How Leaders Undermine Their Own Authority

Summary

Podcast Title: HBR On Leadership
Episode Title: How Leaders Undermine Their Own Authority
Release Date: July 23, 2025
Host/Author: Harvard Business Review
Description: Leadership isn’t a trait, it’s a set of skills. HBR On Leadership provides insights and inspiration from the world’s top leadership practitioners and experts to help you manage up, motivate a team, and unlock the best in those around you.

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Episode Overview

In this insightful episode of HBR On Leadership, Harvard Business Review’s Senior Editor and producer, Amanda Kersey, along with hosts Alison Beard and Dan McGinn, delve into the nuanced ways leaders can inadvertently undermine their own authority. They explore three distinct listener dilemmas through the expert guidance of executive coach Peter Bregman, founder and CEO of Bregman Partners. The discussion offers practical strategies for addressing ineffective leadership styles that hamper team performance and morale.

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Section 1: The Challenge of Indecisive Leadership

Listener Dilemma:
A listener describes their boss’s transition from a questioning, behavior-focused manager to an indecisive leader who struggles to make decisions, leading to frustration and reduced team effectiveness.

Key Insights:

• Nature of Leadership:
  Peter Bregman emphasizes that leadership is inherently challenging and often feels unnatural. Unlike followers, leaders must navigate ambiguity, take risks, and make tough decisions without always having clear training for these responsibilities.

  "Leadership is hard. I mean, it's very hard, almost unnatural." [02:43]

• Unrealistic Expectations:
  Bregman points out that society often projects unrealistic expectations onto leaders, setting them up for failure when they cannot meet these idealized standards.

  "We also often have unrealistic expectations of leaders, meaning we project a lot of... high expectations of what we expect leaders to do for us." [01:32]

• Strategies for Support:
  Instead of directly criticizing the leader, subordinates can offer specific suggestions to enhance decisiveness. This includes implementing decision deadlines, documenting decisions, and reinforcing confidence in the leader’s ability to make and stick to decisions.

  "Here's this decision that we need made and can we kind of talk it through and come to a decision that we know that we can keep." [04:53]

Notable Quote:

"The hardest thing to do in organizations is influencing decisions and people who are not under your control." – Peter Bregman [14:37]

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Section 2: Navigating Office Politics and Brown-Nosing

Listener Dilemma:
Another listener shares frustrations about a colleague who compensates for a lack of technical skills with networking and brown-nosing. This individual is favored by leadership despite neglecting substantive work, causing tension and demoralization within the team.

Key Insights:

• Understanding the Colleague's Approach:
  Bregman suggests that the colleague’s ability to influence and build relationships, despite lacking technical prowess, indicates a valuable skill set that others can learn from.

  "There is something to learn from this guy that actually can make me more effective as I grow." [14:37]

• Balancing Technical Skills with Political Savvy:
  While technical expertise is crucial, being able to navigate office politics and build relationships is equally important for career advancement.

  "People aren't all good or all bad. There's some things this guy does where he's very skilled, and there's some things where he's obnoxious and a value mismatch." [18:36]

• Recommendations for the Listener:
  Instead of leaving the organization, the listener is encouraged to stay and develop their own relationship-building skills. This includes being authentic, sharing credit with the team, and finding ways to effectively communicate with leadership without compromising personal values.

  "Staying in the organization and trying to learn what you can from this political operator is probably the best course." [22:59]

Notable Quote:

"It’s probably like one of them is a show horse and not a workhorse, and the other one might be a workhorse and not a show horse." – Dan McGinn [15:05]

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Section 3: Dealing with a Gossipy and Politically-Prone Boss

Listener Dilemma:
A listener working in a startup describes their boss as technically brilliant and a great mentor but deeply involved in office gossip and politics. This behavior demoralizes the team and creates an “us vs. them” mentality.

Key Insights:

• Impact of Gossip and Politics:
  Bregman acknowledges the difficulty of navigating a relationship with a boss who engages in harmful gossip, highlighting the power dynamics that make it challenging to address such behavior directly.

  "There's a power dynamic... it’s hard to work with." [24:29]

• Establishing Boundaries:
  The listener is advised to set clear and respectful boundaries by directly communicating discomfort with the boss’s gossip. This involves expressing how such behavior impacts team morale and requesting a more professional approach.

  "Finding your voice to create the boundaries without shame, let him know what you're uncomfortable with." [30:35]

• Encouraging Transparent Communication:
  Alison Beard underscores the importance of leaders owning their decisions and maintaining professionalism to foster a cohesive and aligned team.

  "Business is a team sport. If she can find a polite and respectful opportunity to say that she thinks her boss is hurting her team when he publicly voices his dissent, that’s something she should raise." [33:45]

Notable Quote:

"When you're making this business decision... you're supposed to own it." – Alison Beard [32:56]

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Actionable Strategies and Solutions

1. Provide Constructive Feedback:

   • Offer specific, actionable suggestions rather than general criticisms.
   • Frame feedback in a way that reinforces the leader’s strengths while addressing weaknesses.

2. Implement Structured Processes:

   • Use deadlines and documentation to hold leaders accountable and reduce indecisiveness.
   • Publicizing decisions can help mitigate the tendency to flip-flop.

3. Develop Emotional Courage:

   • Engage in difficult conversations with empathy and clarity.
   • Lead with the main point to open up dialogue and address issues directly.

4. Balance Technical and Political Skills:

   • Encourage authentic relationship-building without compromising personal values.
   • Learn from both the strengths and weaknesses of colleagues to enhance personal effectiveness.

5. Set Clear Boundaries with Gossipy Bosses:

   • Communicate discomfort with inappropriate gossip.
   • Redirect conversations towards productive problem-solving and maintain professionalism.

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Key Takeaways

• Leadership Requires a Balance of Skills: Effective leaders need to blend technical expertise with emotional intelligence and political savvy to navigate complex organizational dynamics.

• Constructive Feedback is Crucial: Subordinates can play a pivotal role in helping leaders improve by providing thoughtful, specific feedback and supporting their development.

• Personal Development Over Organizational Change: When faced with ineffective leaders, focusing on personal growth and adapting strategies can often be more productive than attempting to change organizational culture.

• Maintaining Professional Boundaries: Establishing and communicating clear boundaries is essential when dealing with leaders who engage in negative behaviors like gossiping and indecisiveness.

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Notable Quotes with Attribution and Timestamps

• Peter Bregman:

  "Leadership is hard. I mean, it's very hard, almost unnatural." [01:32]
  "We also often have unrealistic expectations of leaders, meaning we project a lot of... high expectations of what we expect leaders to do for us." [01:32]
  "The hardest thing to do in organizations is influencing decisions and people who are not under your control." [14:37]
  "It probably does seem from this writing that she has the kind of relationship with him where she can give him this kind of feedback where he might appreciate it." [05:33]

• Alison Beard:

  "Business is a team sport. If she can find a polite and respectful opportunity to say that she thinks her boss is hurting her team when he publicly voices his dissent, that’s something she should raise." [33:45]
  "We’ve published research that shows that among the traits or characteristics that an employee want in their boss, one of the most important ones is the boss has to have the ability to actually do the job." [20:01]

• Dan McGinn:

  "He is supposed to do the same work he does. So I think if the organization continues to reward him, even if our letter writer gets better at all the things we're Talking about that's a huge red flag." [20:18]
  "I think we all probably agree that he should focus more on himself than on this peer." [19:29]

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Conclusion

This episode of HBR On Leadership offers a deep dive into the subtle and overt behaviors that can erode a leader’s authority and disrupt team dynamics. Through real-life scenarios and expert analysis, listeners gain valuable tools to address and mitigate the impact of ineffective leadership. By fostering open communication, setting clear boundaries, and balancing technical and interpersonal skills, both leaders and their teams can navigate challenges more effectively and create a more harmonious and productive work environment.

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For more insights and strategies, subscribe to HBR On Leadership on Apple Podcasts, Spotify, or your preferred podcast platform. Share this episode with colleagues and friends who can benefit from expert leadership advice. Visit hbr.org for additional resources, including articles, case studies, and books by the world’s top business and management experts.

Transcript

[Peter Bregman]

Just promoted Wharton Executive Education's People Management for Emerging Leaders gives you tools to manage teams, projects and performance. Live online six weeks. Learn more at whartonemergingleaders.com.

[Amanda Kersey]

Welcome to HBR on leadership case studies and conversations with the world's top business and management experts hand selected to help you unlock the best in those around you. I'm HBR Senior Editor and producer Amanda Kersey, succeeding Hannah Bates as your host. Do you work with people in power who have a hard time making decisions? Or whose only expertise seems to be office politics? Or whose gossip demoralizes the team? Those are three listener dilemmas that Dear HBR hosts Alison beard and Dan McGann talked through with executive coach Peter Bregman in the 2018 episode originally called Ineffective Leaders. Through their discussion, Allison and Dan and Peter don't just help the listeners who wrote in seeking their advice. They offer ideas that anyone can use when they're working with an ineffective leader.

[Alison Beard]

Peter, thanks for being on the show.

[Peter Bregman]

Thanks so much for having me. It's fun to be here.

[Alison Beard]

Why are there so many ineffective leaders?

[Peter Bregman]

Leadership is hard. I mean, it's very hard, almost unnatural. We're not really trained to be leaders from a young age. We're actually trained to be followers from a young age. Even when we look at what we do to train leaders, we're often training people to follow a certain process and to, you know, to not actually lead, which is all about taking risks and moving forward in ambiguity and making hard choices and decisions. And that's on the one hand. And on the other hand, I think we also often have unrealistic expectations of leaders, meaning we project a lot of, you know, ideal behavior and high expectations of what we expect leaders to do for us. And it's a little bit of a setup for failure.

[Dan McGinn]

And generally how hard is it to help people change or help people encourage their bosses to change?

[Peter Bregman]

You know, there are people who I have tried to help change and I have failed. And you know, ultimately, if someone wants to change, they almost invariably are able to. But if they don't want to change, they almost invariably will not.

[Alison Beard]

Well, we've got three pretty common complaints from our listeners today. So let's get to it.

[Dan McGinn]

Dear hbr, My boss was promoted to the top level position in my organization a few years ago. In his previous role, he was constantly asking questions that behavior was an asset. But now that he's the leader, he has a hard time making decisions. It's hampering our ability to move forward as his management team. We're Routinely asked to seek further information. Worse, he sometimes flip flops, changes his mind about one of his own decisions or one we had made together. I truly believe he's trying to do a good job, but I'm increasingly annoyed with him. It's also hurting other people's perceptions about his competence and making us all less effective. I've given him some private feedback on this, and he's receptive to it, but I don't know that he can change. This indecisiveness seems way too deeply ingrained in his nature. Please help.

[Peter Bregman]

You know, it's interesting because it's not someone asking for advice about their own leadership, but it's someone saying, help me help this other person be a better leader.

[Alison Beard]

I agree with you there. Because it's hard for a subordinate to speak truth to power and say, hey, you're doing a bad job at this.

[Peter Bregman]

It often doesn't help to say, and here are all the things you're doing wrong, because they may or may not realize they're doing it wrong. But I'm betting this leader is probably frustrated with his own indecisiveness and he probably struggles with it. And I would guess that. That it's not a source of pride or a feeling that he is really on top of things. One idea is, rather than reinforce it, to offer some suggestions of things that he could do that would help him to be more decisive. So rather than point out your indecisiveness is hurting the team to say, here's this decision that we need made and can we kind of talk it through and come to a decision that we know that we can keep and frame it in a way that helps him with a decision that you need made for your particular job or the particular work that you're doing that you can help him make in a way that will reinforce his own confidence and his own ability to make strong decisions and move forward.

[Alison Beard]

Yeah, I think you're right. Process could really help this. Giving him a deadline, taking simple minutes of the meeting and distributing them so everybody knows what the decision was, which makes it harder to roll it back or to flip flop. It's almost like nudges. She can sort of nudge and frame things in ways that make it a little less dysfunctional and move things a little bit closer to a firmer decision.

[Peter Bregman]

Totally agree. I love what you just said about this. You know, like publicizing the decision so it's harder to flip on it. And, you know, I think that's a great idea. And it does seem from this writing that she has the kind of relationship with him where she can give him this kind of feedback where he might appreciate it.

[Dan McGinn]

I definitely went to the question of is it better to just subtly nudge him into better behavior or to have a conversation with him more generally about how to change his leadership style. And it seems like, Peter, you're coming down the side of nudging and Dan, you are too.

[Peter Bregman]

You know, I'm not sure I make such great, fast, immediate decisions and the temptation to flip flop is really strong. And I worry that sort of general feedback about, you know, his style, especially for someone who she says like has a hard time changing. I feel like it's too high a bar. Like I think someone who's really skilled at this stuff and something very, very specific by the way, you're not listening so much. You know, it would be better if you just shut up in these meetings and listen more. That's really sort of direct feedback and you could pull that off. But something like making decisions, that's hard. And there's like so many reasons why it might be difficult for him that I would be afraid that the general feedback wouldn't have so much impact.

[Alison Beard]

I agree with you there because his virtue is really his vice in the sense that the other extreme, if he were making snap decisions, if he weren't asking good questions. We've all seen bosses that are the other side of this continuum and they're probably worse. If I had a choice between a boss that's a little too deliberative, a little bit too open minded, or somebody who's closed minded, wants a decision without collaboration, doesn't really want to ask curious questions, I'd rather take the deliberative person anytime.

[Peter Bregman]

The other question that I had was how often do you dissuade him from a decision that he's already made because you don't think it's the right decision. So if he's made a decision and then you come to him and you say, well, I don't know that that was such a right decision because it didn't particularly go your way and then kind of push him to move towards another decision and is that might get him to make a better decision, but it also might reinforce this challenge and this reputation that he has.

[Alison Beard]

So you suspect she's enabling the flip flopp.

[Peter Bregman]

I've seen that happen a lot and I think it's just worth considering whether you're doing things to help him get better at this or whether you're doing things that might reinforce it. By the way, I Don't know what we're doing. But are we living in an arena of ambiguity? Are you in a competitive marketplace in which the tides are changing really quickly, the competition is changing really quickly? Are you in an agile kind of environment in which, you know, ultimately it's hard to make a decision and maybe you need to change it at times? You know, I've seen that in organizations a lot where employees of a leader are really frustrated with the decision making. And then you talk to the leader and you realize that the leader is engaged in a lot of challenging decisions in a shifting field that requires some change. And the issue isn't decision making, it's communication. Right? The issue is I'm making it. I'm changing this decision for really good reasons. But I'm not telling people, I'm not telling everybody, or I'm just telling one person and not the other people and then they're thinking I'm flip flopping and they're not understanding the reasons why. So, you know, part of it is, is there legitimacy to not making the decisions? And is this a communication challenge as opposed to a decision making one?

[Dan McGinn]

Part of my inclination was to tell our letter writer to take a step back and ask herself, should I give him more time to adjust to leadership? Is his style of questioning really that bad? Is it just my need for immediate action that's causing me to question his leadership? But he was promoted two years ago and so one would think that he would understand what his team needs and sort of have gotten used to the role he needs to play by now. Is that an accurate assumption that I'm making, that, that he's had enough time? He should have figured it out by now.

[Alison Beard]

That's the piece that troubled me the most too, was this. He's been in the job a few years. If he were a brand new boss, you would expect he might take some time to adjust to making these decisions. Is this just a piece of the job that he's never going to get very good at or is there anything that she can do to try to accelerate his learning to give him a better sense of either confidence or get him the information more quickly? Is there anything she can do to give him the experience that he doesn't just seem to be getting organically?

[Peter Bregman]

Yeah, I think that's a great question for her to ask him. And I also, I agree with both of you. Like, I think that if you haven't gotten it after a couple of years, then it's clearly the thing you need to get meaning. If I was doing a performance review on him, then I would drop everything else from the performance review. And I would say this decision making thing is the thing that we should focus on. Let's throw our resources there. Let's really look at what's getting in the way.

[Dan McGinn]

Unfortunately, she's not in a position where she is giving him the performance review. So how does she do that?

[Peter Bregman]

You know, she can't. You're right. And she can't be the person to give him a performance review. It does sound like she has his ear right when she sort of says that she's given him some feedback personally. So that might be where, I don't know, the relationship she has with him, but it might be where there's an opportunity to say, you know, given my vantage point and totally in support of you, it seems like, you know, you're amazing at all these other things. Here's the one thing that would make the biggest difference in our lives as your reports. You know, one of the things I would do if she's overwhelmed with the amount of decisions that he's not making is to really ask the question, what specifically do you need from him to do your work? So rather than get caught up in the general challenge of his inability to make decisions and the insufficiency or ineffectiveness of his leadership, to really think about what you specifically need from him and ask for that and get that, and don't worry about the myriads of decisions that he's not making that don't actually impact your ability to get your work done.

[Alison Beard]

Alison, what are we telling her?

[Dan McGinn]

So first we'd like her to step back and ask herself whether his indecisiveness might be a result of the context, whether there's value in his questions or leadership style given the industry or business they're operating in, and whether the problem is really communication rather than decision making, is he just doing a poor job of letting the team know what his plan is? We do think that she should try to nudge him into more decisive behavior, especially if it's truly preventing the team from operating effectively. She can provide him with more information. She can, along with her team, suggest clear cut solutions and sort of take the decision making off his hands. And she can offer to try out options and report back to him. Last, she should consider having an honest conversation with him about the fact that she wants to be supportive of him as a leader. And this is the one thing that's holding him back, and she'd love to help him improve on it.

[Alison Beard]

Dear hbr, I work In a technical field. One of my colleagues clearly lacks technical ability. He tries to overcome this through networking and brown nosing. While most of us do our work, he spends his time trying to get one on one meetings with leaders around the company. He's positioned himself to be the point of contact for our group. He's quick to overlook our problems. He's always on the hunt for pretty slides of ours to show the higher ups. He wants to be our boss. The entire team thinks this is a horrible idea. He's all shine, no substance, the way he treats those above him versus those who cannot further. His career is night and day. He tells leaders whatever they want to hear. The problem is that our leadership loves him. They're quick to applaud him, minimize his mistakes and invite him to strategy and planning meetings. He does not share anything about these meetings with the team. I quite like my immediate team and my actual boss. But I question an organization and leadership that puts this charlatan on a pedestal. What's the right thing to do here? Start looking around for a new place to work, Wait until he's eventually found out.

[Peter Bregman]

I have sort of an interesting reaction to this one, and it's a little counterintuitive when I hear all of the criticisms of this person, right? That here's a guy who's positioning himself. Leadership loves him. They're quick to applaud him. When I look at the hardest thing to do in organizations, it's influencing decisions and people who are not under your control. And so here's a guy who seems to actually be pretty good at this, right? I mean, he's able to influence senior leadership. He's able to build really great relationships and it pisses you off. And I, you know, my thought is if you turn that around and said, what do I have to learn from this guy that actually can make me more effective as I grow? And I think leaving, you know, finding another place to work is the biggest mistake you can make. Because I want to say you have something to learn here.

[Dan McGinn]

Peter, I do agree with you that he needs to learn how to play the game of office politics a little bit better. But I think that's very hard to do against someone who's not playing the game of work too. His competitor in this situation is someone who's not doing the actual work and only doing the office politics. And that seems like a rigged system. So I really understand his frustration.

[Alison Beard]

So you're saying he's a show horse, not a workhorse.

[Dan McGinn]

Yeah.

[Alison Beard]

And you want him to be both.

[Dan McGinn]

Exactly, yeah.

[Peter Bregman]

I want both of them to be both. So it's probably like one of them is a show horse and not a workhorse, and the other one might be a workhorse and not a show horse. But imagine that you actually start to play the game. And I don't even really think of it in this negative way of playing the game. I think if you're going to work with a whole group of people, it's really useful to develop the ability to create real substantive relationships with the people around you, especially also the people in power. And then what if you did that and actually brought him in and didn't think of him as an opponent and didn't think of him as someone you're working against, but thinking of someone that you could collaborate with in order to help him to be successful and you also to be successful.

[Dan McGinn]

I don't think this guy needs any help being successful.

[Peter Bregman]

You know, he probably does need some help being successful, at least with his colleagues. So it doesn't sound like he needs help being successful with the higher ups, but it does seem like there's a movement against him.

[Alison Beard]

I do wonder whether this almost becomes a question of values for the person who wrote the letter. If this is an organization that really prizes and rewards glibness and polish and doesn't necessarily respect deep technical expertise, I wonder whether this might be a situation where there's kind of a values, a mismatch.

[Peter Bregman]

I would push back a little bit and say, is it that you're frustrated by this one person and it's safer to say, well, this culture will never appreciate what's really, really important anyway, or, you know, and is that true? Or is it something you do to protect yourself from, you know, the challenge that you're facing with this guy and feeling like you don't have the skills, you know, to sort of operate in this environment in a way that can both leverage your technical skills and also have you seen by leadership? And here's a feeling that I have also about people who want to leave a situation because they feel like they can't be effective in it or change it. To me, that's the worst time to leave an organization because your risk of the consequences of failure are zero, because you are about to leave anyway. But if you choose to stay, you could take real risks with people. You could do what you believe is right. You could take risks to show up the way you've always wanted to show up, which is probably very, very scary. But the consequen of failure, which would at worst be firing, are where you would have ended up anyway.

[Dan McGinn]

From my perspective, this guy could be unstoppable if he applies his technical expertise to his work, as he's already doing, and then he learns how to become more visible in the right way. So I think what I disagree with you on, Peter, is that he should learn from this colleague who seems to be doing it the wrong way. I think what he should do is build those skills that you're talking about, but in a way that feels honest. And I think that that's not by ignoring the problems on your team and taking only the pretty slides to the higher ups, you know, it's by taking those pretty slides, explaining exactly how the work was done and crediting everyone else on the team for it.

[Peter Bregman]

Right. I love that. And where we might disagree is I think. I think he could still learn from this guy without learning the bad stuff with the good stuff. Like, I think people aren't all good or all bad. So, like, there's some things this guy does where he's very skilled, and there's some things where he's obnoxious and a value mismatch. And this might be, by the way, not a values mismatch with the organization. It might just be a values mismatch with this guy. And yet even with someone whose values you totally disagree with, maybe he's all brown nosing, but he probably does some things that's worth looking at and going, huh, you know, what's he doing to develop those relationships? And how can I learn to develop those relationships in the same way, while also bringing the substance and the authenticity and everything that I believe is important to me and my values and creating the kind of workplace I actually want to be in.

[Dan McGinn]

I think we all probably agree that he should focus more on himself than on this peer.

[Alison Beard]

Swim in your own lane.

[Dan McGinn]

Exactly. Dan's favorite piece of advice, the piece.

[Alison Beard]

Of this that worries me is the brown noser. Seems like he's on the fast track, and it seems like there is a reasonable chance that he will end up the boss of this department. And our letter writer thinks he's a charlatan. That's a really strong word to use. That's a really strong position. If this person does become the boss, that's gonna be a pretty tough situation.

[Dan McGinn]

I agree. Because they are swimming in the same lane. Right. This person does or doesn't do, but is supposed to do the same work he does. So I think if the organization continues to reward him, even if our letter writer gets better at all the things we're Talking about that's a huge red flag.

[Peter Bregman]

Yeah. And I think if he becomes the boss, that's a total game changer because if suddenly you're reporting to this person and you have zero respect for them, that's harder to live with than if you're a colleague to this person and you're watching them, you know, get an advantage that you believe has no foundation to.

[Alison Beard]

We've published research that shows that among the traits or characteristics that an employee want in their boss, one of the most important ones is the boss has to have the ability to actually do the job. We tend to be less happy if we think the person above us lacks the chops to actually do the substance of the work. And that's really what the situation is. This, this charlatan is not the boss yet. But, but that trajectory seems to be what's driving a lot of the angst for our letter writer.

[Peter Bregman]

You know, Dan, you made a really interesting point in the last question about being public. And I think that applies in this situation also, which is, you know, so let's say the person goes to a meeting and then doesn't share anything about it. You could always email this person and copy everybody on the team and say, how did the meeting go? Can you give us any specifics? So, you know, a way of publicizing the situation in a non confrontational way, but in a way that makes it harder for him to not share what happened in that meeting. Like, rather than whisper it in the halls, you know, publicly ask the question so that he, you know, would have a hard time not responding.

[Dan McGinn]

So what are we telling the guy with the brown nosing colleague?

[Alison Beard]

So first we recognize that where one person sees a brown noser, another person sees a savvy political operator. As distasteful as our letter writer finds this person's behavior. Clearly this brown nosing, non technical employee has the ability to connect with people. He's persuasive, he's ambitious. It's going to be uncomfortable to try to lean into these behaviors that a technical person who values technical skill above all else finds so distasteful. But we do think trying to find the learning opportunity here is really the first step. The thing that gives us the most pause is when he calls the colleague a charlatan. That suggests there's a values conflict here. And in the long term there is a chance this person will become the boss of the department. And if that happens, that's a game changer. And at that point it probably would be time to look for a new job. But for now, we think staying in the organization and trying to learn what you can from this political operator is probably the best course.

[Dan McGinn]

And now for our last ineffective leader. Dear hbr, A year ago I joined a startup. My boss is brilliant at his job and a great mentor. He's also extremely prone to office gossip and politics. I'm not comfortable sharing my personal opinions about other people at the office. When he vents about members of the leadership team, I find it demoralizing. Some of his comments suggest that our co workers are unprofessional or incompetent. Other comments get personal. He might talk about someone's style of dress or love life. I don't respond and try to stick to discussing the tasks at hand. I think he realizes why I withhold my opinion, but it hasn't deterred him. Maybe he feels that as a professional, I should be able to handle it. In fact, I sometimes get the impression that my lack of reaction frustrates him when it comes to interacting with the team that reports to me. He prides himself on being transparent, but that translates to him sharing more information that I think is necessary. For example, he offers his personal opinions on broader business decisions. This leads the group into an us versus them mentality, which I'm unable to effectively steer them away from. It's hurting their morale. I'm trying to set boundaries with him and my group. I know I can give him candid feedback on certain matters, but the way he gossips and denigrates others and gets emotional in conversations, it makes it very difficult for me to trust or respect him. It also makes it hard for me to stay engaged in my work. What should I do?

[Peter Bregman]

My reaction is there's first of all, this is hard. There's a power dynamic. There's, you know, he's a man, he's the boss. There's a role and rank and societal dynamic that I just want to reference and say it's hard to work with. Right? I mean, this is a challenging situation and position.

[Alison Beard]

I wonder if there's a way, especially given the gender dynamic here, she can take advantage of the fact that we're living in a time when things that seemed like they might have been okay five or 10 years ago in terms of a personal comment probably aren't okay now. When the boss is talking about the way someone dresses or talking about their love life, there's really not a place for that in the office. And I wonder if alerting him to this in a caring and protective way might not only help solve her problem, but Also protect the boss from saying something stupid that might come back to hurt him.

[Peter Bregman]

100% in agreement with you. And it's hard for me to tell the relationship that she has with her boss. One thing that I noticed was that in the question, she says, I'm not comfortable, you know, sharing her personal opinions or something like that. I kind of want her sharing her opinions with him a little more. And rather than withhold her opinion, you know, when she feels uncomfortable, I think there might be room here to be able to help him out, to be able to say, you know, you know, it kind of makes me uncomfortable when you share that, or, I like that person, or, you know, I don't know exactly what the boss is saying and how she should respond, but especially with her team, I would say, hey, I'm trying to run my team a certain way, and I want them feeling really good about each other. So I want us to be really careful, and I'd love your help and being really careful about what you say in front of them about each other. Because that, to me, kind of hurts the morale I'm trying to create on my team. So be willing to. To speak up. Not in a way that shames him. Right. That's hard. But finding your voice to create the boundaries without shame, let him know what you're uncomfortable with.

[Dan McGinn]

Yeah, I mean, I think there's a real opportunity for reverse mentoring here, right?

[Peter Bregman]

Yeah.

[Dan McGinn]

By trying to shut him down or change the subject or walk away when he's trying to gossip. I feel like that really misses the point. He's trying to sort of establish more trusting, more intimate in an office setting relationship with her. And I think that her response to that should be to not gossip with him or engage in what he's trying to do, but just sort of say, hey, so help me understand the problem that you're having with this person. You know, I didn't really see it that way, or, oh, wow, okay, I see that underlying issue. Maybe next time with him, we can address it in this way. You, you know, specific comments, like you're talking about Dan, love life, dress, et cetera. Maybe she should shut down in a friendly way. But I think there might also be real work conflicts that she can help him with in this context.

[Peter Bregman]

I think that's absolutely right. And I think part of the question before she does that or in, you know, as she thinks about doing that, is to ask, why is he sharing with you? Like, what's he like? Is he looking for connection? Is he trying to build his own confidence? What's the point. Now, I wouldn't necessarily talk to him about that, but to understand that. Because you could shift the dynamic in part by giving him what he needs, but in a cleaner way.

[Alison Beard]

That's a fascinating idea. I tend to think of the motivation for gossip is to kind of show off that you're in the know and enjoy information with another person. You saw it as a potential attempt at bonding. And I think there's research that says people who use inappropriate language in the workplace are sometimes doing it to try to bond with the other person because it's a minor rule breaking kind of thing. Gossiping is something you're not supposed to do in a company. The boss might be doing it as an attempt to show, hey, you know, I want to be close to you. It's misguided and it's not the greatest behavior, but at least it's a benevolent kind of motivation to it.

[Dan McGinn]

Yeah, We've actually published articles about the fact that gossip can be good when it's used to share information that's important and even spread it through back channels if it needs to be spread that way. And also, as I mentioned before, to sort of indirectly surface conflicts if it's not done in a negative way. That's denigrating people. Unfortunately, it sounds like he's doing it in that sense. And so what she needs to do is steer him away from that bad kind of gossip into the good kind of gossip. Because it is great to be able to share information with your boss and also to let him vent to you once in a while when he's really frustrated with something because then you can problem solve with him, you know.

[Peter Bregman]

And you just made me think, Alison, that when he's venting to you, one specific language that you can use is to say, hey, I get it. And that's really frustrating. But just so you know, you should not share that with anybody except for me.

[Dan McGinn]

Right.

[Peter Bregman]

And that's a subtle way of saying like, you know, without shame to say like, I get that you're angry, but don't go talking. That's gonna hurt you if you go talking around. You know, he'll begin to get of what's okay to talk about and what's not.

[Dan McGinn]

She also doesn't want to be his confidant anymore. She is uncomfortable with it. So while we are encouraging her to push her comfort zone, at some point, she doesn't want to be having as intimate a relationship with him as he seems to want. So how does she handle that?

[Peter Bregman]

That's right. So maybe what she could say is a version of, well, I completely understand that you're venting. Definitely don't talk about this outside the room. It even makes me uncomfortable. Right, so you're able to kind of still be in relationship with him, still not shame him, say, it's really not something you ever want to share. And I don't even like hearing it. And it signals really clearly this is something that's really out of boundary.

[Dan McGinn]

And it doesn't seem that she has clearly articulated that yet. She says she senses that he understands her discomfort, but she hasn't flat out told him she's really uncomfortable.

[Peter Bregman]

I think she seems to be avoiding having that conversation, and it's a difficult conversation, and I think it's one of those difficult conversations that she should just have. So the absence of a conversation doesn't really communicate strongly enough, especially when someone is in a blind spot. And this sounds like it's his blind spot. And so this is a time not to be subtle. And again, one of the things that I talk about leading with emotional courage is how to start a really hard conversation, which is lead with the punchline. So one way to do it is to actually sit down, not during one of those comments, but to say, hey, I want to talk to you about some comments that I've heard you say that make me uncomfortable. Boom, you've opened up the conversation. You've said it right at the beginning. And then to say, I want to give you some examples. I know you don't mean it badly, but I don't know that you know the impact that it has. And I think this might be a blind spot, and I want to share it with you. So be super direct and be caring as you're super direct, but don't make the assumption that when you're uncomfortable, he realizes it, because that's probably not happening.

[Alison Beard]

Let me underline something here. She says in the first line, my boss is brilliant at his job and a great mentor. He has a weakness, and it's a weakness that on some days might be driving her crazy. But it seems like in the overall context here, this one seems completely fixable.

[Peter Bregman]

And if you think about the two other questions that we've had, both of them were much more difficult in that way. One, indecisiveness. His goodwill might be there, but it's very, very hard to shift from indecisiveness to clear decisiveness. And the other problem around being political and maneuvering and unsubstantive, that's also a very difficult thing to resolve and solve. This is really clear. And in terms of offering advice as to how to handle it, you could create some very clear and simple boundaries.

[Alison Beard]

How big a problem is it when he makes clear that he doesn't agree with business decisions that are made? Is a boss supposed to fall in line and sort of stay with the company line after decision is made?

[Peter Bregman]

Ultimately, when you're making this business decision, you could disagree as much as you want to, but when the decision is made and you walk out of that room, you walk out of that room as though you own the decision itself and it's yours. And the worst thing that you can do in terms of productivity, in terms of collective and aligned action moving forward, in terms of the culture, is to walk out of that room and go, well, I disagree with the decision, but we're going to disagree and commit. That is building both tension and discord between parts of the organization, which is one of the things that gets in the way of organizations moving forward most profoundly. So I would say that's a really serious issue. And I would say when he walks out of the room having made the decision with whomever he made the decision with, he's got to own it.

[Alison Beard]

Peter, I think you're right about that. Business is a team sport. And I think for our letter writer, if she can find a polite and respectful opportunity to say that she thinks her boss is hurting her team when he publicly voices his dissent, will take some courage, but I think it's something she should raise. So, Alison, what are we telling the woman with the gossipy boss?

[Dan McGinn]

So we think she should understand why he wants to gossip with her? Is he trying to build a more trusting relationship? Is he trying to get her feedback on difficult situations? Does he really just want to vent and figure out whether she can help him in a way that feels comfortable for her? We think that the idea of walking away or refusing to engage might be a mistake because it's really an opportunity for reverse mentoring. She can push back, not in a way that shames him, but that does explain her position and her perspective. Also, tell him when he's making her uncomfortable and might make others uncomfortable. Really, her ultimate goal should be to correct the bad kind of gossip and steer him to more productive problem solving.

[Alison Beard]

Peter, thanks for helping us find solutions for these people and finding a more effective way forward.

[Peter Bregman]

It was really great, really fun talking with you guys. Thank you.

[Amanda Kersey]

That was Peter Bregman, the founder and CEO of the executive coaching firm Bregman Partners. Peter's the author of the 2018 book Leading with Emotional courage, and he's the co author of the 2021 book you can Change Other People. He was speaking with Dear HBR hosts Alison beard and Dan McGinn. HBR on Leadership will be back next Wednesday with another handpicked conversation from Harvard Business Review. If this episode helped, you, share it with your friends and colleagues and follow the show on Apple Podcasts, Spotify, or wherever you're listening right now. While you're there on the app consideration, consider leaving us a review. And when you're ready for more podcasts, articles, case studies, books and videos with the world's top business and management experts, find it all on hbr.org this episode was produced by Kurt Nickish and me. Amanda Kersey on Leadership's team includes Maureen Hoch, Rob Eckhart, Erica Trexler, Ramsey Kabaz, Nicole Smith, and Anne Bartholomew. Our music is by Coma Media. Thanks for listening.