Women at Work - Ask the Amys: Sabotaging Bosses, Irritating Employees, and More

Episode Date: June 30, 2025

What if your boss turns against you the minute you ask for a promotion? Or you struggle with strategic thinking and keep getting feedback that you’re “too in the weeds”? Or the person dragging down your team is doing just enough to stay out of trouble? The Amys give advice for dealing with sabotage, shifting how you're seen, and setting expectations with difficult colleagues.

Welcome to Ask the Amies. This is when our listeners write to us about their frustrations at work and we give them our best advice. This time those questions are about making the leap from tactical to strategic, handling unfair treatment from a manager, coaching someone with a difficult personality, and a few other issues. So let's start with this question from a woman who's wondering how to push for a more formalized review process at work. She writes, I work at a mid-size family-owned company that has had some growing pains

as we've expanded. One area that has not evolved is our review process, which is done twice a year and involves filling out a form with two simple questions. There are no means for evaluating ourselves in terms of our performance on a more quantitative basis, and there is no opportunity for a 360 review of our peers. A revamped, expanded review process is something we could all really benefit from. But top leadership is resistant to change, despite multiple requests from multiple levels at the company. As someone in the middle of the hierarchy, she says she'd love a chance to provide some

effective feedback in a formalized way to her peers. She asks, how can I make the case for doing so in a way that will get leadership to really listen? Well, she has to build the case. Yeah. She has to build the business case and then she has to sort of assemble a coalition of supporters. Because I can imagine being in the leadership position in this organization and thinking, you want us to do what?

Like, we have so much to do. That's going to create layers and layers of bureaucracy. Why would we invest in this? Right. And she also needs to understand that no manager ever said, oh, great, I get to do more reviews and they need to be more complicated. I mean, it's clear that this is a company that could probably use, based on what she's telling us, could probably use a more formal process.

What that process is, what the investment needs to be, why they would do it, that really is falling to her to make the case as the one who's pushing it. I also think you don't have to wait until the moment of the annual, or in her case, semi-annual review to give feedback or to ask for feedback. This is something that should be in the flow of regular conversation.

So if what she is looking for is a way to give feedback to others, she should give it, right? Well, and I wonder if she could reframe what she's pushing for away from something formal, which sounds like a lot of work, a lot of investment, to we want to create a feedback rich culture. And how do we actually create a feedback rich culture? What do we need?

Do we need those informal discussions? Do we need to empower leaders and managers to understand what good feedback is? Do we need to empower employees to ask for feedback beyond these two questions that they get every year? And I think she could also try to model the behavior. I like that. That she'd like to see and see how that plays out. Yeah.

I like that. The thing I think requires a formal process though, is the giving feedback upward. Oh yeah. If your manager's not asking for it, the leadership's not asking for it, it's really hard to be like, by the way, I have some feedback for you, right? So I think the formal process there could help to have some structure around that. Yeah, I agree with that. That's smart.

The other thing I think about anyone pushing a change in an organization, when you've, you know, people have told you to put the brakes on, ask why. What are their hesitations? Is it around cost? Is it around fairness? Is it around unnecessary bureaucracy? Is it around cost? Is it around fairness? Is it around unnecessary bureaucracy? Is it around bandwidth? What are those? And then try to address those specifically when she builds her case. And also be open to the idea that you might have been

missing something, right? Yeah. They may have a good reason why they've never done it. And then she can engage in a conversation about that. My other favorite advice when you're trying to do something that hasn't been done before, instead of saying, we need to roll this out to the entire company and say, let's run an experiment. Let's do this in one division. See how it works. Test it out. It's a small investment.

It's time limited. If it works, great. And if it doesn't, then you learn. You can make your case different. Exactly. Exactly. All right. I'm going to reach you the next question. All right. Let's do it. This woman is wondering how to know which battles at work are worth fighting. A perennial, right?

I work in education as part of a team of paraprofessionals, but I think this question spans across many different industries. Over the course of a career, most of us will probably encounter a decision or situation we don't like or don't agree with. However, if nobody's hurt, nothing's damaged, how do you know when to speak up and when it's not a big deal? Amy, this seems tailor-made for you. You've written about this in the very distant past, 2013 or something like that. That's right.

And you've acknowledged that this is something you grapple with. Yeah. I have never seen a problem I didn't want to fix. That said, I do take a little of my own advice from that 2013 article. And really, the very first thing I try to do when I'm frustrated by something, when I think something is

unfair or unjust or should be fixed, is I go and talk to a few other people. Mm-hmm. Just to see if it's you. Yes. And to pressure test, like what am I missing? Why would this be okay? Mm-hmm.

How do you think about this? I mean, you're someone who has to pick your battles all the time. All the time. Remember that article about managing your energy, not your time, that classic? I think about that sometimes because it's not just time, it is energy. But I always ask myself, is this a one and done thing? Or is whatever I disagree with going to come back to hurt others or to hurt the organization in some way.

And if there's a long term effect, if there's a long tail to this thing, I might, I might jump up and say something about it. You know, we're talking about something in silhouette. I don't really know what the that is, what the thing is, but if you have a weird feeling about something or if something really seems unjust, plain wrong, you know, it's kind of your job to bring it up, particularly as you rise in an organization and your instinct is part of what makes you you. And it's part of what gives you value and sets you apart. Things don't bother me the way I think they bother you sometimes. And I think of that as a strength of yours and sometimes, and sometimes

it's a strength of mine. So there's, there's no good or bad about this. Well, and I also have to think about it's not just the managing your energy, but it's also managing your political capital because I have certainly been in positions where I raised every single concern I had and then I was treated as if everything I said was pulling a fire alarm for a fire that didn't exist. And so when there was what to me felt like a more important fire, no one paid attention. Right. And so that's the other thing.

She's an alarmist. Exactly. Or I'm, you know, I'm crying wolf. To me, they were all actually wolves, but I had to recognize that you need to modulate the feedback and the speaking up so that when you do have something you're genuinely concerned about, that people listen. Let me bring in a point that Nancy Rothbard made when I talked to her not too long ago. Researcher, academic at Wharton, right? Yes.

And I think this is really important. If you are raising an objection to something on moral grounds, remember who your audience is. You're bringing this objection to your manager, to your executive committee. Recast your objection as a business case, right? Yeah. I remember in your conversation with Nancy, what Nancy's research found was that that was especially imperative for women. Absolutely.

And it actually made them much more likely to be heard if they were objecting on behalf of the organization and not themselves or a small group. The small group, I'm thinking about our paraprofessional here who works in education, right? Maybe there's an unfair policy, maybe there's a staffing issue, maybe there's an interaction with a parent that was handled incorrectly, right? I'm thinking about how instead of saying this is unfair to me or to the paraprofessionals or to this particular staff group, this is not good for the organization. Is anyone addressing this? Because there might be a lot going on behind the

scenes about this policy decision, whatever it is that you feel is not right. Right. The problem might not be the decision, it might be the communication around the decision. Exactly, and that's why you enter it as a conversation, information gathering, not telling people exactly why this is wrong and how it has to be fixed right now. Well, you know, that old rule about assuming positive intent is important here.

Yep, always. All right, hopefully we've given her a little guidance. Let's go to the next one. This is from a woman who feels like her manager is sabotaging her career growth. She tells us that she's been in her current role for four years reporting to the same manager. Lately, when she's been asking him about career growth

and what she'd need to do for a promotion, he's started to spin a narrative about her to his colleagues that she's difficult to work with across teams. She says, I have never received this feedback in my 25 years of work, let alone over the last four years. When I asked for specific examples, the ones he gives me are vague, dated, and based on moments where I, at most, had a misunderstanding or respectful disagreement with someone. I have received top performance reviews, including 360 feedback from my peers, who I work closely

and cross-functionally with. I also have more management experience than him. He's only been doing it for a few years years and I've been doing it for 15 and have always had positive feedback. I can't help, but feel like my gender is an issue. My manager is also known for being very political and others on the team have noticed how he seems to have better relationships with men versus women. She's considered going to HR, at least to make sure that her perspective is

documented and because she's concerned about retaliation. She ends by saying, I'm also considering finding a new job altogether. I'm just not sure what to do. I think her instinct to go to HR is probably smart. I think documenting what's going on, making sure her side of the situation, especially the spinning, the narrative thing he's doing, right? You don't want all of your good work, all of your good reputation undone. making sure her side of the situation, especially the spinning the narrative thing he's doing, right, you don't want all of your good work,

all of your good reputation undone by this person. I don't think this marriage can be saved. Yeah. But I do think it's the right thing to do just because if this guy is behaving this way toward her, how's he behaving toward other colleagues, right? Yeah. And if it's gender-based,

all the more reason to bring it up. Exactly. It does sound like this all started with her saying she wants to grow. Right. You know, it's one thing if he was just not taking action, but he seems to be taking proactive action to dismiss and undermine her.

You know, I'm glad you brought that up because that's just not adding up for me. Which part? The part where she went to him seeking growth opportunities and guidance, and he turns on her and he starts behaving this way. What is going on there? Well, I have a few theories.

Okay. One of which I think is most typical, which is that he's threatened, right? He's like, who are you? Stay in your lane. Continue to make me look good. Exactly. Okay.

Don't take my job. Another is that he just doesn't know how to grow her. So it's highlighting his incompetence or his own insecurity about how to deal with this. And so he's just making it seem like instead of me being able to grow you, I can't possibly grow you because you're difficult to work with. You're not doing these things. And then when she's like, wait, what's going on? He's just sort of grasping at straws to give her this feedback that doesn't add up with

everything else. My other advice to this person is, I can't emphasize this enough, focus on your other relationships. I know this relationship is important. It matters so much to your career and to your daily experience at work, but spend time, invest in relationships with the other people you work with, which it sounds like a good relationship. Cause that's going to save her mentally, but then also hopefully give her some

networking opportunities. Maybe if things go sideways with HR, we'll give her another level of protection. Yeah. OK, should we go on to the next question? Let's do it. All right. So this listener wrote in about a tough dynamic with her soon to depart manager.

I've been working as an assistant property manager for five months. And despite being new to conventional property management, I've picked things up quickly. I'm eager to grow and have expressed interest in the property manager position after my current boss, who is the property manager, submitted her two-month notice. However, since I showed interest in the role, things have become extremely challenging. Some context. When my boss stepped away for a few months to work on another property,

I was left to manage nearly everything solo. During this time, she was not very supportive. When I asked for guidance, she'd say, I asked too many questions and need to figure things out independently. But in the end, I got positive feedback on my performance. However, I still have a lot of room to grow and I've asked her to help train me. And now that I've expressed interest in being considered for the property manager role, she's told me she's not responsible for teaching me. Deep breath, keep it. The situation has escalated to the point where she's taken over most of my responsibilities,

leaving me with very basic tasks. She's also been passive aggressive and rude. Awesome. I feel belittled and emotionally drained. I greatly appreciate any advice you have on how to manage this kind of toxic dynamic, particularly in terms of staying professional, maintaining my confidence, and not losing myself in the process. All right, Amy. Well, first of all, I think I and not losing myself in the process. All right, Amy. Well, first of all, I think I would not focus my energy on this soon to depart boss, I would focus it on who's there, who's going to be there when this person leaves and what sounds like less than two months.

Is there someone else who can show you the ropes? Yeah. Is there someone else who can help build your confidence? A mentor, maybe not everyone does exactly what your student department manager does, but is there someone who does some aspect of it that you can learn part of it? The only thing I would add to your excellent advice is I would suggest that the woman who wrote this letter go talk to whoever's making the decision about this job. To say, hey, I'm very interested in this. I know I have a lot to learn.

Here's how I propose to learn it. I would love to get some guidance from you on what you're looking for. And if you could connect me with people who you think do the job really well, I will make it my business to learn from them. You're making me think she could even do something as concrete as a list. Here are the things I'm really good at. Here's the things I would need to learn.

Here's who I would hope to learn them from when I take on this job. Maybe you know a property manager who works in a different company who you can network with and mention that relationship. Just being very clear that you have a picture of what it would take for you to do this role and that you would be able to execute on what that vision looks like. And also you know make the connections go out there and meet other property managers and ask ask for guidance. Yeah. And say that that's what you're doing. Show that you're really, really intent on moving into, if not this job, a job just like it,

because no one wants to lose that person, right? Yes, and I'll go back to my experiment tactic, which is that if there's some hesitation because of your soon to depart boss, maybe not saying great things about you, maybe just propose, could I try doing the job for a month the way same way I did it when she had to step away? Could we try it for two months, see how it goes and then readdress it?

Let me show you what I can do. Yeah. Yeah. I like that. So our next question is from a doctor in the UK and she writes, how can we start a conversation on gender equality in a department where the higher ups seem to be biased against women workers? I love this classic women at work question. I work in a place where male workers get better training opportunities.

Of course, they are able to stay longer and can put in longer hours to learn a surgery. Despite having similar surgical skills, male surgeons often display more confidence than their female counterparts. This gets them better opportunities and over time can create an unfair advantage for them. Any tips on how and where to start a conversation on this or how to collectively help the women I work with navigate this? Well I'm gonna give a classic women at work answer. Yep. Which is start by gathering data. Yes. Right? Yep. Because what she's saying would be

backed up by all the evidence, right? Like that they can stay longer, they're forgetting better training opportunities, have more confidence. So all of that, she's probably right. Her suspicions are right. But without the data, right, to show that there's inequality, right, then she's unlikely to, her suspicions are right, but without the data to show that there's inequality, then she's unlikely to get the ear of the higher ups. Right, exactly. And then once you've got the data in hand, go to the higher ups with it.

Yeah, there is research, and I don't have it at the top of my head, but I know we've published research that also shows that when people who don't have a stake in the equities, they aren't the target of the inequity. When they raise the concerns, they're more likely to be heard. So I would also say, are there any of these male surgeons that you would consider allies, who you could have the conversation with, who you could say, look at this data I found, any chance you'd be willing to help

me start this conversation? Yeah, that's a good idea. Yeah. This is someone who I really want to write back to us and let us know how it goes, because this is a long process, but even starting the conversation, that's the other thing. Just to help her deal with this and navigate it, and also, as she says, to help the other women navigate, is set small goals, milestone goals. Just raising the issue, collecting the data, having one conversation

that leads to one positive commitment. Because if you're set on rectifying the entire situation in a short period of time, you're gonna feel demoralized and disappointed. So find a small goal that you can achieve that will help lead up to a larger change. Good advice. This listener wrote in about her desire to grow from a strong tactical manager into a more strategic leader. She writes, I work in change management where I guide cross-functional teams through complex change initiatives. Throughout my career, I've been recognized

for my ability to execute and implement effectively, but I'm hoping to soon land a more senior role that would allow me to help shape strategy, not just execute it. As I prepare for that next step, I'm realizing I need to elevate my thinking to be more strategic. But making that leap has been tough. I recently contributed the change management section of a document intended for our C-suite, but the document owner shared that my content was too in the weeds and needed to be higher level. I struggled to determine the right level of detail and what to prioritize. I also recently interviewed for a job where I was a top three candidate, but ultimately didn't get the job.

The feedback was that I'm too detail-oriented and the team was looking for someone with a more big picture perspective. How do I build and demonstrate strategic thinking, especially when I've been relied on for execution for so long? What does the shift look like in day-to-day work? Over to you. So I think a lot about Nina Bowman, who is a executive coach and leadership development person who has written two articles for us that did really well. I think they were back in 2016. One was four things to improve your strategic

thinking skills and then how to demonstrate that you're a strategic thinker. And a lot of what she describes, and we'll share those in the show notes, but a lot of what she describes is really trying to put yourself in the shoes of the senior leader. What are they thinking? What are they asking? The minute you start to go into detail, ask yourself, is that a detail that's relevant to this question? Will that help us make this decision?

And maybe, you know, on conversation five of our 10 conversations, that's a relevant detail, but in the first conversation, is it? Right, so trying to really see things from that perspective. The other thing Nina talks a lot about in those two articles is asking the right questions. Right. And that's not how much data do you need to make this decision,

but what would influence your ability to make this decision? What factors do we want to consider? Who else needs to know about this decision? Who else has a stake in it? I think of you, Amy B, as someone who's very strategic and I'm curious, and yet also very good with details. So how do you balance those two things? Well, I'm actually terrible with details and anyone who is a direct report of mine will tell you that. And I forget, I forget things all the time, but I think the mark of being

a strategic thinker is your future back. So you start with where you want to go, the outcome you want to accomplish, the change that you want to bring to life, and then you work back from there, right? And everything is framed in those terms. So you're thinking about the vision and the goals and the stated strategy of your organization. And this is about pulling the camera back. Right? So where I would go is understanding the game that your organization has stated it wants to play and how it says it plans to win that game. Right. Yeah. We published a great book called playing to win.

Right. By A.G. Lafley and Roger Martin. And that's become a classic, but I think about that. And she should actually read that book. It's totally worth to read. Even if she just skims it. Because I think that will help her understand what are the big picture questions the

leaders are probably asking themselves or should be asking themselves? Well the other thing I would read is Mike Porter's classic on competition, the five forces. But you have to understand the competitive environment that your organization is operating in because that will sensitize you to opportunities and threats and those are the terms you should be thinking in. Yeah. Right? you know, I said you're working from the future back. You're always thinking about the long term. You're thinking about the long term success and health of your organization. And you're framing your thinking in those terms. When you're making a suggestion, you're proposing a change, it's always for the long-term success and

health of the organization. Yeah, I love that. And I have a very tactical recommendation for her knowing that this report did not work out for her and knowing that she's two in the weeds is that she can write the first draft, which will probably be too much in the weeds and then think of that as the appendix. Right. So, okay, if that's the appendix,

what are the two, three top takeaways that people reading this document need to know? Right, perfect. Okay. All right. Problem solved. We solved our problems. Amy, I'm gonna ask you this question.

We're gonna go out of order because this is your bailiwick, all right? So it's from a woman who's wondering how to coach a team member with? A difficult personality. Love them. All right. She writes, I'm struggling with an employee

who isn't openly insubordinate or violating any clear policies, but still creates turmoil. During meetings, the employee makes passive aggressive comments framed as facts, is argumentative, avoids taking responsibility, and lacks self-awareness about the impact of their behavior. Wow. At times, they seem to subtly target a co-worker, but it's done in a way that feels subjective and hard to prove. How do you manage someone whose behavior is corrosive but not clearly coachable or fireable?

Is it really true that you can coach performance but not personality? And what can you do when there's no defining moment to act on? Just a pattern of undermining. That is juicy. And that is written for you. Well, we have three hours, right? Because I have a lot of thoughts. I mean, my very first thought is this word personality keeps coming up over and over. And I think that's really leading her down the wrong path, which is who knows? Maybe this person has a difficult

personality, but when you treat it as a personality, there's nothing to actually address. Right. Like you can't say to someone, you have to change completely who you are because it's really annoying everyone else. Like you just can't do that. Tempting as it is to say that sometimes. And in my head I've said that, but you have to figure out the behavior that's problematic

and you don't have to prove it. This is the other thing, she keeps trying to prove. You don't have to prove it. You can say, there's an impression that. Yeah. I get the feeling that when I saw you do this, it made me think this. Right. You don't have to prove beyond a reasonable doubt, even though this person will argue with you till the end of days that they're not wrong, you as their manager can say, this is the impression you're giving, regardless of whether

it's true or not, we need to work on the impression. So what can we do differently that will change that impression? The other piece of feedback I would give is that it is part of this person's job to get along with their coworkers. And you can say, it's your job to get along with others. And you don't have to say, here's where you're not getting along, here's that annoying thing you did. You can say, here are some things I'd like you to try in order to get along with others. Give this person some proactive steps to take, right?

You might even say, you know, when you do this, it's construed as lack of collaboration. But if you do this, right, if you ask an open ended question, if you build on someone's idea instead of undermining it, if you don't say anything in the meeting and just listen, right, that builds collaboration. And that's what I want you to do. Try these steps to build collaboration. I think managers are so hesitant when they feel

like, oh, this passive aggressive behaviorgressive behavior is, it's, that it's part of who the person is. And you have to separate the behavior from the person. The behavior is not acceptable. Right. If you see behavior that isn't building the organization, that isn't somehow adding to a positive esprit accord, then you can call it out. You know, you can say, I heard what you just said and that was not very constructive. Yeah.

Well, it may not be easy. That's, I think the other thing is I think we often say, oh, they're not coachable. And the reality is this person may not be coachable, but you have to try. I get the sense that she hasn't yet tried because it feels like this person's too combative, too argumentative, too unwilling to admit they're wrong. And they don't have to in order to move on. I agree with you. And I think that the thing to remember is

that attitude is every bit as important as technical skills and an employee. And if this person isn't bringing the right attitude, then this person doesn't belong on your team. And you can do something about that. That's right. I have sympathy for our letter writer in that nothing's quite fireable and they often have a reason why they said something or the argument of why it was okay but that doesn't mean you have to tolerate it. Well this is where you go to HR. Yeah. Because HR deals with this all the time.

Yeah. The other thing thinking back to our very first question around formal review process I also wonder if there's a 360 review process if there's something where she can get a little bit more of quote-unquote objective feedback that would help give her a little bit of data to bring to this person to say, you know, you say it's this, you say it's this, but what the patterns we're seeing in the feedback is that this is how you're perceived. I agree with you a hundred percent, which is very wise given how you're perceived. I agree with you 100%, which is very wise, given that you are the expert on this stuff. You did write the book. I feel a little guilty at how excited I get

about a question like this, because I know there's someone suffering, but it is what I love to talk about, so. ["Women at Work's"] Women at Work's editorial and production team is Amanda Kersey, Maureen Hoke, Tina Toby-Mack, Hannah Bates, Rob Eckhart, and Ian Fox. Robin Moore composed the show's theme music. Bye, everyone. Bye-bye.