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.