transcript of “I’m the Boss’s Daughter” (Ask a Manager podcast episode 17)

This is a transcription of the Ask a Manager podcast episode “I’m the Boss’ Daughter.”

Alison: Getting direction from one manager can be difficult enough, but what if you’re getting direction from two different people and they’re not always telling you the same thing? And then to further complicate it, what if one of those people is your dad? Our guest today is in that situation and as you might imagine, it’s complicated. Hi and welcome to the show.

Guest: Hi, thanks for having me.

Alison: Why don’t you start by reading the letter that you sent into me and then we’ll talk about it?

Guest: I’m the daughter of a small business owner and have worked at the company for about seven years. Somehow, I’ve ended up as a sales and marketing manager, despite rarely feeling like I really know what I’m doing. That being the case, I constantly ask questions. Most of my questions are asked twice – once to my father, the owner and renowned non-manager but excellent salesperson, and again to our GM (Jim, for the sake of names) who oversees me and all employees in the office while my dad rarely visits the office. I do this because they are both highly experienced in the industry, trustworthy, and intelligent – but they have vastly different and equally important perspectives. I deeply value both of their opinions.

Recently and more frequently, I am getting conflicting answers to the same questions, as well as conflicting direction. This puts me in an awkward position on a regular basis because my dad proposes any and everything to make our services more palatable and affordable to the consumer, while our GM is pulling his hair out because we’re not making enough money. To layer onto the situation, there’s obviously a power dynamic that I haven’t quite grasped yet. My GM occasionally gets worried that my dad is thinking about firing him (he’s not), and my dad expects me to walk around like I own the place – but my GM is clearly uncomfortable with the idea of me holding power, worried that I’m trying to steal his desk. Do you have any advice on navigating this weird mixture of disagreement and power struggle?

Alison: There is a lot going on here. There’s the issue of the conflicting answers that you’re getting and the conflicting direction, but there’s also the weird dynamics of working in a business that’s owned by your dad, which I’m sure isn’t making this any easier.

Let me ask you this: if your dad were not your dad – if you weren’t working with family and he was just the owner of the company, same guy, but no relation to you – would you still be taking the number of questions to him that you take to him now? In other words, how much of what you’re doing is driven by the relationship that you have with him?

Guest: I don’t think that I would be asking him as many questions as I am now. Sometimes he can be a little intimidating – I’ve noticed that for the other employees that I’ve hired. And they don’t frequently feel comfortable asking him questions, and he doesn’t come into the office because he feels like he doesn’t get anything done there, which makes sense, and he’s good at being with clients. He wants to do what he’s good at. So I don’t think I would ask him as many questions.

Alison: Let me throw a curve ball at you. This might be a terrible idea. I know you really value your dad’s perspective, but if in a non-family version of the situation you wouldn’t have this kind of access to him and had to send most things through the GM, what would happen if you did that here too? If you stopped taking most of your questions to your dad and only took them to the GM, what would be the effect of that?

Guest: For some questions, my GM would definitely direct me to my dad because he would kind of say, “I’m not sure, you should probably ask your dad, he’ll know better.”

Alison: Got It. The reason I’m asking it is because I think it might be at the root of this. I think it’s really hard to report to the GM day to day, but also still treat your dad like your dad when you’re in a work context. I think it’s probably a very difficult spot for your GM to be in, to feel like he’s sort of supposed to be managing you, but you’re the boss’s daughter, which would be tough for him no matter what. And then on top of that you’re pretty regularly checking in with your dad about work stuff and getting this conflicting advice and direction. If you imagine being the GM in that situation, it’s got to be pretty tough for him. And I wonder if he feels like he’s being undermined even if no one involves intends that way.

Guest: I definitely get that feeling from him. And I feel guilty because my dad only speaks good things about the GM, and he’s worked for my dad for the entire time we’ve been in business – for 20 years this guy has been the brains behind implementing everything that my dad wanted to do. So he’s a huge part of the company and he’s really important, but he still feels frequently like I’m trying to steal his job or I’m telling my dad to fire him or something. And that’s never the case, and I him them that, but understandably he doesn’t believe me.

Alison: Do you know where that’s coming from? What’s giving him that impression?

Guest: No, I don’t. Besides the fact that my dad could just be a little rough sometimes, I’m not entirely sure why he has that idea.

Alison: I will say that is a tough situation to be in. All three of you could have nothing but respect and admiration for each other and you could have given him no reason to feel the way it sounds like he might feel, and I think a lot of people, maybe everyone in his situation, would still have a certain amount of insecurity because it’s hard to manage the boss’s daughter and to know that you have your dad’s ear in a way that he might not and might never have. And especially if he sees that sometimes he tells you one thing and then your dad gives you a perspective that’s a little different, I think that would make almost anyone feel pretty insecure. So that might be what’s going on is just when you mix the family dynamics with the work dynamics, he’s in a tough spot.

Guest: Yeah. I know that having my dad’s ear is a vital part of it, because I go dinner with him, or lunch with him, and I bring it to the office and talk about x, y and z, my GM probably thinks that we also talked about him.

Alison: And I think even if he’s not worried that you’re talking about him, he’s probably seen the same evidence that you’ve seen – that sometimes he tells you something different than your dad tells you. I think it’s a recipe for insecurity for anyone in his spot. I don’t want to discount how valuable the kind of relationship that you have with your dad can be in a work situation. It’s great to have someone who you have that kind of rapport with at work, and where there’s that built in trust and where you can speak in shorthand. Those are all really good things. I don’t want to say, “Oh, you should just stop talking to your dad about work stuff,” because you would be forfeiting all of the benefits that I’m sure come to both of you from being able to do it. I think it’s more a question of being really realistic about how that can complicate things and figuring out where to go from there.

Guest: Yeah.

Alison: I will say, if you were not related to the owner of your company and you just had a question about getting conflicting instructions from two people above you, I would say, “Okay, sit down with your boss. Describe the problem, explain what’s going on and ask how your boss wants you to handle it.” Because the idea is that often when it’s happening, the two people who are giving the conflicting instructions don’t realize that it’s happening, or they don’t realize how often it’s happening. And so, your role as the person caught in between would just be to flag it so they know what’s going on and can address it.

Guest: Yeah.

Alison: And I want to talk a little bit about how your boss would respond to that if it weren’t a family situation, because that’s helpful to just have in your head. Assuming he was a good manager, once you flagged this for him he would then work to figure out where the difference in perspectives was coming from. So that would mean he would probably talk to his own boss. He would flag that they had been giving these conflicting instructions and figure out where were they seeing things differently. And they might then solve it at the root by coming to some agreement between the two of them on the issues that they’d been approaching differently. Or if it was a bunch of things that were just constantly changing, they could agree on a different process to use going forward. And that process might be that your boss would check in with his own boss on those types of things before he brought them to you to make sure they are on the same page at the outset. Or that his boss would agree to back off and just let him handle these things on his own and wouldn’t get as involved. Or it might just be that they would tell you to flag it when it happened so that they knew they had to work it out between them and you weren’t just left feeling like you were in the middle of this conflict.

But in a situation where your boss’s boss is your dad, that gets more complicated. I do think your boss can still do those things and probably needs to, but it’s just less straightforward because he can’t act entirely like your boss when you are the daughter of his own boss. Does that make sense?

Guest: Yeah, unfortunately. It’s something that kind of looms over me at work all the time. Every interaction that I have with any one of my coworkers always seems to be tainted by the fact that my dad owns the company. So, I’m well aware of the implications that that has, and the effect that it has on people. Maybe I should just be more sensitive to my GM being in the middle of that too.

Alison: I do think that is a piece of the answer. I think it’s a double-edged sword in a lot of ways. There are benefits to having that kind of close relationship with your dad, who you work with and then there is also real downsides. And some of those downsides are for you and some of them are for the other people who you work with. And I don’t think there is a perfect solution. I think if you talk to anyone in a family business, you will hear that they struggle with some version of this. Theoretically, the cleanest solution here is probably for you to pull back on how much you take to your dad about work. Ideally in this hypothetical solution – that might not be something you can carry out in reality – you’d be interacting with him the way you would if you work together, but he wasn’t your father and if you didn’t have special access to him. I’m going to assume that doesn’t feel feasible, that that’s just not how things are set up to work. Is that right?

Guest: Yeah. We both work a lot and we both work very hard, my dad and I, and I think we do that not out of obligation, but because we care a lot about the company and we enjoy working. So it’s kind of difficult, because when we get together we talk about it like a hobby – it’s something that we’re passionate about and we enjoy talking about. And I have tried to not talk to my dad about work things when I’m not at work, but it’s like our biggest thing in common, it’s the big thing we do together. So, it is a little bit difficult unfortunately.

Alison: Do you plan to stay in the company long-term or do you see yourself moving on at some point?

Guest: I do plan to stay long-term.

Alison: If you had told me you thought, “I’ll be there for a few years, but then I think I’m going to move on,” I would have a very different suggestion for you and I’ll just tell you what it is because maybe it’s interesting (laughs). If you were planning to move on, I would say that you might be hurting yourself professionally in the long term by continuing with the way that things are structured right now, because if you do want to move on at some point to another company, you want the work norms that you’ve internalized to sync up well with a non-family business. And I would worry that by staying in a situation where family changes the dynamic so much, you wouldn’t necessarily be preparing yourself to thrive in a more traditional setup, and I would also worry that you’d be missing out on some of the professional growth that like a non-family setup would provide – and actually, this part might be true for you. Now knowing that you do plan to stay long term, this is just stuff to think about and it’s not necessarily anything you have to take action on, it’s just stuff to have in your head as one piece of the situation. For example, if your manager ever had a pretty serious criticism to give you, I don’t know that you could trust that he would feel comfortable giving it to you because you’re the boss’s daughter and because you have your dad’s ear. So there’s a risk that you’re potentially forfeiting some of the benefits of a more traditional relationship with your manager. Which is not to say that every manager does that well – I mean, you could go somewhere else and you could have a terrible manager who doesn’t give you any useful feedback anyway. That certainly happens to a lot of people, but it’s something to have in your head as just one piece of the situation.

That said, there’s also huge advantages to the type of situation that you’re in: you’re being given really interesting opportunities, like you said you had ended up in this management position despite feeling like you didn’t quite know what you were doing. And there can be real advantages to just being given that kind of opportunity and having to figure it out. You can learn a ton that way. And then the flip side of that is, maybe you’re missing out on the kind of support and training and more measured growth that you would get in a non-family context. It’s complicated and there’s good and there’s bad and if you are going to stay there long-term, the best thing you can do for yourself is to just have your eyes wide open about what the good is and what the bad is. I think it’ll remove some of the stress if you’re just a really realistic about that.

Guest: I think that’s a good thing. That’s really good advice to give: any feedback that my GM might give me, take it with the understanding that he may being sugarcoating it more than he would anyone else.

Alison: Yeah. Thinking about your relationship with the GM, do you feel like you could ever have a conversation with him where you were just really candid – and maybe you’ve already done this, but to just sit down and say, “Hey, I know this is kind of a weird dynamic. Are there things that we could do differently or that I can do differently on my side that would make this whole setup more effective for you?”

Guest: I have not.

Alison: That might be interesting. There’s got to be a certain level of trust there to do it, or at least to do it and get candid feedback, but he might appreciate hearing that you recognize the spot that he’s in and that you’re reaching out and saying, is there stuff that would make this easier on you?

Guest: Yeah, that’s a good idea, and I think he’d be open to it. He’s a good listener, he’ll listen to me. I don’t know if he’ll respond right away, but I know I can be candid with him.

Alison: And you might think of it too as an investment in the relationship longer term. Maybe he doesn’t have something that he gives you on the spot in response to that. But by saying those things and demonstrating that you’re interested in hearing it, it may pay dividends later. And I wonder too, it may be worth saying to him, “Hey, I would really value your feedback. You’ve been doing this for a lot longer than I have. I’d be really grateful for any guidance that you can give me if you see something that you think I’m not doing quite right or where I could be stronger, I’d really appreciate hearing it.” Because so few people ever say that to their boss, and especially with this guy who is in this kind of awkward situation because of the relationships, it might make him more willing to be forthcoming if there is anything like that. And if he does feel kind of threatened by you, reframing it as “I see you as a mentor” might be really helpful.

Guest: I do see him as a mentor and I think he might appreciate it if I tell him that, because I’ve never told him that outright, but I do feel very strongly that he and my dad are these two huge features in my life that impact me a lot and I care about their opinions tremendously. So maybe I just tell him that, ask for the feedback.

Alison: Definitely. I think too, because you are picking up on this sense that he might feel awkward about it or worry that you are going to get them fired one day, I think telling him how you actually see him and that you do see him as a mentor would go such a long way hopefully toward putting him at ease.

Guest: Yeah, that’s good advice.

Alison: The other thing I would say is kind of like I was touching on earlier. If you’re going to be working in the business long-term and you’re working with your dad, just recognize: all right, it’s complicated, it comes with complications. It’s not always going to be great for the people who are around you, especially for the GM or anyone who’s supposed to have some authority over you – and that’s okay. I talk a lot about family businesses on my website and I talk a lot about the problems that can come up, but that doesn’t mean you should never work in one. I think you’ve just got to be realistic about some of the things that are a little harder about them. It probably will be a little weird for the GM no matter what you say, but you can make it less weird by recognizing what’s going on and bringing it out in the open and just sort of operating with an understanding of what it might be like for him.

Guest: Yeah, I don’t think that I’d ever acknowledged out loud these types of things, and that might be part of a family dynamic. We’re not a feelings family, we’re more passive, so we don’t always tell people what’s going on. Even in my relationships with non-family members like my GM, I carry that over. So maybe this is a time where I should actually express, “Hey, you’re important to me, I value you and your opinion, and I realize that this is weird for you. Let’s work together to try to make it less weird.”

Alison: I love that. I would love for you to do that because I bet it will have an impact. I would love to hear how it goes if you do try it.

Guest: I think I definitely will. I don’t think there’s any reason why I would not. I don’t know why I haven’t, and it seems like such a simple and effective thing to do to just reach out to somebody and say, “Hey, you’re important to me and let’s work on this together – I’m requesting that you tell me what it is that I can do to help.” And even if he doesn’t respond immediately, it can at least give him the idea. Maybe I’ll just tell him and then give him a while to digest it and kind of decide when he’s going to respond, or if, on his own time.

Alison: Yeah. And depending on his comfort level with this stuff, he may not respond explicitly, but it might just change his perspective on things and you might see evidence of that. But I think if you are not explicitly ensuring that the you and someone else are on the same page about how you each see things, you’re leaving room for them to come up with their own narrative and their own explanation. And sometimes they get it right, but sometimes you’ll see evidence that they’re getting it wrong. And I think that’s what’s happening here with your mentions that it seems like he thinks that you might get him fired someday or that you’re trying to take over his job. If he’s thinking those things, I think that is him filling in the blanks about what the situation is, because it hasn’t been talked about openly. And so if you do talk about it openly, he won’t have to fill in those blanks on his own. Hopefully the two of you can get more on the same page.

Guest: Yeah. No, that’s definitely very helpful. Thank you so much.

Alison: Well, thank you so much for coming on the show.

Guest: Yeah, thank you. I appreciate it.

Alison: Thanks for listening to the Ask a Manager podcast. If you’d like to come on the show to talk through your own question, email it to – or you can leave a recording of your question by calling 855-426-9675. You can get more Ask a Manager at, or in my book Ask a Manager: How to Navigate Clueless Coworkers, Lunch-Stealing Bosses, and the Rest of Your Life at Work. The Ask a Manager show is a partnership with How Stuff Works and is produced by Paul Dechant. If you liked what you heard, please take a minute to subscribe, rate, and review the show on Apple Podcasts, Spotify or Google Play. I’m Alison Green and I’ll be back next week with another one of your questions.