Episode 335: Steve Legler on 100 1-minute conversations

May 21 2025

Episode Description

Steve Legler joins me for a return visit. Steve was an early guest, in Episode 32 back on August 7, 2019. Today we talk about the value of moving away from the concept of one big, multi-hour conversation on an important topic toward ongoing bite-sized conversations. I appreciate Steve’s work and value his friendship. As you will hear, Steve was kind enough to be willing to record this episode when my voice wasn’t at its best.

You can learn more about Steve’s work and sign up for the blogs and newsletter that I enjoy here: https://stevelegler.com/. You can find Steve on LinkedIn here: https://www.linkedin.com/in/steve-legler-mba-fea-cpcc-259065a/

Do you have comments or suggestions about a topic or guest? An idea or question about conflict management or conflict resolution? Let me know at jb@dovetailresolutions.com! And you can learn more about me and my work as a mediator and a Certified CINERGY® Conflict Coach at www.dovetailresolutions.com and https://www.linkedin.com/in/janebeddall/.

Enjoy the show for free on your favorite podcast app or on the podcast website: https://craftingsolutionstoconflict.com/

0:46
Steve Legler joins me today for a return visit. Steve was an early guest in Episode 32

0:54
back on August 7, 2019

0:58
today, we talk about the value of moving away from the concept of one big, multi hour conversation on an important topic for ongoing, bite sized conversations. I appreciate Steve’s work and value his friendship. As you will hear, Steve was kind enough to be willing to record this episode when my voice wasn’t at his best.

1:31
Hello, Steve and thank you for coming back to the show.

1:35
Well, thank you for having me back. I don’t even remember how long ago it was, but it was a while so absolutely fresh things to talk about,

1:44
I am counting on that. And even if they weren’t fresh, I think they would be interesting. And I will tell you way back episode 32 and that was August 2019

1:57
oh my god. And now you’re at episode 300 something.

2:00
300 something, exactly. So pretty exciting and a lot of fun along the way. I am grateful for my early guests when I was still figuring out a few things, and I probably was still figuring out quite a few things at that point. But in case someone has not heard that, and because life changes and we all evolve in our work. Please tell folks a bit about the work you do and how you came to be doing.

2:29
Okay, well, I work with families, and I work with families who own assets or a business together and are attempting to eventually transition the ownership of those assets from one generation of the family to the next. So sometimes I work with parents and their offspring. I didn’t say children, because when they’re adults, they’re no longer children, and I work with them in a bunch of different ways, facilitating family meetings, coaching rising Gen family members, helping them plan family retreats, all the continuity planning around the family and the ownership, not so much the business, although I do still work with some companies that have an operating business and work on them, what we call the business circle Sometimes, but I concentrate on the Family Circle. My business card says I’m an independent advisor to families. I’m not affiliated with anyone. I’m a free agent. I love working with other advisors and team up. And I came to do this because I grew up in a family business, and then somewhere along the line, in my late 40s, stumbled into a program called family enterprise advisor here in Canada, and that’s where I had my calling. I didn’t realize that there were people who did this kind of work, and I finally figured out what I wanted to be when I grew up when I was 48, not bad.

3:57
Well, what do they say? Better late than never. I think it’s also true that the journey to get to where you are when you find that’s what I’m supposed to be doing, can be so valuable. Looking back on it sometimes to say, Oh, I didn’t know at the time that that was going to be useful, and yet it was.

4:18
Yes, so many parts of my life come together now in my work, if I had to sketch out in reverse a good career path to get to be able to do what I’m doing, I did pretty well. Had different kinds of experiences and training and situations I was part of that all add up to my life experience and the way I am now able to be with clients to help them have the conversations that they know they need to have, but aren’t necessarily able to have left just to themselves.

4:56
Excellent. Well, I did hear, of course, the word offspring. I know that one of your favorites is to get across this idea that it sends a message when we refer to someone who’s 40 years old as a child.

5:11
It drives me nuts when I hear people talking about families, and they’re, you know, they’re the parents are in their 80s, and then they say, well, and then the kids, and the kids are in their 60s, and we grant our grandparents themselves ready. So I don’t love the word offspring, and it’s because it’s off putting sometimes to some people, but I say it more often to make that just a distinction. And as somebody I forget who came up with this one though that adult children is an oxymoron. They’re either adults or they’re children. They’re not I

5:45
love that. So communication, I know, is one of your strengths. I know that because you’ve written books, and I know that a particular relevance today is the wonderful messages that come across my screen with regularity. How

6:03
did you get started sending out these wonderful blog posts? It’s

6:08
really interesting because I started, I think even before I discovered this field, before I entered that family enterprise advisor program, I knew I wanted to do something with families. I think I thought more about the business side than the family side at first, but I decided that and my kids would ask me, they’d see me every weekend, I’d write a blog, and every Monday, the blog goes out to subscribers. My kids were still young teenagers, and they’d see me writing these blogs, and one day, one of them asked me, dad, who reads these things? And my answer at the time was, well, I don’t know, probably not very many people now, but with time, more and more will. But what I do know is nobody’s going to hire me if they don’t trust me. True, nobody’s going to trust me if they don’t know me, so I am sharing about me, and if we had cameras on you would see that I’m now tapping my heart, and now I’m tapping my temples. I write from here and from here, and I try to combine those two parts and share about myself, but to talk about this work and how important it is that families do this work, how hard it is to do this work, and all the things I’ve discovered along the way, as I’ve engaged with more and more families over the years and spoken to other advisors over the years, there’s so much to know and so much to learn. I keep learning, and I want to share with others, because there’s a huge need for people who do the kind of work I do. There is, unfortunately, though, not enough demand for it. Families have the need. Don’t know that there’s a place and there are people who can help them with that need. Yeah,

8:01
yeah, stumbling along in the darkness, not knowing there’s light right around the corner, it is a little frustrating. Well, I can speak for one reader that I am grateful for. What you share is always of interest. And as I told you when I asked you if you would please come back to the show, there is one particular concept I cannot remember the name, the headline, the subject line that went with it, but the concept I cannot shake it comes back into my head so frequently. And I will paraphrase it. You can clean it up. That’s great. And then I’ll ask you to tell us what you were thinking and what message you were trying to get across. Just maybe not what I heard, but it is along the lines of this, not one 100 minute conversation,

8:57
but 101

9:01
minute conversations.

9:03
Yeah, that’s you did a pretty good job. And in fact, you’re paraphrasing me, and when I wrote it, I was paraphrasing someone, and I don’t remember who to give the credit to. Okay, wish I could. So you’re giving me the credit, but I should be passing it to someone else, and I can’t, because I don’t know who it was, but so let’s just talk about that. So much of this work involves families who have things that they should be talking about, and they know they should be talking about, and yet they aren’t talking. Why is that? Probably because they’re worried, they’re scared. They think it might go bad. Maybe it already went bad another time when they tried it. There’s all kinds of reasons. And so often the elders, the parents, are apprehensive about the conversation, and so they it gets sort of stored up and delayed, and then they want to just get it over with. They want rip off the band aid, and they want have one meeting. We’re going to have a family meeting, and we’re going to tell them all about our estate plan, and then it’ll be done, and the band aid will be ripped off, then it’ll be finished. And it’s like that expression about plans are useless, but planning is indispensable. It’s the planning, it’s the doing, it’s the talking. People think it’s the destination of, okay, we revealed our estate plan, but it’s it’s all the conversations that the family should have been having, should be having, should be dripping along over weeks, months and years, not trying to cram into a three hour meeting. So all concept is do a little bit at a time allow people to adjust. It’s that old timber switch versus flipping the switch on the flood lights so often the family is in the dark, and then Mom and Dad decide they want to just turn on the flood lights and share. And then what happens when those lights come on? Everyone’s blinded and they’re kind of out of it for a minute. Well, if you take the dimmer switch and you you turn it up a little bit and you let people see a little bit, you turn it up a bit more. Their eyes have time to adjust, and it’s the same thing with these 101 minute conversations. And actually the place where I think it applies the most is really in parenting in general. Now I’m talking about parenting children right where they still are children who live in your house and walk out your door and hop on the school bus and come back those, those kind of children. It really applies that people, you know, I get invited on on people’s podcasts, and they want to talk about, how do you talk to your kids about money and all this and it you don’t sit down one day and say, Now we’re going to talk about money for the next two hours true. You have conversations in everyday life, when you go to McDonald’s, when you go to the store, when you watch a commercial on TV. I always tell families they should watch Shark Tank or some show like that, because when my kids were Tina, you know, someone come on and say, I want $100,000 for 10% of my business. And I would pause the TV and say, okay, so how much does this person think their business is worth just talking about money? And it’s often wealthy families, right? They don’t want to talk about money. It feels taboo, sure, but if you if you can normalize that money is something that it’s an essential tool in our society and how it works, help them understand how it works. And then along the way, if you could say, and you know, mom and dad are really lucky we live in this nice house, and that’s because grandpa, who did really well in business or whatever, you can talk about those things a little bit at a time in a bunch of little conversations to normalize it and allow people to adjust to the message and learn from it, and then take in another part of the message a week or a day later, and you can see people learn, and you can adjust what you’re telling them to how you see how they have understood What you’ve already said. And if you try and do all that in a two hour meeting,

13:24
oh no, no. I love the word normalize. I think it applies to so many topics that when you dump everything all at once, that’s there’s nothing normal about that. This is a pivotal moment kind of thing instead of, well, here’s an opportunity today. We might have another one next week, and then we might create one next month to talk about whatever it is, to talk about estate planning, to talk about as they’re younger. Of course, the more frequent ones of, how do we feel about generosity? How do we feel about our good fortune? So different from I’m going to give you a lecture now, and as as you say, the whole Okay, thank God. It’s all over now. I did it once we had the talk, whatever the talk was about, ever again, which makes no sense. One thing that comes to mind, and it hadn’t really, because I have been, as I said, this thing just keeps rolling around in my head, but this is something I didn’t really think about until you started talking. It is scary for a lot of people to tackle these topics, but it seems like it might be less risky to do it in tiny, tiny increments, instead of here comes the whole dump truck. Do you think that’s true? Yes,

14:45
absolutely. And in fact, I read a weekly blog. I also put together a monthly newsletter where I start off with just the tip of the month. And so I dream up something that’s, you know, maybe three sentences. There’s, like, a seasonal component to it. So like, getting up to Christmas, it’s like, how can you engage some of the other members of your family to help with the holiday planning? Right? To just drip in little ideas of connecting with the kids. And then in December, it’s like, well, now that you know if you’re going to be seeing your family, are there some topics that you can hint at that you can then plan to have a meeting in January or February to follow up on something you just said about another having another meeting. To me, the family meeting. The trick for any family meeting is that you leave there with the next one scheduled, and you want everyone to want to come yes to that meeting, and so it needs to be fun and enjoyable. And I tell the story about my dad heard the message that you’re you should call a family meeting. And he called one in 1985 and then the next one was in 2006 and that was only he was diagnosed with cancer, 21 years between family meetings is not the recommended interval. No, no, no. He tried to have the 100 minute conversation over a couple and it was not well received, mostly because it was mostly a monolog and there was no dialog. He also didn’t hear the part about hiring an outside facilitator to run the meeting you himself, because he was a self made man, so he thought everything was better when he did it, sure, which, from his perspective, maybe it was. But from my not so much. And I think

16:33
that the other piece of it is, if you have these sort of one offs that happen, oh, gee, we did the estate planning, we won’t think about that again for whatever the recommended period of time is, five years, 710, years, or until something change happens. It does not allow for flexibility, for life changing, for families evolving, and for people evolving.

16:59
What do you think about that overall

17:00
tone that we’re setting. If we say important conversations don’t happen very often.

17:08
Well, they don’t happen very often because they’re hard, but you have little bits of them from time to time. They’re easier to digest. When I work with families, and I try to get them on a regular schedule of meetings, even if it’s annual or quarterly or monthly, it’s always the key is that everyone then knows that there will be a place to bring something up, yes, so I know that we’re gonna have that meeting. So there’s something that’s bothering me. I don’t have to worry about, oh, do where like I know there will be an opportunity, there will be a forum for me to bring up this concern that I had. And so for me, the first few family meetings are all about creating the culture and the vibe and the openness and the safe space so that people know that this is a place where, if I have a concern or a worry or something that I want to ask about, that there is a place for me to do that. And I think that’s part of the greatest comfort that we can give families that we work with, and that fits so nicely with your more frequency shorter conversations.

18:26
Absolutely. I love the idea of creating that space and giving everyone a voice. And as you know, there are families who are fearful about giving everyone a voice, because it’s misinterpreted as giving everyone a vote or a veto. They are not the same. Talk to us a little bit about this idea of how the more frequent conversations can help everyone in the family feel heard. Having

18:59
everyone feel heard is a huge part of what a facilitator brings right, and it’s disrupting the pattern of one authoritative person speaking and everyone else listening, which is very often the case in the early stages, usually from a first generation family business, that’s there’s a lot of that once you get if you get to work with families that are down, second, third, fourth generation, some of that often dissipates because they’ve understood the importance of having more democratic decision making and hearing the voices. But for families to learn, to go from that one authoritative leader, to hearing, to even wanting to listen to the others. That’s where an outside facilitator earns their money in silencing the ones who talk too much and encouraging and even forcing people to speak who normally speak less. And so the more you do that, the easier it get. It’s you build that must. And so that’s part of the secret, is to do it in small pieces. And

20:08
I would like to think that when

20:12
there is that vessel I’m thinking of it of this is the forum where conversations are going to happen, that those itty bitty ones can start to happen because people are getting practice with help with a facilitator. They get some practice, and this is how I communicate with other people in the family, without stepping on toes, without infuriating anyone,

20:35
and without just sitting here, clammed up, and

20:38
the facilitator does that work, some of that work in the meeting, but then if that facilitator is also coaching the family members in between meetings and helping them prepare to bring up topics that they want to bring up, but aren’t sure how a lot of the stuff happens in between the meetings, right? So, so the best families that I work for are the ones where I’m with them together on some periodic basis, but in between, I’m with them one on one, or I’m with them in smaller subgroups, and we’re trying to do other things. And then we come together in the meeting to discuss them. And then we go off and do some one on ones or small group stuff again, and then we come together again. And it’s that back and forth, one on one, everyone together, that sort of keeps everything in bite sized pieces and allows people to adjust, gives people a level of comfort of how they can speak to each other, as you said, without stepping on each other’s toes. And all these things are not something you just read in a book, and they’re not something that you learn in a one hour workshop, and then you practice, and then you come back and you try again, and you think about it some more, and you try it again, and eventually you learn a lot, just like when you’re doing your 30th podcast, you have a certain level of practice and expertise, but when you’re doing your 300 and something, a lot of things come more naturally. True enough

22:07
and thinking too, as you describe this, how well

22:10
it lines up with something you said early on, which is the plan. Whatever the plan is matters. The planning process is at least as important. Expand on that a little bit. It’s more important.

22:24
It’s the whole the destination versus the journey, right? And I saw a quote once years ago, and I did write a blog about this too, about it’s not it’s not the destination, it’s the journey. It’s all journey, all of it. Too many times people are looking to get somewhere, get something done, pick some box, and if that’s all you’re looking at and you don’t enjoy the journey along the way, like 99.99% of life is the journey. And so learn to enjoy the journey. Learn to enjoy spending time with your family members together, discussing important things. Learn that this is not a one and done thing, and that spending the time together to learn about each other and learn why certain people like things some way, and other people another way. And how can you figure out who should be responsible for what, and who’s going to take care of what? And these things, as you were saying before, these things evolve. Right layout goes on. True things happen. People get older, people get married, people get divorced, people have kids, people die. Things are changing. Sometimes they don’t change for a while, but all the little things that are happening in our lives are changing every day. And so being able to have a lot of touch points as a family to come together and compare notes about where they are and what they want to do and what their priorities are that needs to be done on some regular basis. Yes, absolutely.

24:09
It allows people to evolve instead of being in our 50s, but I think of you exactly the same way as I did when we were teenagers. Well, both of us have changed a little. Maybe we need to keep at that, to remember, for better or worse or or just change, not the same.

24:31
You’re bringing us right back to that thing about children. Right when the people are in their 60s and they’re being referred to as the kids. The problem is that often the parents are treating them as if they were still children. And people do evolve, and sometimes it’s hard to recognize that, yeah, this person has evolved. And gee, so have I. Yes, our relationship should also

25:28
People, often the parents are treating them as if they were still children. And people do evolve, and sometimes it’s hard to recognize that, yeah, this person has evolved. And gee, so have I. Yes, our relationship should also evolve,

25:49
yeah, yeah. And the other thing

25:52
that comes to mind is this continuing concept we

25:57
learn together, we figure out who’s good at what,

26:00
who hates what. All of that is such an important foundation to have in place and to nurture, so that when something comes up that is a problem, it is a disagreement that’s going to be a big disagreement and needs to be handled. I have a sense of who these people are. I care about them, and I actually know them.

26:27
Yeah, it’s all about. Actually, the key word here, we haven’t really said it, is connection, maintaining the connection so that it’s always still fresh enough that you don’t feel bad to reach out to someone, because, oh my god, I haven’t talked to them in six months. You need to have and it’s always more fun to deal with families when they come together and you can feel the vibe in the room that they’re happy to be together. Oh yeah. Now there’s company. Those are the fun families to work with. Sometimes, though, you end up with families where you walk into the room and you just feel this tension between them and more of a challenge. And I guess in your mediation work, you see some of those as well, but sometimes it’s easier to show our worth in situations like that, where we could actually even just bring people together who otherwise would not even be able to come together Absolutely.

27:23
And I’m now reminded and again, similar to what you said early on, it can’t give the credit word due, because I can’t remember, but it was essentially research that had been done, I want to say, in the family business arena, that was talking about the connection, and the frequency of the connection being much more important than what was said and The boat. So if you send a happy birthday text that is important and valuable, similar to this idea of many, many, many short conversations, instead of, well, I’m going to wait an entire year, and then I’m going to send everyone I don’t see all the time in the family this glowing holiday letter about how swell everything is in my family, I don’t know about you, but we’ve received some that are just so fabulous that we were rolling on the floor in laughter. You are truly the perfect family, but we would really enjoy hearing from someone more frequently about the ups and downs. I was thinking of you when I saw this oracle, those itty bitty, frequent touches. Yes,

28:34
the touches to keep people connected and being connected with your family members often needs a little bit more work. Sometimes you need a little excuse. Some families do it really well, though, yeah, but each family has their own way of being. I was with some people over the weekend and they were talking about chatting with their offspring every day and several times a day with some of them, and for others, it’s oh my god. I sent my son a text three days ago and he still hasn’t answered me, but that’s normal. Yeah, I think more is usually better and shorter rather than frequent, but longer, but whatever works for whatever family, just like, like I said, some families have an annual meeting where they come together. Others are quarterly, others are monthly. And then there’s still the families where every Sunday dinner, everyone is expected around the table for dinner. And if you can pull that off, good for you, as long as they enjoy coming. Yes. And if

29:37
you know one of these families, you know one of these families,

29:42
as we’ve heard, that aren’t as many as we might hope.

29:45
So. Steve, this has been great. I, of course, will ask you how people can contact you, and more specifically, how they can get on board and get these fabulous missives coming to them.

29:57
Okay, well, I’m lucky that I have an easy name to spell, Steve Legler. There’s L, E, G, L, E, R, there’s only one vowel. It’s an E. It shows up twice in my first name, twice in my last name. So if you Google me, you will find me, and my website is Steve legler.com and then if you go to my website right there in the top right corner, the place that says subscribe, and then you have the choice of the weekly blogs, the monthly newsletter, or both. Most people choose both, but I don’t want to force anything on anyone, and you can find me on LinkedIn as well. Steve Legler, if you put anything about family business, I’m lucky I have a name that’s not common but not hard to spell.

30:37
Yes, you are lucky. That is quite the combination. I have to say.

30:41
I’m blessed with that and some other good qualities as well. I think many

30:45
indeed. Well, thank you for coming back to the show, Steve. It’s been a lot of fun talking with you, and I will, of course, put that information in the show notes for today.

30:53
All right, anytime. Jane, thank you. Thank you

30:57
for listening. If you enjoy the crafting solutions to conflict podcasts, please tell a friend. Share it, leave a rating or review. When you spread the word, more people have a chance to enjoy the show. You can also sign up for new weekly episodes on your favorite app, whatever setting works best for you and is free. You don’t need to pay to listen. You can also find the show at crafting solutions to conflict.com comments or ideas. Let me know, until next time I’m Jay Jane Bedall.