Getting Along with an Insecure, Know-It-All Pessimist

KIM: I got hired and told, “We hired you for these skills. We hired you for this reason. We hired you to do these things.” So, I’m like, Yay, great. I get to do what I love. I come in and I start doing it, and it’s not met how I thought it would be met. George is so defensive about everything and attacks every idea. So, then I’m just constantly at this point considering, okay, is it worth it to say anything because what’s the likelihood of getting a response that will feel good versus a response where I’m going to go home and scream into a pillow for an hour?

AMY GALLO: Kim runs operations and human resources at a small consulting firm, or trudges through that role, really, because of George’s pushback. He’s the founder and one of four owners, all men who’ve worked together for years. The other three owners, she says, have given up on trying to persuade him to adopt new processes or programs. She describes their position on his behavior this way.

KIM: “Yeah, we just let him do what he wants because it’s easier than fighting with him”, which I completely see. I have already discovered myself personally that yes, it is absolutely easier to just roll over.


KIM: And I’m not the type of person who can easily just say, “Okay, I’m just going to roll over and do what he says, even if I know it’s wrong or even…” There are things where I feel like sometimes I’m being asked to do my job poorly and that’s difficult for me.

AMY GALLO: That’s really tough. Yeah. George’s my way or the highway attitude makes me think that Kim’s dealing with a know-it-all. Know-it-alls tend to monopolize conversations, position their own ideas as superior, and refuse to listen to or heed criticism or feedback. These tendencies cause others to hold back ideas so they can avoid being demeaned, and when a know-it-all calls your expertise into question in front of others, they’re giving them permission to disregard your opinions. How do we deal with the Georges of the world? I’m Amy Gallo, and this is Getting Along, a series where I help a guest and you and everyone else listening, learn to work with anyone, even difficult people. By difficult, I mean rude, unprofessional, or hostile. Bad behavior that wears us down. No one should have to grin and bear it. Change is possible, but the answer isn’t to suppress our emotions or hope the problem person leaves, neither is retaliating or shaming them. These are lessons I’ve picked up from being a career coach, studying conflict and spending the past couple years reading about behavioral science and interviewing researchers for a book. It’s also called Getting Along. Tending to our toughest work relationships is worth the trouble. After all, they loom large in our lives and have a disproportionate impact on our experiences. The path to improving them starts with understanding why certain types of difficult people act the way they do. Then using tactics and phrases to match that type. Little by little you can build a functional relationship for the sake of your sanity and career. Across the series we’ll cover how to put yourself in a productive mindset, model the behavior you want to see, and hold people accountable when they’ve promised a change. We’ll also acknowledge that we can’t force anyone to change. All we can do is nudge them to be a little less insecure or pessimistic or whatever their issue is. Note that every guest is using a pseudonym so that they can speak more candidly about their situation. But back to Kim. I asked her what success would look like.

KIM: So, I feel like success would look like I could have more constructive ways to answer the attack. I’m not good at that, I don’t think. I don’t know if there’s a way to be good at that, but if there’s a way to be good at that, I’d like to get there and feel good walking away from the situation that not only am I true to myself, but that I don’t make anyone else in the room feel like I’m attacking them.

AMY GALLO: Achieving the sort of success she’s after will likely require her to manage not only George’s know-it-all side, but other aspects of his personality as well. We’ll get into those in a few minutes. For now, let’s stick with his know-it-all side and one of the common behaviors that stems from it, micromanaging. Where does she think that’s coming from?

KIM: I think that some of that relates to he founded the company. It’s like this is his baby and it’s a very successful company. It’s been around for a while now and has grown and is in seven figure revenue and it’s doing great. He’s done great things from a small start, so I think that he’s very protective of the company. He’s done things a certain way for a long time and it’s “worked”. And so, my coming in as an outsider and saying things like, “This maybe isn’t a best practice” or “at the scale of the company right now, we need to consider changing this piece of software or this security feature or this HR practice.” It feels like a battle every day because no matter what I say, he’s going to just rip it to shreds. I don’t know that I feel like I have it in me to go in and fight every single day when it’s like, Hey, you guys vetted me. I went through an extensive interview process. You checked my references, you checked my education. Why do I have to keep proving that I know what I’m doing and why can’t he be open to the idea that… Some of the things he did worked because it was a small company and it was brand new, and there was at that time one or two employees and they just don’t work in a company with 30 plus employees. I was told, I was hired, “Hey, we want you to change this. We want you to implement this.” But everything they hired me to do is a battle. I really, really am at a loss of… how do you handle somebody like that? Because so far, all I know to do is say, “Well, I know what I’m doing,” but telling him I know what I’m doing, that’s clearly not the way to handle this.

AMY GALLO: Is your sense that some of this comes from insecurity, though?

KIM: I don’t know. I had a previous job where I encountered a nearly identical situation and everyone around me says, “Oh, he’s just insecure. Oh, he’s just threatened by you.” And especially at this moment in time, being a professional woman and I’m working in a 95% male company in a male dominated industry, I guess it could be he’s intimidated by me. I guess it could be that he feels insecure. I feel like at this point I’m a bad judge of character and I just don’t even know what to think.

AMY GALLO: Why do you think you’re a bad judge of character?

KIM: As I mentioned, this isn’t the first time that I’ve taken a job with someone who when I interviewed with them, I thought, Oh, this person is awesome and we’re going to get along great, and then I get into the job and I have to deal with this situation. So, I am starting to feel like, Huh, maybe I’m not really the best judge of character with all of this. And so, I just don’t know. I don’t know why he’s acting the way he’s acting. I just know that I don’t think it’s sustainable to deal with.

AMY GALLO: Got it. Okay. So, before we have you take on the responsibility of being a poor judge of character and actually being the problem here, let’s just acknowledge there are a lot of difficult people and also oftentimes people will start organizations because they haven’t worked well with others and they think, Oh, it’ll be easier if I’m in charge, if I get to be the entrepreneur. So, I’m not surprised you’ve had this problem in more than one circumstance. However, I do want to ask, if I were to tell you, no, you’re the common denominator here, you are causing this problem, what would your answer be about how you might actually be contributing to this issue? Again, just as a thought experiment.

KIM: I’ve absolutely… At this stage in the game, I have to think about that and I have thought about that and I am very direct in my communication. It is something that professionally I have very actively worked on for years. I have people who’ve known me a long time who say that that is a skill I have improved. However, I am somebody who is committed to telling the truth, and that is often uncomfortable for people. So, I would say that how I contribute to the situation is that I can make people uncomfortable with how I communicate and what I communicate, and I feel like I’ve worked on that. I feel like I’ve tempered it. If we’re looking at me as the common denominator, I would say, “Okay, well I haven’t gotten there yet. I haven’t done all that work I need to do,” but I am at a loss of how to be authentic and how to be true to myself and how to not make myself smaller for a bunch of insecure men. And how do I communicate with them so they’re not threatened or feel attacked by me?

AMY GALLO: Right. That’s a great way to put that question. How do I behave in a way that feels true to who I am, which is an honest, straightforward, direct person? How do I not make up for others insecurities in a way that diminishes what I find best about myself and how do I make this sustainable?

KIM: Because I wonder if me saying, “Hey, this process could use improvement because we have exposure in this way, this way, this way.” I think he’s taking it personal. He invented a process 10 years ago that worked for him for a long time, and me coming in out of the blue and saying, “Actually, this really isn’t great. We need to do it differently,” – how do I do that so he doesn’t feel attacked and I can do my job and do what I was hired to do and show them, yeah, I know what I’m doing. I can do this. I need less attacking and more confidence that you hired the right person.

AMY GALLO: Sure, you want confidence in you, but it also sounds like you want collaboration to actually come up with processes that both of you feel work for the organization.

KIM: Yes, absolutely. That is the other very difficult part of this. In my role, I’m supporting our entire team and I need that, and it’s not helpful to just rip everything, every idea that I have, to rip it to shreds. We get into these conversations and I don’t even know how to guide the conversation in a direction that lends itself to being productive and drawing those ideas out of this particular person because it feels like he instantly gets defensive and then… So, there’s a wall there. So, no collaboration is happening.

AMY GALLO: Yeah, yeah. There’s no exchange or equal exchange. It’s just criticism, criticism, criticism, criticism. Which is why the behavior you’re describing is very much aligned with sort the know-it-all archetype. But the reason I’m also wondering about the insecure boss archetype is because it does sound like there’s a lot of defensiveness, and that’s what we see with insecurity. And it may be that defensiveness is not linked to insecurity, but let’s just for the sake of this conversation, assume there’s probably some defensiveness fed by a feeling of being either criticized or being exposed as having not set up this company as efficiently or as productively as possible. And I think we can also assume there’s a little bit, the sort of tearing down the ideas does also have a pessimist tinge to it. I don’t know if you would describe him as a pessimist. You’re smiling.

KIM: Very much. I came home from work one day after early, early when I started and told my husband it’s like I work with an aggressive Eeyore. He’s just… Everything… When we are in a group in the management team and discussing an opportunity, he’s always the first one to pipe in with how it could go wrong or what is wrong with it or why it won’t work. And sometimes I just want to grab him and say, “Pause. Tell me why it will work. Let’s think about why it might work. What could go right?” Because if we’re just going to tear down every idea, then we’re not moving, we’re not growing, we’re not progressing.

AMY GALLO: Right. So, do you actually ever do that? Do you, not grab him, but do you ever say, “Oh, tell me how it could work” or “Tell me what positive you see in this?”

KIM: I did once in a meeting. It was the leadership team and we were there and he was saying something. He started down the road of that and I did say, “Well, yeah, but what could go right?” And he just kind of ignored it and blew it off and then went on with the conversation. It was in a bigger conversation. And I didn’t press the issue.

AMY GALLO: So, that’s actually a tactic I talk about in the book that I do think works well with pessimists, which is you’ll try to say, “Okay, well what would it take for this to actually work?” Or “what positive things could come from this?” And they may just ignore it or they may go back to their negativity. But it’s something I would continue to try. I would also try to do it when it’s not loaded, because one of the things that happens with any difficult person is that you can often get polarized, whereas, I’m collaborative, you’re combative, I’m optimistic, you’re pessimistic. As you start to, at least in your mind, and then in their mind, you all are at opposite ends of a spectrum and there’s nowhere to meet in between. So, one of the other tactics that often work with a pessimist is to validate their perspective. Truthfully, genuinely, I don’t want you to say, “Oh, you’re so right.” Again, I don’t want to get into you diminishing yourself or your ideas to compensate for his behavior, but to say, “I see what you’re saying and I agree there are risks that could happen. I also see some upsides. Let’s talk about those.” So, trying to, instead of polarizing and saying, “God, here he goes again with all his negativity, with all his pessimism,” is just give him a moment of, I get that. Here’s the risk I see too. Right, okay. That gives a sense of, We’re in this together, and then you can transition or add in the positive stuff as well. And I think engaging in the conversation of, Well, what would it take for this to work? What would have to be true? If we imagined a situation in which this would work, what would that look like? And then you’re sort of getting him to actually participate. He doesn’t have to agree it will work, but he’s hopefully participating in a more positive constructive conversation. Do you see that possibly working with him?

KIM: I do think that could work, especially what you said, just presenting that idea of, “if we just imagined” – I’m paraphrasing a little bit – “but if we just imagined a best case scenario where this would work, what would that look like?” And I feel like he would have a hard time. That seems like a difficult question to come back with a negative to. So…

AMY GALLO: Yeah. Because you’re not asking him to agree it will work. You’re asking him to imagine if it will work. And then that’s a theoretical conversation which you can hopefully then transition to, Okay, now that we have an agreement about how it might work, here’s how I see that playing out in reality. And again, the goal with any of this… because it sounds like the dynamic has been set up that you propose a new idea, he gets defensive, you are assertive, as you should be because you’re defending your ideas, you’re defending your competence. And then it’s just feels like a back and forth, a tug of war, attack. The goal is to think of yourselves on the same side of the table. You are in this together, in your mind, even if it’s not yet, in your mind, you are collaborators trying to solve problems together. And I think the way you’ve told me a little bit about him, it sounds like understandably you’re showing up to work every day prepared for a battle. And I think if you go in with that mindset, he’s going to pick up on that. He’s like, Okay, battle, here we go. So, if you can start thinking – and that hopefully will mirror in your actions and in your language that you use with him – that we are in this together, we have a whole set of problems to solve, processes to set up, and we have to work together to make it happen. We’ll talk a little bit more about how to counteract his attacks, but I think that going in with that mindset is a great place to start.

KIM: Yeah, I think that could be helpful.

AMY GALLO: Yeah. Good. I’m glad. And I think one of the communication tricks is also to often use “we.” So, rather than I think this, you think this or in my last job we did this or best practice is this as saying, Well, we want this right? We want these things to happen. To get to that vision I just laid out, we have to do this, right, or we should do this or we should consider doing this or can we try this out for six months, see how it goes.

AMY GALLO: That’s another thing sometimes when people are constantly putting down ideas or refusing to try new things, rather than saying “We need an entire new performance review system,” which can feel overwhelming and like you said, might feel like a critique of, “I’ve run this company for 10 years. We’ve never had a problem with the performance review system,” is say, “Can we try out a new system for six months, see what we learn? It’s an experiment. We’ll see how it goes and then we can refine from there.” So, you’re iterating on his current systems rather than saying, “These systems don’t work,” but, “we’re iterating on them in a way that helps us all learn and hopefully get to a more effective, productive place.”

KIM: I like that idea of, Let’s do X, Y, or Z for a trial period. I think that probably feels less scary and might be better received.

AMY GALLO: Yeah. Yeah. And again, I don’t think these are things that will diminish your ideas. I don’t think they’re things that will require you to not be straightforward, but they’re sort of communication or persuasion tools that will help you reduce his ego defensiveness. Because that’s really what we’re dealing with when we’re dealing with someone who’s insecure and often someone who’s a know-it-all – is that they’re defensive of this… of what they’ve created or what they believe or how they act. And so, trying to give them feedback or trying to even propose a new idea feels like an attack, and I really hate that this is true, but the research shows, especially with insecure people, that flattery helps because it reduces that insecurity. Now I don’t want to tell you that you have to go in and be like, “I love your shirt. You’re so smart.” That’s not, I don’t want you to… I mean research shows those things would work, but that feels awful. So, again, I’m thinking of your goal of wanting to be able to be true to yourself and authentic. I would think about what strengths does he have? He’s done something right, right? He’s built this company, he’s brought in partners. So, I would try to focus both mentally to help your frame of mind, What is he really good at? And I would also articulate those things because George may be sitting here thinking, Nine times out of 10, Kim is telling me I’m doing something wrong. And so, for him, he’s also probably preparing for the battle with you, and if you can change that balance where it’s maybe three times out of 10 you’re telling him he’s doing something right, or you even say, “I love what you did with this. Well, here’s how I want to build on that.” Right? Or, “What you’ve done is worked really well, let’s continue that and add to it by doing this. Right?” So, you’re trying, again, to reduce the ego defensiveness, get him into a more open collaborative frame of mind and the flattery helps, but it has to be genuine.

KIM: Can I ask a question about something you said? So, you’ve mentioned rather than saying, Here’s a best practice. And I will say that as this situation has gotten muckier and muckier, I have tried that. I have tried to rely much more heavily on it not being my idea because more often than not, the things that I’m proposing are not things I thought of and they’re not my idea. They are things that I’ve learned are… you said it exactly, I use that phrase a lot – “The best practice is,” or, “here is a best practice here.” And now I feel like, Oh, yikes. Maybe I’ve been sabotaging myself by relying too heavily because I was trying to make it not about me. And I was trying to not say I’m right. I’m trying to say I don’t have a dog in this fight. I didn’t invent this thing, but I can tell you that the best practice is this. But it sounds like maybe that’s not helpful.

AMY GALLO: Well, normally I would say with a know-it-all, sometimes that can be really helpful. You can say, “Well, there’s data that shows, right?” Or, “I’ve seen this” and it does take it out of the interpersonal, I’m right, you’re wrong. The problem is, in this situation, because he’s the founder and because he’s set these things up himself, my concern is that when he hears “this is best practice,” he’s still hearing “you’re doing it wrong. You didn’t do it according to best practice.” And so, even though it’s technically neutral, it’s coming off as a criticism. That’s my guess based on what you’re describing his reaction to that is. Does that make sense?

KIM: Oh, that makes a ton of sense, and I had honestly never really even considered it, but it makes so much sense as to why it’s never been met well for me to say, “Here’s best practice, here’s the data.” Me saying “this is the best practice” is him hearing “you didn’t do the best practice.” So, it’s…

AMY GALLO: Yes, it’s a criticism.

KIM: A criticism.

AMY GALLO: So, then that’s why I’m thinking something more like “What you’ve done here has worked really well, let’s add to it,” might help, or, “hey, could we try something different out and just see how it works?” It’s much less threatening to do it that way, even though in your head you’re like, This is best practice, this is how it should be done. You don’t always have to say that, and I think that might make him more open to those ideas. And once you’ve actually done that a few times, I think this defensiveness he has, this seeming lack of confidence in your ideas or what you’re presenting might become less problematic. I think he might develop a little bit more of a rapport of, “okay, Kim knows what she’s talking about. We tried that thing, it worked. I didn’t have to admit I did anything wrong, so it was easy for me to do.” And if he is not stuck in that mental battle with you – of, Kim just keeps criticizing me, then I think you’re going to be better able to not only present more ideas and get more traction with them, but you’re also going to be able to be less careful about how you present them. Because the idea is, let’s say you stick in this job for five years. I don’t want you for the next five years to have to be walking on eggshells every time and think so carefully about how you present things. The goal is to get you to a point with him where you give each other the benefit of the doubt and you have enough confidence in one another that you can be less careful and you can say things that maybe rub him the wrong way and he can point it out. You want to get to the point where it’s just a little more comfortable.

KIM: Yeah, yeah, absolutely.

AMY GALLO: There’s one other possibility I want to throw out there. And it may be that this won’t work, but I wonder about having something I call the meta conversation. So, is there an opportunity when George is in a good mood, when you guys maybe have had some win together where you could say, “I feel like a lot of times I’m proposing ideas and you’re resisting and I get defensive too, and is there a different way we could interact? Is there something I could change about the way I’m proposing ideas that would be helpful to you?” And that’s a hard conversation to have. I would definitely rehearse it, but I wonder if you get some useful information from George about how he prefers to be interacted with, that would be relatively easy things to change that would change that dynamic. I don’t know. What do you think about having that sort of bigger conversation with him?

KIM: I love that idea. I absolutely do not mind having hard conversations because what you’re saying is, yes, that’s the information I want. And I’ve read books. I reached out to you, I’m Googling things on the internet. But at the end of the day, that’s what I want to know – is, Okay, how do I relay this to you, because I’m just trying to do my job. My job is to support the company. I love my job. So, it’s not that I hate what I’m doing and it’s not that I’m bad at what I do. How do I communicate with him so that he’s more receptive and understands, because I’m clearly doing a bad job at making him understand that I’m not trying to attack him. I’m never thinking in my head, Oh my God, he’s so bad at his job, and, Oh my God, he screwed this thing up. I’m never thinking that. But I think he thinks I might be thinking that. So, how can we start from a place where he knows that I am on his side, I’m on the side of the company, they want growth, I want to help. How do we work together and make that happen? But right now we’re not working together. We’re working against each other practically. So, nothing’s working.

AMY GALLO: Yeah. Well, and I want to reframe something for you because you said, “I’m clearly doing a bad job of having him hear me.” And I think there’s a combination of his insecurity, his maybe overconfidence, his defensiveness, plus your direct style and plus your frustration with him that’s making that situation happen. I don’t want you to take responsibility for it solely. And that’s the attitude you need to go into that bigger conversation with is, I don’t love the way we’re interacting. I know I’m contributing to it. I’d love to hear your thoughts on how we do this better. And then it’s like, We’re on the same side of the table. The problem is our dynamic, our interactions, how do we solve that together? And he might get defensive in that conversation, but he might also give you, through his defensiveness, he might give you some clues about how to better interact with him.

KIM: Yeah, anything would help. Honestly, I’m just trying to take all the information I can. How do I make this better? Because it is not sustainable, I don’t think it’s sustainable for either one of us. I would suspect he would say the same thing. But it’s really depressing to get into a job and realize six months in, did I make a mistake? Because I don’t know how to fix it, but I feel I have some better tools now.

AMY GALLO: So, Kim, what do you want to do differently now?

KIM: I honestly feel like sitting down with him in a non-charged setting, maybe going out to lunch or something and just saying, “Look, our interactions clearly aren’t working for us. How can I communicate with you better?” And probably lay out there my fundamental reason for being here and explicitly tell him, “I’m not trying to critique you or what you’ve done,” and saying, “tell me how you want to be communicated with.” And I think the other really important thing for me is – and I know I’m going to really work hard at this – but I have turned into walking into work every day preparing for battle. And you’re right, that vibe is going to go out into the office. So, I’ve really got to work on changing that mentality, personally, before I leave my house, to not prepare for battle but prepare for collaboration. I think those two things are going to be super helpful.

AMY GALLO: Yeah. I’ll just leave you with one last tip. You’re not going to have, I don’t think you’re going to have that conversation and everything’s going to change overnight. I don’t think you’re going to change your mindset and go in and it’s like, Oh my gosh, look, we are collaborators now. So, I think what you have to do is really celebrate the small wins. So, if he, instead of resisting your idea four times and he only resists it twice and then says “okay,” that’s a victory. I just would really focus on what are the small steps and keep at it. Because it’s so easy to just try one thing and get rebuffed and be like, Forget it, I’m done. Behavior change is hard. And even if he was here with us right now and said “I’m committed to change. I want this to go better.” He would have slipups. So, allow that. We’re all flawed humans. You’re flawed. I’m flawed. George is flawed, and just accept that there’s going to be bumps along the way, but you’re headed in the right direction. You’ve got your goals, you’ve got some tactics to try and you’re going to tweak your approach along the way. And if you’ve set a time period, if in four months, six months, eight months, things have not changed, then it’s time to reevaluate.

KIM: Yeah. Yeah.

AMY GALLO: Kim, thank you so much for sharing your story. I hope you’ll stay in touch and let us know how this all goes.

KIM: Yeah, absolutely.

AMY GALLO: If you want to learn more about how to work with a know-it-all, insecure boss, pessimist, or an otherwise difficult person, you can order my book Getting Along through HBR’s online store, Amazon, or your favorite bookstore. And if you prefer to listen, there’s the audio book I narrated. HBR has put together a toolkit to accompany the book that includes more of these episodes, as well as worksheets and an assessment to help you put the book’s advice in practice. Find the toolkit by going to and searching “Getting Along.” Let me know what you think of this series by emailing

Also, HBR has more podcasts to help you manage yourself, your team, and your organization. Find them at or search HBR in Apple Podcasts, Spotify, or wherever you listen.

Women at Work‘s editorial and production team is Amanda Kersey, Maureen Hoch, Tina Tobey Mack, Rob Eckhardt, Erica Truxler, Ian Fox, and Hannah Bates. My co-host, Amy Bernstein, will be back with me for Season 8 starting October 17. I’m Amy Gallo. Thanks for listening.

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