Navigating Family Business: Millennials, Boomers, and Bridging Generational Gaps at Work

Briana Dai [00:00:00]:

And then what we find is we're making really costly mistakes that end up costing you more time, more money, more headache in the long run, right? Than had you taken maybe an extra hour to take a step back and to really think about it. I get asked about more than my brain injury. I get asked about it more than what it was like to work with Mariah Carey. And that is All right, well, welcome to She Means Millions. This is your girl Briana, and I'm coming at you with a solo episode today. And this one is going to be funny because I am feeling a little spicy this morning, to be honest. If you know the kind of morning I've had, you would understand. And I know you all have— I know you understand because we've all had one of those days.

Briana Dai [00:00:49]:

So you're getting ready to see a real and very unfiltered episode on a topic that I get asked about more than my brain injury. I get asked about it more than what it was like to work with Mariah Carey, and that is what's it really like to work with baby boomers who happen to also be your parents? And they're not here for this one, so I can really go in. But in all honesty though, it's not gonna be, I'm not gonna dog on them because I love my parents and I love working with them. Um, but there are some fundamental differences and I think that this is a really hot topic, not only for the millennial perspective working with an older generation or even Gen Z that's working with an older generation because now you know, I might as well be a boomer to a Gen Z, you know what I mean? Like in terms of the way that we think and the way that we process. So cross-generational working can be challenging just because of fundamental beliefs, uh, the way that we do things, the way that we process information, the speed that we process information, all of the above. And I have been in this company now for 8 years. Oh my God, it's been 8 years. Wow.

Briana Dai [00:01:57]:

That's wild to think. But I have learned a few things and it wasn't always pretty. I mean, I, and one of our early episodes, like our episodes, I think I shared the story of, uh, one of the women who was a project manager. She reported to my dad, the OG, who was the president at the time. Now he's the co-founder because, hi, I'm the president now. Um, but she, she actually reported to me but worked closely with him. So I was having a one-on-one with her, just asking her like, how are things going? You know, how are you feeling? Just, you know, doing a vibe check with an employee like one does. And she said, sometimes it's really uncomfortable how you talk to Kim.

Briana Dai [00:02:38]:

And I was like, oh, I get it. You wouldn't talk to your dad that way. And she goes, no, no, no. I wouldn't talk to my boss that way. And I remember that being a pivotal light bulb moment for me in terms of compartmentalizing between the environment that I'm in. It's one thing to— you can't treat people the same way in every single environment. An individual is a function of the environment that they're in. So, and you might act differently.

Briana Dai [00:03:03]:

This is just another example to go on a completely different rampage, but I think it paints the picture the most cleanly. So you might act differently as an individual when you're functioning in a church with your spouse. That's a totally different environment, right? When you're going to church together versus after date night with your spouse and you're in the bedroom, right? Like you're gonna have a completely different energy and a completely different set of, um, for lack of better words, uh, functions than you would if you were an individual in a different environment, right? You're going to behave differently based off of the environment that you're in. And for me, I really had to understand that I had to function differently in the environment of the job versus the environment of the home that I grew up in. The way that I would talk to my dad, or maybe sass my dad when he's getting on my nerves when we're just having a conversation outside of the workplace, is a different function that I had to show up with when we were in the office, and I had to really master that skill. And I'm grateful that, um, you know, my, my family understood that I was learning. You know, when I joined the company, I was 27. So granted, you're supposed to have a certain level of maturity, but you're still learning some things.

Briana Dai [00:04:16]:

You're still learning business acumen. And I had never been in a professional, like, corporate-like environment. I was a solopreneur my entire life. So learning the politics, learning how to compose yourself, learning how to behave not just amongst your peers, but peers that also to be relatives is so important. And I feel like this is a conversation that is so important to have because I know many of you are either boomers who are bringing your children into the business, or you maybe are the child that's listening that's coming into the family business, or maybe you're not the child at all. You're just cross-generational working with older individuals and they sometimes feel like your parents and you just want to like strangle them a little bit, but you can't because you're at the workplace. And so that is a conversation that is essentially the one that I want to have. And I think that takeaway number one is learning to behave based off of the environment that you're in and being able to take a step back, take a breather before you respond.

Briana Dai [00:05:11]:

I'm much more methodical now when I am feeling like triggered or heightened or like I don't agree. I'm less likely to quickly snap back about my disagreement and sit with it for a minute, think about how I wanna respond, and then come back in a more professional way. And that has been a game changer in terms of my evolution, my growth, and just my leadership, not just working with my parents, but with every single one of the team members, because at the end of the day, we wanna want to create an environment where everyone's ideas are heard. No idea is stupid, even though sometimes you might in the back of your head be thinking it. You can't say that if you want a healthy environment. And I think that that culture is so— I don't want to say unique to eWomen Network, but based off of feedback that I've gotten from employees that have come from other companies or had other experiences, you know, we do have a really great culture. And it's because of our core values. One of our core values is we are committed to clear and transparent communication communication guided by the rule of good intention.

Briana Dai [00:06:10]:

And we start every meeting with more than 3 people with our values. And that is, I think, been such a good level set and a reminder just when we go into the meeting, before we launch into it, we always recite all 10 of our values. And that has been really helpful, I think, in terms of not just having them on the wall, but actually reminding ourselves of them on a multiple times a day basis and being able to then live them because you start your meeting off with that preface, with that mindset. So that is number one. Um, so let's talk a little bit about times that, you know, more specifically, maybe the boomer and the millennial, millennial generations clash. So growing up, I was in a very traditional household, right? You obeyed your parents, right? You listened. Yes, ma'am. No, no.

Briana Dai [00:07:01]:

Yes, ma'am. No, ma'am. Yes, sir. No, sir. But don't ever say no. It's always yes, right? Because otherwise you're gonna get grounded. You're gonna get privileges taken away. Like there was, It was not, it was a very traditional upbringing based off of how they were brought up.

Briana Dai [00:07:14]:

And so it was really hard for me coming into the family business at first, getting comfortable disagreeing, you know, standing my ground, saying what I really felt because of the programming of, I'm not just saying no to a boss, I'm saying no to my parents. And I always learned that if I do that, I'm gonna get in trouble. So there was a lot of reprogramming when I came into the business that I had to relearn. And I think that one of the most valuable things that we did as as a family unit was, okay, we're starting this relationship. I'm in the office full-time. I'm coming in as a manager, and sometimes I don't agree with what my parents have to say. And at the beginning, I really held a lot of emotions in. And what happens when you hold an emotion in, right? It just keeps piling up, and suddenly you find that you get to a boiling point.

Briana Dai [00:08:06]:

And once you hit that boiling point, then you have an explosion. And I'm a Sagittarius, so when I feel the need to explode, it's usually messy, and that is not something that we wanted to create. That's not the dynamic that we want to have, because at the end of the day, I love my parents so much. I have a great relationship with them, and I realize that that's not something that everybody has, and I realize that I'm privileged for that. I have had a phenomenal upbringing. I've had a very blessed life in many ways, and I'm extremely grateful for that. So coming into the business, I didn't want to get to a point where I was so frustrated with the family dynamic that it was impacting our dynamic outside of the office. I never wanted to get so upset about something in the office that it would compromise our family unit outside.

Briana Dai [00:08:54]:

I never wanted to avoid the calls from my mom because I didn't want them to be about work. I never wanted to not come to the family dinner because I was mad about something that came to the office, that happened at the office. I never wanted to be in a situation where now I'm not doing holidays with the family because we had a a tiff about something that happened at the workplace. I never wanted that to be the case. And so for me, a couple of things had to happen. Number one, um, and it's gotten a little bit easier now that we're 8 years in. I don't, I'm not as conscious about this, but for the first, I would say 5 or 6 years, I had to, I literally still to this day have my mom saved in my phone this way. She's Mama Sandra Yancey in my phone.

Briana Dai [00:09:33]:

The reason is because based off of who I'm talking to, I might say, hey Siri, call Sandra, or hey Siri, call mama. And that's, for me, it's a distinction because in my mind I almost had to separate the 2 entities, right? Because just the same way that I had to change, I'm a function of the environment. I noticed that my parents are different in this environment and everyone is operating at a different level from a different vantage point when they're in work mode. And so for me, I had to recognize that it's not just me that's different, it's them that's different. And instead of holding things in that I don't agree with and letting them bleed into that personal, right, we had to have an opportunity that we could air things out. Because to say that, oh, you just leave everything at work and you don't bring it home, that is a fallacy and that is utter BS. Because I don't know, maybe men can do it, but as a woman, you don't just leave it at the workplace. You don't just leave it in the car and walk in the door and forget about the day.

Briana Dai [00:10:35]:

When you're a highly empathetic person, you carry that, and those emotions would carry over. And there did come a time at the beginning when I wasn't good at speaking up and speaking my truth and standing up for what I really believed in. And I was going along to get along and doing things, particularly in marketing, that as a millennial that was very proficient in digital marketing, maybe I didn't agree with the direction, but I didn't feel confident enough to speak up. And that was pressure that was building and building and building. And so I had to start to not only compartmentalize the difference between mom and dad Sandra and Kim, but also to be able to say, hey, we need to have a family meeting. And that meeting rarely ever happened in the office. It was always, we have a family room at my parents' house, which I grew up in from the time I was in high school on out. And we would have meetings in that, in that little family room, and there's 4 chairs in it, ironically.

Briana Dai [00:11:29]:

And so there's 3 of us, but I also have a brother, my younger brother Ryland. And people often ask, is Ryland ever gonna join the business? And I don't think he ever will unless maybe once mom and dad are out. And maybe I can see a world where Ryland and I team up. But then again, maybe not, because he's a Taurus and I'm a Sagittarius and we butt heads quite a bit. But who knows? I, I wouldn't put it past us. We'll see what happens. He's great at sales. He would be a really great asset to the team.

Briana Dai [00:11:51]:

I would love to get him in here, but let's not go down that path right now. Ryland, if you're listening, let's talk. But all of that to say, that 4th chair was a really helpful chair because that became Ryland's chair, and he's kind of the unbiased 3rd party. Ryland has really kind of been the secret like, I wanna say weapon in terms of making this family work office home dynamic work. Because when Ryland's in the picture, Ryland isn't involved in the business. And so he can see things extremely black and white, and he's almost like a, like a little bit of a, a referee. And he's not afraid to call me on my BS. He's not afraid to call our parents on their BS.

Briana Dai [00:12:29]:

And whenever it is the family together, we're also really intentional about the fact that We can't let dinner time, family time get sucked up talking about business, which is easy to do when you love your business. It's easy to start to wanna talk about things that happened at work or things that are going on or things, things that are, you know, ideas that we're having or going off on tangents about the company. It's easy when you love your work to do that, but it's also really hard to do that when there's somebody at the table who's not involved in the business at all. And so Ryland, like I said, has been a secret weapon, not only in terms of helping us level set when maybe we're not agreeing all the time, but also in making sure that family time stays sacred and that it doesn't get, it doesn't start to turn into a work dinner, which like I said, it's, it's easy to do when you love what you do because it doesn't feel like you're talking about work. It feels like you're talking about a passion. And so for me, I've loved having Ryland kind of as a, um, quiet, although he's not quiet at all if you know him, but kind of like the, he's kind of like the steady behind the scenes that no one really sees. People are like, we ever gonna meet Ryland? He actually came to Icon for the very first time this year, which was really special for him to come on stage for people to see him in person. And, um, and he's, he's amazing in that way.

Briana Dai [00:13:49]:

So when I was at the beginning having a hard time finding my voice and my footing in the family business, we would have these family meetings. Ryland would always be present and it would oftentimes be me that's like, hey Ryland, I need backup. And sometimes he wouldn't be backing me up. And I needed that. And it's hard. It was a hard pill to swallow. And as a stubborn woman, Um, like I said, I'm a Sagittarius. I don't know if anybody gets down with astrology, but we're, we're pretty stubborn and set in our ways, and it's hard for us to receive feedback.

Briana Dai [00:14:20]:

But I really had to get better at receiving feedback.

Sandra Yancey [00:14:24]:

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Briana Dai [00:14:54]:

I think a lot of millennials in general struggle with feedback from senior positions because maybe they're like, well, that's not how we do things now. But here's the thing, I had to learn the rules like a pro before I could break them like an artist. So when I came into the company, it was so easier for me to say, oh my gosh, this is a headache, this is overwhelming, this is too much, we need to burn this down, we need to do this. But I hadn't really learned all the nuances of the company yet. I think a lot of millennials come in and they want to move so fast that we don't take the time to take a step back. And that is the beautiful thing about the baby boomer generation and probably even the Gen X generation as well, and that is They are very methodical, and even though they don't make decisions and move as quickly as the millennials and especially not the Gen Zs, there is some beauty in slowing down in order to speed up. And I think that that's been the biggest silver lining in terms of my personal development in the company is working so closely and learning directly from my parents, who yes, they're baby boomers, and it's easy to say you know a baby boomer has. I'm, I'm gonna say my parents don't.

Briana Dai [00:16:01]:

My parents are very much with it. But there is definitely, I think, a stereotype, just like there's stereotypes about millennials, just like there's stereotypes about Gen Z. There's always people that aren't— that don't fit the stereotype. But the stereotype says that baby boomers are outdated, baby boomers make decisions too slow, baby boomers don't get on board with technology. My parents are all over technology. Um, my parents are definitely decision makers, but they do tend to, uh, process things a little bit slower. And I have found that I'm a better person because of that, because they have forced me to slow down. And so millennials, Gen Zs, if you're listening to this and you're the type that has a hard time working with somebody that might have a little more years on you because they don't process or they don't move as quickly, maybe there's a reason for that.

Briana Dai [00:16:52]:

Maybe that's the opportunity instead of getting anxious or frustrated or annoyed To sit back and say, wait, maybe I should weigh the pros and the cons of this scenario, because sometimes you do have to take a step back. And maybe that step back is an extra hour or an extra day to really think about all of the plays before you can truly take a leap forward. Because that's the thing in business is sometimes we're so quick to just want to jump to the thing, but we haven't taken the time to really think about what is the ripple effect? How might this impact something else? It's kind of like playing a game of chess in business, right? And when you put, So when you move this piece, it opens up that possibility for something else to fall down. And everyone wants to protect what? The queen, right? And so you have to ensure that no matter what step you're taking, you're not jeopardizing the bigger picture. And oftentimes I have experienced millennials, they wanna move so fast that they're not truly looking at the play and how it can impact all of the other pieces. And then what we find is we're making really costly mistakes that end up costing you more time, more money. More headache in the long run, right, than had you taken maybe an extra hour to take a step back and to really think about it. I have become much more methodical, and I 100% owe it to the fact that I have been directly mentored by baby boomer parents, people who are brilliant business people, people who have built multi-million dollar businesses.

Briana Dai [00:18:21]:

You know, yes, millennials are fast. Yes, we can find anything on AI. Yes, we can do all the things, But that's information. What you don't have from AI is wisdom. And there is undoubtedly some, like, off-the-charts wisdom from somebody who has a few years on you, who has been around the block, that knows a thing or two, you know? And so I really love and value my parents and the baby boomer generation from that perspective because you wanna make sure that when you're taking wisdom from people, They're people who have done what it is that you want to do, you know. And in my case, I do have parents who have had very successful careers, built a very successful business. It would be foolish of me to not want to learn from their wisdom, to learn from their mistakes. And in taking that wisdom and coupling it with my digital savviness and my innovative thinking and my ideas, together we have really formed a true superpower.

Briana Dai [00:19:18]:

And it's all because we respect each other and we respect each other's differences. And so, So again, this episode really is meant for not just the boomer, but especially the millennial, especially the Gen Z, especially the person that's coming up in an organization. I really, I really hope and pray that if this has landed in your podcast feed today, that you're really taking this in and you're recognizing that sometimes the biggest lessons come from slowing down before you speed up. This also kind of ties into another fun little thing, things that that I wanna protect versus things that I wanna change. You know, and mom and dad, if you're listening, we'll meet about this at the EJT on Tuesday. But, um, you know, I think that growing up and having the— I'm actually really grateful that we're all in alignment on this. Recently in this past year, we've been very public about the fact that we're currently in the thick of 10x-ing the business, right? We're 10x-ing the business. We have a goal to do it within 1,000 days, and we're getting ready to enter Q3 of the Of the 1,000 days of doing that.

Briana Dai [00:20:25]:

So I don't know how many days that is in terms of the 1,000 days, but we're almost halfway there. And so what I would like to talk about a little bit is the evolution. And so oftentimes, and this is, I think, the opportunity for a baby boomer that maybe does have years of experience, it's really easy to fall into the trap of, well, this is how we've always done it. This is the way we do it and this is what works. But even if you're on the right track, you'll get ran over if you just sit there. So I'm grateful that this isn't the case with my parents, but we are always looking at, okay, this is how we've done it for the past several years, but maybe this isn't the way that we should continue to do it. And I find that that conversation has been extra well received now that we are in the midst of 10x-ing because all of our systems that we currently have, we can't operate at the 10x level. So everything needs to be reevaluated.

Briana Dai [00:21:16]:

How can we streamline? How can we move faster? How can we multiply our results? And so every single thing in our business right now is truly about not just just executing on what's worked for the past 26 years, but what— how— what— how can we do this differently? And so it's not a matter of saying, well, we've always done it this way and it works, and if it ain't broke, don't fix it. That is the kiss of death if that is your mentality. That is the secret to truly getting left behind, particularly in the world of AI, because I can guarantee you, if you've been doing something that's worked for a while, there is 1,000% a way to do it 1,000 times better faster, more efficiently, less expensively, all of the above, if you're willing to take a step back and look at what you've always done and say, how can we do this in a better way? So we're doing that with every single system, every single campaign, every single event, every single new workflow that we're executing on. How can we do this better? And that's the conversation that I think is really important to have. So for me, that's not a conversation that should be had just in the midst of wanting to 10x. It's a conversation that should probably be had every quarter once we're getting ready to plan out the next quarter. Like, okay. We're getting to roll out X, Y, and Z campaigns.

Briana Dai [00:22:31]:

We've always done them. We've kind of just done a rinse and repeat, updated dates, updated photos, but kind of ran the same campaign. Well, maybe it's time for a refresh. And what I think is so interesting about how we have all changed in this past year of really honing in on this 10x journey is every single thing we're looking at that way, you know, and we're looking at it consistently. And I hope that it's not just something that we revisit this year. But it really is something that should be revisited every single year. Okay, it worked really great last year. We don't wanna break it, but is there an opportunity to make it better? Is there an opportunity to execute this in a more efficient way? Those are really critical components that I think that num— number one, as the key takeaways for this episode, looking at the function of the individual in your environment and being an individual in an environment, how do you function differently? Especially if you're working with cross-generations, especially if you're working with family, looking at If it ain't broke, don't fix it.

Briana Dai [00:23:29]:

That is not the mentality of somebody that's really looking to grow their business or really trying to evolve. And I think that there is a very professional way if you're a younger person trying to put pressure on a system. I think that there's the biggest mistake that I made coming into the business at first was wanting to do that before truly understanding the system, before truly having a complete and total grasp on the ripple effect of when I change X, how does it impact Y? And that is really critical. And then also just having really great communication when things aren't feeling right, calling that meeting. And sometimes having it in the office isn't the place to do that. If you don't work with those people, those people that you work with that you're wanting to have the conversation with aren't family, don't do it at a house. That's not professional. But maybe go out and do it at a restaurant, do it on a neutral ground or somewhere outside of the workplace where it's less charged, and just have the conversation.

Briana Dai [00:24:23]:

Call that meeting and just talk about What's on your mind, because I guarantee you most people, most companies, particularly if you're working for a good one, they want to create a happy, healthy culture, and they want to see the people that they've hired win. And if you're feeling like you're in a situation where you are bringing ideas but you can't speak them, or you don't feel empowered to really push back on them, and you feel like you're not winning, but you know at your core that this could not only impact maybe you but the company, if you truly have the company's vested interest to grow and to help it. Then you owe it to that founder, or you owe it to that manager, that superior, to let them know like, hey, this got squashed, or I didn't feel empowered to say it in the moment, but I really believe that this is the direction that it needs to go, and here is why. Backing it up with the why and what value that you think that that could bring is so critical. But oftentimes we just accept it, we just throw our hands up. Well, that's above my pay grade. And that's— oh, that's the other piece I'm going over on this episode. But I do want to say one more thing.

Briana Dai [00:25:21]:

This kills me. This kills me about millennials. I've experienced it with hiring and hiring Gen Zs is you almost want to act as though you deserve the promotion before you've earned it. It's almost like you don't want to do the work because you haven't— you're not getting paid enough for that yet. That's the mentality. Every single promotion that I've made has been a result of me showing up as a person worthy of a promotion before I've gotten the promotion. Every single uplevel, every single opportunity has come from me going above and beyond, not the opposite, not saying, well, I don't get paid enough for that. So I'm not going to do it, or I'm not going to put in the hours.

Briana Dai [00:25:57]:

Girl, come on. That, that to me is the sign of somebody that it's not promotable. If somebody is not willing to put in the extra work, if somebody is not willing to go the extra mile, to me, you're signaling that you are not somebody that is worth me promoting because you're not. If I, if I can't see that you're going to put in the work now, what's going to make me believe that you'll put in the work later? So if you're somebody that maybe is working in an environment where you're trying to climb the ladder, Then put in the time. Make sure that it's known that you're a hard worker, that you want to do the work, that you want to be promoted, that you're going to bring new ideas, that you're going to bring new revenue streams. If you can't prove those things, then you are not promotable, period. And so that is my mic drop moment because you know what? She does not just mean business. She means millions.