Balancing Act: Managing Relationships with Your Boss and Their Boss

Episode Transcript

Julianna: Hello and welcome to the Uncommon Career or Daring to Succeed podcast depending on where you’re listening from. This is Julianna and I’m here with Patricia.

Patricia Hey.

Julianna: And today we’ve got a really juicy topic for you. We want to talk to you about what to do or kind of the considerations when you have a great relationship with your boss’s boss. Patricia, do you want to kind of lead us in a little bit? Because I know we got into some juicy stuff before hitting.

Patricia: Yeah. No, definitely. I think this is so interesting because, you know, sometimes it’s a situation of, oh, how do I, you know, work the politics and how do I figure out, you know, which relationships to build? But this is like the opposite side. It’s almost like when they say too much of a good thing and you’re like, wait a second. So I’m in good with our leadership, but there’s this boss that I have that’s in between us. right? And it’s, you know, it could make for a little bit of an awkward situation. You could even cause, like you mentioned, insecurity in your immediate boss, which because they are your manager, do your evaluations and are your day-to-day leader, you know, you want to navigate that situation with sensitivity.

Julianna: Absolutely. And I mean, this happens a lot, especially if um you and your boss’s boss have been bumping into each other a lot either at that company or within your industry or whatever obviously as everyone’s careers grow and move around there’s always those connections that you made earlier in your career that kind of follow you along so that’s usually how these natural relationships work but it can be very obvious to people that you have those relationships and like Patricia said that insecurity kind of floats up with the person in between and you know hopefully if they are a fantastic leader you’re just like this doesn’t apply to me and my boss is great they’re supportive But in a lot of situations, especially with either newer bosses, like people newer into the management role in general, newer into that dynamic. So if they’re coming in as someone replacing a prior manager, or if they’re just new to the company, that can be a little bit threatening to them because then they’re kind of wondering like, what does this mean for me? So I wonder Patricia, if we kind of look into more of like the emotional state of that, that in between boss, your direct manager, kind of take us into what that might look like for them.

Patricia: Yeah, no, absolutely. I always think of, you know, that communication piece, right? We, we judge other people by the impact they have on us, but we judge ourselves by our intent. And sometimes other people can’t see our intent. So in that same situation, it’s like, okay, let’s look at their behavior because we can’t really judge exactly how they’re feeling. And that’s where assumptions really start to come in. And this is, you know, when they make assumptions and then we make assumptions and there’s not any real communication. I mean, that’s just the grounds for awkwardness and conflict and things that elevate in our minds. And imagine there’s a situation that’s elevating in both your mind and your immediate leader’s mind. and all these assumptions. And because there’s this sense of potentially threat on their end, they might be like threatened by the fact that you have their boss’s ear. I would very much observe their behavior, number one. So do you see any signs of defensiveness? Are they avoiding you in situations where normally a leader would go directly to you? Do you see that micromanaging that we talked about a couple of episodes ago? Or do you see passive aggressive behavior? So part of it is assessing their behavior. So that’s the input, right? But then you also have output. So when we communicate, we go in and out, right? And so the output is being really open. about communication, technically, they are your leader. But because you have their boss’s ear, there’s this like, interesting dynamic where now you technically can take that, that proactive intentionality to open communication with that leader, because they feel that the power dynamic has shifted. And so because of that, I personally, if it were me, I personally would then say, I’m going to take the initiative to open up communication with my leader more so than I would if I didn’t have that relationship with their boss.

Julianna: Yeah, those are some great points, and I really love how you started with making sure that we remember not to make too many assumptions about what our boss is thinking too, because although we kind of started, Patricia and I, with talking about all the, you know, crunchy bits, I’ll say, that might be possible with this type of dynamic, maybe your boss is okay with it, and the way they communicate doesn’t actually bring that to light, and we’re just misreading their signals possibly, so Really great points there.

Patricia: Oh my goodness. Okay. Seriously, like that’s exactly what came to my mind as you were sharing that. You know, one of the pieces is to get really clear on if the insecurity is based on your direct actions because part of it might be based on that and their relationship with their boss. But the other part might be, you know, we carry things in with us in every role and this could be something they’re carrying and they’re just extra sensitive about it. So, you know, don’t take more responsibility for the issue than is actually on you, but I would look at, you know, is the insecurity or the actions they’re taking, is it a result of something that they brought in with them? How much of it is you and how much of it is just a broader workplace culture? Because some organizations are pretty flat and this might not be an issue at all.

Julianna: And that’s a good point because I do notice these days organizations are trying to flatten out a little bit so that there’s less of that hierarchical dynamic that kind of sometimes gets in the way and causes more issues than they intended. So definitely I think trying to assess your unique situation, what’s happening with that dynamic within the organization, so so key.

Patricia: Yeah. Yeah. And, you know, Julianne, I’m curious to hear your thoughts on like a couple of strategies or things you can do to help manage your relationship with your boss in these situations.

Julianna: Yeah. So I think one thing would be definitely based on the relationship you have with your boss is to see, is there an opportunity to have a very transparent conversation with them?

Patricia: Right.

Julianna: If it’s something you’re worried about, even if they end up saying, oh, I’m not worried, and you still think maybe there’s an inkling of they still are, at least you’ve taken that step to proactively say, hey, look, I know this might be a concern. Maybe this was a concern for my previous boss, or it’s just a concern in general. I’m aware of this, and I’m going to do everything in my part to make sure that there’s not favoritism. Right? At least you’ve taken the opportunity to have that conversation so that later on, if something becomes an issue, it’ll be like, okay, well, maybe we need to revisit this conversation. Because I tried to bring it up. You said that there wasn’t an issue. Let’s hash this over again and see what we can do. but obviously you’re not always in a position to be quite as transparent so maybe speaking with your boss’s boss could be an option as well right to say hey look um i want to make sure that there isn’t a feeling of favoritism because we have this pre-existing relationship whether it’s in the level of authority I have, or your direct impact on my career as my boss’s boss, right, influencing kind of from above, how do we manage that and seeing if there’s a way to kind of agree to being as objective as possible, which I know is difficult, but at least having those conversations, I think, will put it front of mind for people. And that’s, that’s really all you can do.

Patricia: Yeah. Yeah. And I, you know, I really like how you mentioned not just strategies, you know, for managing your relationship with your boss, but also managing your relationship with their boss. You know, you mentioned having an open conversation and how it sometimes isn’t possible to have that open of a conversation. I mean, in marriages sometimes it’s not possible to have that open of communication, right? with like, you know, personalities and emotions and conflict and all these things. But I think it’s, I agree with you that it’s important to have conversations with them. If you can’t be as direct, which would be ideal, but if you can’t be as direct, maybe you don’t have that relationship, you haven’t built that trust, doing little things to reinforce their authority, reinforce their role, check in with them on things that And maybe you would normally feel inclined to check with their boss on by getting their input because as your leader, they also have that specific view that their boss may not be paying attention to because their boss is focused in their things. But then one thing you mentioned was like managing that relationship with your boss’s boss. And I find that so wise, right? Let’s be honest, like it feels good to have a relationship with the mentors and leaders who are influential. And let’s be honest, who have the power to help our careers. And it can be so easy to, in public spaces, be like, Hey, how are you? You know, like just be really. friendly and showcase this favor. But I think that the wise thing to do is to hold it close to you and to message them via email and arrange private conversations to develop their relationship and really not use it to your advantage politically in unnecessary day-to-day things. I would first set boundaries in terms of how publicly or how not publicly you have this relationship so that when you truly need their help, need their mentoring, need their advocacy, it’s in something that’s really going to matter. So it doesn’t affect the day-to-day with your immediate boss and being too public can actually disrupt your relationship with your boss’s boss to where you lose trust because you’re taking advantage of it, right? And so You just want to kind of manage those pieces so that you build a relationship on trust and you’re able to use it strategically when you truly need it.

Julianna: Yeah, I really love that because it’s true. We are usually actively looking for these people in more senior positions who can be our advocates, who can speak on our behalf in other in in rooms when we’re not present. But I love that advice you gave on making sure that you’re using it strategically and not for day to day stuff, because that can kind of dilute it where it’s like, oh, well, they they always just favor this person. So if you can find that right balance to Maybe offset a bit of that when you agree with your boss on something and you’re both in agreeance with each other but disagreeing with your their boss. Right, your collective boss, that might be a good opportunity to kind of forge a partnership with your direct manager to say okay. Yeah, I’m not always in agreement with our boss. And when I agree with you, I will wholeheartedly support you. So that an ethical and very objective way to build on that relationship with your manager to be like, Hey, I’m proving to you that I’m not going to abuse my relationship with your boss to win their favor or to kind of shove you into a corner and make you less shiny as, as the person in charge of this entire team.

Patricia: That’s so wise. Essentially what you’re saying is continue to be your own person, right? And just because the boss’s boss has more leverage, you don’t sell your soul to have this relationship, right? It reminds me of this thought of like not shrinking back in order to make your current boss feel better, but at the same time, not going with that, you know, so you are your own person. And the reason why you probably have the boss’s boss’s ear is because they respect you and they respect the character and the work ethic and what you bring to the table. So I think it’s important to remain yourself. And if that means that you agree with your boss on some points, then own that as well. Absolutely.

Julianna: And I think that really is kind of the crux of what both of us are saying is that you really just have to be true to yourself and not allow that either relationship, the one with your direct manager or with your boss’s boss, to get in the way of making the right decisions and doing the right things.

Patricia: Yeah, definitely. Definitely. Okay. So, you know, now we’ve talked a little bit about the overall situation, how to recognize it and some strategies to take to sort of avoid things escalating. But what if it does escalate? What are some strategies or responses that you think someone should take if it does start to become a problem?

Julianna: Yeah it’s a great question and I actually had a client recently who had that situation where she could tell her boss was getting super uncomfortable with what was going on so what she did was pick out a specific scenario where he disagreed with his boss and said, OK, well, I don’t really care personally what the two of you decide. So she went to her direct manager and said, look, with the situation, I know you and your boss disagreed. What would your preference be? Because with me managing this program, I have the power to kind of decide what we do with that. So she actually, not necessarily circumvented her boss’s boss, but went directly to her direct manager to involve that person to say, hey, okay, well, I personally want your opinion on this. and kind of make that room for them to be involved in a more formal context. So that’s one thing you can do. Other options might be to kind of see again, if you can have that transparent conversation, can you bring the two of them together and say, look, we’re seeing some issues here. I don’t want my prior relationship with this person to be an issue. What do we do here?

Patricia: Yeah, open it up for conversation.

Julianna: Open it up, trickier, but it’s really dependent on whether you can actually have that conversation with the two of them.

Patricia: Yeah. I mean, especially having two people in the room can be kind of tricky or even having individual conversations with each person to kind of figure that piece out. You know, I’ve had clients and colleagues who their boss has become hostile, has started to withhold information or have started to purposely, intentionally, and obviously block opportunities or bring in HR. So those kind of like pushing you out kind of thing. And part of it is having that private one-on-one conversation and just being like, hey, you know, I sense that something’s going on. And if you know already that that might be an issue before you have a conversation, that begins with conflict. Hey, what’s going on? How come? How come this? How come that you can start by, you know, like we said earlier, reinforcing their role, reinforcing their authority, building trust, building relationship and easing your way into that conversation. But then the other part too, that could be helpful is as you’re having these conversations is remember to always bring back the common ground because you both work on the same team in the same organization, you have the same mission, you have the same goals and your success is their success and vice versa. And so kind of bringing that back to the forefront before you even start that conversation and then leading into that conversation I think could be, um, I think could be really, really helpful.

Julianna: Yeah, I love that idea of trying to find that common ground because honestly, and I know we’ve talked a lot about toxic bosses and things like that in some of our recent episodes but goes back to some of what we’ve talked about in those episodes where sometimes that toxicity is something that you personally cannot solve, right? There’s a certain point where you have to decide, is this a solvable conflict? Or is it a conflict that you simply need to get out of? And if you’ve done all the things that are reasonable to kind of find that common ground, try to involve your direct manager as much as possible to make sure that they know that you’re not trying to abuse your prior relationship. And if they’re still blocking your career and withholding information and doing other unethical things, that might be something that you really have to think about in terms of your long-term career and continuing to work for this person.

Patricia: Oh, yeah. Yeah. I mean, that’s, that is the point at which you reach out to their boss and you don’t say, Hey, your director is giving me some problems here. But it’s more of a conversation of, you know, I really wanted to grow in X area and I was curious, I saw something in this department or I’m curious if you’ve got something up the pipeline. I would love to just develop some new skills and how can we work together on that? You know? So yeah, I mean, from recognizing if you have a situation, how to mitigate the situation, how to determine if it’s becoming a real issue, right? Or if it’s just your boss or just the environment, or if it truly is something that your relationship with their boss is impacting, right? And then we also talked about what happens when it’s escalating. So as we kind of get to the end of this episode, Julianna, what would be your final thoughts on this situation, this tricky situation? Tricky, but beneficial.

Julianna: Tricky, but beneficial. So I think the key to all of it is really making sure that you are doing your personal best to be ethical about the entire situation. As long as you’re doing that, I mean, there’s only so much you can do to manage, especially dynamics that are that complicated with two people who are senior to you in the hierarchy, as well as, you know, all those interpersonal issues. But as long as you can sleep at night knowing that you’ve done your best not to abuse that prior relationship, that you’re trying as much as possible to build that relationship with your direct manager, That’s really all you can do and all you can hope for.

Patricia: Oh, that’s so good. You know, ultimately, it’s about your motive, right? It’s kind of like a while back, it was like, you can’t lie and you shouldn’t lie. And it’s not just because it’s good and bad, but it’s also because if you lie, then you have to keep that snowball going to keep your life from being found. And that’s just so exhausting. And it’s the same thing if your motive is in the wrong place. then you either are going to be acting or forcing something that’s not genuine. And now you’ve got to recreate this everywhere you go. And this is essentially lying, right? So you have to figure out like, where’s your motive, get that in the right place. And the rest of the pieces will fall into place in a way that, like you said, you can sleep at night because your motives are right. And therefore your actions and your behaviors are right as well.

Julianna: I love that.

Patricia: Yeah, it was good. It was good.

Julianna: Yeah. So I think that’s all we have on this topic this time, but definitely as usual, let us know if there’s something you want to talk about and connect with us on LinkedIn or through our websites. We would love to hear from you.

Patricia: Absolutely. Thank you all for joining us. We look forward to seeing you on the next one. Bye. Bye.