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Navigating Complexity in Enterprising Families

Let’s Talk Family Enterprise Podcast Episode #72

Host: Steve Legler
Guest: Michelle Osry

Host Steve Legler speaks with Michelle Osry about how families need to deal with both complicated issues that require specific solutions, as well as complex challenges that require different skills to navigate to help the family make progress. They discuss the challenges in getting both advisors and families to understand these distinctions and find ways to work on having each family’s best outcome emerge from co-creation.


 You’re listening to the let’s talk family enterprise podcast for everyone in the family enterprise community, families, advisors and thought leaders, sharing ideas that help enterprising families thrive across generations. Brought to you by family enterprise Canada.
Hello and welcome to another episode of The let’s talk family enterprise podcast. My name is Steve Legler, and I’m honored to be your host once again this month, we’re going to try and shed some light on the complex nature of enterprising families and how we need to distinguish between the idea of things being complex and things being complicated. Our guest is Michelle osri, who is one of the instructors in the FEA program and a longtime friend and colleague of mine. Michelle led an in person FEC event in Vancouver a few months ago titled navigating complexity in family enterprises. And her presentation there is what inspired this episode. We’re going to get into some areas that will help families and their advisors better understand the differences between resolving complicated technical problems with solutions and helping families co create better ways forward together. There’s plenty to cover, as usual, so let’s jump in. Michelle Audrey, welcome to the let’s talk family enterprise podcast.

Thank you, Steve, so happy to be here. I’m

glad that we’re doing this, and as I framed it for you in our prep call, this is a conversation between two people who do this work that a lot of people who are curious about this work and understand a little bit about it, I want them to hear us talk about it in a way that gives them a little deeper understanding of what’s involved. So we are both involved in training feas, and you are part of the faculty, and I’m one of the project team advisors. So we see lots of people who come from the technical domains of this work with families, and we often look at the differences in the three circles that a lot of experts come from, advising the business and the ownership. And when they do the FAA program, they’re exposed more to the family side, and that’s where a lot of the big differences come in. Do you agree with that?

I do, and I came from technical too, so I understand that.

So did I. And some of our listeners would be familiar with the 10 domains of family wealth model, and if not, we will put a link to it in the show notes. But there are four domains at the top of the model that are called wealth creation and stewardship, and the ones at the bottom are called cultivation of family capital. And I think I’m mentioning this just because it’s germane to the question about the complexity versus what’s complicated. And so this event that I talked about, that you did in Vancouver. So grant Conroy, who’s an FEA that was involved in organizing that mentioned to me, Oh, Michelle did this great event where she talked about the difference between complicated and complex. And as soon as I heard those words, I said, Oh, we’ve got to do this. So here we are, and I want to just talk about some of those differences, but before I do that, how did this complicated versus complex come to be an idea around which to center that event?

Let’s see. Granted said, I think we need to do event, but we can’t do the same old thing and do so much talking and make it about slides, and I said to grant, why don’t we try something? It’ll be a little risky, but why don’t we try something, maybe to do with movement or role play? And so grant being grant, said, I love the idea. And then it actually became too complicated for us, and we said, we’ll never pull this off. We had wonderful ideas about role playing. And then we thought, not everyone’s going to love this idea. And then I think, rather than ditch it, we started to actually realize what’s the simplest way that we could possibly give an insight or an AHA to family members and advisors attending. And one of the things that just came to us in the course of a conversation, was, if we could give a experience of complexity, then that would be a win. And we realized that the exercise didn’t need to be very complicated to give that insight, meaning we could actually do a very simple case study. Because initially, when we started, we were thinking of, oh my gosh, we’re going to have to give scripts and make sure everybody get their parts. And it was so complicated that it would take a lot of learning in the evening and very little insight. But instead, we had three or four lines, and really it was about. Occupying a role of a family member and just experiencing the table, which was a family through the lens of that family member that you had been assigned. And you know, may sound a bit daft and not very interesting, but what came through was that several people who participated, some said it’s the first time I’ve understood my brother or I completely now understand why I’m not being clear. So we shifted very little, and the marvel of a complex situation came through. So I don’t know if it sounds a bit cryptic Steve, but that’s how it came to be. And to start the session, I just did a short overview on what is the difference between complex and complicated, or how would we define complicated and what is needed for complicated, and how do we find complex and what is needed for complex? And so I tried to set the scene that allowed everyone to practice how to behave and complex, and everyone exceeded our expectations by far and had a fabulous time, which is why the insights came Excellent.

Okay, so let’s just I did a little quick google complicated versus complex, and it spat me out this beautiful thing that I just want to touch on quickly, so complicated many parts, but predictable, a complicated system or problem has numerous distinct components, but if you understand all the pieces and processes, you can often predict the outcome, which sounds to me like a lot of the technical advice that families need and get. And then the complex is complex. Systems have many interacting parts whose behaviors are often non linear, meaning small changes can have large, unexpected effects, and the overall system’s behavior is emergent. It arises from the interactions of its parts and cannot be fully understood by looking at individual components alone. And so I think the way you described how you set up that exercise, people were put into a situation of complexity that was simple enough for them to role play in, but that allowed them to experience the fact that you could not predict what the other people in the role play were going to do. Is that part of what the magic was

so well described, that’s exactly it, and the experience is realizing that you are interacting with the other and are being impacted by the other just as they are being impacted by you, which is so obvious, but we forget that that’s about to happen in any relationship, right?

There’s an interdependence, and as things play out, you don’t know what someone’s reaction is going to elicit in someone else. And so there’s that whole systems thinking part about recognizing that it’s not a linear one plus one always equals two. And so the people who are used to working in taking things that are complicated and finding the most elegant, beautiful solution in some areas of the work done with families, that is absolutely what happens, and experience and expertise are valuable to resolve those kinds of situations, but when it gets to the complex where it’s the family members dealing with each other, now more expertise actually can work against you, and it seems adaptability is the most important component when dealing in those situations. Is that correct?

Yeah, again, super well summarized that. You know, we for many years, many of of the feas listening in, including myself, we were trained, and that training, the more trained we were, the better we became. So all we needed to do was hear three or four parts of the fact pattern, and we’re pretty sure that we could predict the rest of it. And thereafter, our job was to solve the problem, whether it was a finance problem, a tax problem, a legal problem, and you wouldn’t want someone to do that, you know, without the technical training, and so you would look to see who is the most technically trained here to be able to solve this problem. And yet, when we move into the world of complex, as you said, very often, that training unfortunately closes our visual or our thinking, and we start to expect certain things or predict certain things, which is not that’s you know, it’s still useful, but if you’re unable to be extremely present and to listen extremely carefully and deeply and experiment and have the humility to work within the system, knowing that. You can’t predict it, but bring all your expertise. That’s good. But have that humility to know that the relationships in the room are key. That’s what we’re listening for, and that’s what we’re working with. So it takes, it takes both skills working at the time, and sometimes you need to put the one down and pick the other up. And this is the rewarding field of being the FEA, it is also I find it at all times I have scary parts of the day, and at all times I’m faced with conundrums, and at all times I’m faced with my gosh, I have no idea what is about to emerge now, but to have the capacity to be ready for it. And then there are some days where you think it’s complex, but actually it’s just complicated. So, you know, I still am a bit worried speaking too cryptically here, but taking your guide on it to those listening know that at times, lean into their technical and their training and their expertise, that’s why you’re in the room. And then there are times where leaning into that is going to make everything more muddled and everything worse. And we’re going to take five steps forward. I’m going to take 10 back, because we have just made the problem worse. We’ve added to the problem, right?

I like the way you talked about the fact that you need to put one down and pick up the other, because it’s not nobody saying that you don’t need this and you need all of that. It’s It’s knowing when to apply each and it’s often the people with the most expertise and experience that are so valued for those things that have difficulty putting that one down and picking up the other one. And so the complexity requires creativity, agility, experimentation and willingness to learn. I’m reading this off one of the slides from your Vancouver event, and then this is the takeaway line at the bottom of that slide. One of the core paradoxes of complex systems is that a lot of effort can have no impact, and a little effort can have a big impact. So you don’t even know where the important extra work that you’re going to do, you might do a lot and get nothing out of it. And with the right brainwave or right noticing of something that’s emerging from somebody who’d said something, and somebody else’s reaction to it, might just open up a whole new area of clarity for the family.

Yeah. And this is where the, you know, the amazing work, some of the resources I quoted or have in that deck, which was sent to the feas, and, of course, happy to share with all feas, is the work of Arthur Sharma and his theory, you and a lot of the work that he does at MIT in social innovation, the incredible phrase he has of learning from the future. You know, he said, we’re taught how to learn from the past, but there is also a way to learn from the future, meaning really being attentive to what is emerging. Use the word emergent a little earlier. So being attentive to what is emerging. And if we come in with expertise that keeps us close to that we will not spot it when something new is emerging. And the incredible thing in working with families, where you are creating and crafting and forging a way forward, or if a family is stuck and you’re becoming unstuck, it’s the ability to listen carefully and to take from the conversation, or to take from the meeting what you need to find your way forward together. And if you’re not listening for that, you’re all going to stay stuck,
right? And you’re reminding me of one of my favorite words, which is co creation, and the fact that we are often there as facilitators trying to elicit all the best thinking in the room so that the people for whom all these expert plans are being made are available to co create how things are going to work together for them going forward. And so you talked about Otto Scharmer, but you also quoted this other book, unleash your complexity genius. And I want to just spend a little bit of time on some of the ideas that book talks about, can we go there now?

We can go there? And Steve, before or after? I’d love to have given example, an actual example of today, where my fellow FAA called me and asked for my view, using my expertise. He said, could you tell me what models you’ve seen work? Okay, go with that. Keep going. Okay. It was an example, very typical a trust situation, and let’s just go with mom and dad or trustees and are trying to determine the success of trustees, and a lot of nervousness around, can our four children be the trustees? What will happen if they’re in deadlock? What if they are actually opposite of deadlock? They all agree with each other and decide to take all the money, you know? So the question then leading. The expertise? What models have you seen? Okay, so if I have no models and no expertise, I won’t be able to answer that question. Or I could say, here are the spectrum of solutions on successor trustees. Now that, of course, makes your colleague on the call feel a lot more relaxed. I’ve got a whole lot of options to work with. I hadn’t thought of a few of them super helpful. And if we end there in our collaboration, I have equipped someone to go into a complex problem with a lot of solutions that would address things in a mechanical way, right? And so the equipping I wouldn’t be able to do it because I’m not in the room. Would be to support through coaching of together with the family based on their circumstances, their context, the sibling relationships, the sibling parent relationships. What if Dad passes before mom? Mom persons before Dad. What is the relationship between the parents?

 What are the wishes? What’s the context of the wealth? What’s the significance of the wealth? What are the values of the family? What are the generational stories? What are the wealth myths? There’s any number of things that the co creation of the solution will take place together. Now, very helpful to have the seven options, or the 10 options that I have, including voting options and checks and balances. And you know how that might work with their board, but really it’s in the room, determining based on the relationships and the unique nature of that family, finding the model based on all of the practices, finding the practice for the family. And what I particularly love is that I can say this to be true almost every time when you do that work well, the family will surprise you by coming up with something that you have not experienced before. And you say, this is utterly brilliant. This is exactly right, and it’s the perfect solution for that family, because that family was able to co create it amongst themselves,
yes, and you’re helping them with expertise and experience, and then you’re helping them by creating the space for them to see in a much bigger way than they have before. So they will. They will. You know, some families say, help us do our best thinking together. Help us do our highest thinking together and with checks and balances. So we don’t want to all be delusion about what can work. So I think that might lead into you now talking about this book, because how do you create the conditions for that kind of co creation? Because we can all co create, but do badly. How do you co create so that you are taking the highest wisdom of the family and the advisors. Nothing better than doing a wonderful brainstorm with many advisors in the room and many family members in the room, then you really are set. But, you know, sometimes you want to close that group. But Okay, so back to the book. How do you create the conditions for it? You know, do we study? Is there a course? Can I read a book?

Well, there’s a one of the slides that quote that you’re had in that session, or lists eight things you can do in the from unleash your complexity, genius, and we won’t cover them all, but number one is noticing. And you mentioned that a few minutes ago, and that’s often the facilitators role is to notice things that the family doesn’t notice themselves, right? So some one of the quieter people in the family says something, and people kind of blow it off or they don’t even listen. But there’s a nugget in there that we can notice and that we can share. Is that an example of what we’re doing to help with this,

it definitely is, but it’s one of many. So let me start on noticing. Such a beautiful word, noticing. And you know, I’m having read that book, I thought, well, noticing is such a big part of things. And here’s how I would recommend advisors and family members, if they’re listening, start their meetings, and it’s by noticing themselves. It’s not just the facilitation noticing. So if each of us can notice, how am I feeling right now? How am I showing up? What is the agenda? Do I even understand the agenda? Just it’s the noticing at the start that sets the conditions. So noticing is either going to send us in a direction that says, I realize I’ve come here with an entire story of how this meeting is going to go, or I notice that I’m feeling very relaxed, or I noticed I’m very nervous. So one of the small exercises that you can do is to ask a family member, or every family member you know, take a page and write seven things that you’re feeling right now. And many families can’t even write one, because they’re not used to actually being in touch with how they’re feeling right now in the meeting, which is very odd, the average board meeting, they don’t do this sort of exercise. But it’s not actually silly. It’s actually connecting your head and your heart. It’s making aware of your body. It’s, you know, all of if we did a different podcast on dialog, you know, productive dialog starts with, actually, no.

Feeling and the stories you’re telling yourself based on other people’s conversations. So back to your noticing, Steve, it’s not only noticing who’s speaking who isn’t, but it’s how we’re feeling and how their stories are impacting us and how their words are impacting us, and how we’re showing up and whether or not we’re being open minded. So how to then create the conditions for staying open minded and open hearted. That’s where we wanting to go.

And when you talk about noticing ourselves, I’m going to take a guess that we’re wanting to share some of that with them, to model the behavior that we want to see from them as well, that it’s okay for all of us to talk about how we are arriving in the meeting.

You know, that’s a facilitators choice. So interestingly, I have almost never had felt the need to share how I’m feeling okay. It is strangely because I know, you know many facilitation courses say model vulnerability. So you know, I’m realizing that now, speaking to you, maybe at the end I’ve gone, but I it’s, it’s oddly felt not particularly relevant. Family members are very good at going. When you create the conditions for them, they will do their very best to honor that moment. So if they’re saying, well, actually, I’m feeling not very much, or I’m not sure, or that’s okay, but at least we know one level of awareness higher, and our awareness is that you impact me and I impact you. Another tool actually that, and I think I included the slide in that particular session is I love making use of the Johari Window, which I’m sure you all know Steve, and you know the wonderful four quadrants where, if you draw it up on a flip chart, and so I encourage advisors to look up Johari Window, because I can’t really describe it on a podcast that well, but if you look it up, it’s a beautifully simple tool that describes sort of quadrants that are divided as follows, what I am aware of and what you are aware of. And there might be parts that we are both aware of, and that part is called the arena, so I disclose to you, and you can see it, but there could be parts that I’m not showing you. So it’s the hidden parts that you are not aware of, but I am. And then there’s the parts that you are aware of that I’m not, and I would call that my blind spots, right? And so if you draw that chart at the start of a meeting, it’s very interesting to ask someone at the end of the meeting, which of those quadrants moved for you, do you feel you reduced your blind spots, and in what way do you feel you could reveal more of what was hidden? And what we’re wanting in a family is for family members to have the ability to reveal more and more of who they are. And the arena, not only the individual’s arena, but the family’s arena becomes larger. That’s what we’re wanting.

We’re wanting the family to know more about themselves and be known to others exactly, get rid of some of the opacity and add more clarity to everyone. And it’s not just about what the family is working on, but it’s about how they relate to each other exactly. And when you do that, you’d be very surprised, because there are times when I host retreats that I can feel the the sort of action oriented thinking, Oh my gosh. How much longer is this stuff going to take? Right? What they will experience is where you can create the conditions for showing up and unleashing your complexity, genius, and I’m not making this up, those same high performing a types at the end of the retreat will say, I cannot believe how much work we’ve covered, that they don’t realize that they’re making progress while they’re doing it.

Not that they don’t realize it is that they created the conditions to make the progress. It’s not by stealth. They actually start to realize the conversations become productive. They’re able to put things on the table. They’re able to solve and move through together. I mean, this isn’t a magic pill. There are times when we say stuck for a while, but it is a path where you’re working this way together, where you can rather than, as we talked about in the beginning, the technical route, people aren’t showing up. The arenas are very small. The technical solution is not fitting. We try another technical one. It’s not working. Or we all politely say it looks fine, and leave many a shareholder agreement looks fine. Try to get to signing. It takes us three more years, right? So what we’re saying is, when you do it, well, you can actually pick up speed,

right? We’re getting we’re helping families get into a flow state. And some of the things we’re doing, I guess, are, I’m looking at your list of from the book there, laughing, wondering, experimenting, moving, loving, these are all things that if we can bring more of those elements into a meeting and get people to be more open with each other, we can then start to make a lot of progress with the complexity. Yeah.

So another tool to share is quite often where you are attempting to describe, let’s say, a governance chart, or a governance functioning actually to do it physically, rather than have your clients sit on their chairs looking up at a screen, have them standing and occupying their positions on the org chart, there is something about the visual and the movement, you know, you can elicit ahas, and that’s what you’re wanting, because then you can move on. It becomes very possible to start picking up speed after that,

right? Just getting people out of their chairs. Sometimes these meetings where people are sitting in the same spot for hours can really get stuck a lot more, and sometimes just getting people to move around and try different things can be really helpful. We talk about advisors Understanding these differences, but the families need to understand them as well. Sometimes it feels like to me that more and more advisors and families are starting to get these ideas of the importance of doing the family work and not just having the most perfect technical solutions. Are you noticing that in your work as well,

there’s so many 1000s of families, and we have small subsets of them, so I don’t really want to, of course, have too broad a brush here, but I would say there’s still families that ask for the template, and if Sure, we can get that template. And what I love now, actually, now that I’m thinking of how to answer your question, what I couldn’t do before, that I can do now, is I could actually do a quick spoof by saying I’m going to ask at GBT for one right now, right? And here it is, family of four. They said, Please, could I have a charter terms of a subcommittee? And here it is. And then, how is this helped? Right? Because you actually have to live it. So I still, I’m a big believer in writing charges, I find them quite hard to do well, and they take time. And I definitely like starting with chat GPT. So I always go with the and I like charters, I like term sheets, and I know that it’s in the practice of them that we will discover more about them. So we can start with, how do we aspire and what do we think will create the terms of engagement that will support us? But then, as we practice these terms of engagement, what do we learn? Because it’s all about the practice of them, and it can get tricky when you practice. So that’s the empathy we have for families, and that’s where we learn alongside our families, is to how to do this well,

we are always learning alongside them, and hopefully we will all continue to learn together. Michelle, this has been a great discussion, and unfortunately, we need to start to wrap it up. Now. We’ve just started, I know, but as usual, we’ve got our two final requests that we have of all our guests. So I’m hoping you can please give us a book recommendation and also one piece of advice from someone who works with families to others who work with families and to the families themselves. So can we start with the book?

Now, in full disclosure, you mentioned that to me one minute before we started our conversation. And I went, Oh no, what book am I going to recommend? And you have based this lovely conversation on the book. Unleash your complexity, genius. And I kid you not my I went to a book on my bookshelf that I went and grabbed in the 60 seconds before you started. And it’s the book that I thought, if our fellow feas do not have this book, I want them to have it. And it’s we can do this. And you’re not going to believe the subtitle. The subtitle is 10 tools to unleash our collective genius. And I had absolutely no idea two titles when completely connected book is, we can do this. 10 tools to unleash our collective genius is written by a wonderful friend of mine called Kate Sutherland, and it has inspired me, over the last 1012, years that I’ve had this book in my work with families, there are 10 tools that I looked at again and again and again in doing the work, because each of the tools supports work in complex environments. And so I would be happy to pick a conversation up with any FEA who buys the book and feels bit befuddled by any of the tools, or wants to talk more about the tools. I’d be happy to do that, because I use almost all of them in my work all the time.

Interesting, because I bought that book, I believe, on your recommendation at some point, I thought it was really cool, because it’s not a book you read. You don’t read chapter one and chapter two. It’s it’s a reference book. So when you’re in a situation and trying to figure out, what am I going to do with this family, you’ve got 10 different approaches in that book that you

could use. Great that’s a double endorsement. There you go.

All right, one piece of advice for listeners out there. Boil down all the 1000s of great pieces of advice you have, and just give us one.

Well, it’s a hard one, Steve, and maybe it’s advice I give myself. I’m going to try and think of what that could be. And, you know, I still feel so nervous. Sometimes going into an important meeting or two day retreat, I feel like, how am I going to deliver this? Or, you know, almost the same feeling I had when I was an investment bank or an academic, or my previous career roles where it was up to me to solve the problem, and so my advice is to remember that we can’t solve the problem. It’s not ours to solve, it’s not ours to fix. That we have a very different role when we wear the hat of a facilitator, if you’re wearing the hat of a tax professional, please solve the problem if you’re wearing the hatch of a lawyer? I’m so happy that you’re on the team. Bring your full heft of your experience, but the advice when we go in is to remember, you know, what are the capacities that help us? Humility, noticing, you know, deep, listening, deep gratitude. And you know, these are the sorts of things that people go, come on. How’s that going to help us? But you would be amazed what you can accomplish when you rest into looking at a system and respecting a system and working within that system. And I think that this work comes after we’ve done all of our technical because, of course, you can pull on that all the time. I pull on all my technical all the time. But it’s these other skills. You know, the advice I give to myself is don’t try. Oh, wait a minute. I found the advice I want to give Steve. Okay, let’s go. Okay. It’s called trying not to try. That’s another book title. The advice I often give myself is try not to try here, because it’s not yours to do. So my advice to others are and it’s not blanket advice. I hope I’ve caveated that enough. Take in your technical but in that special territory, don’t try, because sometimes you won’t let the silence be silence, and sometimes you’ll interrupt when you should not.

Beautiful, that’s the advice. It is a special space when we are working with families, and we have to honor their complexity and try and hold the space and help them through their situations to make things better for everyone in the family. Beautiful. Michelle ausri, thanks so much. Thanks again for joining us to share your insights with our audience. Thank you, Steve, very much for inviting me. I appreciate that.

Listeners, if you have not already subscribed, please do so make sure you never miss any of these monthly episodes. Thanks again for joining us. I’m Steve Legler, until next time,