we have what we call delicate circumstances. And that is the junior boss, someone who is younger than you, significantly younger than you; the former colleague, a colleague who gets promoted above you; the unconscious discriminator which is, these days, a very hot topic; and the persecutor. That’s the cast of characters.

Pete Mockaitis
Okay. Well, thank you. I think it’s handy just to have a sort of typology in terms of, “Okay. I recognize that.” So, we could talk about these 20 in depth. But, maybe, you could zero in on maybe one, two, or three of these that are both particularly demoralizing for people as well as super prevalent? So, there’s both a high frequency and a high intensity of damage, so let’s talk about those three in terms of how we deal with them.

Katherine Crowley
Yeah, I would be happy to. I actually want to start with the sacred cow, Pete, because this is one…what’s interesting is this is a boss who will feel so frustrating but they’re often like nice people. You know what I mean? So, a sacred cow is someone who’s been in their position for a long time, they’ve climbed up the ladder of the office, whatever it is, the company, whatever it is. They usually are…the people at the top are loyal to this person because they were loyal to them, and they’re now in a position where they probably don’t have the competence really to do anything significant. So, what they want to do is just toe the line, not make any ruffles, and just do a basic job but not cause any problems.

Pete Mockaitis
And so, in this instance, the boss is the sacred cow that a lot of people say, “Ooh, maybe I don’t want to cross them because they’ve historically been really good to me and…”

Katherine Crowley
That’s right. The sacred cow has friends, usually, at the top. They’re protected in some way. And so, what could happen is, let’s say you’re a very inventive or creative person and you get hired by this person, and as you’re getting higher, they’re saying to you, “We really need innovation in this department,” which may be true. But then once you get into the position, you experience that you are blocked at every step of the way. Any new ideas, they’ll say, “We’ve done that already. It won’t work.” They’ll ignore your best thoughts about how to solve a problem. They will tell you that upper management doesn’t want that kind of thing. So, they’ll do whatever they need to do to sort of put a road stop onto anything you’re trying to accomplish.

And for people who are real performers and who like to achieve and contribute, this kind of boss is deadly. Yeah, and so the thing with the sacred cow is that, going back to detect, the four Ds: detect, detach, de-personalize, deal. With the sacred cow, the first is to detect, like, okay, if you find out that someone has been there for many years, and they’re not going anywhere, and you keep pushing up against this person, which is usually what happens when you’re working for a sacred cow, you get in power struggles of constantly trying to push your ideas forward. Then you detect, you’ve got, “I’m working for a sacred cow. They’re not going to become comfortable with change. They’re not going to want to do anything innovative.”

Then the detaching would be, “Okay, this is not about me. This is about them.” And de-personalizing would be to say, “All right. So, this person is afraid of change, but maybe they need to look good.” Sacred cows still want to look good in whatever position they’re in. And so then, the deal, what can you do, would be to find out, and this is very hard if you’ve already pushed hard and been rejected and feel resentment, but the deal part would be to find out if there are any projects that the sacred cow is interested in, like things that they would love to accomplish if they had the ability, and get behind those ideas or try to make your ideas their ideas. So, if you’re willing to make the sacred cow look good, you may actually be able to make progress.

Pete Mockaitis
Okay. Thank you. All right. So, that’s a handy one then. Can we hear another boss here and how we’d approach it?

Katherine Crowley
Yeah. So, a commonly occurring and destructive, I would go to the very top of the list, which is the chronic critic. And it’s funny because we have another version of the chronic critic in Working With You is Killing Me called the pedestal smasher. And these are the bosses who have very high standards for everything, and often when they first bring you onboard, they tell you that you’re wonderful and that you’re finally going to solve their problems and that they really admire your work capacity.

Once you start working for this kind of boss, the chronic critic, they then begin to find fault with everything that you do. And so, they slowly start to erode your confidence because they can always find the wrong thing. One client we had who worked for a chronic critic used red highlighter, under-liner, even online with documents to show where the mistakes were. And, literally, it got to the point where the client was like, you know, they’d go to meetings with their neck in a brace because it was so hard to deal with this person.

So, they slowly can erode your confidence and, therefore, detecting as soon as possible becomes a really important thing when you find out, and you can always ask around to see, “Is this person, have they always been so critical of everyone or is it just me?” You detect but nothing. They don’t ever find things good enough because part of what they’re doing is trying to keep you below them so that you don’t threaten them, right? So, you detect that.

Then, again, detaching, realizing this is not about you. And chances are you’re never going to have the experience where they say, “You did an amazing job.” De-personalizing is, “Okay, so if that’s how this person operates, then my job is to continue along and try to create, try to do a good job but not take their statements personally.”

And then dealing would be to do your job, to go to other places to get recognition. So, you may want to join a taskforce, or go work with another department on a special project, or go outside and join a professional association. Nowadays, those are all happening in online and meetups and things. But you do something like that to pump up your confidence again so that you can figure out what your next best move will be.

Pete Mockaitis
Okay. Well, now, could you tell us an inspiring story of someone who did just that, they figured out, “Okay, we got a troubling thing in this behavior,” what they did, and then the cool outcomes that unfolded from that?

Katherine Crowley
Yes. So, actually, I can tell you about someone who worked for a sacred cow and it was actually for a very prestigious institution, he was very excited about the job, got there, and then had pushback for every single thing that he did. He was able to befriend that sacred cow after much frustration, a lot of hitting walls. He was able to befriend that sacred cow and found out that that individual, the boss, had a very specific project that she’d always wanted done but had never had the resources to do. He made it happen and, as a result, their department won an award, and he went on to be offered another job at another institution.

Pete Mockaitis
All right.

Katherine Crowley
So, there’s a good story.

Pete Mockaitis
Beautiful. And I’d also love to zoom in and hear sort of navigating these tricky situations, are there any particularly powerful scripts, phrases, questions, that you recommend and see are helpful over and over again?

Katherine Crowley
Yeah. Well, I think that’s such a good question. When we wrote, in both of our books, when we talk about talking to whoever the individual involved is, we always talk about how important it is to prepare yourself. Like, one thing that’s valuable, I think, actually in knowing, like, let’s say you know that you work for a boss who always has to be right, for example. And there are those bosses, so you don’t want to go into the conversation looking to convince them that you’re right. You would prepare for that kind of a conversation by thinking, “Okay, how can I join with this person and their approach?”

So, you could say to this individual, “I know your opinion is very important to me, and I know that you usually understand things in a way that I don’t, but here are my thoughts about doing X, Y, and Z.” So, you confirm the individual’s capabilities, you try to talk to them in a way that makes sense based on how they hear and reason with things, and then you make a concrete suggestion about how you can move forward.

Pete Mockaitis
Okay, cool. Well, now, can you tell us a favorite quote, something you find inspiring?

Katherine Crowley
My favorite quote may seem odd but it is by Hoagy Carmichael, a jazz musician, and it is, “Slow motion gets you there faster.” And I like it especially because in the digital age we’re all constantly running – I certainly am, I’m sure you are as well – and constantly on the go, and wanting things to happen quickly. And so, I find that quote “Slow motion gets you there faster” really helpful because it helps me slow down, focus on what needs to happen in the moment, and have patience with the process. I think that’s one of the biggest challenges in any situation, and certainly in a difficult work situation is to be patient with the process.

Pete Mockaitis
And now could you share a favorite study or experiment or bit of research?

Katherine Crowley
Yes. So, one of the studies that we did actually was for our third book, which was Mean Girls at Work. And there, we put out a request for any stories that women had about other women who they found difficult to work with. And what we were able to glean was that, I would say, 40% of the studies, or 40% of the stories rather, what was interesting was they were not about blatantly mean cruel individuals. They were what we call passively-mean situations where people were excluded, where they were taken out of an email link, where they were not asked to join an event, a work event, or even a social event, where they were contradicted at a meeting but in a nice way, it’s that sort of passive-aggressive looks like.

And so, we found that really interesting that 40% of the women who had difficult relationships with other women, it was more of a passive-aggressive experience, and it really informed a lot of what we wrote about in the book because women do a thing called tending and befriending. We believe we need to be nice to each other and yet what happens in the workplace, because we’re not that comfortable with direct confrontation, is that people end up tending, acting friendly, and then doing subversive things.

Pete Mockaitis
Well, thank you. And how about a favorite book?

Katherine Crowley
So, my favorite book is Eckhart Tolle, Towards a New Earth.

Pete Mockaitis
Okay. And a favorite tool, something you use to be awesome at your job?

Katherine Crowley
So, I practice what we preach, so I will say that I do, on a daily basis, every morning I exercise and I write a list of what are my top three priorities. And at the end of every day, I also exercise again, and I practice gratitude. And I know that those things don’t sound like business tools per se, but those set the tone for the rest of my day.

Pete Mockaitis
And is there a particular nugget that you share that really seems to connect or resonate with folks, readers, listeners, they quote it back over and over again?

Katherine Crowley
Yes, there are two. And one is…

Pete Mockaitis
Nice job.

Katherine Crowley
So, I’m a psychotherapist by training, so one of the things that I will tell people is that, “If you’re feeling hysterical, it’s usually historical.” Now, I did not make that up but it is such a truism that whenever I say it, people are like, “Oh, my God, that’s so true,” because it’s not the person showing up late for a meeting. It’s probably the 35 times they showed up late, and the time they were late on a deadline, and the time, you know, whatever. And that’s a valuable statement just in the sense that, again, going back to the things we were talking about, unhooking, detaching, you have to calm yourself down so that you respond in a right-sized way to whatever the situation may be.

Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?

Katherine Crowley
I would point them to our website KSquaredEnterprises.com and also to our podcast which is My Crazy Office.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Katherine Crowley
Yes. My final challenge, actually my call to action is to whatever your situation, if there’s someone who is really bothering you, there are two things that you can do. One is that you need to stop and see whether you are in a power struggle with this person, because power struggles you will not win. The second thing is you need to consider whether you’re expecting this person to behave exactly the same way you do. So, it’s always important to examine your expectations. We often get furious of people who do things that you say, “I would never do that,” and yet the most important thing for figuring out how to work with people is to understand that each person is operating from a different set of expectations and behaviors.

Pete Mockaitis
Well, Katherine, this has been a real treat. I wish you luck and success, and hope that working with people is working for you.

Katherine Crowley
Thank you, and talking with you has been lovely for me.