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How to Manage Your Boss | That’s a Good Question

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People don’t leave companies, they leave managers. This means that your ability to develop a highly effective and respectful working relationship with your boss is key to your job satisfaction.

But what happens when your boss is a roadblock making it feel impossible to function and succeed as a team? In this episode of “That’s a Good Question,” our listener finally reached a tipping point after four years with a boss who struggles daily to manage the team, projects, emails, and meetings.

Through active problem solving, practical advice and shared experiences, we will offer tips and tricks for managing up, addressing personality differences that impact manager/staff relationships, and effective strategies for better working with your boss.

Guest Expert: Mary AbbajayMary Abbajay

Mary Abbajay is the president of Careerstone Group, LLC, a full service organizational and leadership development consultancy that delivers leading-edge talent and organizational development solutions to business and government. As a sought-after author, speaker, consultant, and trainer, Abbajay helps clients develop the strategies, skills, and sensibilities needed for success in the 21st century. She is a frequent expert contributor for television, radio, and print publications in the greater Washington area where she provides practical leadership and career advice. Abbajay currently serves on the Market President’s board of BB&T Bank, and is a past chairman of the board for Leadership Greater Washington. In 2010, she was named as one of Washington Business Journal’s Women Who Mean Business, and she was a Smart CEO Brava Award recipient in 2017. Abbajay is the author of Managing Up: How to Move Up, Win at Work, and Succeed with Any Type of Boss. @maryabbjay

Our Host: Celeste Headlee

Celeste HeadleeCeleste Headlee is a communication and human nature expert, and an award-winning journalist. She is a professional speaker, and also the author of Speaking of Race: Why Everybody Needs to Talk About Racism—and How to Do It, Do Nothing, Heard Mentality, and We Need to Talk. In her twenty-year career in public radio, she has been the executive producer of On Second Thought at Georgia Public Radio, and anchored programs including Tell Me More, Talk of the Nation, All Things Considered, and Weekend Edition. She also served as cohost of the national morning news show The Takeaway from PRI and WNYC, and anchored presidential coverage in 2012 for PBS World Channel. Headlee’s TEDx talk sharing ten ways to have a better conversation has over twenty million total views to date. @CelesteHeadlee

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Episode Transcript:

Celeste Headlee:

So, Lynn first give us an idea of what kind of work you do and what kind of workplace you work in.

Lynn:

So, I am in the pharmaceutical industry and I work in quality assurance for document control and quality systems, which also does include the training aspect of things.

Celeste Headlee:

Okay. And your issue essentially, is that your manager isn’t functioning as efficiently as they can. Is that accurate?

Lynn:

Yes. Most definitely.

Celeste Headlee:

Okay. So, give me some specifics here. What is going wrong?

Lynn:

Truthfully, I feel that she is in a state of … It’s an unstructured and undefined environment. So, unstructured in that the team, we’re right now we’re a group of four. We were five at one point. So, we’re a group of four. There’s no specific, aside from knowing that I handled the doc control side and one of my counterparts handles the training side, there’s not a lot of definition in who’s doing what, structure of projects, meetings. We have a lot of last minute ones-off five minutes before a meeting, “Hey, can you jump on this meeting with me?” And then you’re asked to drive the meeting without knowing … Yeah. Yeah. There’s been times I have to remind her, “Are you jumping on this meeting.” Or, “Hey, did you see this email?” The responses are typically, “Wait, what meeting? What email? I have 4,000 emails.”

Celeste Headlee:

Okay.

Lynn:

Yeah. She’s very involved, which is a wonderful thing, but sometimes too much is not good. A lot of external, both personal and clubs or activities, as well as everything internal that she could possibly join, she joins. I am looking at it as maybe it’s a distraction. There’s been times I’ve been on meetings, addressing situations, and she says, “I have to go.” And when look at the calendar, I see it’s one of the club meetings. And I literally said the last time I said, “Oh, is it this club?”

Lynn:

“Yes, yes.”

Lynn:

I said, “Oh, I have that on my calendar too. But I don’t have time to join it because I have to figure this out.”

Lynn:

The response was, “I got to go, I have to go.” And jumped on the other meeting.

Celeste Headlee:

So, it sounds like she is just taking on too much so that she cannot take care of her core responsibilities.

Lynn:

Right. And I think my … Let me apologize in that I probably should have started it off by saying she is a quality systems manager with no quality systems experience. She has vocalized to numerous people multiple times.

Celeste Headlee:

Okay. And have you spoken with her about any of this?

Lynn:

Absolutely. I’ve asked for structure. I’ve asked for, let’s go through all of our projects, let’s you and I work together to build this team, we know what’s going on. I even went and checked your … We did one of those evaluations of her personality. I said, “I even went so far as to go into your office, look at your blocks to try to figure out a better way that maybe I can communicate to you.” And I said, “At this point, I don’t know how else I can ask for structure in any other way, shape, or form.”

Celeste Headlee:

And what was her response?

Lynn:

She takes it well, she apologizes. “I definitely want to work with you and try to create this environment.” I explain to her, I am a very structured person. I like structure. I like process. I’m willing to admit that maybe I have to loosen up on that a little bit. I have no problems doing that. But we have to start somewhere. And then we fall right back into the same process.

Celeste Headlee:

Okay. So, it sounds like chaos. Let’s bring in our expert because I feel like I have a good, at least a beginning, sense of what’s going on. And we have exactly the right person for you. Mary Abbajay. Her book is called, Managing Up: How to Move Up When At Work And Succeed with Any Type of Boss. She’s the president of career stone group. And she’s got 20 years, at least 20 years, of experience in this area. So Mary, this is your wheelhouse, is it not?

Mary Abbajay:

Oh my gosh. I am just sitting here biting my tongue. So, this is such a classic case of managing up. So, I’m just going to dive right in if that’s okay.

Celeste Headlee:

Yeah, absolutely.

Mary Abbajay:

So first of all, Lynn, I want to say you have my deepest empathy on this situation. I too am a very structured person. Chaos, impulsivity, scattered braininess drives me cray cray. And so before I give you some kind of tough love and some advice that is going to be very pragmatic, let me say this would drive me to distraction. So, a couple of things that I just want to recap that I think we know.

Mary Abbajay:

One is that her style of management isn’t your cup of tea. It’s a little scattered. It’s not very structured and it is not really working for you. Okay, is that right?

Lynn:

Absolutely.

Mary Abbajay:

Okay. And I believe that you have talked with her boss about her style management. Is that right?

Lynn:

I did. I mentioned it. I brought it to his attention about three years ago and I was greeted with, “Well, I understand. She’s got a lot on her plate.”

Mary Abbajay:

So, what we know then is that her bosses are okay with her performance in some way, shape or form because they’re not going to do anything about it, right? And so we know that. And here’s the other thing that we know based on your story, that she’s not really going to change who she is. So, given that reality, we’ve got to figure out a way that you can work with this person, whether she’s going to change or not. So, she’s not a bad person, right? She’s not like a tyrant or a narcissist or a gaslighter or a bully or a freakshow like that, is she?

Lynn:

Absolutely not. Love, love, love her. Wonderful person outside of work.

Mary Abbajay:

All right. So, here’s my tough love for you. When we are dealing with a boss, a boss that doesn’t work for us, we have to realize that they’re not going to change who they are. We can make requests for how we want them to manage us or interact with us. And it sounds like you’ve done that. And like any request, some people aren’t capable of making them.

Mary Abbajay:

So, when you’re faced with a situation like this, I want you to think about it, that you have three different choices. This is what the Buddhists tell us. Your first choice is to really just deeply accept it. Accept who she is, accept her flaws, and just be okay with it. Don’t get all wrapped around the act. That’s who she is, that’s who she is, and so finding a way then to actually be okay with that. That’s choice number one and that can be really hard.

Mary Abbajay:

Choice number two is to find something that you can change about the situation. And since we can’t change her, we’ve got to figure out what you can change either in your attitude towards her, or in the way you interact with her, to make the relationship work for you, for her, and for the organization.

Mary Abbajay:

And the third choice that you have with something like this is quite frankly to leave the situation. And that is to find a different position in the company or to find a different job because we know the management of the organization isn’t going to do anything about her style of managing, and we know that she isn’t going to change. So, it really then comes up to you. What do you want to do? Do you want to find a way to work with her? Can you accept the way she is? Or do you feel like you are at the point now where you need to leave?

Lynn:

So, I’ve voiced my opinion about looking for other position within the company to both her, and at the time, her manager. We had a little bit of a structure change, an interim, so her manager stepped up and another manager stepped in to be her interim boss. So, I’ve definitely voiced that I want to look for something else.

Lynn:

I’ve also just recently spoke with my counterpart, who’s been very nervous about being vocal and I’ve gotten him to a point where I said, “Look, maybe if we get together,” I said, “And this is not an attack. This is not, we’re trying to get her fired. We just want to make things better. Maybe if we both go in with a united front, discussing the issues, giving bullet point examples, maybe we can go to our interim manager who does seem to want to make changes, present this scenario and say, look, how can we restructure this team for better outcomes?”

Mary Abbajay:

Yeah. That sounds like that could work. What is the rationale for that? So, when you’re going to make a request like that, what is the business case for it? Can you pinpoint to how her management style is actually making the team less productive or less positive?

Lynn:

Absolutely. In the times that we are told to jump on meetings, we’re pulled away from other work. The lack of structure has us working on multiple things. Our efficiency, our timing is just all over the map. Again, what are we producing? If we’re being pulled over here and sent over here and told to stop here. There’s things that are falling through the cracks that are not being addressed in a timely manner. So, it really touches on a lot of areas of the business.

Mary Abbajay:

Okay. So, your strategy is to try to remove her or to try to get what?

Lynn:

I don’t want to remove her unless management feels, “Hey, maybe her strengths could be better used in this area.” Our area of QA is comprised of multiple departments. A better structure. Perhaps, maybe we put her more into, if she’s a senior manager, that’s another thing. She’s always diving down into all of our activities, rather than focusing where she needs to be and letting us run our shows technically. So, if we could restructure it and have management be more specific and give her specific guidelines and structure, then we can then have our structure and we can all work in a more cohesive environment.

Mary Abbajay:

Yeah. And so what are the odds of, you think, them doing that? And are you going to present a structure?

Lynn:

Yes. I’m going to present a structure. Like I said, I literally just spoke to my coworker, my counterpart this morning. He’s in agreement. We’re going to put together, again, a carefully designed layout with no threatening tones to it, just really for the betterment of the department, which will overall benefit the business and ask for, perhaps, she gets some more alignment in her realm where she should be as a senior manager and stays away from the levels with the exception of a higher level just following up.

Mary Abbajay:

Yeah. Well, I think that’s absolutely a strategy to use. What’s the danger of that strategy though?

Lynn:

I’d like to say, I don’t think there is one.

Celeste Headlee:

I’m laughing only because there’s always a danger.

Mary Abbajay:

Always a downside.

Lynn:

Exactly. Potentially if they do speak with her, depending on how they choose to go about it, it could backfire. But at this point, if that’s what happens, then that’s what happens. And I’ll adjust. I cannot do another year of in 2022 as I have ’21, ’20 and ’19. I can’t do it.

Mary Abbajay:

And that’s where I really want to go next in case it does backfire. So, on a scale of one to 10 Lynn, with one being I’m totally chill and 10 being I am going to kill someone or my it’s going to pop off, what are your emotions towards this person in this situation?

Lynn:

This person in this situation I would say is definitely a nine.

Mary Abbajay:

So, one of the things that happens to us, and maybe this won’t be that meaningful to you, but for other listeners. And this is a very common situation, sadly, that I find with my clients where there’s a real serious mismatch between the management style and the person being managed, the team. And so what happens is that when we start getting really frustrated with the other person, because as you said, she’s not a bad person, she’s just a bad boss. She just ain’t very good at managing people. She’s not a good manager for you. And so what happens when we get into these situations is that we actually get trapped by our amygdala, our reptile brain. And we go into the negative emotional state, which is not good for you. And it’s not good for your performance because that literally, when we’re in the amygdala, when we’re emotionally hijacked by somebody else, then our cortex, our smart part of our brain ceases to exist.

Mary Abbajay:

So, as you’re going through deciding on your strategy, I really would encourage you to try to get out of the hijack of the emotional situation, this is really for other people experiencing that, and try to look at the situation with a little bit of emotional distance. Oftentimes I will tell people, this is really about emotional intelligence in some ways, which I’m sure you have tons of. But it’s about really looking at this person and thinking, “Wow, what must it be like to be them?”

Mary Abbajay:

Having a little empathy. What is this person going through? Giving somebody a little grace and a little empathy as you’re dealing with them can be very helpful. Because we know that organizations promote people to management based on whole bunch of reasons. Most of which aren’t whether they’re going to be a good manager or not. They’re about their technical skills or their experience in something else. Not necessarily their experience in managing. So, if you were this woman, I’m just going to double check this for you. If you were this woman, what’s her experience working with you?

Lynn:

I think that she definitely picks up on my frustrations, but she is also aware that I have her back.

Mary Abbajay:

Yeah.

Lynn:

I will always go above and beyond to do what I need do. She knows that. That’s why she comes to me often. Yeah … I’m trying to visualize it. So, I’m trying to be fair. I’m sure she gets frustrated with me sometimes. I’m sure she does.

Mary Abbajay:

Yeah. I had a young woman once who had a boss, very similar to yours, and she was just so angry at this woman and just making this woman out to be this villain, which you are not doing with, with your boss, Lynn. And I said to her, “For two weeks, I want you to go to work and I want you not to be so damn angry at her. Have a little empathy for what her your boss is going through.”

Mary Abbajay:

I gave her a bunch of other strategies. And about two months later, I’m at an industry event here in DC and her boss comes up to me and says, “I don’t know what you did to my employee, but she’s a whole new person.” So, I always want to council people when they’re dealing with someone who’s really frustrating, to try to see what your contribution is and how that person may be experiencing you.

Mary Abbajay:

It sounds like you’ve done a lot with this person and tried to work it, so this is really more for other people. But the another thing I would say is, have you considered going to her and saying, “Hey, I know we’ve had these conversations and it’s just not working. Quite frankly, I love ya, I want to support you, and I don’t think you’re right for this job. I am going to go make this recommendation about a new structure.” Have you thought about doing that to her? Really letting her know what you’re going to do ahead of time?

Lynn:

So, I would say that I’ve had the conversation up to where I say, I’m going to recommend that you go to another line. Again, she has exhibited some territorial actions that I’ve picked up on. And by the way, I loved everything that you said earlier about having the empathy because I have definitely over the last four years, ran that train. I was angry. I was frustrated. I’m like, “She’s got to go.”

Lynn:

And then one day I finally … I’ve been doing a lot of work on myself as well doing, as you mentioned, the emotional intelligence and I’ve now taken that step. And I think having gone through those courses has gotten me to this point now where I said, empathetically, I do need to address this, but I need to address this in the best way for not only myself, but for her as well, because I understand her personal needs.

Lynn:

There’s things outside of work that are also influencing. She has a ton of personal responsibilities that she’s managing and trying to manage everything else. And when I took that time is when I realized this woman’s just got so much going on. We need to relieve her. Let’s take the plate and instead of one big plate, we make a bunch of little plates. And that’s why now I’m proposing, let’s go talk to her now interim boss with the proposition of, “Hey, maybe we need to move her into something a little different.” And try to pull back the scab on this situation, as much as it might be a little bloody or a little hurtful, a little painful, but I truly am going at it with the most empathetic way that I can for myself as well as her. Because as I said, as a person, I love her. I do.

Mary Abbajay:

Good for you. That’s really important. And I’m glad you’re approaching it this way. So, let’s talk a little just about the political dynamics at play just before you do this, just want to make sure. And Celeste, jump in if you have any thoughts on this.

Mary Abbajay:

So, you’re going to go to her interim boss. So, tell me about how the interim-ness works at your organization. My experience is interim bosses are loathed to make any big changes. Is the timing right? Or is it better to wait until there isn’t an interim? So just talk Celeste and I through that a little bit. Am I right, Celeste, about the politics of that?

Celeste Headlee:

Absolutely.

Lynn:

Oh, definitely. Politics is a slippery slope, for sure. So, the interim, I’m assuming it works the same in most companies. Somebody leaves, somebody steps in, potentially they then secure that position. Not sure that’s going to happen here. However, this individual, I’ve also taken some steps to reach out to another manager, senior manager in our group who is wonderful and loves to mentor people and we spent about an hour on the phone and she goes, “I hear you. And we’re working on things.”

Lynn:

So, he is actually identifying that the quality organization as a whole, we have a lot of work to do and they’re now recognizing that some things need to change and some structures need to happen, including restructuring. So, that’s why I think this is the best time to approach this situation with him as he’s building these new structures and new dynamics.

Celeste Headlee:

Can I just jump in for a second? Because I want to build off something that Mary has already said. And she’s already given you a clue into how you can use your knowledge of brain science to who your advantage. And there may be a place that you’re missing here because I think Mary’s right that going to an interim boss, it can be a tricky proposition to carry that off effectively.

Celeste Headlee:

However, if you guys have a good relationship, there’s reason why you can’t engage her in the problem solving. So if you go to her and say, “Here’s my issue.” Not framing it as in, “Here’s the way you’re not meeting the needs I have.” But, “Here’s the issue I have getting I’ve done efficiently. This is what is getting in the way of my success in my job. Can you help me? Can we work together on this? Here’s my idea for it. I’d love to get your feedback on my proposal and I feel like maybe we can help each other because you’re clearly overwhelmed and maybe we can help each other with this. What do you think?”

Mary Abbajay:

Well, I love it, Celeste.

Lynn:

Yeah. And I will say that I definitely have attempted that, but I will preface it with I’ve attempted it, but at a much softer level. And to your point, maybe I need to beef it up more. And instead of what I’m going to bring to her interim manager, maybe I present it to her, to your point.

Celeste Headlee:

Yeah. And again, whereas people have a tough time … If you go to somebody and say, “Here’s all the stuff that you’re doing wrong.” They are literally going to be in a defensive position. And by that I mean exactly what Mary was saying. You are going to engage their amygdala, they take that verbal feedback just as though were a physical attack.

Mary Abbajay:

Correct.

Celeste Headlee:

And so the conversation is basically over. But we also know that people who disagree with each other on almost every possible level will work together to solve problems and puzzles.

Mary Abbajay:

Yeah. And the other thing Celeste, I completely agree with you. My other concern for you, Lynn, is I don’t want this to damage your reputation. I don’t want people to think, “Oh, that Lynn, she just did an end run around her boss and got her boss canned or whatever.” So, I want you to be able to go through this process and come out smelling like a rose and not the other way. And I agree with Celeste. If you can engage this manager in problem solving, in restructuring, you’re probably doing her a favor. Because she is overwhelmed. So, I really am digging what Celeste said.

Lynn:

No, I like it as well and I am happy to give that a try. So, here’s my question. There’s two aspects. One I’m still trying to work through. What about the situation where … The quality systems that she’s managing is not her realm. So is that irrelevant of everything because look, this is the situation we’re in now so let’s just live where we’re living and just try to make it better? Or is that something that still needs to be addressed? That she’s out of the realm?

Mary Abbajay:

Well, I think that depends on what her role as a manager is and what the organization expects from her. So, at its very basic, a manager is about setting the conditions for his/her/their employees to be successful. It’s about removing obstacles, it’s about making sure the team has the resources and the direction they need. I’m not the kind of person that thinks you need to be a technical expert to be a great manager. It can help, but it also can hurt.

Mary Abbajay:

So, I am not sure. This would depend on your organizational culture. Do they require managers to be technically expert or at least experienced in their realm? I would say your better case, and you are building a case against her, which, let’s just say what it is, is really around the impact of her management style and how that impacts either productivity or positivity on the team and how the team could be better.

Celeste Headlee:

Right.

Lynn:

Okay.

Celeste Headlee:

And also you have to figure out how you sell that to her. And I don’t see that going over fairly well. And going back to the empathy part, the empathy actually can be super informative for you. And by this, I mean keep in mind that she gets home every, and she thinks to herself, “I did the best I could. I had to cut some corners, something slipped by, but I took care of the things that took priority and I did the best I could.” That’s how she’s most likely seeing it.

Lynn:

Right. And I think my other concern is that because she already has a heightened state of protecting her ground. So to add a little bit more to this situation is that she’s the only breadwinner in her home and she’s also older, which she’s expressed. She realizes, we’re getting older in industry and we all know, like it or not, some industries, people can age out, we’ll say. And I want to definitely approach it from the most friendly, concerned, empathetic way that I can. Because I know myself well enough that I can be a bulldozer in my frustrations. So, I know I’m going to have to work on dialing it back, and just really going in there from her side of it maybe is the best way to present it.

Mary Abbajay:

Yeah. Well, I will just say it is a big move that you’re about to make and I just want to make sure that you’re really thinking about the pros and cons if this doesn’t go well for you. If it doesn’t go well, if they look at and they say, “Yeah, no. We’re not going to do this. She’s just fine.” What kind of position does that put you in?

Lynn:

Yeah, that’s true. And to your point, I don’t want to stir the hornets nest.

Mary Abbajay:

Yeah. You don’t want to burn any bridges.

Lynn:

I don’t. And that’s really the saddest thing is I truly, despite my frustrations, I truly, truly just want to make it a better environment and a better again, I keep using the word structure. Not just for myself, for her, for all the whole team. And I’m really going at it with that in mind. But it could backfire.

Mary Abbajay:

It could.

Celeste Headlee:

Yeah, but here’s the thing, Lynn. As much as you are thinking of the team, you are equally thinking of yourself in your own situation, which is 100% natural. That’s not a knock on you. That is natural and that is of course how we all think. So, you might want to take a tactic that has been used in a number of hospitals when they are trying to figure out what went wrong and how they prevent things from going wrong again.

Celeste Headlee:

And the way that they do that is they all sit down to the table and they say, “Okay, here’s what happened.” And each person around the table is going to say their narrative. From their perspective, what happened from beginning to end. Beginning, middle, and end. And the reason I say that is because rather than making assumptions about what’s happening with her, what her priorities are, what she’s thinking, how she makes these decisions, you need to hear from her and that’s going to make the problem solving better because we all only have our own perspective, right? It’s the cliche of, if two people watch a parade, both of them are going to see two different things.

Celeste Headlee:

So, at this point you’re missing some valuable information, which is why is she managing like this? What are the choices she’s making from her perspective? What is happening on your team? And then you can begin to problem solve.

Lynn:

So, would we do that in a group setting? I would worry to a degree that she could feel more threatened that way. Perhaps if we’re all, she may look at it as being ganged up on.

Mary Abbajay:

Well, I think this is something you’d probably want to have an external facilitator come in and have some problem solving conversation. We do this all the time with clients. And it’s really about, all right, what’s working well with this team. What could we do more of, less of, or differently? And there’s ways to make it less threatening. It’s the sort of conversation where you don’t just have it one time, you have it multiple times.

Mary Abbajay:

And if she doesn’t have enough structure and you all want structure, then let’s have a conversation as a group about what that structure would look like. And it sounds like you might, if she goes to you for things, it sounds like you could actually move into be her fake deputy. Here’s the structure the team wants to have and here’s the processes. We’ve really thought this through. What do you think? So, it’s slowly taking some of the things out of her response, her role, and having the team create it.

Celeste Headlee:

Yeah.

Lynn:

And I started doing that with my counterpart and the other woman who works with me. I check in with her every day. “How’s everything going? Do you need anything? What are you working on?” To try to get a feel for what their day is like, how they’re doing. And I don’t have a problem doing that. My only concern is just hitting the wall because as I said, I’ve already asked her for structure. And haven’t just said, “I need structure, period.” I’ve said, “We need to go through projects. We need to see who’s responsible for what. What do we have coming down the pipeline?” I’ve laid it all out and said, these are the things we’d like to work on. But to your point, get more feedback from my counterparts and put a plan together.

Mary Abbajay:

Yeah. Stop asking her, start telling her.

Lynn:

Yeah. Yeah.

Mary Abbajay:

Like, “Do that.” She’s never are going to give you what you want, Lynn. She’s never going to be that person. So, what your team has to do, they need to create that structure and present it to her. Be more proactive. And by the way, it’s going to take her a couple times to get it. So, you can stop asking for that from her. Start saying, “We’ve put this together. We’d love your feedback. Here’s how we think we should proceed.”

Lynn:

Okay. Listen-

Celeste Headlee:

Yeah, because you’re asking for structure and she doesn’t know how to deliver it.

Mary Abbajay:

Yeah. She doesn’t.

Celeste Headlee:

You’re at an impasse.

Lynn:

Right. And even though my thinking that, by saying, “Let’s structure our projects.” But if she’s not even aware of what we’re doing, which is sometimes … Like right now, we have to do weekly trackers of everything that we do in the course of a day and provide this to her weekly. So part of me goes, “Does she even know what we’re doing?” I know she understands the basics. She knows I work in this system and my counterpart works in this system and has a very general knowledge. But there’s also been experiences I’ve had with her where I’ve taken the reins and done something. And I get, “Well, that’s funny. I thought I was the manager.”

Mary Abbajay:

That’s fine. Say, you are. What more can I do for you?

Celeste Headlee:

Yeah.

Lynn:

My response was almost, “Well, then by all means, please manage.” But I did hold back.

Mary Abbajay:

Yeah. And when she says stuff like that to you, you just say, “I’m really trying to help you. I’d love to take more off your plate.” In some ways, I’d like you to see what are the upsides of this kind of a boss? It sounds to me like the upsides of this kind of boss might be that you have a lot of wiggle room to do what you do and be an expert, or am I wrong?

Lynn:

I think I do. Yes. And I just have been taking things on and pushing through and sometimes it works and other times it doesn’t. So to your point, maybe we just need to communicate more. But not just more in words, in actual details.

Lynn:

I feel like what I’m hearing from you is maybe there’s just too much talking and people aren’t really listening. Maybe we need to present more details and that’s how we’re really going to sort it out and iron it out.

Mary Abbajay:

Yeah. And just stop asking her for structure, Lynn. You’re not going to get it. Instead, create the structure. You and your team can band together and create structure. She’s a little bit on the impulsive side, and what we always say when you’re working for an impulsive is whether you like it or not, it’s going to be your job to put guardrails around it. It’s a better team sport than an individual sport. So, with her scatteredness and her impulsivity and her lack of structure, I really do encourage you and the team to pull together and create a structure that’s going to work for you, that’s going to work for her, that’s going to work for the organization. And it’s not a formal structure, but it’s enough structure that you all can really be productive and positive in your careers, in your workplace. Stop waiting for her to give it to you. She’s not going to do it.

Lynn:

Well. And here’s the thing too, to be fair. We have mid year reviews, we have year-end reviews and she does always say, “Please, if there’s anything I can do better, let me know.” So, if she’s asking for that, then we should extend her that. I think we’ve all just been a little cautious, a little nervous. We want our jobs. We like our jobs.

Mary Abbajay:

And one of the things, when we make requests and I’m sure you know this, this is really more for our listeners, people aren’t necessarily really good at making what I call effective requests. And an effective request, especially an effective upwards request is: Here’s what I need, specifically. Here’s what it looks like, specifically, really details. Here’s why I need it, specifically. And here’s how I’m going to make that happen.

Mary Abbajay:

So when it comes to the structure, you could say, “Here’s what we need. Here’s why we need it. Here’s what it looks like. And here it is.” The more legwork you can do for bosses like this, the better off you are. And I also want to be really clear. It’s not fair, it’s not right, it sucks. You get to experience that for a moment. But then we have to pull ourselves away from making the other person the villain and us the victim and figure out what actions can we take to get what we need to be successful, to get what they need to be successful, and for everybody. So it’s really about getting past how they should be and figuring out how you can get what you need.

Celeste Headlee:

Yeah.

Lynn:

I do agree with that. And again, I try to put myself in her situation. Would I want my employees doing this to me? Again, it’s not that we’re doing it to her. We’re just reaching a point of what do we do? What else can we do? Because we think that we’ve conveyed it to her. But to your point, maybe we haven’t effectively conveyed it.

Celeste Headlee:

I just don’t think structure means the same thing to her as it does to you.

Mary Abbajay:

I think Celeste is right.

Celeste Headlee:

So, when you ask for more structure, she may be thinking, “Why do you keep asking for me for this? I’ve given it to you.” So, when you talk about communication, things don’t always mean the same thing to different people.

Lynn:

Agreed.

Celeste Headlee:

So yeah, you’re going to have to use a different tactic. And instead of treating, every single time the chaos reigns, instead of treating it as though it’s a new surprise every time, just know that this is how this is. It shouldn’t surprise you each time.

Lynn:

True.

Mary Abbajay:

You know she’s going to be late for meetings. So send her a note saying, “Hey.” Take turns, “Don’t forget we have this meeting. What do you need from me?” It’s really about thinking ahead of the game for people who aren’t structured or who are chronically unprepared or chronically overwhelmed.

Celeste Headlee:

Exactly.

Mary Abbajay:

And it’s not fair, but it is your reality.

Lynn:

Absolutely. And that’s probably one of my most frustrating things. You are a 100% right and that’s exactly what I do. “Hey, hey. Don’t forget about this.”

Lynn:

“Oh, darn!” Or, “Hey, don’t forget about that.” And I feel like I’ve spent my last four positions managing my managers and part of me is going, I’m so tired of doing it. Can I just get a manager that manages me?

Mary Abbajay:

Of course. I totally understand that. And Lynn, someday you’ll have one. Someday you’ll have the unicorn boss who’s really perfect. But you just haven’t had that lucky moment yet.

Celeste Headlee:

Yeah.

Lynn:

And really at the end of it, once we do all of these things, to bring it back to the very beginning, I have options and they are what they are. And if this doesn’t work, then it may be I have to look for another job. .

Mary Abbajay:

And you know what? That’s okay. What you want to ask yourself is, when you reach the point where you actually cannot have a fulfilling career or fulfilling work life because the relationship just doesn’t work with the boss that you have, then you need to really consider thinking about moving on. Often times, people get all caught around the axle around the sunk cost of it.

Mary Abbajay:

“Oh, but I’ve spent four years with this person. I’ve put all this time.” Well, that time is gone. What you want to think about, Lynn, is the opportunity cost of not moving. So, what are you losing out on in your career or in your happiness, by not around for something that would bring you more happiness, more joy, more ability to do what you want to do at work? So, it’s really important when you’re thinking about this to also take into account the opportunity cost. Where could you put yourself to its next best use?

Celeste Headlee:

Super great advice.

Lynn:

Yeah. And I think the mindset that I’ve been in, and my counterparts even expressed it, is the devil you know versus the devil you don’t. So, to your point, yes, I have put in four years. So then part of me is going, you know what? I’ve already put four years in. I got to do something more. Or to your point, do I go elsewhere? It’s a tough call. Because it does. It’s the devil you know-

Celeste Headlee:

That’s saying only makes sense if there’s only devils out there.

Mary Abbajay:

That’s right.

Celeste Headlee:

That’s the only way that’s saying makes any sense whatsoever, is if the world is full of devils. And it’s not.

Lynn:

I consider the devils to be the situations, is not, maybe-

Celeste Headlee:

Again, only true if every situation is a form of devil and it’s not.

Lynn:

True. Okay.

Mary Abbajay:

It’s not. And the other thing Lynn, you could think about, is called job crafting. But is there a way that you could create a job at your current or organization, maybe in the current unit, where it takes you out of her line of authority? Maybe as an independent person or something. It’s one of these things that people don’t think about, but if you could actually craft a job that does exactly what you love to do, it makes the contribution you want to make, but it isn’t under her sight line, her authority line, have you ever thought about that?

Lynn:

I have. And I’ve started looking at some potential opportunities where I see areas that need to be, air quotes, fixed, where I can jump in and dive in and fix the problem, so to speak. Where I can take take control of situations and make them my own and do better with it.

Mary Abbajay:

That’s something to think about. And when you do that, the same kind of thing around requests. Really craft out what the job would look like, show the value to the organization, the business value, show how you would be able to implement that idea. Talk about your transition into that, and make sure you’re pitching it, get some feedback from some people before you pitch it to the powers that be, and then make sure that you could even pilot it. You could be like, let me 30% of my time doing this. And once you can show the value of it, then you move yourself into a newly creative position that you have created.

Lynn:

I like that idea.

Mary Abbajay:

It works. It’s one of these strategies that not many people think to do. It takes a little bit of leg work, but when it works, bam, you’ve just taken control of your career and your workplace experience.

Celeste Headlee:

Yeah.

Lynn:

Is it possible to maybe turn that into my current situation? Meaning maybe what I do is look at the chaos that’s going on and say, “What chaos can I essentially manage?”

Mary Abbajay:

Yep.

Lynn:

And I may still fall under her, but maybe if that’s the better way to do it. What chaos can I take and make my own?

Mary Abbajay:

Yep.

Celeste Headlee:

Yes. I think that’s good. Although you’re limiting yourself. Before you’ve even started, you’re already limiting yourself to what if I did something narrower where maybe I’m still underneath this boss that I can’t work with. But-

Lynn:

Yeah. You’re right. You’re right.

Celeste Headlee:

In advance, you’re limiting yourself rather than thinking big.

Lynn:

And honestly, I think a little bit of that is a little nervous of making those changes and those jumps. And to your point, what are the potential hazards of doing … Whether it’s talking to her, talking to her manager, making a new job. They’re all big items, big actions.

Mary Abbajay:

And so what I love about this conversation, Lynn, is you came in with just one option and I think now you have four, five, or six options.

Celeste Headlee:

Yeah.

Lynn:

Yeah, definitely.

Mary Abbajay:

And you know, I just read an article, it’s probably in Harvard Business Review or something, where they were talking about when you’re faced with the decision, it was so classic, they’re like, “You make a pro and cons list.” And I was like, “I love that.” So, take each of these options, name them, give them a name, and write a pro list and a con list. And I think that’s a great way when you’re sorting through some of your options. And Harvard Business Review thinks so too.

Celeste Headlee:

Sometimes the simplest solution is the best.

Mary Abbajay:

Right?

Lynn:

Keep it simple. Absolutely.

Mary Abbajay:

Yep.

Lynn:

And sometimes too, by writing out the pros and cons, it makes the cons not so scary and it can make the pros really evident.

Mary Abbajay:

Yeah.

Celeste Headlee:

Yeah. All right, so you have some homework to do, Lynn.

Lynn:

I do.

Celeste Headlee:

But at least exactly how to move forward. And just as Mary was saying, you do have options. What happens next is not entirely up to your boss.

Mary Abbajay:

Yeah. I love that. Was this helpful, Lynn?

Lynn:

Oh my gosh. Absolutely. And I think that’s the thing is feeling empowered that I do have options, that I can take action. So, thank you for all of the guidance and the feedback. It’s definitely opened up of areas that I didn’t think about and provided me with a lot of options.

Celeste Headlee:

Great. Well, what we aim for is to be as helpful as possible. So, I want to say thank you to you first, Lynn, for bringing us a situation and an issue that I bet lots of our listeners are either in, or have been in at some point in their career. So, thank you for that.

Lynn:

Most definitely.

Celeste Headlee:

And thank you for your expertise, Mary, as always. Thanks for sharing your experience with not just Lynn, but everyone listening.

Mary Abbajay:

Well, thank you. Celeste and Lynn, it was an honor to be here. I’m always really touched when … Because I think your work, it takes up most of our waking life and I’m always really honored when people share what’s going on with them for me. So, it was great to be on this so thanks for inviting me. And Lynn, the best of luck to you. I’m going to be thinking about you. So, you’re going to have to find me on LinkedIn and tell me what happens.

Lynn:

Absolutely. Thank you again, both Mary and Celeste, for being able to present this option. Not only for myself, but again, if my situation can help other listeners, then we’re making progress.





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