my brother is my business partner and he keeps going MIA

by Alison Green on November 11, 2024

A reader writes:

I wrote you way back in 2021 when I was trying to decide whether or not to stay in the family business, and in 2024 I sent you my update. I’ve since stepped into the role of CEO, for better or worse, and am now facing an ongoing issue for the first time as the leader of this company.

We have three family members who are part of the business now — my father (majority owner and president), myself (CEO, minority owner), and my brother (VP, minority owner). My brother and I have the same ownership stake and the idea was that the company will transition to us, and we will be equal business partners.

But my brother is undependable. My guess is that he has depression, anxiety, or some type of mental health issue that he has never addressed, and it means he’s often mildly unreliable and then every once in a while he drops the ball in a spectacular fashion that leaves other people to clean up his mess.

We’ve had conversations about this on a number of occasions over the past decade. But about three years ago, it really seemed like he was doing much better. He was showing up, answering his phone, responding to emails, doing his job well, and actively participating in executive planning. He said he wanted to be here with me to lead our family business for the long term. And that felt wonderful. The idea of having a partner in this family business, where it can feel very high stakes and very lonely, was such a relief. My brother is smart and thoughtful, and I trust his judgement and views, which often differ from mine, which is great in a business partner. Shortly after that was when long-term plans for ownership were being put into place, and actual ownership stocks started to change hands. I thought my brother and I were going to be a great team.

But 18 months ago, there was a incident where he went uncommunicative for a week and left a project manager in the lurch. We had to scramble to find a subcontractor to complete our work. Eventually he showed up and said he wouldn’t do it again.

And then a year ago, he left on his honeymoon having completely failed to get a project with a hard deadline started, leaving me having to scramble to make apologies to city officials, track down materials, ask for extensions, and generally get really ticked off at my brother. Once he got back, I, in the presence of my father, told my brother that he needed to see a therapist or in some other way address his lack of dependability or I would not go into business with him. He agreed and said he’d already talked to his doctor about getting a referral. Over the last year, I’ve asked a couple times if he’s made any progress with getting help, but he’s always said he was waiting on insurance or for an appointment, etc.

Over the last month he’s gotten shaky again, being less and less responsive. Then two days ago, I found out he was leaving the country the next day for two weeks. He never told me. I found out from my mother. We once again have a project left in the lurch, making other people scramble. He left one of our crews short a member (he gave his guys only one work day of notice) and another employee is scheduling things that he should have scheduled. And I’ve come to discover that he’s put off scheduling a kick-off meeting for another project for the past three weeks, ignoring the emails from an angry PM for the state.

How do I deal with this? I know I don’t want to be in business with my brother under these circumstances. I said that last year, and I meant it, and I set a boundary… and here we are and it’s time to enforce this boundary. I know all that, but I don’t know what to actually do and what to actually ask for.

My dad sees all this, and is supportive of me. My brother has been doing this to my dad for nearly a decade, and I think my dad is even more fed up and upset than I am. My dad is also a bit of a hothead and a dictator. He wants to straight-up fire my brother. I don’t know. Maybe that’s best? But my brother has good qualities, good skills, and he is an owner and he is my brother. What about a PIP? A leave of absence? A change in role, take him out of leadership? Or did that ship sail last year?

Part of what is so hard is that I love him. And he’s falling apart at work because of very real, very challenging stuff in his personal life. The other part is, I lived the same childhood as my brother. We had an alcoholic mother and my parents went through a terribly messy divorce, and all that created issues around communication and confrontation and self-worth and shame for all of us (issues that I’ve worked hard to overcome through my own therapy and coaching). So I’m deeply empathetic to why my brother is the way he is. And I don’t want to blow up my relationship with him or my sister-in-law. But I can’t do it like this anymore. And ultimately if we keep going like this, the relationship is already destroyed because I’m so frustrated and angry. And I could work with him, somehow, probably, if he would just communicate with me — if he had just told me he was going to be on vacation, that he had been ignoring these emails, that he was stalling out. But we’ve tried saying, “Please, for the love of everything, just communicate!” for nearly a decade, and nothing has changed. It’s never really gotten better, except for that brief period three years ago.

I’ve read through your archives, looking for family businesses hitting similar issues, and this and this really hit home. We’re experiencing these issues, the hit to morale and people talking about leaving based on family members being treated differently. So I know we need to change and I know there is no way to do it without this being sad and painful.

Any advice you could offer to help me figure out some options to move forward that fall between “keep doing what we’re doing and getting the same result” and “fire him as soon as he steps off the airplane” would be much appreciated. My brother gets back in two weeks, and I need a game plan for what our conversation is going to look like.

You have a few choices.

You could give him one final warning: if this happens again, he’s out of the company. He can retain his minority ownership interest, presumably, but he can’t work there.

Or you could figure you already gave him that warning last year and it’s happened again anyway, so it’s time to part ways now.

But did you give him that warning last year? It sounds like you told him that you being in business together was dependent on him seeing a therapist, which is a different thing. And I don’t think that’s the right requirement since he could see a therapist regularly but still continue jerking you around, and it would be just as impossible to continue having him as a business partner as it is now.

So if you give a final warning now, don’t pin it to therapy. It certainly sounds like therapy would be a wise step for him, but that’s up to him. The part that you control, and the part that’s at the crux of this, is that you’re not willing to be in business with someone who periodically disappears without notice and lets major projects slip. So that’s the part to attach the ultimatum too — if that happens again, he’s out.

That said, I don’t think you’re obligated to give him that warning. Your conversation last year made it clear how disruptive his behavior was and how strongly you felt about its impact on your partnership, but he’s still done it again. If you’d rather just be done now, that’s fair and you can be.

A third option is that you lay out what will and won’t work for you and for the business, and then ask him to decide if he can commit to meeting those needs or not. You could simply say in very plain language that you’re not willing to accommodate another instance of this so if he wants to stay he needs to commit to XYZ and if he messes up again, he’s out. Ask him to be realistic with you and with himself: does he genuinely believe he will pull it together and sustain that with no additional mess-ups or, for the sake of your relationship, should you both be pragmatic and acknowledge now that it’s not going to work? It’s okay to be forthright with him that if he recommits but then repeats this anyway, it will affect your relationship — in fact, that it’s already affected your relationship and you hate that because you love him. That’s true and he deserves to know that; you shouldn’t be the only one grappling with that.

But you’ve got to set a line, and make it clear what that line is and what happens if he crosses it. That doesn’t mean “fire him as soon as he’s out of the airport” — but it does mean a probably painful but necessary conversation about what you will and won’t put up with, and there shouldn’t be another one after this one.

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{ 201 comments }

{ 201 comments… read them below }

  1. Chairman of the Bored*

    Lots of people have good ideas, good qualities, and good skills.

    They should still not expect to keep a job if they cannot be expected to show up reliably and *do* that job.

    Seems like it would be better for everybody to either buy this guy out entirely or treat him as a silent partner who picks up a check for his ownership stake but has no authority or expectations of doing any actual work.

    1. Alton Brown's Evil Twin*

      Can the “good ideas, different opinions, etc” stuff be packaged into a (part-time, maybe) job that has no management responsibilities or deadlines? OP consults w/ brother as needed, but never delegates anything to him. That’s the only compromise I can envision.

      1. Green great dragon*

        Yeh, this is worth exploring at least. Are there long-term individual projects developing new products/strategies/campaign, say? But only if the company can support it.

        A non-executive director role feels like the ideal place for him, but hard to transition there from the starting place you have and that may not be something the company needs.

        1. goddessoftransitory*

          I agree. Brother may have skills, but they are not being deployed in any kind of useful manner. It’s like hiring the world’s best architect but they only show up with a room’s worth of drawings once a year.

          If he wants to stay, he can’t be in charge of anything, basically.

      2. Kes*

        I was wondering about this as well. OP really wants to keep working with brother, and brother may want to keep working there. but its clear that his current role and responsibilities aren’t working for him (and his failure to be reliable isn’t working for anyone else). If the issues are illness (including mental illness) or addiction related, there may be limits to how much control he has over them, and while ideally he’d get help and figure out how to get them under control, that isn’t something that can be forced. OP wants to do right by their brother but they also have to do right by the company and their clients as well. At this point that means brother should not continue in their current role – either they find a different role where brother’s lack of reliability doesn’t matter so much, like an occasional consultant on non-time-sensitive ideas, or let him go.

        1. Lea*

          Does brother want to keep working there?

          I think I would be inclined to approach it by asking if this is really the kind of work he wants to do. Because he doesn’t seem invested in the work or the team if he can do this?

          He could just be terribly avoidant about stuff which I get but leaving for two weeks without having stuff done doesn’t sound like someone who is enjoying his job

          1. Part time lab tech*

            This. So much this. If this business didn’t exist, what would he be doing instead? Instead of failing at this job, what could he be succeeding at?
            The business sounds like the path of least resistance for him but does he even enjoy it? Could OP buy him out? Would he enjoy being a contractor more so he can relax for 6 months between 2 year stints?

      3. Kevin Sours*

        It sounds like “member of the board” — especially as a minority owner — would fit. The question is what kind of stipend would be reasonable. Or possible if he’s not doing any day to day work.

    2. Antilles*

      I agree with the reliability concern. This paragraph jumped out at me.
      But about three years ago, it really seemed like he was doing much better. He was showing up, answering his phone, responding to emails, doing his job well, and actively participating in executive planning.
      Half the description of “how he’s doing better” is that he bothers to show up to work and answer normal business communications. This is literally the bare minimum expected of an employee, the lowest possible bar imaginable.
      Except that he can’t even meet that low standard, repeatedly vanishing without warning.

      1. kiki*

        Yeah, it would be difficult to stay motivated as an employee if I saw that one member of the leadership team is allowed to go MIA for weeks at a time and not do baseline expectations of their job repeatedly. Especially because that wouldn’t be allowed for anyone else, but this particular leader is family.

        1. RC*

          And especially since it sounds like employees have repeatedly had to scramble to cover for his disappearing shenanigans. By the second or third time I get a “ok so, Brad has disappeared again, can you drop what you were working on to do this kickoff meeting for an important project, btw it’s due tomorrow” I’m vigorously looking for another job.

          1. Starbuck*

            Right, LW might be willing to give her brother another final chance but I imagine the rest of the staff have all written him off at this point. It’s an obvious double standard assuming no other employee is allowed to be this flaky and keep their job. I doubt he’d ever have their respect or trust again.

            1. goddessoftransitory*

              And their best employees will soon be writing off this company. I would be shocked if at least half of them aren’t actively job searching.

              1. MM*

                Not to mention clients! There are two stories about angry clients in this letter, and that is certainly not a comprehensive list. I’m kind of surprised there’s not more concern in the letter about being able to keep the business going at all at this rate of getting their reputation rightfully dinged.

        2. reputationcoded*

          Exactly this.

          I’m with Dad – I think it’s time to cut your losses. Honestly, maybe working for/with family is contributing to his mental health issues and consequently his lack of dependability. He might thrive in another role with a new organization and you might be doing him a favor cutting him loose (thought I understand it won’t feel that way).

          1. MigraineMonth*

            Or getting fired might be what he needs to realize that he really does need to get help.

            Or not, it might exacerbate the shame spiral and make him even more resistant. It’s so hard to help someone when their illness is telling them they don’t deserve to get better.

            Either way, he can’t be kept in a position where he’s disappearing and doing so much reputational damage inside and outside the company.

      2. goddessoftransitory*

        I spotted that too: reading it I was thinking “well, isn’t that what any worker is supposed to be doing?”

    3. Chief Bottle Washer*

      Right. If there were any other employee, he would have been fired already. And OP needs to realize this is having a negative impact on the business and the morale of other employees. It sucks, but I think OP needs to cut him loose.

    4. Anon for this one*

      I worked for a company that had been started as a family business. By the time I started there, it was a publicly traded company, but there was still a family member employed with the title of “VP of Special Projects”. The role reported directly to the CEO and had no employees that reported to it. In all the years I worked there, I never saw that person or heard of them actually doing a project, though I did hear rumor that they would occasionally show up on a phone call, add their thoughts, then disappear again. It annoyed everyone a bit that someone was getting paid to do nothing, but overall no one cared because it meant that family member wasn’t causing issues. OP, this is what the title VP of Special Projects was made for! Give your brother that title, occasionally ask his input on things, and if he’s able to get himself to a functional state, he can start having more responsibility. Is it ideal? No, but it preserves your relationship while reducing the liabilities he carries.

      1. Smith Masterson*

        I worked for a family owned ISV. The owner/founder’s second husband’s family (his father, mother, and brothers) used to fly in once a year (on the company) to pick up their checks and vacation. They all had bullshit VP titles. Only one of them occasionally caused issues.

  2. different seudonym*

    In my own family (which does not have a business) comparable issues result from active addiction. I mention that not to diagnose at a distance, but because if that’s at issue, it definitely cannot be solved by the sort of mental-health treatment that targets depression and anxiety. To be clear, addiction usually coexists with depression and anxiety! But it’s not something you can chip away at, the way you can chip away at, say, patterns of negative self-talk. If there’s an addiction, you get into recovery or nothing changes.

    1. A Library Person*

      It does sound like the letter-writer has some idea of what, specifically, might be causing these issues in their brother’s work life and is sympathetic but has reached a breaking point *because of the way their brother’s personal issues are affecting his work output*. Speculation like this seems particularly unhelpful in this context, where the letter-writer has essentially decided on a course of action but is trying to figure out the best way to handle it.

      1. Big A$$ Rock*

        It seems helpful if multiple people had a similar thought. It’s sometimes helpful to throw out another option. ds made it clear that it was a thought to consider, not an actual diagnosis.

      2. Double A*

        The reason it’s helpful to think about this for the LW is because the way you approach active addiction and the way you approach depression are different as a family member. With an active addiction, anything you do to soften the situation just makes it last longer. ironclad boundaries are really the only way to deal with an active addiction. And really those boundaries need to be, “I will help you get into recovery and nothing else.”

        Since this is a family situation, I think reaching out to the sister-in-law is going to be important to find out if there’s more going on.

        1. different seudonym*

          Honestly, it was the description of the family system that rang the bell for me, not the nature or degree of his flakiness. One million “last” chances, the worry that consequences will cancel love or disrespect the person’s good qualities, the effort to find complex “reasons” for repeated, simple abdication of responsibility…those are all things people do when their loved one is using and they don’t yet understand what recovery actually looks like.

          To reiterate, I don’t know what is true of the LW’s family. I only notice similarities with my own experience. But I do think that the confirmed presence of an addiction would change the advice radically.

          1. MassMatt*

            I have no idea if there’s an addiction issue or if it’s something else, but the business is suffering in multiple ways from the brother’s lack of reliability. The most obvious is the work that he isn’t doing and his absenteeism. The other is the resentment this is causing among the rest of the staff, who see one rule for them and another for boss’s son.

            LW a needs to make sure her father/main owner is in agreement and get rid of the brother. It doesn’t mean you don’t love your brother, it means he needs to take responsibility and suffer the consequences for his unreliability.

            1. gyrfalcon17*

              I think also that LW needs to separate what needs to be done for the business, vs. whatever family things they might want to do.

              They’re all tangled up in knots about how to care for their brother, and massively neglecting what they need to do to care for the business and the other employees.

              1. AcademiaNut*

                Demanding that he seek therapy is a prime case of that. Getting a medical diagnosis and treatment is the kind of thing a family pushes for, and would be an overstep for an employer. Showing up for work reliably is something an employer pushes for, leaving it to the employee to figure out how.

                It’s also worth detangling the job stuff from the therapy, because it’s entirely possible that the brother going to therapy won’t turn their performance around. It depends on the details of the issues, the type of treatment that’s available, compatibility with a therapist, if/how well medication works, and how all that interplays with the brother’s personality and desire to be a reliable employee.

                1. MigraineMonth*

                  Agreed. It’s one thing for an employer to offer medical (or other) leave to an employee who seems to be struggling with a medical issue. Maybe instead of saying they fired an employee, they can say that they separated “due to a medical issue”. However, an employer should never tell an employee what treatments to pursue or make their employment contingent on getting a particular treatment.

                  I know he’s your brother, OP, and you want to care for him. If he asks you to help him by calling therapists’ offices until you find one without a long waitlist, that’s a great thing to do *as his sister*. However, getting him into therapy/other help is no guarantee that his job performance will improve in the timeframe you need it to for work, so don’t make any promises around that.

      3. stop diagnosing*

        Several times in letters like these, speculation like this is useless. But other commenters will flock out of nowhere to explain why it has to be mentioned and how they’re not actually diagnosing anyone (which is against the site’s commenting rules). You’ll get used to it.

    2. Margaret Cavendish*

      I had the same thought. And unfortunately, it also can’t be solved with “this can’t happen again” kinda of conversations. You’ve had the conversations, and I’m sure he understands what’s at stake here – and he still keeps disappearing on you.

      I hate to say it, but I don’t think you can give him one more chance. He may say all the right things about not doing it again, and he will probably even believe them and want to do better. But right now, he just can’t. He will do it again, because he’s motivated by something other than your business.

      I believe you when you say he’s smart and funny and that you love him. All those things can be true – and he can still be a person who bails on important parts of his job. So as much as it sucks, I do think your plans should start as soon as he gets back from the airport.

      This does suck, a lot. I’m so sorry you have to deal with all of it like this.

    3. JSPA*

      Directing him, as family, to medical leave / continuing to cover insurance for several months (including cost of whatever inpatient treatment may be needed) and being open to rehire, are about as far as the LW can rreasonably bend, I think. Plus if board members are paid for their time, he’ll still have that.

      IMO, a spouse may well be just as much of the end of their rope, and trying hard not to blow things up with the family business! When people are disappearing for a couple of weeks at a time on no notice, it’s commonly disruptive for multiple aspects of their life.

      And if you’re terribly worried about blowing up their income, I guess you could see if there’s a part-time job that the sister in law is qualified for and has time to do??? Whether or not she takes it, the offer would have been made, Which goes a long way towards preserving family harmony.

      1. Jasmine*

        “And if you’re terribly worried about blowing up their income, I guess you could see if there’s a part-time job that the sister in law is qualified for and has time to do??? Whether or not she takes it, the offer would have been made, Which goes a long way towards preserving family harmony”

        Having another family member who would be difficult to fire if they were not up to the job might be asking for trouble. Help or encourage her to find a job somewhere else. (My FIL had up to 12 relatives working at his company so I say this as someone who has seen it and as someone who was NOT interested in working there!)

    4. Momma Bear*

      I was also wondering if there was more than depression going on, given the family history of addiction. I would make an action plan with the father and give the brother final notice. He’s going to burn the company for everyone if this is allowed to continue and then where will that leave any of you? He had dropped the ball again and was already sneaking out, again. He’s learned nothing. It’s hard when it’s family and there’s a trauma bond. Maybe LW needs to seek their own therapy to break the cycle they grew up with, too. I think brother needs to find other employment. He’s had way too many chances for way too long.

      1. Polly Hedron*

        But I think brother is unemployable. No non-family business would put up with him.
        Cut him loose at the airport and give him a trust fund.

        1. WS*

          On the other hand, if he has genuine consequences, not just a stern talking-to, he might put the work in to be more employable. The half-in half-out role he has now is not helpful to him either.

    5. Lisa*

      That was my thought as well. Especially with the family history, it would be unsurprising. Sadly being raised in dysfunction often means finding unhealthy ways to cope. Ask me and my chocolate supply how we know! But OP needs to also not fall into the codependency trap, which it sounds like has probably been an issue, including feeling the need to protect the younger brother from their father’s volatile temper. My heart breaks for them, because I know the struggles of trying to make a good life when your childhood was bad. I hope that OP has the strength and compassion to do what needs to be done. Especially compassion for themself.

  3. Lamont and Rollo*

    You and your dad need to agree on a plan ASAP. This sounds like a mess and can’t continue – an employee, let alone an owner/VP, cannot just disappear with no communication. If a regular employee did that they’d probably be gone yesterday.

    If you can’t or won’t fire him , can you give him less responsibility somehow?

    1. Pastor Petty Labelle*

      This. Dad is the majority owner, he can tell yoru brother this cannot continue and he will change the succession plan to reflect that.

      For yourself, do you really want a partner in business you can’t rely on? Sure it can be lonely at the top, but having someone you can’t depend on won’t help that. Because you can’t count on him to be there when you need him.

      You need to approach this as a business decision not a family decision. If he weren’t your brother would you still be wondering if you want to cut him loose? Doesn’t matter his childhood, you need to be able to depend on him. He’s your brother so you can personally support him and encourage him to get help, but businesswise, its time to cut him loose.

      1. BellaStella*

        I tend to agree here. Any other VP who did this would be fired. Give him a severance package and let him go.

      2. goddessoftransitory*

        I agree. It may be lonely without brother there, but he’s not providing stability, just a distraction.

    2. T2*

      If I was him, I would ask dad to sell me 1% of his share so that when Dad dies, I am the majority owner. I would also talk to an attorney to clear any survivorship issues in the ownership structure.

      The I would go into caring for my brother mode.

      1. gyrfalcon17*

        As long as “caring for my brother mode” doesn’t include “let my brother stay in a position with critical responsibilities that can tank the company if they’re neglected, and brother keeps neglecting them.”

        Given the family mess and angst, and regardless if brother’s problem is addiction or not, I recommend Al-Anon meetings to OP as a place to start learning she cannot fix her brother, and it harms people for her to keep trying to the point of almost tanking the company, several times.

        1. gyrfalcon17*

          And while I’m here: an Adult Children of Alcoholics group, if OP can find one.

          Alcohol was not the cause of the dysfunction in my family, but I have found Al-Anon to be super helpful. But even more so than general meetings, the meetings for ACOA were — WOW! These were my people!

          2. T2*

            Third this. I myself never drink alcohol, drugs or any other psychoactive substances directly because of my parents issues.

            It is fine for other people. But for me, what it did was turn otherwise good people into people who cannot be reliable.

            I like to think that I am generally reasonable. Good bad or otherwise, I can put up with a lot, as long as you are reliable. But I find I cannot allow anyone who is unreliable and cannot be counted on to affect my manner of living or have any form of power over me.

        2. T2*

          It doesn’t.

          But my view is that you have to ensure your own survival first and then look after others. In my family, my wife comes first (the one who picked me and will be with me when everyone else is gone), and then my kids who I am training to be able to live independently eventually) and then the rest of the family.

          Sometimes supporting the brother means being patient, kind and loving while he gets his act together.

          Sadly, many people’s values get twisted when it comes to money and power.

  4. Successful Birthday Rememberer*

    I get the family dysfunction and how damaging that can be – I know from personal experience.
    That said, it is not an excuse to behave this way.

    Sigh…I work hard and struggle to make ends meet. It must be nice to travel internationally and do whatever else you want, then continue to collect an exec-level salary. I can see why employees are resentful. I am kinda resentful at your brother and I don’t even work there.

    1. Elsa*

      There’s a difference between “I love my brother” and “I love my brother and part of that love is ensuring that he never faces any consequences for his actions.” It’s wild that the more power you personally get, the harder it is to tell the difference between those two positions.

      1. Elbe*

        +1000

        I feel like somehow it’s become increasingly common for people to equate kindness, compassion, and understanding with bending over backwards to ensure that people never experience any consequences for their actions. More often than not, that’s just enabling. It’s actively hurting that person (and everyone around them) by taking away the natural pressure they would feel to improve things.

        1. goddessoftransitory*

          In dysfunctional family systems, “consequences” too often get linked to “wild lashing out by an authority figure” and are seen as profoundly unfair things to be avoided/shielding your loved ones from at all costs. Add that to running a FAMILY business? Woof.

      2. Antilles*

        The other wild part is how that “ensuring there’s no consequences” strangely seems to only benefit those already in power.
        Does anybody believe that not a single employee of the company also has a crappy home life, alcoholic family members, or their own mental health struggles? Of course not, it’s just that they manage to drag themselves into work because they know they’d actually experience consequences because they don’t have the perks of dad-is-founder and sister-is-CEO.

        1. anon24*

          So much this. I’m sympathetic to anyone who is struggling, but I have both physical and mental health issues, and I’m still dragging myself to work 50+ hours a week because I have literally no one and if I don’t do it I’ll be living on the streets and that won’t exactly help my problems any. Sometimes you just have to pull it together, even when that means working 12+ hour shifts and coming home and sobbing uncontrollably on the floor because you wish it would stop already.

        3. Tea Monk*

          Or they just get fired, but its the circle of life. at least brother will be able to get some treatment with the time away from work being fired will give him.

      3. Daria grace*

        A concept that’s really helped me in some of my relationships is that love is not primarily about protecting people from discomfort, it’s about acting in other people’s best interests. Occasionally it’s appropriate to shield people from discomfort but more often it means putting people in temporarily uncomfortable situations to help break patterns that are doing them harm

      4. Boof*

        Usually the dynamic is the person tends to make the consequences seem wildly distressing; probably because they don’t have good coping skills and/or their coping skill is to broadcast distress until someone comes in to help. And we tend to want to avoid distressing our loved one so, it’s really hard to know when the distress is temporary/necessary especially when you’ve been in the thick of it so long and in theory, you could relieve that distress, at least temporarily. (at the cost distress to a lot of other people but again, that is the trick, that one person’s distress seems like the worst instead of that really it’s ultimately avoidable / or worse is being inflicted on everyone else in the long run)

      5. MigraineMonth*

        I’m not sure I agree. I know people without deep pockets who have drained their savings trying to keep a family member alive and out of jail. If they had the power to guarantee that family member had a job, health insurance, and a mental health care provider that wasn’t the US prison system, they would do so in a second. It’s sad that everyone doesn’t have those resources, not somehow shameful that OP does.

        I also don’t think OP’s brother is running away and cutting himself off from all contact with his family for fun. It sounds like recurring shame spirals, in which case the inside of his head is probably an awful place to be. (That would also track with his failure to get mental health help. Have you ever tried to navigate find a therapist who would take your insurance and didn’t have a waitlist, all while your brain told you that you were worthless and none of this would help? Take it from me: it isn’t fun.)

        The advice to OP is the same: she cannot keep her brother in a business-critical role when he isn’t able to do the job. That doesn’t mean she’s a bad person for wanting to help her brother when he’s struggling, and it doesn’t mean her brother should be, what, punished on behalf of employees who don’t have the privileges of wealth?

        1. AF Vet*

          Oof. The ONLY reason I finally found a therapist who would listen AND take my insurance is because my mom had worked with her for years and knew we would mesh, so she made the appointment for me. I will curl up in a ball and very when she eventually retires.

    2. CommanderBanana*

      Right? I’m imagining an employee being told there’s no money for a raise, while they know Executive Brother is getting a salary for doing nothing.

      I have known more than one family business where problematic family members basically got paid to exist (and stay away).

      There’s a reason most family-owned business either get sold to a bigger corporation or fall apart 2-3 generations in.

      1. Reluctant Mezzo*

        Yes, one time when I was let go and the boss’s daughter got to stay, whom I knew was not reliable, it wasn’t any surprise when that office closed a year later.

    3. Web of Pies*

      I agree, if brother is well enough to travel internationally frequently, then his addiction/depression/whatever isn’t a real factor here. He knows he can do whatever and get paid because faaamily. See also: weaponized incompetence.

      OP: You need to accept that his behavior will not change, ever. It’s been a decade of this! If you want to reward his behavior, give him the board seat and the stipend and no decision-making or work responsibilities. I don’t like it because it feels very enabling to me, but he’s not my brother.

      1. owen*

        please don’t equate ability to travel sporadically with ability to be reliably at work (not just showing up but also completing the job duties)! they are two very different things and one can be ill enough (mentally, physically, or both) to travel internationally for short periods of time, but not sufficiently well to be able to reliably work. linking the two does a huge disservice to many people who deal with disabilities subject to unpredictable flares.

        for the OP, however, the basic situation is as you say, it’s been a decade of his father not following through on consequences for this kind of behaviour. it is very unlikely to change. so the OP needs to decide which of Alison’s three options is the best for them and their business. it is unlikely to involve keeping the brother on over the long term.

      2. Kella*

        If the brother has some form of mental illness where one of the primary coping mechanisms or disordered thought patterns is avoidance, then being able to travel *in order to avoid work* would likely be easy for him to do, while answering an email could be insurmountable. Mental illness does not always look like your capacity for *all* activities deteriorating. Sometimes it looks like exclusively being able to do one or two activities, to the severe detriment of all the others (including ones that keep you alive.)

        That doesn’t change the fact that OP needs to draw a line and stick to it. But there’s not enough to definitely demonstrate that it’s weaponized incompetence instead of a mental illness.

  5. pcake*

    LW, you say your dad wanted to fire your brother? I suggest you let him.

    Your brother is leaving not only you but people who work for you in the lurch, sometimes when it really counts. It’s causing you and your employees stress and scrambling or leaving you to pay extra to vendors to take up the slack. No doubt wondering whether your brother will flake causes worry not just to you but to your employees – and possibly to your customers.

    You can’t force a person to function, no matter how much you want to. You can’t convince them to be happy or functional, regardless of your intentions or whether it would make them happier. And many people really do mean well when they make promises, but something gets in the way. Your brother has shown repeatedly that something will get in the way. If an employee behaved this way repeatedly, wouldn’t you let them go?

    1. Dawn*

      This. Sooner or later, he’s going to do something the company can’t bounce back from; let your dad take the hit while he’s still in charge.

      1. I own one tenacious plant*

        This is an excellent point. The problem started while Dad was fully in charge, he should be responsible for the solution.

        1. Not Tom, Just Petty*

          I see what you are saying. Dealing with brother in the company is above OP’s paygrade. Boss Dad should be handling this. If it means firing brother, then OP can help him as brother, outside the company.

    2. Hot Flash Gordon*

      Yeah, you can’t care more about your brother’s job than he does. I get that it feels gross to fire a family member, but think about all your employees who have families and depend on the company functioning well and staying in business. It sounds like your brother is starting to jeopardize the stability of the company and you and your dad need to prevent that from happening.

      1. pcake*

        But is it gross? If the brother damages the company so that it makes less money or loses customers, the brother will also take the financial hit. Not having someone who leaves everyone in the lurch protects everyone’s job or money INCLUDING the brother.

        1. Hot Flash Gordon*

          Well, I said that I understand that it “feels” gross because it’s her brother, whom she loves. Most people aren’t terribly logical when it comes to a family member, which I get and it’s probably why he hasn’t been fired already.

    3. H.C.*

      not only vendors, but clients too! After all those apologies & extension requests because of his dropping the ball, they might think again before considering doing business with your company again.

  6. Artemesia*

    Does his minority share provide cash flow? Dividends? Whatever. Could buying him out give him transitional money as he finds something else? Obviously Dad is key here, but I would not drag this out. Time to move him out of the business and preferably time to buy him out entirely.

    The only way I would consider keeping him on would be in a very constrained job where he can’t derail projects if there is such a position. But best if he is not longer associated with the business.

    The issue then is how to do this so he keeps insurance and financial resources for a transition to something else.

    1. Seeking Second Childhood*

      A severance package including COBRA coverage or the right to buy into the company health car coverage covering his own costs.

    1. Successful Birthday Rememberer*

      Never put more work into someone else’s well-being then they do. Unless they are unable to, of course. Trauma does not mean incapacitated. He needs to go.

    2. bamcheeks*

      I think this is a great point, and I mean that in a deeply serious way, not in the kind of cliche way.

      LW, do you actually believe your brother wants to be in this job? You say that three years ago “[h]e said he wanted to be here with me to lead our family business for the long term”, and that that felt amazing *to you*, but do you believe he still feels that way? Do you believe that is still his long-term goal? Are you sure he’s not just trying to live up to yours and your dad’s approval? Are you sure that getting “fired”, if it was done kindly and compassionately, wouldn’t be gutting-but-also-something-of-a-relief?

      I don’t know, I just feel like there is an awful lot in this letter about how much you want him to be part of the family business, and much less evidence that it’s what he wants. I am sure he does on some level, and he probably has a lot of the same positive feelings towards the business and its role in the local community and you and your dad as colleagues that you talked about in your second letter. But I also feel like, jeeeez, it must be so unbelievably stressful to have all these people and projects depending on you when you’re not able to sustain the reliability you need. I could imagine him writing a very similar “one the one hand – on the other hand – on the third hand – but then again – idk, should I stay or should I go? ” letter to the one you wrote in 2021.

      And obviously if you were just a normal boss, the correct course of action would be to let him go and figure all this stuff out on his own! But as you’re also his sister, and from that point of view I think the conversation I would have is, “Look, this role isn’t working. I love having you in the business, I love the discussions I have with you, but we need someone in this role who is capable of X, Y and Z, and that’s not working out. I don’t know what you need here – -whether you want to stay involved in this other capacity, whether you want an income without being directly employed, whether you want to cut free and do something totally different — but whatever you want, it can’t be the status quo. Please take some real time to think about this and find someone to talk to about it, or talk to me. I want to make this work for both you and the business and right now it isn’t.”

      1. Madame Desmortes*

        I once asked my feckless ex-husband, while we were still married, what he wanted to do with his career, since I was looking at a career change myself.

        He lied to me. Straight-up lied. And I believed him, and it sent me into something of a tailspin, because what he said and the career change I wanted would ultimately be severely incompatible.

        He admitted to the lie some time later, claiming that “he wanted to say something that would earn my respect.” I wish I’d divorced him then, honestly. But yeah, lying for approval is a thing some people do, apparently.

    3. Elbe*

      Agreed. The LW is trying a lot and, from what has been described, the brother isn’t trying very hard at all.

      She wanted advance notice of vacations so that coverage could be put in place. I mean, that’s incredibly basic. If he’s able to organize and purchase a vacation, he’s able to do that.

      1. Filosofickle*

        Being personally familiar with mental illness and executive dysfunction, my experience is that he could actually be trying very, very hard! It’s not always true that being able to do one thing means being able to do another. But regardless of his intentions, the impact when he falters sounds disastrous. Time to let him go, or find a role for him where he can’t do harm to the business.

    4. Not Tom, Just Petty*

      And the dad. I think the dad is done. OP has to let him. It’s his company and his brother’s life. Maybe being let go will be a kick in the pants for brother to get his life together. Maybe it will free brother from a career he hates. Maybe it will come out neutral or he ends up not doing well. OP doesn’t know because OP is not in brother’s head. That’s the problem with trying to help someone. We tend to think our solution, like OP’s “keep him an active employee at all costs” is best. Love your brother, OP but respect the company.

      1. Ellis Bell*

        The problem is OP’s dad could have done this years ago. After ten years of thinking everyone will forgive you for letting things slide, you come to believe that’s acceptable. Even OP thinks firing someone who goes AWOL on their job is harsh, because she’s seen ten years of avoidant water treading. Possibly the dad’s patience has finally worn down, but as OP is the only new ingredient here, that’s why OP feels responsible.

    5. JustaTech*

      Sadly, yes to this.

      Sometimes people just aren’t in a place to accept your help.
      Sometimes the help you are offering, what you think they are asking for, isn’t what they want or need. And sometimes what they want isn’t what they need.

      OP, I’m so sorry. I really hope that by separating your brother from the business as gracefully as possible (and allowing him to save as much face as possible) you can keep your brother even as you lose a co-owner.

    7. Hot Flash Gordon*

      Yup, I thought the same thing. OP can’t care more about their brother’s job than him. He could be a rockstar in the field, but that means nothing if he’s not reliable or loses the company money or damages their reputation.

  8. Not A Manager*

    *I don’t want to blow up my relationship with him or my sister-in-law…. Ultimately if we keep going like this, the relationship is already destroyed because I’m so frustrated and angry.*

    Fire him now. Do it compassionately, make it clear that this isn’t a punishment or a rejection. My guess is that on some level he will be relieved. People don’t engage in this kind of avoidant behavior because they enjoy it. He can still be a minority owner, he can still benefit from the company’s success, he just won’t be in a position that is unhealthy for him and unsustainable for you.

    1. Ellis Bell*

      If you’re keeping someone in a job simply to avoid upsetting them, there’s something deeply wrong. The job is not the same as the same thing as the relationship; they must not be confused. He’s noping out of the conditions required for the job; would he also nope out of the relationship? None of that would be on OP.

    2. J. random person*

      I was fired about ten years ago. One third of my brain was thinking what you’d expect, along with wondering should I mention I started therapy a month ago that might help with issues that are affecting work. The other two thirds of my brain were like, “OH THANK GOD I NEVER HAVE TO COME BACK HERE AGAIN.” I don’t think I realized until that moment just how much I disliked that job. We can’t know what brother is thinking, and I’m certainly not saying “therefore fire him,” just saying if that does happen it wouldn’t surprise me if he wound up feeling something similar.

      1. Paint N Drip*

        If I were the brother, and I maybe felt like I was handed a job because it was a family business, and I’m now stepping closer into my dysfunctional family, and I had proven over a few years to be unreliable and in some ways a liability to my company, and my sibling was the heir apparent seemingly happy & successfully doing the job and anything asked of them…. I think “OH THANK GOD I NEVER HAVE TO COME BACK HERE AGAIN.” would be just about right

        The pressure he is under must feel immense, and the relief would be immense as well. Maybe he can even come back once he’s addressed his baggage or mental health or whatever is going on – it seems OP would really LIKE to have their brother running things with them, but only when brother is at capacity.

    3. Elle*

      I really love the point that people don’t do things like this because they’re having a great time and feeling successful. He knows he’s not doing well. Sometimes a break is the right thing for everyone, even if it feels awful.

    4. Starbuck*

      “I don’t want to blow up my relationship with him”

      Also, is brother putting this much effort and sacrifice into maintaining the relationship as LW is? Sure doesn’t seem like it. It’s possible he does care very much and is feeling these failures deeply, however… at a certain point behavior matters more than intentions and it’s time to match his. He’s done with the job, clearly.

  9. PDB*

    Fire him. It’s that simple. And yes, I know it’s a family business. I’m familiar with them because my father ran our 100 year business into the ground. He should have been fired.
    Since he’s an owner he still gets cash flow, I assume, but get him away from the day to day.

  10. Smurfette*

    LW, I really feel for you on this one. It’s definitely not sustainable for you or the business to continue like this.

    But I also wonder whether it would not be better (and even a relief) for your brother to be able to detach himself from the family business and look for a job that is lower stakes. Currently if he messes up, he’s not *just* messing up. He’s also disappointing his dad and his sister and causing harm to the family’s legacy. That’s a lot of pressure on someone who is clearly struggling already.

    Who knows? He might actually want to leave but be afraid of letting you down, or disappointing his dad. Talk to him, and see how he feels about staying in the business, and if he wants to, how he sees things changing for that to be possible. Maybe a different role in the company would be a better fit – something that plays to his strengths.

    Best of luck!

    1. Alton Brown's Evil Twin*

      That’s a really good point about ‘harm to the family’s legacy’ etc. Maybe that can help the conversation.

  11. e271828*

    LW, if your father will not fire your brother, you need to leave the business while you still have a reputation, yourself.

    Inability to manage family members sends most family businesses out of business. Your father and brother are getting into position for the classic spiral downward.

  12. Mermaid of the Lunacy*

    There is someone out there who would be excited to work with you, excited to represent this company, competent and trustworthy. Firing your brother would be a favor both to him (so he can get his act together) and a favor to the person out there who would be a good partner for you. You can always hire your brother back if he gets it together and wants to re-join the company. But you need reliable help.

  13. Looper*

    You have to fire him before he destroys any goodwill you or your company has with your employees, clients, and vendors. It has been over a decade of this, people are likely not going to trust you to make tough calls at this point or to hold people accountable. The lack of consequences is also enabling your brother not to address his problems.

    And though you didn’t ask, it would be a good idea for you (and your dad, if possible) to seek counseling for yourselves. The cycle you are describing is very familiar to anyone who loves someone with mental health and/or addiction issues. You don’t have to be trapped in this cycle and you can have a relationship with your brother, but it takes work and fortitude. Find your support community so that you will be equipped to help your family.

    1. Lana Kane*

      And though you didn’t ask, it would be a good idea for you (and your dad, if possible) to seek counseling for yourselves. The cycle you are describing is very familiar to anyone who loves someone with mental health and/or addiction issues.

      I think this is a very good point. OP, going into therapy yourself could help you see the path forward more clearly.

      I still don’t think he should work there anymore, though.

  14. Caramel & Cheddar*

    I think not firing him sends the same kind of message to your employees that we see in a lot of letters where the LW is working for a family owned business: that the dysfunction will continue indefinitely no matter how poorly it impacts both clients and staff, and that’s a recipe for making people miserable and tanking the business.

    You’re already dealing with angry PMs who work for your clients. He’s not only jeopardizing your current projects, but he’s also jeopardizing future work! And if they’re not already, your staff are going to start looking for other work instead of having to constantly clean up after your brother.

    This is not sustainable.

    1. Momma Bear*

      I worked for a company that did a lot of contract work. Our home office repeatedly failed to meet contract deadlines (it was more administration/invoicing than our actual work). The team got fired from multiple contracts not from our poor performance but because the clients got fed up with HQ’s inability to do their part. This will absolutely impact future work if it hasn’t already.

  15. Lana Kane*

    Think of the strain being placed not just on you, but all the other coworkers who have to put out huge fires regularly and with no notice because Bro can’t be trusted to show up. This is your workforce and who you should be looking out for. You’ll end up losing good people.

    After that, think of the reputation being built around your company. Word will get out that it’s unreliable and stressful to work with.

    Like Alison mentioned, can he retain his stake as owner, just not work there? This has been going on for 10 years and he has been made well aware of the problems he’s causing. I wouldn’t give any more warnings because honestly, he’s had them in spades.

  16. KWu*

    Would it be worth considering that firing your brother may not be a one-way door? I wonder if firing him feels like you are giving up on him ever getting into a better place health-wise, but you could fire him without putting him on a never-rehire blacklist. If he gets things together and keeps it together for many years and is interested in coming back at that point, perhaps things can work out in the very long run for the initial dream you all had for the family business. Just something to consider for trying to lower the stakes a little bit for the current decision.

    1. JustaTech*

      Or have the option of him coming back as some kind of contractor or consultant – let him be an ideas guy on an ad hoc basis , but don’t put him in a position where people need to be able to depends on his follow through.
      Pay would have to be a lot lower, but it would be something.

      And again, dependent on 1)him *wanting* this and 2) him getting it together.

  17. Timothy*

    It sounds like the brother has checked out. He should be replaced by someone who can do the job, perhaps on a temporary basis. You can proceed after that depending on how the brother gets his life sorted out.

    Right now, the brother is hurting the business more than he’s helping, so he has to go.

  18. S*

    I respectfully disagree with Alison’s advice: you’re unambiguously past the point of warnings here. Even if he heeds your warning and turns things around, it’s overwhelmingly likely to be only temporary, like before. Even if by some miracle he does turn things around for good, will you ever be confident that the change is permanent? Do you really want to make long-term plans with such a huge question mark around?

    Buying out his shares and dismissing him from his role would also be the best thing for HIM. This situation, where he knows he can screw up majorly and not get fired because he’s working for family, is enabling his worst tendencies.

  19. My Brain is Exploding*

    Keep him as a silent partner, with whatever comes to him due to being a shareholder, but NOT as an employee. You should be a shareholder and a paid employee.

  20. Msd*

    I’m not on board with firing him but I do agree with the comments of moving him into more of a consultant role. Have the hard conversation about unreliability and that he can no longer be in charge of projects but keep him on as a sounding board.

    1. kanomi*

      I am pretty sure if I screwed up multiple times over a decade and took vacations whenever I wanted to without warning my boss, I would be fired, not given some cushy consultant gig. He’s already part-owner, which is legit. A dubious consulting gig where actual employees have to meet with and implement the useless suggestions of someone who could care less about the business is a waste of time and money and an insult to those workers. What sounds “compassionate” unfairly imposes on others.

      1. Joron Twiner*

        Same, if the brother was anyone else he’d have been fired long ago. How insulting to your non-family employees to make them still put up with your brother when you and everyone else know that he is unreliable and costing your business time, money, and reputation.

  21. Circus Monkey*

    It sounds like your brother may only be able to do what he does because he works at your’s/his father’s company.

    1. Middle Aged Lady*

      This. You might be doing him a favor in the long run if he’s forced to treat his issues because you and dad won’t tolerate it anymore.
      I think you should ask what would you do if this was a beloved ling-term empliyee?
      And how gis behavior affects the rest of the staff?
      You dealt with your issues from the dysfunctional family. So can he.

  22. Spicy Tuna*

    If it wasn’t a family business, would he already have been fired? If the answer is yes, then you have your answer.

    I own a business with my husband and it can be really, really hard to work with people you are married / related to.

  23. E*

    Brother needs a different role before his actions impact the reputation of the business. A consultant role might work but don’t continue the way things are now. I worked for an 80 year old company and watched how the owner’s son, who was not a good leader, managed to torpedo the company’s reputation by not fulfilling contracts on time and under bidding projects. They went from 200 employees and $75 million of revenue a year to maybe 50 employees and $3 million of revenue in the span of 5 years. I will be surprised if they last 5 more years. Don’t let this happen to you.

  24. Keymaster of Gozer (she/her)*

    Look at it as a pure risk analysis.

    By keeping him on you risk losing staff who are fed up with having work dumped on them at the last minute, losing suppliers and venders who are tired of you lot being unreliable, having uncomfortable talks with the bank when the finances start to look shaky.

    By keeping him on in a non active but paid role it’s less risky but you may still lose staff who are not okay with putting in work but being paid the same/less as someone who does little.

    By letting him go you risk some very uncomfortable family fights, maybe for years.

    Saying this as someone with several very severe mental issues who nearly DID do herself out of a career at one point – being kind can only go so far before it starts to hurt. If people had just let me get away with my behaviour then I’d have had no incentive to sort myself out for good.

    Sometimes the best thing you can do for someone with severe depression is enforce boundaries. We don’t WANT to be coddled.

  25. Elbe*

    If a non-family employee did this repeatedly for years, they would certainly be fired. Keeping him around is not only causing major issues, but it’s also probably crushing morale. Let dad fire him.

    Sometimes people are reluctant to change when they never have to face any consequences themselves. Right now, everyone else scrambles and covers for him, providing him the illusion that it’s not so bad and that everything works out in the end. Being let go (by people who love him and wanted him there) may be the push he needs to make changes.

    The LW should keep in mind that letting him go now doesn’t mean he can’t be brought back later, when he’s more responsible. It doesn’t have to be a permanent thing unless he never gets help, in which case the LW will be happy that they didn’t allow that to tank the business.

  26. disconnect*

    Oh my god fire him please. I know he’s family, but he cannot function in this role, and you know it. He’s done this time after time, and he’ll continue to do this. He’s not suited to this role.

  27. Friday Hopeful*

    Make him a hands-off silent partner. Make sure you have more shares than him so you can maintain control then just pay him his part. However, make sure you not only take your part (as shareholder) but also a salary for working in the business. You won’t be shutting him out totally but you will be taking the responsibility away. Then either hire or promote someone responsible into his job.

  28. Nonsense*

    My direct, to-the-point response: you’re the CEO and part-owner of the company. Act like it.

    My somewhat-indirect, leading question response: would you put up with this from any other high level employee? Or any other employee, period? Are you more concerned with keeping your business’s reputation intact and retaining your employees and are you more concerned with making your brother change behaviors he’s proven over and over and over again that he doesn’t want to change? Because the only way you get to have it all is when all you’re left with is a failing business.

  29. Consequences*

    This letter cuts pretty close to me. I was the flaky sibling for a long while – not in a family business, but in schooling and other situations. Mentally I was having a really rough time, and it’s taken drastic changes to my self and environment over the years to escape the worst of that.

    I have a relative who isn’t flaky, but engages in other behaviors that have hurt me over the years. Talking to him never caused him to change his behavior in a meaningful way. It’s when I took the drastic change of cutting him out of my life that he’s started to work on himself (so I hear from others).

    This is all to say, LW, that you can’t do the same things and expect different results. Maybe what your brother needs to finally internalize the need to work on himself is a drastic change.

  30. Sparkles McFadden*

    This is so hard because you have to separate the professional from the personal. This is difficult enough to do when you’re not related to the person. In this case, you value your brother and you want him to be a partner with you in the family business. Understandable. But, your brother is not business partner material. Your brother is not even management material. Someone can have a lot of stellar qualities but if the person is not reliable, the good qualities don’t matter anymore. One cannot do a good job if one does not actually show up to do the job. You are prioritizing the personal relationship over the professional (I think it would be impossible not to). The proof of this is that you are trying to make therapy a condition of your brother retaining his job. You’re trying to use the job as leverage to get him to address his personal issues. That really won’t work.

    I think another issue is that you probably realize that your brother would never be able to get away with this behavior at another job. If the family business is the only place he’s ever worked, it’s highly likely he won’t be able to get another job, and I am sure that’s part of the calculus. But you are the CEO here, which means you also need to think of how your employees and business partners are getting screwed when deadlines loom and your brother freaks out and leaves the country without notice. When work gets to feel like too much, he just runs away because he knows you’ll fix everything and he’ll get to come back and start the pattern over again. Have employees quit over this sort of stuff? Have you lost contracts? As CEO, you need to look at those things too!

    What to do? First of all, you need to recognize what you can fix, and what you can’t control at all. You cannot make your brother into someone reliable. It doesn’t mean he has no good qualities. It means he can’t be your business partner however much you want that to be the case. How you deal with him now depends on what you are willing to do. If it were me, my immediate solution would be to put him somewhere where he can’t do quite as much damage. Maybe let him retain his share in the business but not work there. I think you need to decide what you can and cannot tolerate and set serious boundaries.

    1. Elbe*

      If the family business is the only place he’s ever worked, it’s highly likely he won’t be able to get another job, and I am sure that’s part of the calculus.

      Agreed. And if this is true – the LW is worried that he will not be able to find a similar job at another company – it’s even more of a reason to let him go. If his performance is so bad that’s he’s literally unemployable, then it’s a huge indication that he’s not going to be able to make the needed changes.

      No everyone is cut out for all jobs. Just because someone is born into a family who owns a business doesn’t mean they have the skills to be a CEO. If he is genuinely struggling with long-term issues that make him unreliable, he’s just not a good fit for jobs that have strict deadlines and involve a lot of management and planning. This is likely not a job he would have ever succeeded in if he had been a regular employee, and keeping him on is preventing him from finding a better match to his abilities.

  31. Garlic Microwaver*

    All of these angles suggested are contingent upon the brother’s change in behavior. It does not sound promising. Can OP not cut their losses and walk away to pursue another path all together?

  32. WellRed*

    “I said I didn’t want to be in business with him and I meant it” and a year later nothing has changed. This perfectly illustrates the problem with family biz. You wouldn’t put up with thus BS from anyone else. He’s shown you how it’s going to be. Listen up!

  33. learnedthehardway*

    People with depression or bipolar disorders can cycle through different stages. Sounds like your brother has long cycles – a few years doing well or at least okay, then a depressive episode that comes on quickly and is pretty long term.

    Since this is a family business, I think you have a little more leeway to be creative. And you probably want to be as supportive and non-judgmental as possible. Perhaps this is not exactly legal from an employment point of view, but what if you and your father make it an unofficial condition of employment that your brother be evaluated by a medical professional for his mental health issues on a regular basis, and comply with treatment (whether that is medication or therapy). Approach it that he needs to manage this the same as he would any other health condition – eg. diabetes or cancer. When he realizes he is starting to cycle – and his therapist can help identify that to him – then put him on a leave of absence / disability leave. Give him the space to recover, then resume his employment. In the meantime, build up a pool of contractors who you can reach out to to manage his projects, as needed.

    This approach will allow you to build in some resilience for your company, help your brother to manage his mental health issues, take away some of the shame/stigma he feels about having depression/anxiety (which may help him to be able to keep you in the loop about his mental health and thus manage the workload impact on you/your father/the company better), and give him space to recover when he needs it.

    You might also look at putting in a benefits policy so that other employees are also taken care of when they have major issues – that would go a long way to helping people feel like they are being treated equitably.

  34. ubotie*

    Since OP is not a majority owner, I guess option 4: “sell off the company and do a career that is totally unrelated to anything related to your family (pun very much intended)” is off the table?

    So I guess that leaves option 3C: OP sells their shares or whatever to the dad and brother and leaves anyway, still finding a career that has nothing whatsoever to do with this tomfoolery.

    Because seriously WTF.

    I know that’s blunt and not necessarily what the OP was writing in about but like, it seems like the OP’s family’s business can’t survive without fundamental changes and/or frequent hand-holding by Alison. The former doesn’t sound like it’s going to happen (mainly because the family isn’t capable of making those changes) and the latter isn’t really sustainable (or fair to anyone, especially Alison). So really, maybe it’s time to cut the cord for good here.

  35. Hey, I'm Wohrking Heah!*

    OP you are in a tough spot. Would your brother have cut you this much slack? I’m wondering if he’s hoping you’ll fire him so he doesn’t have to be the one to pull the plug, and getting more and more flaky. I’ve seen people do it when they’re just maxed out. Good luck.

    1. Falling Diphthong*

      I’m wondering if he’s hoping you’ll fire him so he doesn’t have to be the one to pull the plug.
      I wouldn’t be surprised if brother has a history of “I won’t pull the plug, but I’ll keep screwing up until the other person does. And then it won’t be my fault” in other contexts.

  36. CubeFarmer*

    Sounds like your father has been dealing with/enabling your brother’s issues for at least a decade, and now it’s up to you to enforce a boundary for the sake of your business. You have a potentially big problem on your hand and an ever narrowing window to address it before it hurts your company.

    As someone who also works in construction, I know how reputation-dependent the industry is. We recently had two architects with whom we have worked closely for over a decade start to get flaky. We think that they took on too many projects and then when something went wrong (an associate quit, someone had personal difficulties, etc,) the firm collapsed. There were missed deadlines, MIA principals, broken promises, and confused clients. It became really embarrassing for us–because we made the connection between professional and client.

    As a result, we stopped referring these firms to potential clients, and quickly found out that we weren’t the only people having problems with these two architects. One architect disappeared for a time without explanation. He’s slowly been reemerging, hopefully he dealt with whatever problems he was having, and we are cautiously optimistic (but still won’t be referring anyone to him for a while.) The other architect chose to lash out and tried to malign OUR reputation. So, essentially they are dead to us for the foreseeable future. We don’t see how we could responsibly work with them again. That’s a great lesson in what not to do when you’re having organizational difficulties.

    Good luck, LW! My sense is that you know what you need to do.

  37. Nola*

    My husband’s best friend Tom got fired from his family’s business about 10 years ago. Tom has Bipolar II and when he’s between cycles or even in the early part of a manic phase he could do the job, show up, be personable, cross tasks off the list, even participate in long term, high level planning. But then he’d disappear for a week because he’d decide to visit a friend out of state or there’d be a band he needed to see or he’d decide to spend his nights playing online video games and forget to come into work. And then he’d crash and could barely get out of bed. Even if he made it into the office he was only semi functional and couldn’t be expected to handle much of anything.

    And meds would only work until they didn’t.

    He spent half his time, in his words, screwing up, and the other time living with the shame from his screw ups. This isn’t how his family saw it, they loved him and knew about his illness, but that was his reality.

    Eventually he dropped one too many balls and even his most loving family knew they couldn’t work around him anymore. He was fired.

    It was tough – on both sides. He was angry and resentful. His family felt guilty but also felt resentful due to so much chaos that had to be cleaned up. Tim and his cousin that lead the charge in firing hm didn’t speak for more than a year.

    But a decade later it’s definitely worked out for the better. The family business is thriving now that there’s consistent leadership. Tim has done a lot of work in therapy. Meds are still only partially helpful and has manic periods where he chases after butterflies and then weeks were he just sits on the couch watching Netflix. He drives for Uber now and picks up some part time shifts for a friend’s tour company. It’s gig work but, with his brain chemistry, that’s what works best for him. More importantly, he no longer feels like he’s letting (multiple generations of) his family down.

    OP firing up our brother may be horrible in the short term but it may be the best in the long run.

  38. Forensic13*

    I say this not to exactly excuse the brother’s behavior—but I wonder if any of his behavior might be specifically influenced by working with your dad.

    I looked at the previous questions, and you said something along the lines that your dad is not a good manager, mentor, or delegator, though he is a good project manager. I wonder if your brother’s behavior is related to this—is this the only job your brother has ever had? Did he learn to run things from your dad? I know you’ve been taking over management/running the business, so I’m guessing your brother has been exposed to your presumably better skills now. But has he ever really learned how to lead well?

    And then again the way you’ve described your dad, I wonder if he’s sometimes unforgiving of failure or mistakes, or at least impatient with them. Of course your brother still has to be responsible for his actions! But his actions seem a lot like he’s avoiding confrontation, and that kind of dynamic might explain it.

    I don’t know how actionable any of this is, so sorry if it wasn’t helpful. I just noticed that nobody else seemed to have discussed the extra complication of the dad yet, especially in relation to the other questions, so I wanted to raise the idea.

  39. Generic Name*

    You’ve gotten a lot of good advice. I know you love your brother, and I’m sure part of your reluctance to fire him is guilt. But think of it this way, if your brother stays and continues to screw up projects that leave other people scrambling to cover, those very people who pick up the pieces will eventually get tired of being the clean-up crew and will find other jobs. The best ones will leave first, and I’m sure it’s the best ones who jump in to fix.

  40. Kevin Sours*

    “My brother and I have the same ownership stake and the idea was that the company will transition to us, and we will be equal business partners.”

    This stood way out and I don’t see where Alison addressed this. Regardless of where you land on your brother’s continued employment, imagine trying to manage the business as equal owners in the future and ask yourself if you honestly see that working out.

    1. Elbe*

      This is a great point. Something has to be done NOW before the LW no longer has the power to make changes.

      The worst case scenario here is that he never changes, but he becomes untouchable. The LW will be doing all of the work trying to keep things afloat to save everyone’s job. Who needs that kind of stress?

    2. goddessoftransitory*

      It does seem like a recipe for disaster. I doubt Brother can buy OP out and she’d be stuck with him.

  41. The Ginger Ginger*

    If you do keep him on, you at least have to immediately change his responsibilities. You just canNOT have him as the sole person in charge of projects any more. So at least a demotion/reassignment is required, and will go a little way show your employees that something has been done. You need to ensure he can’t put you or his coworkers in this kind of situation again.

  44. Jellyfish Catcher*

    Your brother is jeopardizing Your job, Your financial stability and Your loved ones.
    And – he doesn’t care.
    The person who needs therapy Right Now is you. I say that as someone who has had therapy and it can be an amazing help.
    You are emotionally trapped in the “good” brother role, if you and only you, work harder, try harder, blah, blah.

    Your good employees can see this clearly – and will leave. Your family can see this and that they are coming in second.
    Your clients will see this and leave.
    Another time of late delivery, you’ll will be blacklisted with that customer and your company’s reputation starts sliding into the gutter.

    Right now, find a very good business attorney.
    Sit down with your dad and insist that he gives you his portion for majority ownership in the company – to save it.
    Also, from this day on, document ALL brother’s antics: late times, no shows, dropped work, the effects of it, revenue lost, one and on, etc.

    Give your brother severance/ buy out, whatever legally works to get him out of the company. He may blow through the money – at that point, he gets a job somewhere else.
    You can’t save him – that’s on him.

    1. Jellyfish Catcher*

      You need to do this, before the company spirals.
      Or, if your dad suddenly dies or is incapacitated.
      The hardest part of a difficult decision is starting; once you start, the dread dissipates and the light comes through.

    2. goddessoftransitory*

      And remember, OP: your brother’s feelings and motivations are at this point irrelevant. He may not care a whit, he may be beating himself up on the daily because of his inability to function. It’s beside the point–what matters is what he’s DOING. And what he’s doing is jeopardizing your livelihood and business reputation.

      You are his sister and love him. But your clients and employees do not. They may feel bad for him, but that’s a distant second at best compared to what his actions are doing to their own reputations, profits, and peace of mind.

      You have to do what Jellyfish Catcher recommends or you will lose everything.

  45. Therapist*

    I am not optimistic that your brother is going to change.

    What happens when your dad is no longer with the business? If you and your brother are 50/50 but you do most of the work and in addition need to clean up preventable messes that he makes, your relationship will be harmed amd you may not be able to get rid of him. Going forward if your brother stays you and your dad need to put into place something that allows you to maintain control of the company. That would be better for both of you. If your brother ran the company it would have been run into the ground. Maybe when your dad gives up his portion of ownership you get a larger amount of ownership? Bottom line – your brother has showed you that he cannot be an equal partner. At any other business he would have been fired. Many times over.

    I am a therapist and I am not optimistic that therapy for your brother is going to 100% fix this problem. First for therapy to be successful it would require your brother to be honest/insightful about what is going on. Second he would need to be motivated to change. He seems to be neither of those things. Therapy is less effective with people who feel like it is a punishment. That doesnt mean its not a good idea – maybe he will start to open up and find it helpful. But I wouldnt put all of your eggs in that basket.

    Alison is right that you should not be solving this problem for him. You need to treat him like any other employee. You wouldnt tell another employee how to live their life. You would tell them what they need to do to be successful in their job and what the consequences will be if they dont step up.

    There seem to be some messy family dynamics at play here. Are there other options where you dont all work together?

    1. Ellis Bell*

      Yeah, I think “go to therapy or you’ll lose your job” contains more job-related motivation than motivation to get well. If he were ready for change, no threats would be required. There’s also juuust enough wiggle room for “I’m trying to make an appointment”, or he actually goes to therapy, but without becoming a better business partner because he’s just check boxing a requirement without really caring about making it a success. Just go straight to tearing off the bandaid of “It’s not working out, the company is in danger”. I know OP is worried about family relationships, but I think it would actually escalate tension to hold the job over him as a bargaining chip. The sooner you get to the inevitable consequence, the sooner you can switch into “focus on getting well because we love you” messaging, rather than making it about the company.

  46. Goody*

    I have not read any comments yet, so apologies if I’m echoing others.

    Edit his email settings so you get copied on everything inbound and see if you can do the same for outbound messages. On your side, set up a folder for those messages so your own work doesn’t get completely buried. Obviously this won’t catch phone calls or in-person conversations, but it will help get you in the loop on a chunk of his work.

    1. Antilles*

      At that point, why even employ him though? If you’re going to be checking all his emails and reading all his responses and keeping detailed tabs on all of his work, at that point, you’re basically doing his job.
      Might as well stop the charade and either fire him or move him to a “VP Emeritus” role with pay but no duties.

      1. Elbe*

        Agreed. Trying to prop him up is just too much work from the LW. It’s time to either make him leave or for the LW to leave.

      2. Goody*

        because, depending on what’s going on, just knowing that your manager is fully aware of everything in your email maybe enough to make a change. it certainly did work for me. I went through a period of about 3 months where I was struggling you stay on top of everything and brain weasels would not allow me to ask for help. Manager set up a copy rule, would skim my emails a couple times a day, and asks pointed questions about things that needed more more immediate response. That additional accountability and support helped get me through the hump without the formality of a PIP or other actions.

        1. Jellyfish Catcher*

          You wanted to improve and felt responsible to do so.
          You showed up for work on a regular basis, knew that you were not keeping it all together at that time, appreciated your managers help and you improved.
          The brother isn’t doing any of that, after years of shenanigans.

          1. Antilles*

            This.
            I’ll also note that Goody struggling for “about three months” feels way more fixable than the OP’s brother who’s been doing this for “nearly a decade”. Like, I’m sorry, but if you’ve been going AWOL for years and still have it happen three times in the past 18 months, that’s well beyond anything that CC’ing people on emails could possibly solve.

    2. Goody*

      and now that I’ve caught up …

      Definitely still set up the email copy. and take advantage of his vacation to deep dive into his mailbox to figure out what’s outstanding ( if you haven’t already done so) and get caught up.

      Ultimately I think Brother needs to be released from his current, hands-on position, and someone should be hired to fill the role that can keep up with the duties. I don’t know about excising Brother entirely from his ownership share, that’s a lawyer and Dad discussion IMO. Perhaps there’s a way for him to retain a minority interest without operations input, maybe a board position or consultancy as others suggested.

    3. Starbuck*

      This is sensible to do while transitioning him out of his role, which should happen ASAP, but obviously can’t be a long-term solution.

  47. AnotherSarah*

    A cautionary tale from a family business in a related industry: My great-uncle built a wonderful company, and a few of his kids worked there/owned it. One of the kids, J, was a loose cannon and everyone knew it. He was great…sometimes. And then he’d do things everyone else had to pick up after. I’m sure there are Reasons why. But ultimately they don’t matter in terms of morale. Great-uncle passed on ownership/operations to some of the kids equally, because he…felt badly for J? Unclear. He knew he shouldn’t have done that. He thought he more responsible siblings could handle J. 15 years after great-uncle’s death, there have been multiple lawsuits, restraining orders, the works. Good employees have left. The business is still wonderful but only because FINALLY the other siblings were able to do what Alison suggested as an option and get J out while retaining some ownership stake. None of the rest of the solutions (mandated therapy etc.) helped. Very few of the other siblings or other family members speak to J and his family. But it didn’t have to be like this–great-uncle and the other sibs could have taken the road they ultimately chose much earlier, and J could be a wonky but still loved member of the family, without messing up the business. Don’t be like us!

  48. Grace*

    One solution I don’t see mentioned here: are you sure YOU want to inherit this business, OP? Maybe one (or more) of your employees would leap at the chance to buy you out. That would give the business a chance to start afresh, your brother a chance to start afresh, YOU a chance to start afresh. You could work on your family dynamics without the financial and logistical dynamics of the business in the way.

    1. Elbe*

      If, for whatever reason, the LW and dad are unable or unwilling to fire brother, I think that the LW should get out now. They should try to sell the company before brother gets 50% of it and cannot be stopped from running it into the ground. It’s worth something now, but may not be in 10 years.

    2. Lab Rabbit*

      I don’t really think this is the solution to the short-term question LW asked, but I think this question could help them come up with an answer to their current dilemma. It doesn’t sound like they were terribly committed to this business in earlier letters. If they are committed now, then yep, the brother can no longer be working here. If they would rather cut their losses and get out, then that is where they should be focusing their energy, not trying to manage the dynamic between their brother and everything else.

  49. *daha**

    Make sure you’ve got a business structure that differentiates between ownership share and employment salary. So the CEO gets a salary before business profits are computed, and so does whoever replaces your brother after you fire him. After salaries and other expenses are paid profits are distributed by/to the owners.

    (Some family businesses intertwine these payments.)

  50. BigLawEx*

    LW I want to gently push back on the ‘same childhood’ theory. Each child experiences it differently. Plus you are different people with different temperaments and different personalities. How one sibling experiences childhood and carries that into adulthood can be radically different for another sibling.

    Therapy and coaching may not make him more like you in terms of dependability, responsibility. I think you have to think about impact even if you know the cause.

    1. goddessoftransitory*

      Agreed. I would swear my sister and I, growing up in the same house, came from different planets sometimes.

      1. allathian*

        Yes. I have lots of memories fighting with my sister, partly because we lived in very cramped conditions when we were teens. Being forced to share the same bedroom is no fun when you’ve lived for several years in a larger home with your own room. We adapted eventually, but I don’t remember anything except constantly fighting with my sister when we were teens. We have very different personalities, and at some point in our 20s when we were no longer living with our parents or each other my sister said something like “I doubt we’d ever be friends if we weren’t sisters” and I agreed with her.

    2. allathian*

      Yes, this. Siblings raised in the same household can have wildly different experiences growing up for a variety of reasons. This includes birth order, where the older sibling often has to fight more with their parents to be allowed to do things their peers are doing and the younger siblings getting to grow up slightly earlier. This can especially be true for older sisters and younger brothers.

      Personality is also a factor, irrespective of birth order. I firmly believe that no matter what parents say, they will never be able to treat their kids fully equally. Equitability is a good ideal to aim for, but children have different needs that mean they don’t necessarily benefit from the same treatment. For example, I was a book-loving, shy introvert when I was a kid (I still love books and need lots of time to recharge on my own, but I’m no longer shy), and I would not have experienced being sent to my room as a punishment. Not being allowed to read would have been, but my parents never even considered that. My more extroverted sister hated the idea of being sent to her room.

      This happens even in families where the parents don’t favor any of their kids more than others. Favoritism can be gender-based. Or siblings who have no particular issues may resent the attention the parents give their disabled sibling and feel like they aren’t allowed to be kids with needs because they don’t want to be an additional burden to their parents. Or as may be the case here, the always responsible sibling will almost always eventually start resenting that they have to fix the messes the irresponsible one made.

  51. Festively Dressed Earl*

    LW, I wonder if your brother is in the same place you were when you wrote your first letter, but reacting to it differently? If his heart isn’t in it and the business feels like more of a burden than an opportunity, the two of you should talk about that and decide what that means for both of you. There’s no shame in wanting a different path, for either of you.

  52. Kat*

    I don’t think she should give a final warning. His behaviour is chronic. He’s done nothing about it, despite being told how it’s affecting other people. What’s the point of giving him a warning when she’s gonna be waiting for the other shoe to drop? Does OP really want to wait for another mess of his? Just fire him. Let him keep a minority share that entitled him to profits but he doesn’t work there or get to make any decisions about the business. Firing him doesn’t mean she doesn’t love him.

    Remember OP, you said YOU were the one taking on HR/admin stuff on your own, no one made you. Well here too, you’re making your own life harder all on your own. No one is forcing you to keep cleaning up your brother’s messes. You’re the one doing it to yourself when you have the solution in front of you, but you won’t let your dad fire bro.

  53. Sihaya*

    I mean, pretend he keeps setting fires in your trash cans and then walking away when no one’s looking. You fire someone immediately for arson. There’s no question, no PIP. So I’m going to ask you, how do the consequences of his actions compare to the unattended trash fire? How many employees escape and never come back? How much work is destroyed? How long is the recovery time? What’s the financial cost?

  54. Theda Marinelli*

    What I’m reading is that both you and your brother had a troubled childhood, but that you are still making excuses for Him (only) based on that. Sounds like you took steps for therapy etc. to deal with that and move forward. He has not.
    Unfortunately, I’m with those who say fire him. He’s going to lose his job one way or the other. The only difference is if it’s now and only him, or later when the whole company goes down.

  55. Parenthesis Guy*

    I would try not to fire your brother in your shoes. Awfully hard to get a new one at this stage. Money and businesses come and go but without family – what do you have really?

    If I were you, I’d try talking with him. Yes, you’ve had a billion conversations about how his irresponsibility is hurting your business. But I’d have a conversation with him about his behavior and what his long-term position is going to be.

    Equal partnership is off the table. He clearly isn’t responsible enough for that. But maybe he’ll agree to something like a 66/33 split where you’re clearly the boss and he’s the subordinate. Maybe he’ll decide he’s not interested in running the business but would like to be a member of the team that contributes in executive planning. Maybe he decides something else that’s reasonable.

    If you guys come to a reasonable agreement, I think it makes sense to keep him in that spot. Otherwise, let your dad fire him and take ownership of the decision.

    1. Jellyfish Catcher*

      No….the OP has done this, over and over and over, for years. It’s who the brother is.

      The only solution, if the brother is still to be connected to the business, is to remove him from ownership, and is never expected to show up at the business site.

      Having owned and (successfully ) run a small business – you can’t do it if 33%
      of owners / employees are incompetent or not even showing up.
      Either the bro gets out or the OP sells out her share. Personally, I’d opt for getting out.

    2. Boof*

      Firing a business partner who is one’s family doesn’t HAVE to be the same as disowning family, unless they decide they have to be that way.
      It sounds like the family relationship is fine, the business relationship is very not fine, hasn’t been fine for a long time, and shows no sign of changing. Time to end the business relationship and hopefully the family relationship will be that much stronger for not having a second, negative relationship bogging it down.
      But ultimately that second half is up to the brother, if they’re willing to own up that they weren’t a good business partner but are still happy to have good family, or if they only care about family when there’s a transaction that helps them.

    3. Kat*

      This is horrible advice. The OP has already done what you suggested; talk to her brother. Ad nauseam. And it hasn’t gotten her anywhere. He hasn’t absorbed or cared about the impact he’s having on her. There’s no “right” combination of words that she hasn’t tried that is suddenly going to get through to him now when it hasn’t before. Telling her to talk to him again is sort of victim blaming in that it puts the onus on her AGAIN for HIS behaviour, as though she’s just not saying it the right way and if only she said the right things, he’d change. How he behaves is not in her control. Another conversation won’t change that.

  56. Happy*

    It sounds like all of the people on the first post who predicted that the LW’s brother would wind up getting the company were effectively right. He’s not in line for 100% ownership, but 50% with split decisions with the LW is a lot more than the plan had been originally, when LW described herself as the heir apparent.

    I understand how it got here, but it’s not a great place to be when LW has a much better history of professionalism, excelling at her job, and emotional investment in the success of the company. But it sounds like it’s still fixable and since dad wants to fire the brother that definitely sounds like the best course forward for everyone.

    I know that’s hard, but it will also probably be easier to be supportive of his health struggles as a sister when they aren’t intertwined with work.

    1. gyrfalcon17*

      Dad needs to transfer at least a small amount of shares to LW (or whatever their lawyer advises) so when something happens to Dad, LW becomes majority owner, *not* 50-50 with brother.

  57. Workerbee*

    It almost sounds like BOTH your dad and your brother are waiting for you to make the hard decision so they don’t have to.

    But I’m not sure.

    -There’s your dad, who is “supportive” of you and has directly had your brother’s behavior visited upon him for almost a decade, allegedly wants to fire him, but…hasn’t. Why? Is he stopping himself? Are you stopping him?

    -Then there’s your brother, who has the time and energy to go off on fun excursions but has zero problems leaving huge, stressful messes for you to fix. Again and again. Because he knows you will, again and again.

    A decent person would resign. Has he ever tried? Was he talked out of it because y’all felt bad?

    I think you should be done talking about boundaries and just go ahead and enforce them. He’s getting back in two weeks. That’s enough time for you to get his exit paperwork or whatever ready and a transition plan, and to start doing interviews for his position. Pension him off or whatever, but get this living encumbrance out of the company before there IS no company or you rack up your own health problems from all the stress and idiocy.

  58. Lexi*

    Regardless of whether he is an owner or not he should have an employment contract with a Job Description. This would make it easier for OP to see how he is failing as an employee and the steps she needs to take.

  59. Lizard Lady*

    At this point, I agree with your dad that firing him would be best. You may not have specifically said “stop doing this or you are fired,” but that does not need to be explicitly stated, and one more chance will almost certainly lead to another cycle of this. Also, I am not familiar with business law or the intricacies of ownership, but if your dad were not in the picture, would you still have the authority to fire him? I get that on paper you are the CEO and he is the VP, but if the company ownership is equal, can that complicate things? If it would be an issue, even more reason not to delay.

    Be compassionate about his circumstances, and point out that you understand the harm he is causing is not deliberate. Ultimately, though, he is damaging the company and causing hardship to the employees and clients that depend on the company running effectively.

    I’d plan for negative reactions from him and SIL regardless of how gentle you are. One of the downsides of mixing business with family is that everything becomes personal. I like the suggestion to leave him as a silent partner, though again, make sure that it will not affect your ability to override his input if needed. Maybe that will help mitigate the blow and show that you and your father still wish to be supportive as *family*.

    There simply is no way forward unless he changes, and if he could change himself in his current circumstances, he probably would have already. From your description, he does not seem to be twirling his mustache on a beach while cackling and exclaiming “those suckers!” Change is hard and takes time. Even with therapy, there is no guarantee he would change at all, never mind on the timetable you would need to keep these incidents from reoccurring. Relationships have to operate where someone is at, not where they could be if they were different.

  61. PX*

    One of the rare times I feel the advice is too generous. If he wasn’t your brother, would you have accepted any of this behaviour from a regular employee? I feel like the answer is pretty obviously no, and so the conversation when he gets back needs to be “Your behaviour continues to be disruptive to the business, it’s time to start putting together a transition plan for you to exit gracefully.” And then let him go and stop enabling this.

  62. Jules the 3rd*

    Does he have to be there all year / all the time? What if he had a rotating schedule, like 3mo on / 3mo off? Encourage him to think through what’s so hard and to become inventive in how to deal with it. Regularly scheduled transitions would be much easier than unexpected ones, for example.

    Best of luck to both of you.

    1. gyrfalcon17*

      I think the only way to deal with him continually failing at his responsibilities, is to give him no responsibilities. 3 mo on/3 mo off or similar sounds all well and good, until 2 mo into a “3 mo on” he decides it’s time for an immediate 4 wk vacation.

    2. Kevin Sours*

      It’s one thing realign his role in the company with this strengths and limitations in mind (assuming OP is correct about his strengths). But this sort of bending over backwards to keep him in his current position — even if it works — is going to exacerbate some of the problems mentioned in the letter. The perception that the family screw up is going to get treated with kid gloves and given options not available to other people in that role to continue working is bad for morale. And there is no way you are going to get people to believe that this is something available to everyone unless there is already a history of that sort of accommodation.

  63. restingbutchface*

    @restingbutchface, why don’t you work with family or family businesses? Me – *gestures helplessly to OP*.

    I feel for you, I really do. This reminds me of my own family dynamic – except without the business. I genuinely don’t know what I would do, but is this a familiar dynamic in your family? If you have always been the fixer, the pleasant one, the good child, I would suggest talking about this more with a therapist.

    There was a loud voice in my head all the way through your letter screaming “what about OP?!” and on occasion that voice has a point. If you spend your day covering for him or worrying about him… that’s not right. Who covers for you? Who worries about you? If you were protecting him as a child, who protects you now?

    No judgement here, this is a horrible situation. I just hope you can prioritise what you need.

  64. Boof*

    Unfortunately LW, if he’s been like this for years, you’ve already outlined it’s a major problem, I think you have to assume it’s not going to change. I get what Allison is saying about having One Final Conversation but I think the Final Conversation is here.
    I think what I’m really not sure about from what you describe is if you think there’s a role at your company that your brother would be better suited for – I know a LOT of jobs require tight deadlines, but if there’s something that’s more about long term planning and strategy, something where if he’s having a rough few weeks it’s ok to step back, do you think he would be able to do it?
    I don’t know if that’s being on the board, or an event organizer, or what. Maybe you could leave the door open for him to resume things if he can demonstrate reliability in some place less sensitive/crucial, but it’s also ok to just say no, brother needs to be brother and not coworker, you love him very much but can’t be business partners.

  65. Raida*

    Honestly your brother should continue to draw income from the business as a part owner, and change roles to either team based where he’s part of a group and not a bottleneck, or leave.

    You can focus on your relationship with him as your Brother, not VP Who Is Unreliable.
    Your brother can have less to do with his father as his… kinda employee?

    You can get him to work as a subject matter expert for the new VP/people doing the pieces of his job.

    Maybe you don’t get to have a partner. Or maybe you do, but he’s a soundboard rather than in office with deadlines, etc.

  66. Melissa*

    As a therapist, I can vouch for the fact that “get therapy” is not a panacea. Do you know how many people are actively engaged in therapy and also are terrible at their jobs? Millions, I imagine. Many of my own clients! Therapy is great, but should never be used as a cudgel, as though getting somebody to agree to do it is going to somehow solve problems for everyone else.

  67. gyrfalcon17*

    OP, I’m worried. At your previous update, things seemed to be looking up: you were still the heir apparent, the plan was still to transition you into CEO, and there was no mention of the well-known-for-years character traits of irascible father and feckless brother.

    But now you seem to be doubting yourself as CEO (“I’ve since stepped into the role of CEO, for better or worse,”), and far from being heir apparent, you’re being setup to eventually have to run this company on a 50-50 basis with feckless brother. Why did he suddenly get so much shares? As much as you? It’s been clear for a decade that he’s not contributing, and now he gets as much ownership as you, the hard-working daughter who is good enough to be made CEO but somehow not actually good enough to own the company without the 50-50 deadweight of feckless brother.

    I think you’ve gotten out of some of the bad patterns from your first letter, but somehow other bad patterns have crept in.

    I hope you can step outside of this situation mentally and look at what might be going on that’s fueling this: brother gets equal shares, you have doubts about being CEO, you’re finding it hard to see clearly what to do about an employee who is beyond irresponsible.

    Good luck, I hope you get through all this and things look up again

    1. gyrfalcon17*

      Somewhat to the side, but maybe not:

      One thing to think about: as the older sibling, are you taking on the burden, probably since childhood, of shielding your younger brother?

      I know in talking with my older sister, she talks about that weight of responsibility, so now when we get together, she gets to be the younger sister, and I take the older sister weight (we’re partly playing, but also completely serious).

      Best wishes to you.

  69. EngineerRN*

    Two things:

    1. Your relationship with your *brother* should not be the same thing as your relationship with your *business partner*. Those roles have different requirements, boundaries, and expectations.

    2. The symptoms you’re describing sound a lot like Type 2 bipolar, just as a thought (not depression) – super-productive (the “manic” stage, which in Type 2 can be really hard to spot, because it just looks like someone really excelling at their job & life, vs. Type 1 when it’s much more dramatic), with periods of “down”/”absent”.

  70. Grumpy Old Tortie*

    You need to fire him, end of story, before he drags you and the company down with him. Lots of people have difficult childhoods and lives, they deal, grow up, move on to adulthood.

  71. Catagorical*

    You don’t need to fire him as a brother, but it does sound like he needs to be fired from the business, sorry. Running a business is hard enough without constant random implosions.

    Your life will be better, and you might find more energy to help him get help, to the point he will accept it.

  72. kanomi*

    IMO, he should have already been fired due to the immense amount of damage he has already done to your company’s reputation. Nobody with a better option will work at or do business with a firm that puts nepotism above work ethics. You are forcing your employees to endure your family’s problems. It’s completely out of touch. Any other employee would have been fired, it’s a total double standard.

  74. maxounet*

    you shouldn’t mention therapy, I confirm. In France, in my sheltered workshop, we have an employee (responsible, among other things, for deciding on the admission of new disabled workers, managing sector changes if a disabled worker wants to manage etc). And he totally uses threats of therapy for punitive purposes. One day a disabled worker contradicted him, to which the boss confirmed that the disabled worker was right. The employee concerned called the disabled worker’s care coordinator to request therapy for the disabled worker
    Now, you don’t seem to want to use therapy in a punitive way, but to help him. But imagine, he’s vindictive and decides to say it’s punitive on social networks, there’s bound to be people there to support him, and the family business would have a bad reputation.

  75. Vanamonde von Mekkhan*

    LW, there is a lot of focus on the business, your brother and your father in this letter, but I think you should take a good long think if you yourself should stay in the family business. You say there is a lot of things you love about it, but is all the problems associated worth it? Because it looks to me like you, your brother and your father being in business together is breaking the family apart since your roles as family members are being intertwined with being business partners and those roles are now in conflict with each other.

    Do you have someone outside of the business and family that you can talk freely with? Because I think it will be useful to you to talk to someone to help you get your thoughts together.

  76. Judge Judy and Executioner*

    There are special consultants for family owned businesses and I highly recommend that the OP should engage with one. My partner worked at a family business when it was discovered that one of the owners children (let’s call them Pat) did not have the degree they went to school for because they dropped out. Pat was in a high level role, and had no working experience outside of the family business. While Pat was good at some aspects of their role, delegating and leading were not strengths and the business suffered. Pat’s sibling, the CEO, struggled with this, because they cared about their sibling and didn’t want it to affect Thanksgiving, Christmas, and other holidays. With the help of the consultant, the family was able to make a decision. Pat is now at another company and thriving, and the family business is doing much better without the missing stair.

  77. Bananapants Modiste*

    An old friend of mine once was the older son and heir apparent of a small but flourishing company (the family had money).
    He struggled greatly at college trying to get a business degree, changed his major several times and got nowhere.
    The thing was, he was artistic, and also hampered by a mild form of schizophrenia (distracting voices and impaired logic, but the nicest guy in town).
    Internships and jobs at the business did not go well, as he was bored witless.

    After a long process, his younger brother took over the company. Older brother was installed in an apartment with a regular income, and the family still gets along well.

  79. I Had To Fire My Brother, Too*

    OP, the *only* reasons not to fire him are because he’s your brother, because you’re concerned about the effect firing him would have on him and your family relationships, and because you really want for him to get help and get well. Those aren’t reasons to keep someone in a job they can only do sometimes. They might be reasons to give him another chance… but you already did that.

    There are no business reasons not to fire him. He’s broken your trust and that of his colleagues. You don’t have any confidence that he can be successful in his role, and he’s burned most of his goodwill with his colleagues. He’s caused significant financial, workflow and credibility issues for the business.

    As someone who had to fire my brother, I can tell you that waiting to make this call will not make it any easier — it will just give you a lot more time to agonize and be mad at your brother! Waiting to decide or doing nothing will 100% hurt the company and his coworkers, though.

    The sooner you do it 1) the healthier the business will be, 2) your brother can find a new career, 3) your entire family can heal (that might take awhile, but it can happen). It also means you, your dad, your brother, and your family won’t take on any additional trauma from future behavior that your brother may not be able to change. You’re not helping your brother by letting him stay in a situation he can’t be successful in.

    I truly feel for you. It feels awful to fire a relative, especially one you love and care about so much. It feels fundamentally wrong. But this isn’t really about your feelings. You’re the CEO. You have a responsibility to everyone who works for you to resolve this situation. If you continue to let it fester, you’re failing to make business decisions for the good of the company, and you’re jeopardizing a lot of people’s financial welfare by permitting it to continue — yours included.

    Let him go as kindly as you can; support him financially if the company can do so with severance or buyouts, or restructuring his ownership in the company.

    Good luck, this is hard.

  80. Azure Jane Lunatic*

    So in case you absolutely want to keep him in a working role, does he currently have an assistant, and if not, is there budget to employ one for him? People having executive dysfunction issues can sometimes function better if there is someone there taking care of communication and some routine tasks if there’s a problem or shame spiral or something.

    Is he handling any information where the assistant would need to be a member of the company? Because if not, it might go over better with current company employees if the assistant were employed by the family to handle any miscellaneous life administration thing that Bro is struggling with (including work) than creating a position within the company for picking up after his issues when he gets out of control.

    I have ADHD, and “promising to do better” does exactly nothing long term for me and brains that work like mine. I can learn new coping techniques, and I can learn that most people just want to know if there’s something happening that affects them, and know it promptly. I can learn that the shame from not being able to do the thing I committed to doing is nothing compared to the shame of not being able to do the thing and then having everyone who was depending on me find out the worst way. I can learn new ways of tricking myself into performing the task that I’m having a hard time doing but need to do. (Especially when that thing is literally the easiest possible thing to do, but it’s built up such emotional weight that it’s like shoving that football training equipment all by yourself with a very angry coach standing on it berating you about why you can’t somehow find the strength to push it even an inch.) But promising “I will never drop all my balls again” means that when I find myself having dropped a ball, I will be tempted to cover it up rather than disclosing it promptly.

    There’s a Hyperbole and a Half cartoon about the cycle of escalating responsibilities and system collapse.

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