Family business and legacy adviser

Episode 33: Why Your Kids Stop Listening to Your Wisdom | Steve Legler

Why Your Kids Stop Listening to Your Wisdom | Steve Legler

Episode 33

Have you ever tried to pass your hard-earned wisdom on to your children, only to realize they aren’t listening? I’ve been there. And the harder we push, the more likely they are to pull away.
In this episode of The Long Strange Trip, I sit down with my old friend Steve Legler, who works with wealthy families navigating the complicated relationships between generations. We talk about why parents often struggle to stop parenting their adult children, why the wisdom we want to give is better received when it’s invited rather than pushed, and how successful entrepreneurs sometimes bring the same management style they use at work into their family relationships.
Steve shares why humility, vulnerability, listening, and admitting our mistakes can help rebuild trust—even when years of hurt have created distance. We also explore forgiveness, sibling disagreements, family harmony, and why understanding someone doesn’t mean agreeing with them. I know this isn’t just theory. I’ve struggled with some of these things in my own relationship with my children. And one thing I’m learning is that repairing a relationship isn’t a destination. It’s a journey. Sometimes the best thing we can do is stop trying to be right and start making room for a real conversation.
Transcript

I’m Josh, the host of the show. We’re going to dig into six areas together, finding real work-life integration instead of that brutal 95-five split too many business owners live with. We’re going to approach retirement as an actual reinvention, rather than just stopping work, and we’re facing death honestly and avoiding PTSD around it. We’re also building resilience when life throws us curveballs. We’re sharing wisdom across generations, and finally, we’re understanding the patterns that show up in all our transitions. I’m not coming at this as an expert. I’m a fellow traveler, figuring this stuff out in real time, especially now as I navigate my own dual cancer diagnosis at 73. Welcome to the long, strange trip. I’m glad you’re here. Hey, how are you today? This is Josh Patrick, came with an old friend, Steve Legler, who I’ve known for I don’t know how many years through an organization called Purposeful Planning Institute, and I found Steve one of the more erudite and smart people there, and he is going to help us understand how you not gain wisdom, but how you impart wisdom to others. He works with wealthy families, and there’s a lot of facilitation there. So instead of me talking about it, why don’t we have Steve talk about it? So let’s bring him on. Hey, Steve, how are you today?

Speaker 1 1:26
Very well, thanks, Josh. I don’t know that I’ve been described as erudite very often, but I’ll take it. It’s that’s one of those 50 cent words. It’s a word I really like. Although my favorite word is sesquipedalian, which means user of large words. Okay. Okay. There’s a meta thing going on with that one. Yeah. So any rate, that’s been my. Sometimes I like ridiculous words, but at any rate, let’s talk about wisdom. I mean, you deal with with wealthy families that have really big problems with how to impart the wisdom from the senior generation to the junior generation and have them listen. So, first of all, what is the problem with doing that? There, everyone always asks, at what age do you start? You know, when do you start to tell the children that we’re a wealthy family, and when do you? And I always say, earlier is better, and going slowly and using the dimmer switch is better than having them in the dark and then flipping the lights on and blinding them, right? So, so going slow and sharing over time in digestible bits is very important. The issue that that sometimes occurs is somewhere in the teens to the early 20s, there’s almost this natural whatever my parents are saying is stupid, and I don’t want to hear about it. And you got to be able to get through that and onto the other side where they’re willing to come back and realize that you know mom and dad are actually they have some interesting things to share with me, but the hardest thing for some parents is they feel like they need to push the wisdom down, and the wisdom works better when it’s pulled down. So it’s honestly,

Speaker 2 3:14
go ahead. Sorry.

Speaker 1 3:16
So it’s the pushing on the string problem, and people think, well, I’m pushing, and they’re not taking it, so I better push harder. And the other, the real answer is, I better stop pushing, and I better try and create the conditions where they will want to pull it. And that comes in in meeting them where they are, and learning to listen to them, and not have the discussions be a one-way street, because for young people to be lectured by their parents gets old real quick, especially when sometimes the parents are just a little bit judgmental about things like work ethic and things like that. So many parents end up turning off their kids from what they have to say, and it’s hard to sort of realize that that laying off is better than pushing hard.

Speaker 2 4:13
So one of the areas that yeah, one of my six areas here I talk about is how to run a business without treating your children like employees, and I’m going to bet that many wealthy families are led by a patriarch most of the time, sometimes a matriarch who has built a very very successful business. Probably was really involved in the business when the kids were young, and the kids didn’t get much of mom and dad while they were building that, and the resentment stays way past 23. Stays the whole life. How do you deal with that?

Speaker 1 4:52
So the hardest people to deal with are those entrepreneurs to get them to change their perspective of what they’re doing because what has been successful for them for decades, usually at work, has worked quite well with employees, and the things that work with employees don’t necessarily work with your family members, right? So, getting them to want to listen to what you have to say without you acting like I am the expert, I know this. You don’t know it, so just listen to me. There’s so much more in the delivery of it that it’s not what you say; it’s how you say it. It’s when you say it. I saw something the other day about feedback, and feedback is not what you say; it’s when you say it, how you say it, where you say it. There’s all the little details of how you go about transmitting this wisdom that you have, that you want others to pick up, but acting like I am the smartest and you are lucky to have me to learn from, is not necessarily conducive to having that go well. So having the parents actually, this is one of the things. When there’s been a successful business, it’s rarely been a you know a straight shot from zero to millions, right? There are always hiccups along the way, and one of the things I’m often telling to these people is, can you share some of the mistakes you made? Can you share some of the things, some of the challenges you had to overcome? Because I don’t think your kids recognize that, and they have a tendency. Sometimes the problem is the parent has been so successful that that the offspring are looking and going, “Oh my God, I’m living in the shadow of a giant. I can never live up to that, and that creates its own challenges as well. And so, having the parent be have a little humility and admit that they’re imperfect, show that they have things that they can learn from their kids as well. Which technology kind of helps with that often enough. That like, you know, my my kids are helping me with stuff on my phone all the time, and I could just look like some okay boomer. You don’t get it, I’ll fix it for you. But at least there’s a little bit more of an adult to adult relationship, and that’s the issue. I saw I read something just the other day about parenting, and the guy who wrote it, Mike McGrann, and he wrote, an eight-year-old always needs parenting, an 18-year-old sometimes needs parenting, and a 28-year-old should not be parented. And if you take a certain definition of parenting being, you know, hands-on, I agree with that. And so somewhere, I have clients where the kids are 38 and 48, where they’re still the parents are still trying to parent them.

Speaker 2 7:45
Yes,

Speaker 1 7:45
and that that rarely works well. The later the later the later you wait to stop the parenting part, the harder it’s going to be.

Speaker 2 7:56
So what do people do when they’re 50 or 60 or 70, and they finally realize that they’ve blown it with their kids, and their kids really don’t want to have a whole lot to do with them.

Speaker 1 8:09
That’s hard, and it’s like that best time to plant a tree thing. The best time was 20 years ago, but the best time is today or tomorrow, and I think the big mea culpa, humble, honest. I’m sorry I screwed up. I know I did a lot of things. I did them for reasons that I thought were right at the time, and I’m realizing now that the way I went about it had a lot of shortcomings. I’d like to try again. I hope you’ll let me try again. I don’t know that all parents are able to actually say those words and say them in a way that’s believable. But if somebody said, “I really want to do this. What do you think I should do? That would be probably the first thing I would say, and then don’t expect that you saying that one time will flip the switch and they’ll come running back. You have to demonstrate that probably on a number of occasions, or repeat it and find ways to demonstrate it to build up the goodwill to put back some of those deposits in your goodwill account with your kids that that maybe you depleted over the years with treating them in a way that in retrospect you realize you were probably harder on them than you really wanted to be

Speaker 2 9:38
or needed to be

Speaker 1 9:39
or needed to be,

Speaker 2 9:41
yeah. Which

Speaker 1 9:42
is, and they’re not the same.

Speaker 2 9:43
No, they’re not. I, I’m guilty of that. So I, I know that that plant, that world really well, and it’s a struggle I’m having with you know my kids. Is that, okay, we have a relationship. It’s superficial. They never really want to get in anything deep, and breaking through that has been an incredible challenge. So it’s you know it’s something I think that you work on for years and years and years and years. Maybe you make a little bit of progress, you slip back two steps. So it’s sort of like one step forward, two steps backwards, three steps forward, one step backwards. And as long as you’re going up to the right, you’re probably going to be in a good place. Hopefully, you don’t die before you finish,

Speaker 1 10:26
and you really have to understand as you start that it won’t be a straight progression, and that you’re going to have you need to expect that there will be stumbles along the way, and this is where one of my favorite expressions is you know it’s not about the destination. There is no destination. It’s all a journey. And if you could learn to enjoy the journey and take the small wins and learn from the steps back to try and do a little bit better next time and be open about the fact that you’re not perfect, and admit it. And like the humility I’m talking about, about demonstrating, there’s always another chance to do that, and admitting the struggles that you’re having it, but without blaming the other people, of accepting you’re part of the blame, and asking for forgiveness. And if there’s if there’s things that you need to forgive the others, forgive forgiveness is something you do for yourself, right? If you forgive someone, it doesn’t change anything for them, but it changes a hell of a lot for me, and somehow, in many relationships, there there’s been hurt from both sides, and forgiveness and saying sorry and things like that. If you go first, you make it easier for the other. It’s

Speaker 2 11:58
been my hard

Speaker 1 11:58
to do, and it’s hard to.

Speaker 2 12:00
Yes, and that’s been my experience. My the word I use all the time is vulnerability. I think that the more vulnerable you are, and I think this is a general thing in the world, by the way, not just with your kids. The more vulnerable you are, the better chance you have of people thinking that you’re authentic, including your children. And it’s a process. I will tell you, because I go through it myself.

Speaker 1 12:25
Yes, and I and I bet you anyone who is a parent can relate to some part of what we’re talking about. And one of the things, like I often play a facilitator role for other families, and it’s unbelievable how often like parents will say to me like, why do they talk to you about this but they don’t talk to me? And I and I also well because you’re their you’re their parent. I’m not. I’m like the safe uncle that that they can that they can talk to because I haven’t been overseeing their lives often in too much detail for so long, so I can I get away with you know hearing things, and then sometimes one of the things I do a lot now is I explain that my kids don’t talk to me about this stuff either, like I was at my sister’s beach house a couple of summers ago, and my kids were upstairs on the rooftop deck with their aunt, and I was coming up the stairs, and then all of a sudden I stopped. I said, “Wait a sec, I can eavesdrop here, and you know she’s asking them questions that I would never even ask, and they’re answering it. I’m like I’m getting this information that they won’t tell me because I won’t even bother. I won’t even dare ask because it’ll seem like I’m prying. So it’s not that I have this magic wand. It’s just so hard to do with your own kids for many, many people. Probably most people. I would say most people. It doesn’t matter the level of wealth you have, and you know because you know, people with little wealth, you know, they often beat their kids when they were little, and they made a mistake, and you know that never they never do that. They never get up with that. There are plenty of mistakes to make as a parent, and I don’t know when my kids were born, it didn’t come. They didn’t come with a manual, right? And making it up as you go along, and you do your best, and you’re never going to get every step right. And if you’re vulnerable and humble enough to admit it, and you know admit that hey yeah, there’s a lot of things I wish I would have done differently.

Speaker 2 14:37
Yes, absolutely. So Steve, when you work with a person in your role as a facilitator, how do you go about helping bridging the gap between the two generations, from a facilitator’s point of view, not from you know a family point of view?

Speaker 1 14:54
No. So, for the facilitator, when I started doing this work, I really imagined that the bulk of the work was when I would be in the room with the whole family, and yes, that is an important time, and that’s where I really got to be on. But the secret to doing that work well-that’s like the game-you got to practice before the game, and the practice is all the one-on-ones you do with each family member to get each family member to trust you. So I need to develop the one-on-one trust with every single person in that family, so that when I’m in the room with them together, they all know and believe that I am them there for them. And yes, I’m there for their parents and I’m there for their siblings, but I am there for them, and I have their best interests at heart. At heart, and I always jokingly say I could only do my job as long as everybody agrees that I should be there, because if I manage to spoil something with one person by sharing something that they didn’t want me to share, or whatever. Like I’m effectively neutered. I can’t do my job anymore. As soon as one person doesn’t trust me, so I take that very seriously. It’s something that you can’t read in a book how you do this, but when you’re doing the work, you feel it, and you feel the pressure to, you know, be very discerning in what you say and when, and how you need to bring your calm to the room, and be able to ask people to rephrase something if you see that it didn’t land well, and call out things like, “Oh, did you realize that when you just said that that didn’t land so well? Now, do you want to try again a different way, or can you share with your dad why you had that reaction and now you’re kind of like trusting the person? Like remember two weeks ago when we talked about this, you mentioned something. Now I would like you to say it to your parent, right? So it’s all this stuff of developing this trust and trying to make sure that the right information comes out and is heard in the right way, and to just-it’s really when I first heard this term, holding the space-I didn’t like it, but now I love it because that’s what it is. It is holding this fragile space of family emotions and trying to make sure that all the conversations are productive.

Speaker 2 17:22
So, at the end of your engagement, do you believe that you have created family harmony, or you’ve helped create family harmony?

Speaker 1 17:32
That’s the goal, and it’s the north star. And I don’t know that there is something called family harmony as a destination, but I am always trying to make the family more harmonious. Okay,

Speaker 2 17:48
this is again a very interesting question for me. How do you deal with children that are very different, have a very different belief system about how the world should work, and specifically how their kids should be raised, and it’s really different how they do it. How do you bridge this gap to keep them from hating each other?

Speaker 1 18:10
Oh, so you’re meeting between the sip between the

Speaker 2 18:13
siblings.

Speaker 1 18:16
Okay, because

Speaker 2 18:17
I’m assuming, Steve, that one of the outcomes that you know, first gen one clients want is that after they’re gone, their kids talk to each other and they like each other.

Speaker 1 18:30
Yes, because all those decisions that they were making autocratically now need to be made democratically. Yes, and the people aren’t getting along. It’s going to be hard to make those decisions democratically.

Speaker 2 18:41
Yes,

Speaker 1 18:41
and they are all so different, and then the way they are making life choices start to be in conflict with each other, and so as a parent, the best thing I can do is show acceptance and understanding to each and every one, and understanding and agreeing are not the same thing. Yes, right. To be curious enough to understand, so you say, okay, I understand. I don’t particularly agree with it, but I support your right to do as you choose. And your sister over here and your brother over there, they have different views. And if the parent is taking sides with any views, well, then it’s kind of over already. So the best the best appellant can do is show the acceptance and the understanding of, and again, acceptance and agreement are not the same either, right? So if you can understand and accept even when you don’t agree, if you can demonstrate as a parent the ability to treat someone with respect, even though you don’t agree with them, but because you love them and they are part of your family and they have a lot of other good qualities, then if you as a parent can demonstrate that, you have a much better chance than if you are siding with one brother and sister against the other one over there,

Speaker 2 20:06
it makes certainly good sense. And unfortunately, I see parents too often siding with one side or the other.

Speaker 1 20:14
Yeah, yeah, I see a lot of parents who do things that make me go. This is going to be hard because, because I can see little tweaks that they could do that would make it not nearly as bad, and yet they won’t avail themselves to that because they’ve they that’s just not how they roll, right? There’s some parents. I read a blog every week, and one I wrote a little while ago, where I brought up this concept of the self-righteous parent. You know that oh well, I am right and you are wrong, and I’m hardworking and you’re not hardworking enough. And okay, if you’re going to keep bringing that up and lording that over your kids, then don’t be surprised when they don’t want to spend time. It’s not rocket science. Yeah, though, because you really want the best for them, so you want them to be more hardworking, and you want them to appreciate how hard you work, and you want all that, and you can’t have everything you want. So if you want to have all those things and you still want to have a relationship with them, something has to give, and I’d rather give up on some of those other things and keep the relationship.

Speaker 2 21:30
So when someone starts working with you, and their mindset is, you know, I would assume their mindset has to be somewhere in the wheelhouse that you can actually get some results.

Speaker 1 21:45
Yes. Oh, absolutely. I’ve had I’ve had more clients than I care to admit that I’ve started off with good intentions and thinking that they had good intentions, and then eventually I had to stop working with them because I didn’t enjoy banging my head against the wall, right? There needs to be some movement. Yes, I’ve had my share of clients who are somewhere between the immovable object and the irresistible force, or whatever those terms are, and they and they won’t move, and so these are the kind of people who approach someone like me with a. I’m saying it semi facetiously, but you know my kids won’t listen to me, so I’m going to hire you. So you tell them what I’m saying, and maybe they’ll listen to you. And like if that’s your attitude, like let’s not waste any of our time because it’s not going to work that way. This is a two-way street, and yes, I’m sure I can help you get your message, your important messages, heard by your offspring. And if you’re not willing to change anything in the way in your part of this, then this isn’t going to be success.

Speaker 2 23:02
Yeah, and there’s always two sides

Speaker 1 23:04
to a coin. In those, when people are this far apart, you can’t expect that you know it’s going to be this or that. There’s got to be the easiest ways for each one to approach the other. Now it doesn’t necessarily have to go fast, but they all have to do some of some of the movement, and and sometimes the feelings in the in the rising gen have been so they’ve been so turned off that they don’t want to make a move, and very often the parents are so set in their ways that they don’t want to move either. And my best bet in situations like that is to just try and chisel away a little bit, a little bit, a little bit, as to just micro moves in the right direction, and then pointing out to this side, hey, you notice, you know, your parents actually agreed to something, which you know, a few months ago, if I would have told you that they would do that, you might not have believed it. And on the other side, hey, you know, you didn’t think they would do this, but now they’re starting to show up to the meetings and take a little bit of responsibility. So we’re making progress, and just to me, as long as I can finish a meeting and have the next meeting on the schedule and be 99% convinced that all the people are going to show up again, and we’re going to do this again, and we’re going to talk a bit further, and we’re going to move the ball a little bit further down the field. If I can know that they’re going to come back together and reconvene for another meeting, then that’s a large part of the battle that I have is to just keep them coming back and continuing the discussion, and having thought about the things that were discussed in between on their own, and also with me, and in perhaps in small groups, and then get ready to all come back together and say, “Okay, last time we talked about this. You said you were going to do this. You’re going to look at this. Where is this now? How are things evolving? And just move slowly but surely. It is a it is not a destination. It is the journey, and I am there to accompany them on this journey, and help it go well, and help these conversations happen in a productive fashion. Well, Steve, we’re going to have to leave it there because we are out of time. All right. So, what would you like people to do after they watch this podcast or listen to it, how they contact you, and do you want them to contact you? If anything I said resonates with you, I’m always willing to jump on a call and talk about, particularly a family situation, whether it’s whether it’s someone from a family or someone who works with families who understands what I’m talking about but wants a little bit of guidance on how to help families move forward. I’m very active on LinkedIn. I have an easy name to spell, even and it’s not common, so I’m easy to find. There’s only one vowel. It’s an e. It shows up twice in my first name, twice in my last name. Steve Legler, you Google me if you put family business or whatever. I’m sure to show up. Hit me up on LinkedIn and sign up for my blog and read my blog. Listen to the podcast that I host and I’m on. And if anything resonates and you want to chat, I’m almost always happy to do that. If you’re trying to pitch me something, probably less likely. But if you just want to chat about this kind of work and working with families to help them have better conversations to increase the chances that their transition of their family wealth from one generation to the next will go well, that’s the work that I enjoy.

Speaker 2 26:36
And I’ve got two things I’d like you to do. The first is please go wherever you’re watching this podcast or listening to it, and give us an honest rating review. Love it, she gives five stars. You hate me, give you one star. I will cry big crocodile tears, but you won’t see it. So that’s the way it is. The second thing is, if you think you’d be a good guest with the show, I’m always looking for great guests. Just send me an email. We’ll set up a time to talk and see if this is right for you. My email address is jpatrick@stagetwosolution.com. That’s the number two, and solution is singular. It’s jpatrick at stage two solution.com. This is Josh Patrick. We’re with Steve Legler here at the Long Strange Trip podcast, and I really do need to have a truck and is our outgoing song because this is a Grateful Dead title. But thanks a lot for coming by, and I hope to see you back here next week. Thanks for spending this time with me today. I really appreciate you being part of this journey. I’d be grateful if you’d leave an honest, ready-to-review. It helps other people find these conversations. Lets me know what’s landing with you and what isn’t. If you love the show, give us five stars. If you hate it, give it one star, and I’ll just cry a little bit. Keep asking the hard questions. Keep being honest about what’s difficult. And remember, we’re all just trying to figure this out together. I’ll talk to you next time on the long, strange trip. Thanks for stopping by.

Transcribed by https://otter.ai

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