can I fix how my boss treats people?

A reader writes:

I work for a small nonprofit membership organization and am supervised directly by the executive director. The ED meets with funders to advocate for our members, builds partnerships with other organizations to provide services to our clients, and is generally the “face” of the organization.

The problem is, he’s kind of a jerk. He constantly interrupts and talks over people, over explains simple points like one would to a toddler, points his finger in people’s faces when speaking to them, and is very dismissive of anyone who has ideas that are not his own. (He recently told someone during a meeting, “This is why you’re wrong” and listed all the reasons why a pretty good idea wouldn’t work.) I’ve been in many meetings with him where I’ve seen people completely shut off after listening to him for about two minutes. He’s worse with women, especially young women. While we haven’t lost out on any opportunities (that I know of) because of his demeanor, I have had people approach me privately and comment on his abrasive personality. More than a few people have bypassed him and come to me to set up programs and suggest new initiatives because they don’t want to deal with him.

I have pretty thick skin, so I have no problem pushing back when he starts lecturing me about how much I don’t know, or telling him “I am not finished speaking” when he tries to interrupt me. I know not everyone is comfortable doing so. How can I talk to him about the way he speaks to others? Is it even possible to address without looking like I’m overstepping? As I mentioned, he’s the face of our organization and I hate to think that our funders, clients, and partners think we’re all a bunch of jerks.

You can’t fix this.

I’ve worked with this guy and I’ve been you, letter-writer, and all the energy that you will put into trying to explain to him how to treat people decently — into trying to explain how to talk to other humans, and not to treat young women worse than other people, and not to be an asshole — all that energy will be wasted.

He might — might — make small modifications around the edges. It’s almost worse if he does that, because that will give you just enough hope that he can change that you’ll continue to try to change him more.

But he won’t change in substantive ways. This is who he is. He’s an asshole who diminishes people.

If you want to have one conversation with him — and only one — about what you’re seeing and the problems it’s causing, go for it. There is a very small chance that it will be a wake-up call for him. If it is, great! He can pursue coaching or therapy or behavioral changes on his own. If he wants your advice about what to change, he can come and ask you for it. But if that one conversation doesn’t change much, then hear the message that’s sending you, and don’t spend more of your energy trying to fix him. At that point, you’ll have shown him the problems, and he’ll have shown you he doesn’t care.

If you want to work there anyway, knowing that this is who he is and he won’t change, that’s 100% your prerogative. Some people are fine with this type of personality and can work around it pretty well without being terribly affected by it. If you can and you want to, feel free!

But all that energy you’ll put into trying to be a buffer between him and others (that’s what’s happening when people come to you instead of him), and into protecting other people from his behavior — if it works, that will just keep them in a bad situation longer, when what they really should be doing is getting out. Don’t try to make this more palatable for other people; support them in pushing back or leaving.

Read an update to this letter here.

{ 160 comments… read them below }

  1. Anon for this*

    Oh no. I could have written this letter, and this is exactly what I don’t want to hear. Assuming not great but not abusive management, if you’re in a position reporting directly to an ED/founder, how do you get good feedback/coaching to that person? What are the limits to managing up, especially to someone who doesn’t have a manager, in a young organization?

    1. voyager1*

      It is really going to depend on how upper management sees him. They may no he is an ass, but if he brings in $ then they may be less inclined to do anything.

      On the other hand if they hate his guts, a well placed complaint could do some good.

      1. Anon for this*

        In this scenario, there is no upper management. This is the person who runs the organization.

        1. Lumen*

          Then run far, and run fast. The limit to ‘managing up’ is how much the person above you actually lets themselves be managed/coached/given feedback, especially when there’s no one else above them. And if that amount is “very little/not at all/a bit but it costs me a lot of social and professional capital”, then your options do get somewhat narrow.

          1. AnnaBananna*

            + 1

            Yup there’s a crucial part of managing up and that’s that you’re saving BOTH your faces from looking bad to superiors. If there’s no superior? Not a damn thing will compel them to change unless there are drastic consequences (scandal, losing major funding, being snubbed in the industry, etc).

          2. Swiss Miss*

            Then run far, and run fast.
            Allison has said, “if you want to work there anyway, knowing that this is who he is and he won’t change, that’s 100% your prerogative. Some people are fine with this type of personality and can work around it pretty well without being terribly affected by it.” That is good advice and it applies to Anon for this too.

    2. Observer*

      Allison lays it out pretty well. The only other possibility is the Board. If they are willing to listen and push back, good. Otherwise, this is who they are, and who they are going to stay.

      1. Ask a Manager* Post author

        In my experience, it’s a very rare board that will intervene in an effective way on something like this. If the ED is bringing in money and keeping the org running, the board might pass along some feedback but it’s unlikely they’ll do the work necessarily to truly hold him accountable to changing; they’ll either see it as below their pay grade (although it’s not) or just won’t feel like dealing with it. There are some rare boards who are exceptions to this; most are not. Meanwhile, the personal risk to the OP of going to the board is pretty high if it doesn’t result in meaningful change.

        1. Princess Consuela Banana Hammock*

          I agree. Unfortunately, being an asshole is usually not enough to concern the board. The Board is only going to act if they think he’s doing something illegal that puts them at risk, but even then, a bunch of boards will do nothing. In my experience, an ED like this will never change, and the Board won’t make him change, either.

          1. Swiss Miss*

            I agree. Unfortunately, being an asshole is usually not enough to concern the board.

            Also, there are times when “being an asshole” is in the eye of the beholder. I have seen organizations that are extremely consensus driven, and risk averse (“don’t rock the boat”). They then bring in an executive director or change agent to say just what OP said (“This is why you’re wrong,” “There’s an 800-lb gorilla in the room,” etc.). Presto, the staff labels that change agent an asshole.

            I am not saying this situation is one of those times. On contrary, the letter writer has a very level headed tone, so I think it is not. But to generalize from PCBH’s comment, there are definitely times when a change agent needs to rock the boat.

        2. Observer*

          I definitely agree that it’s rare – there is a reason they are the ED to start with.

          This is more of a last try, “I did my best” kind of thing. But i Anon for This (or the OP for that matter), tries this, they need to do it understanding that it really is a last ditch and low probability of success effort.

        3. Rust1783*

          Unless OP does it on their way out the door, and ensures the Board knows this is a big reason why they’re leaving.

          1. Competent Commenter*

            Agreed on both counts. I was fired while pregnant by a terrible nonprofit ED, then allowed to resign in good standing instead, and because one of the board members volunteered in the office and must have heard about it, I thought the board would know. I don’t think she ever told them anything. That ED was there another eight years or so and the board sat by as she fired many good people and other good people quit because the work environment was intolerable. So, if you decided to leave because of your director and you want the board to know about it, tell them yourself.

            1. That Girl From Quinn's House*

              I worked for an *awful* ED who had multiple employee lawsuits against him, and had sabotaged a highly profitable department for several years running, so that he was running tens of thousands of dollars in the hole each year when he should have been profitable.

              This was his status 4 years ago and he’s still there.

        4. Snarkus Aurelius*

          At the last nonprofit I worked, the ED only got fired when her VP of fundraising (BFF and they took vacations together) screwed up on a major donation. Keep in mind that this VP had been screwing up a lot, but she pissed off a corporate donor. They both got the boot. The ED had been committing time theft for a few years, doubled her own salary during a recession with no justification, cut retirement contributions for everyone but herself, and had her head in the sand to the point we almost went under. But none of that mattered to the Board until money was involved.

          For a lot of boards, it’s out of sight, out of mind. THEY don’t have to work with the ED on a daily basis, and whenever they do work with the ED, the ED is on his best behavior. With a lot of boards, the ED and members were friends prior so there’s that to contend with.

          1. AnnaBananna*

            “doubled her own salary during a recession with no justification, cut retirement contributions for everyone but herself”

            Jeebus, there’s certainly a place waiting for her at Satan’s dinner table….

          2. stelms_elms*

            We were not allowed to talk to anyone on the board of directors except the board chair if we had any type of complaint. (It was a fireable offense, information was posted about it in the copy room if that gives you any sense of what the atmosphere was like there.) And of course the ED made darn sure she was besties with every board chair. A director made a comment in a board meeting that wasn’t even contrary to what she said, but she demoted him the next day because he “spoke to the board”. But the organization has been constantly expanding with stable funding under her leadership, so the board thinks everything is sunshine and roses. And btw, the ED’s husband is the COO.

            1. Princess Consuela Banana Hammock*

              Ugh, this is so frustrating, so unlawful, and so common.

            2. Swiss Miss*

              This is a great example of why anonymous speech can be so important. Why not copy the information posted in the copy room and anonymously send it it a sympathetic board member?

          3. Princess Consuela Banana Hammock*

            I think the most difficult issue is that boards delegate management responsibility to the ED. Generally the ED (and CFO, if one exists) is their primary liaison. That makes it difficult, because they’re supposed to be able to conduct a regular ED performance review and to sign off on all financial policies, exec compensation, etc. But if the ED is hiding that information, and if there isn’t a robust whistleblower policy, it’s relatively easy to defraud or otherwise hide bad conduct from the board.

        5. CommanderBanana*

          Yep, I worked for a small nonprofit (very small) and the ED and one director were active alcoholics who were abusive to staff, including physically abusive. The ED had been with the organization for over 20 years. He was finally removed by the board…five years after I left. And this was after a large publication wrote several articles about his behavior.

          Soooo, the board may remove him. It may take two decades. I wouldn’t make that gamble.

          1. Gatomon*


            I worked in a government office that took over 20 years, multiple lawsuits, a multi-year campaign by our awesome union rep documenting all.the.things. to the union and HR AND a total management shake up (regional, division and division HR) above the branch manager for the bad manager to get fired. It’s not worth spending half your working life waiting for it to happen.

        6. Anon for this*

          Thanks! Going to the board definitely feels like a huge risk to me, but more importantly to the organization itself, given that we have a fundraising-focused board and I’m worried they’d be less excited about going out and raising money for us if they had a sense of the issues.

          In a new non-profit or a start-up with an inexperienced founder, I’d just love for there to be a mechanism to get the ED this kind of feedback that isn’t the organization failing slowly. I believe so deeply in our mission and I’m in a position where I could lead a degree of culture change, but it’s hard to figure out how to do that when your own boss is part of the problem. The type of person who’s an effective fundraiser/risk-taker who will start something isn’t always the type of person who’s naturally a great manager/steward of an organization and I wish there was a way to bridge that gap and help my boss learn those skills.

        7. Staxman*

          The last sentence of that comment is more or less a recasting of this, from Machiavelli:

          “Men should be either treated generously or destroyed, because they take revenge for slight injuries – for heavy ones they cannot.”

    3. Just Elle*

      Jocko talks a lot about ‘influencing up the chain of command’ and its basically about building a relationship where he trusts you to make him look good, so that when something big enough to push back on comes up, he is more willing to listen. That is NOT the same thing as coaching up though, that’s just saving capital for when you really need it.

      You are not going to spark a complete paradigm shift in this person’s personality. Its been formed over many, many years and short of a dramatic life event / “come to Jesus” moment, no person is just going to change that dramatically. Especially since, as far as he’s concerned, its served him well and wound him up in an ED position.

      What you *might* be able to accomplish is picking one or two “symptoms” of his overall world view that you’d like changed. For instance, maybe you really wish he’d stop texting during meetings (to use today’s example) or using a certain word that he likes to use to talk down to you. Push back on those two little things and phrase it as a “you” thing. “Hey boss, I know you don’t mean it like that, but when you use the word ‘stupid’ it makes me uncomfortable. Can you please find alternatives?” and then gently remind him consistently every single time moving forward, like you’re training a dog. “Hey, there’s that word again!”

      1. Maya Elena*

        Oh, my husband likes his books! I’ve heard excerpts (via audio-book, interviews) – a bit too hardcore for me!

      2. AnnaBananna*

        I think gentle would go right over his head. I think I would start with the sexist attitude since that’s actually the quasi illegal one (I say quasi since tone probably can’t be upheld in court. Or can it? Hmm, now I’m curious about that!)

        1. Book Badger, Attorney-at-Claw*

          I am not an employment lawyer, but I could maybe see a gender discrimination/hostile work environment suit. But those are always hard to prove, even in states that have broader protections, and if he’s a dick to *everyone*, that makes it even harder.

    4. animaniactoo*

      Put it this way: They’ve managed to get to where they are having encountered a lot of people in their life.

      The likelihood that you would be the first person to bring this news to them is vanishingly small. The possibility that you would be the person who they respect enough to listen to is even smaller. The possibility that they would make effective change – as opposed to minor change/lip service as an attempt to appease you and keep you happy / happy with them – is even smaller than that. As a risk assessment exercise, you’re looking at something which has such slim odds of succeeding that putting any real time or energy into trying it would categorize as a self-defeating effort. Tilting at windmills.

      This is someone who has heard that feedback from somebody somewhere before and decided it didn’t matter enough to do anything about it.

      Whatever amount of good you can see in this person and their intentions, unless they are *asking* for help, you would be banging your head against a wall to attempt to address it. You are going up against a decision they have repeatedly made in their life and chosen the other option. For whatever reasons, they like the other option. It works for them and they do not want to change it. Even if it stops working for them, they are unlikely to understand that it is the source of their issues. Because there will always be another scapegoat for it.

      1. Human Sloth*

        “The likelihood that you would be the first person to bring this news to them is vanishingly small. The possibility that you would be the person who they respect enough to listen to is even smaller.” This!! This is just wrong. Some people just suck.

        1. AnnaBananna*

          It’s true though. My first thought was ‘I wonder what his spouse thinks’, but then I pictured someone super duper mousy and submissive and went ‘yah, he’s not changing’. I think if one of the org’s partners were encouraged to speak up (instead of quietly chatting to OP about it after his rude diatribes in meetings), it might change.

    5. NW Mossy*

      The limit you’ll hit is that you can’t enforce meaningful accountability on your own boss, and without that tool, your efforts can’t go very far. In a situation where the boss is the top of the food chain, the only accountability on them is forces outside the organization.

      That is really bad scene, because external forces come with their own constraints. They can’t necessarily see inside the organization to get a true picture of what’s going wrong, and the tools they can use (lost funding, disconnecting relationships, lack of willingness to invest time/energy in the organization) are indirect enough that the badly behaving boss has plenty of space to to make an “it’s them, not me” argument in their own head.

      The only response you have in this situation is as Alison describes, which is saving your energy for other things. I’d argue that it’s probably best to consider leaving, because a poorly managed organization is going to tend to stay small and limit your own opportunities to grow.

    6. Staxman*

      I once had an employer (sole proprietor) who liked to say, “It’s my company, and if people don’t like the way I talk to them, they can go to work somewhere else.” I was glad to take him up on it.

  2. voyager1*

    When he begins to correct you incorrectly and rudely , start your rebuttal with the words “Well actually…”

    You may see some improvements in his behavior… or not.

    1. Liar Liar Pants Dracarys*

      And couple that with spreading your knees WAAAAAY far apart so no one could possibly squeeze in next to you.


      1. voyager1*

        That is a good point, but I was taking the assumption that they were standing, but if these conversations are in a seated position, then yes this is a good additional strategy.

      2. Marthooh*

        Ooh, ooh, ooh!

        Tell him you’d like to play Devil’s advocate here. He’ll love that.

  3. tuna*

    I am at my last day working for this kind of person — trust and believe, it feels GREAT to say goodbye!

  4. anon for this*

    I wonder if the boss got in this position if he’s this obnoxious, was he selectively less obnoxious to people on the way up the ladder and now he feels he’s at the top and can act however he wants?

    I encourage LW to find another position (unless it really doesn’t bother you, which I think would be hard to pull off) and don’t allow yourself to be guilt-tripped into staying by any “but what about the children/elderly/disabled/hemophiliac we are helping” nonsense.

      1. The Original K.*

        Yep. I had a boss who was legitimately good at the skills part of her job but she was nasty to everyone who was or who she perceived as below her (which was basically everyone except senior management, even those who were on her level. One of my work friends, who was on her level and actually had MORE experience in the field and way more at the company itself, loathed her.) She was condescending, snippy, and cold. Internal and external people would make comments to us like “Does she always talk to you like that?” But she was great at managing upwards, so senior management liked her. (She hated the company though. Only lasted a year before she moved on. There was a lot of “good riddance” once she was gone.)

        1. Mrs. Carmen Sandiego JD*

          Dealing with an upper-level coworker who fits this description exactly. Has made new hires nearly cry due to her abrasiveness and is almost proud that this is how she is, and she sees no reason to change. Some of the seasoned hires seem to tolerate her jokingly but all the new hires hate her with the fire of a thousand suns. You can’t change someone’s personality overnight..

    1. Escapee from Corporate Management*

      Seriously, compared to my comment above, many of these bosses are often excellent at one thing where their personality did not block them from success. They then get promoted into positions where their personality becomes a detriment. That, or they inherited the company.

      1. Escapee from Corporate Management*

        I knew one at a non-profit that was a favorite of a big donor. He was gone within two months of the donor retiring from the Board. Until then, he was untouchable.

      2. Snarkus Aurelius*

        Which is worse because, in my experience, the board is stacked with the ED’s longtime BFFs.

    2. Pommette!*

      The obnoxious EDs I have encountered all came from “empowering” professional backgrounds where brashness and (over)confidence were expected, accepted, and even encouraged (think doctors leading health-focused NGOs, or lawyers leading justice-focused ones). They also often came from wealth, which had helped them move forward professionally.

      Their obnoxious attitudes actually played well with some donors, partners, and board members (many of whom come from similar backgrounds, and share similar blind-spots). Where we would see a person dismissing and belittling subordinates and silencing the diverse voices whose input should matter, they saw evidence of intelligence, confidence, frankness, and no-nonsense efficiency.

      These EDs hadn’t had to work their way up the organizational ladder: instead, they had either helped found the organization they were leading, or had been brought in by the boards.

    3. ThisColumnMakesMeGratefulForMyBoss*

      I agree on the looking for a new job part. OP says they have thick skin, which is definitely sounds like they do, but working for a person like this is draining, and may be affecting them more than they realize.

  5. Anynomous*

    OP, you say this is a nonprofit organization. Does it have a board of directors? If it does, they ought to be told of his behavior. Let them confront him about how his awful behavior is hurting their organization.

    As someone who’s spent years wishing an asinine relative of would finally see how her horrible behavior was hurting our relationship, I have to agree Allison is right. Asses like this really don’t see the reason to change. Maybe he would if HIS boss threatens to fire him over it. Maybe not even then.

    1. Alton Brown's Evil Twin*

      Was going to post exactly this.

      OP, have you been in meetings with your boss and the board of directors? What’s he like there? Is it a complete personality flip? If so, then you 100% can’t change him.

      1. LetterWriter*

        We do have a board. I have thought about going to the board president in the past, but hesitate because the board president and ED have known each other for decades. I don’t have much faith in the board president to confront the ED, and I worry that going to the president could be seen as insubordination.

        I’ve been to a few board meetings, and while it isn’t a complete personality flip the ED does act a bit differently toward board members. He still overexplains and interrupts, but is more deferential and will listen without arguing. A few board members have heard how he speaks to people he views as subordinate, but they haven’t done anything about it.

        1. SheLooksFamiliar*

          That’s so frustrating. It’s one thing if he’s a jerk to everyone because, hey, that’s his DNA. It’s another, very telling thing when his jerkiness changes depending on the audience. He knows better but chooses not to adjust his communication style for anyone he considers ‘less than.’ RHIP, I guess…

          I feel for you, OP. I’ve worked for jerks who weren’t as jerky as your boss, and hated it. I knew I couldn’t change them, even for the good of the team and company I wanted to support. All I could do was find another job as quickly as I could. Please keep us posted on what you decide to do.

        2. Working Hypothesis*

          LW, that is a HUGE red flag in itself.

          You know what the difference is between an abuser and somebody with an anger management problem is? The abuser won’t mistreat people in front of a cop, or their boss, or somebody else whose authority over them they recognize as capable of delivering consequences.

          That is the proof that they know EXACTLY what they are doing and how wrong it is, and they choose to do it anyway. If they didn’t realize it was wrong, they wouldn’t bother to change it in front of authority figures, because they would have no awareness that the authority figures would see any problem in it. If your boss did not already know, beyond any shadow of doubt, that he was being an asshole to everybody who wasn’t able to hurt him for it, then he wouldn’t be modifying his actions when he was facing people who can.

          So he does know. And he can control it, because he does control it… when it benefits him personally to do so. He simply sees no reason to choose to control his preferred way of interacting with others — i.e. domineering, aggressive, interrupting, demeaning, and borderline verbally abusive — unless *he* would personally be the one to suffer from the choice to do it in that specific situation.

          You can’t make every interaction with a client be a situation in which he’ll personally suffer consequences if he behaves badly. You can’t make him care about the inherent immorality of treating people badly when it *won’t* come with direct personal consequences for himself. And you probably can’t make him care that it comes with consequences to the organization so long as it isn’t actually losing them funding. There is an outside chance that, if he feels a sense of ownership over the organization, he would exert himself to behave better if he saw his actions significantly damaging the organization’s bottom line… but so long as people have a workaround they’re willing to use (going to you to propose initiatives, etc) that keeps them and their money flowing in, he’s likely to see that as a perfectly fine solution to the whole thing. He gets to keep behaving the way he likes to behave, and the organization keeps getting money. The fact that a lot of people end up thinking badly of him, and somewhat worst of the organization, and that you have more work to do to try and mollify them all… now of that is going to make this kind of person believe there is anything wrong with the process. That is the world working the way it *should* work, in his eyes: he does what he wants, and the rest of the world puts up such it, cleans up after him, and doesn’t bother him about the resulting messm

          1. Jules the 3rd*

            +1. Abuse ruins everything.

            Your boss is abusive. The board knows about this and doesn’t care. It’s not going to change.

            1. RVA Cat*

              This. Letter Writer, get out now.
              At least this douchecanoe is just an ED of an organization in a developed country. Imagine the many people like him in positions of authority in, say, North Korea, or at various times in history (think Edwin Epps in 20 Years a Slave).

  6. Lumen*

    OP: you are correct that many people will see this ED’s behavior and interpret it as a reflection on you (and other people). It sounds like you’re wanting to change his behavior for the good of the organization, but also for your own professional reputation. And I don’t think you’ll be able to do much good for either of those, if you stay.

    But he is an asshole and he’s not going to change. The organization may not have lost out on any opportunities (that you know of), but the missing word at the end there is “YET”. Eventually he will cross the wrong line with the wrong person and ruin an opportunity. After all, people are already bypassing him because he’s so unpleasant to deal with.

    And your professional reputation, which may be more or less okay right now, will eventually take (potentially serious) damage for choosing to continue working with him. After all, people are already making comments to you about how awful he is.

    I really wish you the best of luck. You sound like you have a good head on your shoulders, and I hope you get to make better use of it for a boss who isn’t a huge asshole.

    1. montescristo1985*

      Will people really judge the OP by their bosses actions? I could see it working the other way around, but wouldn’t most people instantly understand that an employee can’t control their boss?

      1. Lumen*

        It’s less about people wondering “why isn’t Employee doing more to stop Boss from this terrible behavior?” and more “what does it say about Employee that they choose to work with this Boss, who is terrible?”

        Some people will remember that employees can’t really control their bosses, and will not judge. Some might just be glad they have a reasonable person to deal with when they want to go around the ED. Others who don’t have the whole context might wonder if the OP doesn’t care about the ED’s behavior, or actively condones it, or has poor judgement, or any number of things.

        It may not be fair, but lots of people do judge guilt by association, even in cases where there’s an obvious power differential. It just doesn’t seem a risk worth taking.

        1. Jasnah*

          Or OP talks to a prospective client or applies for a job elsewhere, and the other person has heard through the rumor mill how bad that org is. They don’t know it’s just the ED, they just heard that org sucks… and OP is the face of that org.

    2. LegalBeagle*

      Agreed. I would leave. Non-profit fields tend to be small worlds and word gets around. If the org has a bad reputation, that will rub off on the OP, fairly or not.

  7. Naomi*

    You say you haven’t lost any opportunities that you know of because of his attitude. I would emphasize “that you know of”. Sure, someday someone might tell you right out that they decided against working with your boss… but I suspect there have already been people who silently decided to go elsewhere next time, or who never contacted your company at all because they were turned off by his reputation.

    1. Princess Consuela Banana Hammock*

      Co-signing this. I had a boss who was a micro-managing, sexist, racist asshole. But he was as a liberal/”progressive” asshole, so folks felt uncomfortable calling him out on his shitty behavior. His boss (the ED) had no backbone and refused to manage him. We lost coalition relationships, funding, and all sorts of other valuable relationships/resources because of him. People were actively discouraged from applying to or working for the organization because of him. But the ED and Board had no idea, because you usually can’t count what you don’t see or measure, and it’s hard to measure all the meetings or relationships you don’t build. And when outside groups did tell our ED about his bad behavior, the ED ignored it or would pretend the feedback was about all of us lower-level staff.

      The ED’s behavior is absolutely hurting OP’s organization and its cause. But he’s also not going to change, so all OP can do is decide not to associate or affiliate with a group that has an asshole for an ED.

    2. Don*

      Just basic probability would say it’s surely happened. LW works for this person – gets paid to deal with him – and is writing this letter asking if it’s possible to make him less unpleasant. What are the odds that someone else didn’t have the same feelings and no financial motive to put up with his nonsense? What are the odds that a person is unpleasant to that many people that regularly… and yet none of them have commented on it to someone in a position to decide to go another way? Almost certainly someone who has left the organization has stayed in the nonprofit sector and has been in a conversation at their new organization about how unpleasant and sexist this person was to them.

      1. Samwise*

        Yep. Several profs in my dept in grad school had a business. They were gigantic tools (I worked for them). When I was at my first full time academic job, a colleague asked me about them, because the dept was considering paying them $$$ to come in and do some trainings. I phrased it carefully, but made it clear that they were tools, our faculty would despise them, and my colleague would never get another chance to bring anyone else in ever to do trainings like this.
        They lost a big opportunity — and I’m sure never knew why.

    3. Competent Commenter*

      I encourage the OP to keep an eye out for instances where the ED’s behavior has indeed cost the organization something so that if you do decide to talk to your board, you have some objective data. It’s likely to happen eventually. That might mean missed opportunities to participate in partnerships with other organizations, staff quitting, hard to hire new candidates because of the organization’s reputation, etc. When a staff member quits there’s the cost of staff time to conduct a hiring process and retrain, for example. If a partnership falls through maybe there’s a loss of revenue or exposure from an event.

      I had to reframe this way for our ED and I think it was effective. We needed to hire another marketing staff person. I pointed out that being understaffed was resulting in lost opportunities in social media, news, etc. Then I flipped it and said “here’s what you get if you staff sufficiently: a vibrant social media brand, increased exposure to these audiences, additional publications, an updated website,” etc.

  8. Jules*

    The only tactic I have found remotely useful in getting folks like this to change is to focus on outcomes. “In the meeting you asked for ideas on how to improve volunteer engagement. Jolene put forth an idea, then you told her all the ways that her idea was wrong. After that, no one shared any other ideas. Was that the outcome you wanted in that meeting?” Ask this politely, calmly, as though perhaps that was a desired outcome of some complex management strategy you’re trying to understand.

    1. EinJungerLudendorff*

      It does seem like you would need some amount of authority or standing with the person to do that though. I doubt they would accept being held to standards like that from their subordinates, or even colleagues they don’t like.

    2. WillowWeep*

      I also love this. Some obscure new management style that has not hit the bookstores yet.

      1. Tabby Baltimore*

        Not really new, I think. I became aware of this approach–“intent vs. impact”–at my agency a few years ago when an SES member came to talk at an HR-sponsored event panel. Jules’ example follows the generally suggested pattern a speaker in this situation would take: “I understand that your intent was X, but your impact seems to have been Y.” After that point, whether the speaker continues asking questions to lead the listener to a better understanding of what went wrong–or just baldly lays out the reasons (“when you …”) that contributed to the (undesired) result–will probably depend a lot on the speaker-listener relationship/power dynamic, and whether the listener is interested in hearing them. EinJungerLudendorff made a good point about that.

        1. Jules*

          For sure. When I use this technique with my 14 year old niece who is frustrated that her mom (my sister) “never lets her do anything” she wants, my follow-up is vastly different than when engaging with my (former) big boss who kept trying to have brainstorming sessions in a deathly silent meeting room.

  9. Just Elle*

    People don’t change who they are, fundamentally, as a person unless they go through a “significant life event” that causes them to reevaluate everything on a much grander scale. Because, changing yourself so fundamentally requires a total paradigm shift.

    As Alison mentioned, there’s an (infinitesimal) chance that you could be that spark of a wake up call. So, you can try it. But if your attempt doesn’t rise to “significant life event” level for him, then Your Boss Sucks And Isnt Going To Change.

    1. Anonymously*

      Are there any YBSAIGTC items in the store?

      I have a coworker like this (who is not in management). She throws tantrums, is insubordinate, interrupts others, talks down to people, has been rude to coworkers and visitors, argues with family on the phone. She also gets all the plum projects, raises, more responsibilities, and lots of employee awards. Management is aware of her behavior and they do not care. Oftentimes, I think if employees get results or higher-ups depend upon their knowledge/skills, they do not care if people are jerks.

      1. Working Hypothesis*

        >>Are there any YBSAIGTC items in the store?

        If there aren’t, we could make some!

    2. Heidi*

      I agree with the “significant life event,” and by that I mean like a bunch of ghosts visiting you on Christmas Eve and showing you all the wrong choices you made in your past and what your future is going to be if you don’t change.

      The buffering could be indirectly enabling his continued behavior because he doesn’t get to see the full consequences of his actions. If everyone had to deal with him directly, at least some of them might call him out, and hearing it from more than one person might convince him that he’s doing something wrong. Maybe. Or not. Probably not.

  10. Utoh!*

    I’m curious, is there any group or type that he does not behave this way toward? I’ve noticed my co-asshole treats only specific people with condescension, the others he’ll engage with and bend over backwards to assist (other men, or those who can assist him in some way). This so smacks of him *choosing* to be an asshole or not, depending upon who he’s dealing with. It’s just gross.

    1. Shopaholic*

      Ya this. My boss is like this, although perhaps to a lesser degree and the way he treats people drives me insane. For various reasons, I can’t leave yet but it’s definitely one of the major reasons why I’m looking for something else.

      You can’t change this man. I think you have decide how much you can put up with

    2. LetterWriter*

      White men over the age of 60. He’ll still interrupt them, but is much more deferential toward them and actually listens and considers what they say. It’s super gross.

      1. animaniactoo*

        In cases where someone has made it clear through their actions that what they want is an echo chamber – even if that echo chamber is more visual than auditory – sometimes your greatest power can be in working competitively to them rather than cooperatively with them.

        You can help the death of this kind of person’s ability to be effective by doing the same or similar work elsewhere, with people who do actually listen and treat their staff and people in general well. Failure to succeed is the strongest motivator for someone to change. And if not change, then it at least saves others from having to deal with them in order to accomplish good things.

        1. Librarian of SHIELD*

          Sometimes not even failure can bring about behavior changes. If I had a nickel for every time my former jerkboss said “But I’m better at X than that other manager is! It shouldn’t matter that she’s nicer than me!” I could go coin swimming, Scrooge McDuck style.

          1. Working Hypothesis*

            Even when it doesn’t being about behavior changes, it can sometimes bring about long term changes in who gets those positions. It who keeps them successfully. Being able to hold onto a good staff is a skill that hiring managers look for in management candidates. And the No Asshole Rule, in all its names, is an explicit thing in management these days. So it’s not that this kind of behavior never changes, it’s that it changes slowly and on a societal level rather than on a case by case individual level.

            1. animaniactoo*

              Exactly – and thus the point about working competitively to rather than cooperatively with.

      2. Women need to interrupt*

        I would like to question this idea that “it is always wrong to interrupt people.” You do not need to let people ramble endlessly to derail meetings. As Madeleine Albright has said, “women need to interrupt.”

      3. Jasnah*

        If you are not a white man over 60, what makes you think he’ll listen to what you have to say?

        I don’t think you can help this guy.

  11. Lady Ariel Ponyweather*

    He might — might — make small modifications around the edges. It’s almost worse if he does that, because that will give you just enough hope that he can change that you’ll continue to try to change him more.

    Oh yes. It’s worse and it hurts. Giving you that hope and yanking it away is almost a betrayal. At least if a person isn’t going to change, you know what you’re dealing with.

    Sorry to hear about this situation, OP. He might not be costing you opportunities yet, but he will.

    1. writelhd*

      Yes, I just dealt with this…a boss who had a tendency to be a jerk to people (in a different way than the OP) and would tend to hire jerks (who were jerks in the classic way of the OP), but did sort of realize it wasn’t working and needed to do better and made some transparent efforts to do so…only to be just unable to let go of his deepest tendencies until he burnt out and fed up with how things were that he himself quit, and somebody with a totally different attitude, outlook, and way of treating people has replaced him, and….WOW.

      There are so many things that I just held inside, didn’t critically analyze, didn’t speak up about, didn’t even realize were just so stressful and wrong and soul-crushing to absorb and try to work with, that I’m now having to catch myself on. I’d used a lot of “at least he’s trying” mentality to fail to see how truly ineffective some of the things he did were and I am still constantly re-framing view of how that department should operate now. So it is possible to work with these people if they try to change, but it can affect your outlook on things so deeply if you’re not careful.

  12. Lalitah28*

    Resist the temptation to save anyone from the destiny of their character flaws. Let them sink, let them feel the consequences of their behavior.

    This is his character. He will not listen to an underling if he is routinely dismissive of them.

    Your job is not to fix him. He needs his road to Damascus to throw him off his horse when a major funder get wind of this or the board. But still, it’s not your problem. Protect yourself, protect staff up to a point – but these places are like the Titanic and switching the tune is not going to stop the ship from sinking.

    1. Snarkus Aurelius*

      And understand that there may be no consequences for his actions. Such is life.

    2. JediSquirrel*

      Resist the temptation to save anyone from the destiny of their character flaws. Let them sink, let them feel the consequences of their behavior.

      This is such sage advice, but hardly ever heeded. The world would be a better place if we all learned this. I’m still learning it, and it’s not easy.

  13. 8DaysAWeek*

    I had a similar situation a few years ago. Somehow this person managed to be with the company for 25 years before he was fired.
    When they became my manager it was unbearable. The first year was a lesson for sure. The second year I took a “kill with kindness” approach while job searching. That seemed to turn the tables at least with our interactions.
    I also think I was probably the first person ever to actually give candid feedback on his year end review (we have to review our managers every year). 2 years of me providing honest feedback I think is what did him in. Or so I would like to think. I ended up getting a new position within the same company after 2 years of working for this person. They were “let go” a year later.

    It is a toxic and draining situation. I can handle a lot but this was a show-stopper for me and I found a new job.

    1. voyager1*

      Wow. I wish I could review my manager. A lot of companies would benefit from that. Of course it would have be done in a way to protect from retaliation.

      1. Cafe au Lait*

        My library did a 360 review when I first started but has done away with it since. I really wish this year it was back in place. My manager is nice, I like her a lot, but I’m getting frustrated with the micromanaging. She was promoted from a different unit. While I think there are things that need shake ups, there’s quite a bit of work that’s left undone. She sits on stuff for weeks; I see it sitting in her inbox untouched.

        I’ve tried to manage up, and she declines to pass along projects. (Like updating internal signage).

        Plus, she’s passive when it comes to feedback. We once had the same conversation three times (so six weeks total) before it dawned on me what she wanted changed.

  14. Sophie Hatter*

    This was the director of the site at the nonprofit I did an AmeriCorps term at. He didn’t even take the time to pronounce people’s names correctly and would try to cover for it with bravado. Yelling “James! James!” out your office door and then getting mad because the person’s name is John and they didn’t think you were talking to them does not make you a good boss. When I think of toxic masculinity I think of that guy.

    1. 1234*

      Reminds me of what happened to a lady, Jen, who worked here before me. Another employee, Glenda, would call out “Jane! Jane!” and Jen knew it was for her and then corrected her:

      “Actually, my name is Jen. What can I help you with?”
      “Uh huh, uh-huh, Jane, I need the report on Mr. Smith’s llama.”
      “My name is Jen. Mr. Smith’s llama…”
      “Thank you, Jane.”

  15. Ismone*

    I do think you should push back against the sexism. I know you aren’t his boss, and may not feel that you have the power to do so, but I don’t think that sexist behavior should be allowed to pass without comment, unless you really are in an untenable position, in which case, my only advice would be to escape.

    1. Observer*

      Why? This guy is a disrespectful jerk. He’s mistreating everyone he’s encountering.

      Also, what makes you think that the OP (or anyone in that situation) has the power to push back on sexism when they don’t have the power to push back on anything else? There is nothing magic about sexism (or any other *ism for that matter) that makes it realistic or reasonable to push back on it when you can’t push back on the rest of the misbehavior.

      1. Is*

        Because discriminating against younger female employees is despicable and illegal. Usually on this website, there is a lot of good advice about how to politely push back against illegal conduct without invoking lawyers. The same thing applies here.

        1. 30 Years in the Biz*

          This was my thought. The sentence “He’s worse with women, especially young women.” set off alarm bells. It could take just one person to bring a suit against him and the board that’s supporting him. This would be an expensive problem to deal with. And it will happen when no one’s expecting it. Mentioning your concern with potential liability might help.

          1. RVA Cat*

            ….and now I’m wondering if he’s going full Harvey Weinstein creepocalypse on these young women when the Letter Writer isn’t watching.

        2. Observer*

          It’s no more despicable than the other stuff he is doing though (And I say this having been at the receiving end of jerks who are also sexist.)

          Now, the illegal part of it might actually be useful – not with the jerk, but with the people who can hold him accountable. Even Boards that don’t care about jerks sometimes care about legal threats.

  16. Lucette Kensack*

    Oh, man. I’ve been there. Twice, actually. In both cases, the ED was the founder.

    In the first case, I was the #2 and ran the day-to-day operations of the organization. I was able to manage up and I wasn’t unhappy in the role, but it was remarkable how we all just accommodated it. Evvvvveryone we worked with (internal staff and external partners) knew that the ED was a jerk and had figured out how to work around it. We talked about it openly. I literally had a budget line for flowers to send to folks after he had been especially rude.

    The second time, it was a much larger organization and I was one step removed from the founder, thank goodness. She was semi-retired so wasn’t formally in an ED role any more, which was another problem. She was rude, bigoted, and still thought of herself as the main decider even after she had stepped back into a discrete program-delivery role. I would never have accepted a role in which I had to work with her directly.

    1. Librarian of SHIELD*

      I hate that you had to budget in advance for apology gifts when your a-hole boss exceeded all a-hole expectations. I really do wish the world as a whole would stop accommodating jerks and pretend that their behavior is normal and okay.

  17. Edith*

    I briefly wondered if this was written about my former ceo… we all work for this guy at some point.

    1. Lumen*

      We do. Plenty of organizations are built around toxic assholes. And then the people around them spend most of their time buffering, compensating, and mitigating their behavior instead of doing the real work. End result: everyone’s contributions are less than they could be, and assholes continue to fail upward. There’s not a lot to be gained by continuing to protect and ‘work around’ and ‘coach’ jerkbosses who aren’t going to change.

      1. Edith*

        I also hate when the toxic Elizabeth says, “well Steve Jobs was a toxic asshole so I can be too!” No. It doesn’t work like that.

        1. Lumen*

          Yeah, the proliferation of stories about CEOs who dropped out of Stanford and treat their employees terribly but are “geniuses”?

          All that’s doing is leading to things like Theranos (so it’s all the more ironic that autocorrect gave you ‘Elizabeth’ for that sentence!).

  18. Thea*

    I believe the only way ED’s behavior may change is if he slips up and treats this poorly some stakeholder further up the chain, like being dismissive to a board member. Let’s hope that happens, but until then, continue doing the good work of asserting yourself as you have been doing. He may be oblivious, but at least you can feel better knowing you’re not allowing him to walk all over you.

  19. RainbowsAndKitties*

    I read the comment about other people bypassing the ED and going to OP instead as possibly being about people from other agencies rather than people within OP’s org. If that is the case, how should OP handle that?

    1. WillowWeep*

      I would think most people tend to just ghost away, rather than say ‘hey, we are not going to partner with you because your ED is an @$$hat”.

    2. IT But I Can't Fix Your Printer*

      Definitely. Imagine a LW writing “Dear Allison, my org wanted to collaborate with this great local org but their ED was a jerk – should we explain to them that this is why we went with someone else?” She should correct me if I’m wrong but I’m guessing the answer would be “not worth burning that bridge, just politely decline and be grateful you found out before you signed any paperwork.”

  20. lnelson in Tysons*

    For individuals like this, I really want to steal a line told to me by an HR person who used it with such a jerk.
    “No being as a$$hole is not against the law. But please explain to me why you think this is a good long term management strategy.”
    Apologies for swear word, I am quoting.
    Had a bad manger like this (actually worse) and he never changed. I have no doubt it is because (aside from his self-centered/entitled personality) he was probably never held accountable for bad behavior and therefore never had any reason to modify it. Karma will come around at some point. That guy was fired. Wish I had been a fly on the wall that day.

  21. IT But I Can't Fix Your Printer*

    If any of the people coming to you privately are funders, prestigious collaborators, or other influential folks, and you feel like you have strong relationships with them, you could try to get them to say something (to the jerk or, if applicable, the board) – “Hey, as you know, we’ve given you All Our Money and we’d love to continue doing that but frankly we’ve considered switching to Competitor because of behavior like X and Y.” But I’d only do this if you think it wouldn’t get back to you.

    1. Koala dreams*

      Yes, probably the board will be more likely to listen to outside voices such as major donors who complain as opposed to staff complaining.

  22. WillowWeep*

    Why do SOOOOO many of these letters start out “I work for a small non-profit…”?

    1. Ask a Manager* Post author

      It’s actually not a disproportionate amount. It’s that you notice it more because nonprofit people tend to identify themselves as non-profit people whereas almost no one writes in and says “I work for a for-profit business” even when they do. If you assume that most people who don’t self-identify as nonprofit are at for-profits, then the majority of letter writers aren’t nonprofit workers.

      1. DKMA*

        I’m sure this is true, but I still feel like non-profits have above their fair share of representation. I always assumed this was because they were more likely to have the sorts of issues that make interesting letters. I guess my hypothesis was a mix of:

        1) Small organizations are more likely to be dysfunctional because they won’t have professional management / HR / etc.
        2) Non profits are more likely than even other small organizations to have people in management who really have different skill sets (usually fundraising or something tied directly to advancing a specific cause)
        3) Non profits are more likely to have fuzzy hard to measure goals which make it harder to notice when leaders are not getting results
        4) Employees at non profits are more likely to put up with ridiculous shit because they believe in the mission making it take longer for these problems to be “solved” by failure.

        Oddly all of these also start to become true in pockets of REALLY big companies, but it’s more about getting overlooked, lost in bureaucracy, and employees assuming it must be normal because it’s happening at big name organization.

        1. CommanderBanana*

          ^^ THIS

          I’ve worked for nonprofits or the feds my entire career, and this is sooo true.

        2. Ask a Manager* Post author

          All those things are definitely true! But I still don’t think they’re represented here more than other sectors. *Small* employers definitely are though.

        3. Non-profit noob*

          Amen. I’ve worked at a small non-profit for 2 years and our organization checks every one of those boxes.

          I’d also like to add that non-profits tend to be under-resourced and the ED tends to take on a lot of pressure from multiple directions (staff, board, patrons, etc.), but this does not justify the jerk behaviours.

  23. AnonyMouse*

    I think I work for a similar type of person right now, but I’m getting ready to leave this week. I have an “exit interview” (it’s apparently not very formal) on my last day with our HR person, and I’m debating how much I should share about my frustrations with this job/my supervisor. Even though I have no intentions of ever coming back here (and I’m relocating, so that makes it even more unlikely), I don’t want to burn a bridge should I ever need the reference from here. I also don’t feel super confident it would fix anything. But I can’t sit there and pretend like everything was great. Has anyone else experienced this? How did you handle it?

    1. Real_Ale*

      I’d say:
      Was your performance at this job stellar, that they’d give you a useful ref? Or was your relationship with Soop polite at best? Asking because my current employer will give either a stellar review or a confirmation that the person worked there, but they’ll never give a bad review, and interviewers/HR are cued in to what that kind of confirmation means. I don’t think I could trust Toxic OldJob to give a good rec, even if I thought my relationship with them was ok. Toxicity never sleeps.

      I left a toxic boss once, long ago in the early aughts (this situation was so bad it achieved PTSD and continues to reverberate in my working life). With some satisfaction I can report that I did lay it allll out there in a letter when I left*. I don’t know if it made a change or not, but I can say that about six months later when the new office manager (she couldn’t keep one of those either) called me because they needed more staff (wonder why) and I straight up asked her if she’d read my exit letter. When she said no, I strongly suggested she do so and then call me back if she still wanted me to return. Let me tell you just how surprised I was that she didn’t call me back. I do not regret this, not one bit.

      Moral of story: “don’t do something you can’t undo until you have considered well what you won’t be able to do once you’ve done it.” But once you’ve considered that, do the needful and take satisfaction in your choice.

      *after she verbally assaulted our high-school intern in the waiting room in front of a client for doing something that was Not Wrong. I watched that poor kid crumple and while I’ve seen more disturbing things than that, most of them weren’t in person.

    2. Jules the 3rd*

      Depends on the company. My current employer:
      1) Only provides dates of employment
      2) Does not allow managers to give more details while they are still working for the employer
      3) Has professional HR employees.

      I’d be pretty comfortable providing professional criticism there, like, ‘I felt my manager was assigned too many employees for him to be an effective manager’ or ‘her strengths were A, B, C but she struggled with D, E’.

      I would not give honest feedback on a boss if any of those 3 criteria were missing.

      If I did give feedback, for, say, the person in the letter, I’d have written down every example I could think of and then picked the Worstest Hits. ABC might be:
      Board communication

      While D,E,F, etc might be
      Calm, professional feedback
      Listening to team ideas
      Relationship building

      But you’d need *very* specific examples from those Worstest Hits, like ‘yelled at X during a meeting’, ‘cut off [list of people] during various meetings (bonus points if [list of people] is all women)’ or ‘counterpart from X org commented on boss’s behavior’.

  24. Fergus*

    I had one girlfriend and i use that term loosely scream at me in the parking lot on how dare I bring her flowers to her job and that I didn’t have permission to go to her job, this was valentine’s day and her birthday. So you know this parking was equivalent to the parking lot of your local library. She didn’t get another flower from me. I have learned over time that behavior will show it’s ugly head at anytime and the best way to deal with it is to be as far away as possible from it.

    1. DKMA*

      It sounds like her reaction was extreme, but surprising a “girlfriend and i use that term loosely” at her workplace is actually a pretty…..Fergus-y thing to do.

    2. Narya*

      Sorry, but… what? I think *most* people would freak out if someone who wasn’t their actual significant other showed up at their job with flowers… because that’s what stalkers do. Also… how does this relate to the letter??

      1. Fergus*

        I was dating her at the time. She worked at a public county office. It was her birthday and valentine’s day. Her behavior was so irrational and I was giving her a gift. When the behavior doesn’t fit the situation it’s best to walk away and never look back. It won’t change, only get worse.

  25. starzzy*

    I can think of exactly one time where my interactions with someone fundamentally changed how I perceived work and my interactions with others. It actually happened with a boss I had at a temp job for only four months.

    Up until that point, I was very Type A: Work Must be Done Quickly and Correctly and If It’s Not, I Will GO OFF. This temp job was a section of the business that needed utmost attention to detail and we were in charge of sending people’s work back for corrections (which most were not happy to redo). One day, relatively early in this job, I was having a meltdown because someone wasn’t correcting their work for me fast enough and I was evaluated by my getting their work through to the next step. This boss sat me down and said, yes, we want and expect perfection from you (me), but this isn’t brain surgery. If you fall behind or make an error, no one will die; it’ll eventually be fixed and you need learn from it and move forward.

    Her attitude where she expected my best, but was understanding of errors and circumstances, changed my life. I teach now, and I try to bring this attitude toward my students.

    I doubt that the ED from OP’s post is in a position to be learning anything from anyone and will not deign to learn from someone considered subordinate to him. But someone seeing the correct, compassionate way to handle work situations may have further-reaching ripples than we know, so OP should keep bringing the best practices to bear in all of her circumstances at this job or when she moves on and people may be able to learn from it.

  26. The Man, Becky Lynch*

    I’ve only worked in the for-profit world so my experience is mainly with abrasive, pigheaded ownership, which is about the same as a Founder in an ED position running amok. The best way to do it is to accept that you cannot change him and to protect those around you with all your powers. As the regular #2/3 position, I am usually the one who everyone goes to and then if it needs to be ran up that ridiculously annoying flagpole, I”ll do it because like you, I will tell them to knock if off [and they listen or I wouldn’t be in that position needless to say].

    It’s kind of like when you have an animal that didn’t respond well to training but for some reason, you’re attached and get along just fine. So you keep others away so they aren’t bitten by the rascal.

    If you are unable to position yourself in a place where this person is sort of kept behind glass, so to speak, then it’s just a matter of leaving the situation. Some things aren’t saveable, people certainly are their own creatures and you cannot change them unless they want to change. So you can only adapt to them, keep them away from the vulnerable folks or just rid yourself of the stress by not working for them/around them whenever humanly possible. You cannot take this burden on yourself, as it’s a battle that won’t be won and will only discourage and hurt you.

  27. Blue Horizon*

    I believe I know the story to which Alison is referring in her response. I won’t dig it up again, but suffice it to say that Alison knows what she is talking about and that this can be a very dangerous path to embark on. Simply by virtue of your role you are already in a position of needing to smooth the way and work around this person’s problems. While you may be doing this purely out of professionalism in order to keep the business as functional as possible, it can have the side effect of insulating him from the consequences of his actions and making his long term position in the organization more, rather than less, tenable. You are already running the risk that this will be perceived as enabling by some people. In fact you’re running the risk that you will actually BE enabling him. If you start thinking you can change him or make him better, that will naturally push you much closer to that line. If he were to, for example, give you just enough encouragement that you thought you were succeeding, and you became emotionally invested in that outcome, then it might unconsciously bias you to minimize problems that arise or dismiss them as temporary backsliding. People like this are very good at giving you what look like rational reasons to play along with their game (often by invoking dire consequences due to externalities if they are held accountable, e.g. “the company couldn’t survive without me”) and even the best of us can be caught in the trap.

    If you continue there then you need to be very clear whose side you are on. If you start thinking it’s possible to change him, make sure you keep in mind as an alternate hypothesis that maybe he is just as much of an asshole as you always thought (or more) and is taking advantage of your improvement attempt to manipulate you. Think of what might go wrong as well as what might go right, think about how everyone concerned might tell the story in future, and make sure that your interactions with everyone (and not just this guy) are true to your values and professional ethics.

  28. MissDisplaced*

    It’s rare that Alison starts off with a “You can’t fix this,” and “I’ve worked with this guy and I’ve been you, letter-writer.”

    She’s right. It’s so difficult to fix someone who’s that bad, and you know, it’s not your battle. As you said, you can manage dealing with him, but you can’t really buffer between him and others as it only hides how bad he is. In-house staff is one thing (not cool but it’s more accepted), but I’m amazed how people like this rise to such high levels, especially if he’s like that to the clients!

  29. I Got Out*

    Run. I have been there and I loved my job and watched as my ED got more and more abusive, particularly to women. I never thought I would leave but when everything finally blew up, I ran and never looked back. It is not worth your time, your energy, and your health to try and fix him or to try and endure. He will never change and you will grow more and more frustrated. And I can GUARANTEE you that his attitude has lost your organization money and supporters. When I worked for a jerk, I didn’t know how bad it was. But after I got away, I have literally been in meetings where people said, “I don’t want to fund this agency because the ED is a jerk.” He is absolutely costing you in money, volunteers, and reputation.

  30. Auntie Social*

    My husband had been on the board of a non-profit but had worked there all through grad school. His manager was a terrorist, and donations were low as a result. He was one of the few people who could win an argument with Bob, and he would undo all of Bob’s irrational decisions and insults (no Emily, you’re not really fired, you’re fine”). Bob was SURE that he was going to be made a regional VP but that day never came, and Bob retired. Hubs was supposed to give a speech about Bob, and he said in all good conscience he couldn’t get up and lie. I said “you can always turn it into a comedy routine”, and the lightbulb came on. When he got up he said “How many people here have been fired by Bob? Okay, fired more than once?” “And who here is the laziest person on the planet??” It became this huge catharsis for longtime staff, and actually Bob took it pretty well. Bob’s replacement was a soft spoken gentleman who preferred to inspire and donations tripled in a year, and that seems to have been the seed under his dentures.

  31. Book Badger, Attorney-at-Claw*

    Your boss is this way because it works for him. People tend to act in ways that work for them, either tangibly or intangibly, and rarely if ever deliberately do things that would hurt them. And sometimes, the only thing that makes people change is when the behavior they’re doing starts consistently hurting them.

    Like, I’m a chronically late person. I suck at being on time, to everything, even things that I enjoy. My job is okay with me being late: most people in the office are, and our hours are deliberately flexible to accommodate it. But if I knew that I’d be immediately fired if I was even one minute late to work, I’d probably start taking as many precautions as possible to *not* be late, because my behavior would hurt me, rather than work for me.

    Your boss is like this because, in all likelihood, he has never suffered a consequence from this kind of behavior, or if he has, it has never been so bad as to affect him permanently. The fact that he changes his behavior around old white men shows that he knows *how* not to be a dick, and chooses to be one anyone.

    Here’s the problem: since you’re not over him, you’re not the one to enforce consequences. You don’t have the authority to fire him or reprimand him. Lawsuits are decided by settlement, a judge, or a jury: either way, it’s almost certainly not your call. You’re not his daddy or his favorite grandma or anyone else who could give him a firm talking-to and disinvite him from the barbecue. So he’s not going to change based on what you do, because he has no reason to. And if those consequences do catch up to him, it’s probably not going to be because of you. (And honestly? I’d worry about being caught in the crossfire.)

  32. human fidget cube*

    I’ve worked for people like that before, and trying to change them is always a waste. Plan your exit instead. You will invest so much energy and time trying to fight the windmills that you could spend doing something productive instead, and you’ll become miserable for it.

  33. NonProfit Nightmare*

    I could’ve written this myself. I work for a small non-profit and my boss is, frankly since it is just between us and the internet, a condescending jerk. He belittles women in the office, calling us clique-y and the one time I tried to challenge him I was accused of “scolding him like he is a child” multiple times. I was the previous writer that had written about staff wanting to go to the board about his attitude/some poor choices he has made. Just keep your head up and don’t fall too far into the fray.

  34. theelephantintheroom*

    Ugh. While not my manager, I work with guy like this. He’s amazing at his job as a developer…when he bothers to sit down and concentrate on it (he always has some “this is above your understanding” type of excuse for why it’s not getting done and our not-very-tech-savvy management doesn’t know enough to know it’s all BS) But, otherwise, he’s an asshole.

    I WILL say, though, that this guy USED to be a manager. But when his bosses saw how terrible he was with other humans, they removed that responsibility from his plate and attached his employees to a manager in an entirely different department. (Sounds weird, but it actually worked pretty well.) Maybe your company will also take notice and make the necessary adjustments?

  35. Non-profit noob*

    Wow, I feel like I could’ve written this letter too!

    I’ve been working at a small non-profit under our ED for 2 years, and it honestly feels like an abusive relationship. When it’s good, everything is rosy and perfect, but when she’s stressed out, it’s nightmares for all of us.

    Our ED is a woman who’s been with the organization for over a decade, moving through various roles and ending up at the top. She has trouble adjusting to the stress and responsibility to her new role and letting go of those from her old role. This leads to micromanagement and behaviours that sabotage our (small) team. I have been recording those instances and here are just a few examples:

    1) One day she sent my team a project idea saying that we should “talk about it”, and does not make herself available for meetings. A week later, she shows up at my desk and demands us to draft and execute the idea immediately. When she found out that we were waiting for a meeting with her, she became really annoyed. In the end, we had to shuffle our deadlines to make room for this last minute idea.

    2) She likes to gossip and criticize other staff/board members when they are not there, which makes us wonder if she does the same thing when we are not in the room.

    3) One time she grilled me in front of an intern for not using the calendar properly and that there’s information missing. Well, it turns out later on that she was looking at the wrong calendar.

    The list goes on and on. When she does something like this, she almost always apologizes immediately, only to do something similar the next week. I guess my point is, don’t expect them to change. If there is room for learning and growth, then stick with your job and suck it up. Otherwise, you are better off searching for another place than wasting your time and energy trying to change your boss.

  36. Calamity Jane*

    I worked for this guy as well and his behavior elevated into abuse. Once he directed it at me, I had to leave.

  37. Alice's Tree*

    Just piping in that while Alison is probably correct that it won’t help to explain to your boss how he’s coming across, it worked for me with my boss. So there’s hope.

    In my case, I didn’t sugar-coat it for him. I was blunt and direct that he was offending people and making them feel dismissed. I gave him specific examples, and I told him it had to stop because it was hurting our work. He said he’d watch himself, and he did. I hope OP gets the same result.

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