Interview with Christina Wing, founder of Wingspan Legacy Partners, faculty member at Harvard Business School, and business owner

The art of communication is the glue that holds family businesses together, yet it’s often the toughest nut to crack. Why do families in business dance around the conversations that matter most? Conflict, relationships, illness – these topics are the bedrock of our family dynamics but are often shrouded in silence. This silence can ripple through generations, affecting everything from who holds the reins to how decisions are made.

Enter the world of open dialogue, where honesty and a united front can transform uncomfortable chats into pivotal moments of growth. But how do we get there? The path might be smoother than we think, built on the straightforward principles of honesty and the collective pursuit of a brighter future.

On this episode we are joined by Christina Wing, the founder of Wingspan Legacy Partners, a seasoned faculty member at Harvard Business School, and a business owner herself. Christina unlocks the transformative power of tackling tough conversations head-on in family businesses. From the nuanced role of timing in broaching sensitive issues to the enlightening impact of the COVID lockdowns on our understanding of mental health and the need to set personal boundaries, Christina sheds light on the conversations that can redefine the future of family enterprises.

Image courtesy of Christina Wing

Key Takeaways:

  • Rejection is one of the main fears that prevent honest conversations from taking place between family members. It’s natural to feel apprehensive about discussing a difficult subject with a family member, especially when there’s a risk of damaging your relationship with them, affecting others, or impacting your status within the business. The thought of being rejected, and ultimately isolated from the group, can be extremely daunting.
  • A common misconception is that the peacemaker in the family should take on the responsibility of initiating difficult conversations. However, peacemakers often want to avoid conflict and don’t necessarily understand the necessity of addressing issues head-on, even if it means temporarily disrupting the peace to achieve long-term improvement. In reality, those who are great listeners tend to be the best individuals to navigate difficult conversations.
  • In nuclear families, it often proves challenging when some siblings make choices closely aligned with those of their parents while others don’t. It’s natural for children to compare themselves to their parents’ perceived expectations, which can lead to reluctance to express their true selves. However, if children don’t acknowledge and embrace their differences, and discuss them with their parents early on, the conversation often becomes even more difficult years later, potentially after resentment or regret become hurdles.
  • One of the first steps to becoming better at having difficult conversations is adjusting behaviour around all interactions. Take the time to engage in meaningful discussions about subjects you genuinely care about, rather than resorting to polite or banal dialogue. Additionally, understand that not everyone within a family wants, or is even open to, change. Similarly to a non-family business setting, family members need to establish and build trust within the family unit before they can expect the honest engagement they are working toward.


Ramia: Welcome everyone to another episode of Women in Family Business. I’m so excited about our guest today. Christina Wing is joining us. Hi, Christina. Welcome on the show.

Christina Wing: Hello, thank you for having me.

Ramia: Christina, you and I are going to have a difficult conversation about difficult conversations, and I really love this topic, especially in the context of the family business, it’s a very necessary topic that you take very much to heart and that you’re very passionate about. But first questions first, like, why would you want to be the person to bring up such a challenging topic in the family enterprise arena?

Christina Wing: It is not the most popular topic in general. For me, the passion comes from the fact that I think I could have had so many different outcomes in my own life if my family had engaged in difficult conversations. Not only would I have had different outcomes with my family, but I would have had different outcomes through the different chapters of my life. Because things that my family didn’t talk about at home or in business, I kind of carried with me. And I also didn’t talk about them. And it took until I was almost 50 to start talking about the things that actually really matter. And for me, pushing others to encourage them, push them, nudge them to do this. It’s hopefully so that they can have, you know, more honest and true relationships.

Ramia: And you’re addressing something so important because I think just generally in the family context, we assume communication should be easier because we’re close, but then actually communication is so much harder very often having conversations honestly can be so much harder.

So in the family enterprise arena, we have the business and the wealth, the wealth component that can come with it as well, which add actually two more layers of challenging conversations to have. But like, tell us a little bit more about what you’ve observed when interacting with business families. Like what do you think is the main reason why even though we have so much riding on good communication, right? Like even though so much depends on us having challenging conversations.

Why is it so hard for us to do it, even though the stakes are so high?

Christina Wing: I think that there’s a little bit of a fear factor that people have about engaging in a difficult conversation that nothing will change. And so if you really think about it, if you take the time to have a difficult conversation with somebody, it’s because you care. But you have to go into it with a goal. If your goal is simply complaining, then that’s not a difficult conversation. That’s a complaint.

If your goal is changed behavior and working together to get there, then there is a result that’s worth it. But I believe many of us feel that people aren’t gonna change, it’s been this way forever, why rock the boat or let somebody else do it. And what we end up doing is having these difficult conversations behind the scenes. So everyone’s having their little mini difficult conversations, but nobody really wants to address the elephant in the room.

Ramia: And so what do you think qualifies as a difficult conversation? Tell us about sort of like topics that you’ve encountered where you’re like, you know, generally these are stumbling blocks for families.

Christina Wing: Money is a big stone block, and that comes across in inheritance, comes across in succession, it comes across in governance. All of these things that money touches are touchy, like who gets what. Even things like the beach house becomes something we argue about, even though it’s a beautiful thing to have in a family, but instead it turns into this thing that becomes money-related. So money, religion is another thing that becomes difficult in families, especially if people wanna marry outside of their religion.

Governance in general becomes something people don’t talk about. People don’t talk about competence. We’re not comfortable talking about who’s competent for what role. It almost feels like if I’m competent to do the marketing role, but you know, Tom isn’t that something’s wrong with Tom, but no wait, Tom might be really competent at something else. But because we don’t talk about competence, we just shy away from who’s actually better to do certain things. It’s sad.

Ramia: What do you think we’re really afraid of in that kind of a conversation? Like, I always wonder this, like, you know, do you think the overweighing fear is to hurt others or to, as you said, like rock the boat or sort of like, you know, stir up things that feel like that might lead to unraveling bigger conflicts? Or are we inherently just really always protecting ourselves from rejection and sort of like misunderstandings?

Christina Wing: I think the biggest fear is rejection. And what that means is not just rejection of the difficult conversation, but a bigger rejection, a more permanent rejection. Suddenly you compromised your relationship with said person and that leads to compromising your relationship maybe in the business. And it leads to you compromising your relationship with others. There’s this fear that a difficult conversation with one person leads to potential isolation from the group. And that’s a very scary thing.

I also believe that many people, when they embark on a difficult conversation, the person receiving, the inclination is to be defensive and judgmental. And so our best strategy is to actually have them more often so that they’re not as “Okay, everything’s been perfect for five years and now Christina’s gonna drop the big bomb.” We should talk about difficult things more often and then it’s not as big of a deal. But the other thing is sometimes it’s easier to be peaceful. And I think easier in the moment. And so those moments accumulate. If it’s like, well, I’m not gonna bring it up at Thanksgiving, well, I’m not gonna bring it up at Christmas, I’m not gonna bring it up at Hanukkah, I’m not gonna bring it up… like it becomes the times when families convene are also times that shouldn’t be the time for those difficult conversations. But we feel that for some reason, especially holidays, they stimulate angst and other issues that these conversations typically happen then and they’re not well received. And so then it’s like, go back under your covers for another 10 years.

Ramia: It’s interesting how those kinds of occasions can though provoke often those kinds of conversations as well, right? Because you spend time together and of course, like you’re forced to confront certain things.

But, okay, I’m very wary, Christina, of like, you know, that uncle or that cousin who’s decided that their role is to be the devil’s advocate. And they’re like super proud of that role, right? Like, and they’re like, and they, and for me, like, I just wanted, I want you to tell me what now is the difference between someone doing that where they basically use that role to just say things because they really want to say them, right? And between someone who addresses a difficult conversation in a way that then is constructive for everybody? So not just addressing, but actually conversing. Where do you see that nuance?

Christina Wing: So that difficult uncle is a contrarian and his goal is to be center of attention. And so the goal of this conversation is to have a voice, be center of attention and kind of poke people. He does not have a goal of change in behavior. And so a difficult conversation is typically about a perceived change in behavior, change of information flow, change of how you do things.

We all have that uncle and you’re kind of like, oh, here goes uncle Sam again. But what my view is, we all know that’s uncle Sam. And guess what? He’s never gonna have the ability to have an authentic, difficult conversation because he’s already ruined his ability to converse with the family. He doesn’t have that voice. That person is probably the same way at work. Probably everybody wants to get Mexican food and he says Chinese. It’s just. The contrarians are contrarians and a contrarian is not somebody that it’s easy to engage in a difficult conversation with. However, you have to sometimes. And so a contrarian takes it even more effort to have one with. And what that means is you’ve got to be well thought out and you kind of have to make it on your terms instead of even meeting in the middle. Everyone else, I feel like it should be meeting in the middle, but a contrarian that already has their back up has to be approached even differently.

Ramia: I think you’re addressing something so important here because essentially being a contrarian doesn’t necessarily give you the credibility to be the kind of person who can facilitate or initiate a difficult conversation in a family enterprise. So let’s talk a little bit about who has that kind of credibility or what you have to do to build that credibility in the family to be the kind of person that maybe finds more acceptance for raising a subject like that and what you’ve observed. What kind of people have been successful at it? What kind of traits do they share?

Christina Wing: It really depends on the situation and how the person is viewed by the person receiving it. And so I might view you a certain way and we could have a very productive, difficult conversation. However, if we don’t know each other’s roles, a difficult conversation comes off really, really poorly. In other words, many people think, oh, the peacemaker in the family should be the one to have the difficult conversations. Absolutely not, because the peacemaker is somebody that wants to keep the peace, but not necessarily understand that sometimes you have to break things to make them better. And so the perfect person that engage difficult conversations are people that really listen.

And so people that listen to what’s being said and what’s not being said, and have the intuition to kind of see around corners. Like I said at the beginning, we only should engage in these difficult conversations if it’s going to improve something, if there’s a common goal of improving. That doesn’t mean the person you have it with has to share your goal, but it means you have to go in with a goal and that at least will hopefully enable the person to listen. You know, there are a lot of other topics that we’re not even talking about that are worse, like addiction, like divorce, you know, happiness. We don’t talk about any of these things. We really, in many families, don’t even talk about happiness because it’s almost perceived, if we talk about how happy we are, we’re not working hard enough. And so it’s this intersection of family, money, and work that makes almost no topic safe. We talk about sports, we talk about food, we talk about movies. We can’t even talk about all books because it kind of gets into a political realm. But the things we talk about really are so limited and narrow. Yet, if you watch the news with your family or you view a situation, families are very good about talking about difficult things about others. Well, look at this. Look at Chris Christie. He’s so overweight. He shouldn’t be president. Well, you see that on the news every day. We would never say that at home. We just don’t talk about those things, but we feel comfortable as a group talking. And what we’re really doing is we’re judging these people from the outside. And so we all know these hot buttons are in all of our heads, it only makes sense that we should have to be able to talk about it with one another.

Ramia: But then I think that’s a really interesting point you’re raising, because also that kind of like social gathering and then common observation, I think also actually instills more fear potentially in other family members to say, well, you know, did you hear how aunt so-and-so responded to like, you know, such and such TV series and stuff like that? I’m never going to tell her that I made this life choice or like I never going to. You know what I mean? Like, so it feels like that’s even that’s even less conducive in a weird way to like then actually opening up.

Because we might perceive the other person as much more judgmental or close-minded than they might actually be, right? Like, and I think that’s also, that’s definitely, at least it sounds to me like a recipe for disaster in terms of like preparing for a difficult conversation.

Christina Wing: Well, you know, you’re bringing up a really good point and what it does is it gets to culture. And so when you think about families and people in general in workforce, there’s multiple generations. And so, you know, my mother is a very strong willed, 100% Italian woman. If she gets invited haphazardly to something, she’s not gonna go because she doesn’t think it’s a proper invitation.

Me, if I bumped into some friends and they were like, Oh my gosh, I can’t believe you’re here. Join us. I’d be like, totally. Not only would my mother not go, but then she would probably question why she wasn’t invited. And what that does is it then would lead people that hear her saying that to be like, Oh, well, we didn’t invite aunt Karen a week ago. We better not invite her now. And so these cultural norms also make it hard to change. And generations communicate differently. And so we have to meet the person the same way. I would have a difficult conversation with my mother very differently than I would with somebody my age. And I also would give her less notice about it than I would give other people because she would be somebody with too much notice, she would worry and fester about it.

And so you have to play your cards right. And it sounds so delicate. Like at the beginning, you said, well, kind of like, why bother? Well, the why bother is, gosh, wouldn’t it be nice if my mom could also go to spontaneous dinners or do other things? Because she’d love to attend. Once she gets there, she’d be fine. But it’s like this mental thing in the head. And so it’s a big hurdle. And if you think about it, we always have this tendency to assume people want something or that they’re going to act in their self-interest. I want to have a difficult conversation with you because I want something. And very often, many of my students, the difficult conversation and what they want is information to know how to help. They might want to know, what is my responsibility if something happens to you? What is your wish of what I would do with the business? But if they ask it the wrong way, parents and elders feel like they’re saying, what am I getting? What am I getting when something happens to you? What am I getting? What am I getting money? Like, when am I in charge? You know, you ask somebody about succession, they feel that you want their job and you want them out. But in reality, We have to talk about succession. It doesn’t just ‘poof’ happen.

Ramia: Yeah. But I think, so I mean, but let’s talk about like maybe a few of these choice, like very, very difficult topics, like because I do think, and I think you brought one up at the very beginning, that I actually feel we, even in just a general family enterprise conversation, we shy away from a lot. So I have this sort of like, I would say like this suspicion that around the family enterprise conversation, we have started having a bit of a discourse that talks about, like, you know, we like to talk about family harmony. We like to talk about continuity and, and those, those forever words, right? Like, and it feels sometimes that comes at the cost of diversity and diversity of thought and choices in lifestyle, because it almost sounds like we can only achieve that goal if we’re all the same, and if we all believe in the same things, and if we all do things the same way. And I feel like that narrative is still astonishingly prevalent. And I, I constantly see how this makes a lot of people extremely unhappy. And I’m sure that you can totally appreciate why that is. Um, and I actually think we don’t talk about this often enough about sort of like diversity of thought and diversity of, of lifestyles and how that contributes to how you’re able to be part of a family and how you’re able to contribute. And also what kind of a voice you receive in the family arena. And I think that’s also important to say, if you do choose another religion or you choose to marry someone from another religion, if you do have a different lifestyle than the rest of the family or you make different lifestyle choices, that can seriously impact your standing in the family. So how do we learn to have that conversation and sort of like understand how rich it actually is when the family is open to that diversity and is open to embracing you know all the different kinds of like lifestyle decisions everyone can make?

Christina Wing: You know, it’s something I’ve thought a lot about, and I started to pull these traces. When you think of many first generation entrepreneurs, many of them are immigrants. And they immigrate from another place to wherever their new place is. And what they have is the shirt on their back and their family. They also bring the culture from where they came from. And these immigrants are the hardest workers. They stay unified as a family. And suddenly I think that the next generations think to celebrate what they did, we have to do it the same way. We have to all be of this religion and do these kinds of things. And yet in reality, the first generation left what they had. They brought some of it, but they started over. And so the best way to encourage diversity of thought and action is to remind everyone to be entrepreneurial. Generations need entrepreneurs in every generation. If you have a family that is always making cars, but they don’t innovate how to make them, where to make them, what type of cars, or I might want to be in a totally different business, but I have respect and I can be a good owner, investor, then that car company is going to die at some point. You have to keep innovating. And when you innovate in business and you innovate in what people are allowed to do, like allowed, encouraged, I should say, that starts to bring in diversity of everything. diversity of thought, diversity of religion, diversity of race, diversity of all things that matter. And that’s how we get better. I mean, you go to some place that’s incredibly homogeneous, a family, they pretty much hate each other because they’ve all been put in the, you know, square box and they’re not all square boxes, but they’ve had to act that way. And so by the time you get to generation 11 of square boxes, they resent each other. People are not fulfilled. When you go and you see a family that has squares and circles and pairs and all this, like they actually aren’t competing with each other because they’re doing other things that make them happy and fulfilled. And diversity is the only way to rise up. And so it starts with entrepreneurship.

It started with entrepreneurship in G1. And you know, what does legacy mean? Does legacy mean these big words that G1 is the legacy that me and G5 has to have? Or what is my legacy? My legacy is individual. And a family can have a family legacy, but individuals have to have an individual legacy. And the family legacy has to change. What it was in G1 is not what it’s gonna be in G10. So you can still have a family legacy, but it’s gonna change every 10, 15, 20 years. If it doesn’t, that would imply that any family that sells their business doesn’t have a legacy anymore. And I call baloney on that. I think that there are many legacies to have. Your legacy of a family can be being good people. Your legacy of a family can be being inclusive. Legacy doesn’t have to be about money. So I say entrepreneurship.

Ramia: You talk about the changes, right? Like, so family changes all the time. And of course, some of these changes are deliberate, others are not. And if you think about how the family paradigm changes with each family member that’s added with each marriage, with each, with each divorce, for instance, that’s another one of those topics that tends to be really, really dicey. And like, and, and interestingly, because you think about there probably is nothing more important than to ensure in your family, you can have that conversation safely, right? Like whether it is that you decide not to marry or who you marry or like whether you need to get that divorce or whether you’re having children or not. I just I just want to really finding really interesting and challenging, like why like a frank conversation there can also be difficult. And sometimes even within the same generation I’ve observed, like it’s not just younger generation to older generation, but sometimes within the same generation, this can also represent a challenge. Why do you think that is and how can that be remedied?

Christina Wing: I think there’s two things. There is, why is it a challenge in a nuclear family? And then why is the challenge exasperated when the family grows? Typically in a nuclear family, one of the people in the family will resemble the parents’ choices. And that person seems to be the celebrated one. Because, oh, mom, dad got married in a Catholic church. Now we’re getting married in a Catholic church. And then the other two are sitting there going, well, I never wanna get married or I wanna marry a woman or I want this. And it’s a, we compare ourselves to what we think our parents want. And so first of all, we don’t give parents enough credit to actually be open to hearing who we are. We wait until we’re so far down the path of assuming they’re going to reject our choices, that we’re defensive and they’ve spent 35 years having you as a child and the conversation is difficult for two reasons, not because they’re judging your choice, but also because they feel like they haven’t known you for all this time. How sad is that? So number one, if there’s something that is different than how your parents were, embrace it and talk about it early.

I hope everyone is different than their parents, because we’re not all gonna marry the same way our parents did, or choose those lives. So that’s that. With growing a family, just like a business, a business zero to five has one culture, five to 10 the culture changes, 10 up it changes dramatically. In a family, zero to however many you are, let’s say you’re five, well you go from five to seven to 10.

Massive changes happen. And that’s because other people are coming in with their diverse thoughts, diverse interests, diverse traditions. And the best thing to do is if a family has any principles that are just sacred to them, meaning we have a family business and we only want family to ever work in it, then make that rule before there are any non-blood people in the family. If the owner of a business says, I only want anyone that’s a blood relative, that’s his or her choice to make, but you don’t do it after the second sister gets married and that husband’s kind of not very smart, because then it becomes personal. And then everybody kind of, the apple cart’s tumbling around. If you have things you really, are deal breakers, state them, but have it be before it’s personal. So, you know, a lot of people have prenuptial agreements. If you’re gonna have a prenup, if a family is gonna say, I insist all my children have a prenup, why don’t you make the prenup before anybody’s even dating anyone? Why not make this standard prenup? What people think is, oh, I’ll wait until so-and-so gets engaged.

Well then the first one has to bear the brunt of all of this. If kids know, hey listen, this is mom and dad’s money. We might not ever give any of it to you, but it’s definitely not up for debate. We have a prenup. You can have your own prenup with your spouse of what you earn, but in terms of what you inherit, we have one for the family. It just changes everything. And you know, I’m not in favor of predetermined succession. But if you look at countries that have had predetermined succession, like a country like India, it was always first born male was gonna be the successor. More of their family businesses have lasted into later generations just because it was already decided. There wasn’t a fight. The others went and did things. It’s kind of like the monarchy. I’m not saying that’s right, but knowing it gives the other person freedom to be entrepreneurial. And so I do believe when families have views in their head around these things, if they would just start talking about it sooner, people would accept it. That’s different than a difficult conversation. That’s like preventing a difficult conversation.

Ramia: Well, I think prevention can in itself be a difficult conversation because I think it is hard actually in a situation where it seems, well, it’s not urgent or it’s not the time to bring up such a topic. Right. Like, so as you said, I actually think like having a conversation around preventing something that lies in our potential future can actually be pretty difficult because like a lot of family members don’t want to think that far ahead. Like it’s a little bit the same thing as bringing up someone’s will or something like that, you know, instead of just waiting until they’re really ill or like the situation becomes very emotional. Um, so I actually think that it’s still very much part of the having difficult conversations conversation in a way.

Christina Wing: Well, think about how many times you’ve wanted to have a difficult conversation. And then think about the times that you haven’t. Half of those probably mean you shouldn’t have had them because you didn’t have a goal, but you were ready to have a knockdown drag out with a friend like, I can’t believe you’re always late. But then you just decide maybe that’s not worth it because if the goal is to see the friend more often, then you would do it. But if you’re like, this is so bad, I don’t even wanna see the friend, it’s not worth the difficult conversation. Ones that you delay that the next time the occurrence happens, you react emotionally, those are the ones that really hurt us. It’s the ones that we put off frequently and we’re waiting for that person to do it.

Those are the ones that we have to do because those are the ones that will destroy our relationship with people because we do react emotionally sometimes. Most of us have moments. We try not to as we get older, we try even more, but you know, we do. And those could be so prevented if we took the time to have them in a calm way.

Ramia: You’re describing, of course, the phenomenon that essentially not having these conversations or having these conversations in a destructive fashion can hurt people very much. It can be quite devastating. It can lead to a lot of family members feeling enormous amounts of pressure and burdens of expectation. It leads to devastating misunderstandings, which we see on a daily basis. And sometimes it’s really ironic because it’s not for a lack of love in the family, but like it’s, it’s just a, it’s like deep seated misunderstandings that are for festered for years that have not just not been addressed.

When people are hurt, when people suffer from these expectations, we do have a lot of cases of mental health challenges in the family enterprise system. We have challenges with addiction and a lot of that is connected. I’m not saying I wouldn’t say all of it, but a lot of it tends to be connected from with this phenomenon of being born into this, this family that has these expectations or that you perceive has these expectations or would not accept you as being different. So when you’re actually dealing with something that almost seems like an effect of your inability to have those conversations as a family, and you’re suddenly faced with someone who’s actually faced with like a very acute health situation because of it. I mean, it’s definitely not when you want to start having those conversations, but if you have to, how do you do that? If your family doesn’t really have that culture of having those conversations to begin with? And that’s a really difficult position to be in.

Christina Wing: Yes, I mean, I think that mental health has been so understudied and, you know, so many things contribute to it, including sleep deprivation. Now a chronic issue is something that we have to figure out how to get away from permanent stigmatizing of people. And so a lot of addiction, whether it’s weight issues, whether it’s substance abuse, people are afraid to talk about it, both the person that needs help and the person that you can see needs help because it feels like they’ll be for the rest of their life cast as she’s an alcoholic or she’s this or she’s that. We have to realize that there are chapters in life where we all have mental health needs. And it’s a matter of why not take the air out of it before it gets too big. And in these cases in particular, I think these should be the easiest difficult conversations because it should be, you know, I’d like to sit down and talk to you. Can we get together tomorrow? I wanna let you know in advance. I wanna talk to you about something that’s concerning me just so you’re prepared. We go to a neutral spot so that it’s not my turf or your turf. And it’s basically, the goal of me sitting down with you is I love you to death and I’m worried. And I’ve noticed now that every time I see you, you’ve had too much to drink, or I’ve noticed that in the last 10 meals, you haven’t eaten one bite. What can I do to help? I’m here. And it’s stating the goal. The goal is your safety. It’s showing the empathy. I’m only doing this because I care about you. And then how do we work on it? And I think that if we could start to have more of those conversations, so many of our problems wouldn’t escalate. During COVID, when everybody was home together, not just families that have family business, but everyone, mental health went soaring up because there was no separation of like church, state, work, everything was at home. And so families and business, everything’s in one place. It’s like all mixed in one setting. And so for people that need more privacy or some boundaries, it becomes very hard to cope in those situations. And sometimes they cope through things that aren’t as healthy. And so part of all of this is getting to better behavior. So hopefully in having these conversations, somebody will state, yes, I’m having this problem, but the problem isn’t the problem, it’s what’s causing it.

So by talking about it, we can find out, yes, it stresses me out every time we get together, that all you guys do is talk about the business, because I’m not in the business and I don’t feel part of the family being there. And so I drink when we’re sitting there, you know, or, or whatever it is. I mean, there’s always causes. And if you can talk about what you’re getting as the result of it, we can back into solving other parts.

Ramia: I guess the advantage of that kind of really dramatic change in someone or such an acute case is that it is very visible and what the problem is, is very clear in a way. So I think even though having that conversation is admittedly one of the hardest things for a family to do. It’s also really obvious where to, like what the issue, what the problem is.

For me, I think when I think about people listening to this podcast with you right now, Christina, I think everyone who’s part of a family enterprise, no matter how functional and how great, is going to recognize some topics in here that we’re like, yeah, we’ve either not had the conversation or we’ve not had it enough. Because I think it’s not a cliche for nothing. It’s definitely there for all of us, no matter how successful we become, no matter how well we do.

But repression plays a really big role in this. If someone listens to this podcast and is like, you know, I’d actually like to have these conversations. I’d like us to have a culture that allows these conversations. How would you go about identifying which topics should come first?

Christina Wing: First, our behavior has to change in general, not just around difficult conversations, but take the time. If you take the time to ask somebody something, ask them something you care about or just don’t ask. We don’t have to have these just polite conversations always. So start, you know, leaning into people, start small, but in terms of families that want to see change, everybody doesn’t want change. And so that is the first thing that people have to recognize. And so if everybody wanted change, it’d be so easy. We’d always get together and be like, okay, we’re gonna change things. It’s not like redecorating a living room where everybody wants to get a new rug and now we can debate it. And so you need to build trust with your family that your intentions are good, just like in business. Family business or other business, you can’t just come in and be like, I’m the new kid, I want everything to change because people have been there doing it. So you have to earn your place and you earn your place by being a good, kind family member, listening and respecting what people that have come before you have thought, understanding their perspective. You do not have to agree with it, but take the time to understand where it comes from. You know, you might just be like, oh, grandma’s so stubborn. Well, why is she that stubborn?

Maybe she wants you to eat all your food because she didn’t have food when she was young. Like just take the time to listen. And then once you’ve done that, then don’t treat people like they’re not smart. So don’t try to manipulate them into what you want. Be very blunt. Grandma, I really wanna talk to you about something and this is so uncomfortable for me and I have so much respect for you, but would you mind if we got together? Cause there’s something I’d like to address.

And if grandma says no, then give her a month and go back to her again. And this time it’s, grandma, I brought this up a month ago and I really care about us and our relationship. I’d like to sit down and talk to you about something. She will say yes, eventually. Here’s the thing, most likely, your first difficult conversation, you’re gonna fail, in your opinion. Because if you have to, if you’ve waited, you’re pent up and the other person’s not ready. But that doesn’t mean you give up. You have that difficult conversation. You express that love and you express the goal for why you would like to see certain things change. It’s not for self-benefit. It’s for communal benefit and you keep trying. And the more it happens, the less people talk behind everyone’s back. And the more the person that you’re having this conversation with is part of the collective conversation.

Cause let’s be clear. Families gossip, work people gossip, you know, grandma’s difficult. I’m not the only one that thinks so. I’m probably talking to my cousins and my brother, my this. That’s kind of unfair. Um, it’s when you think about it, how would you feel if you were on the receiving end and everybody is too, um, nervous to talk to you, but everyone’s gossiping about you. And so you care enough to want something to change care enough to include that person in it instead of excluding them by doing it all behind their back. And we all do it, I do it. You know, you get on the phone with one parent, you talk about a sibling sometimes. And it’s not malicious, but then it just kind of gets out of whack. Instead, just source.

Ramia: So to all the families out there, Christina is advising you to make small changes to enable big conversations. Christina, thank you so, so much for joining us on the podcast today. We really appreciate it.

Christina Wing: Thank you. Have a great day and lean into those conversations.

Ramia: We shall.