What Does "Ready" Really Mean for Rising Generation Family Members?
Jennifer East advises leading global families and family enterprises on the complexities of sustaining wealth, leadership, and cohesion across generations. Over the past two decades, she has worked with multigenerational families and family offices navigating moments of transition, helping them clarify purpose and wealth identity, approach succession with intention, and strengthen the relational foundations that underpin long-term continuity.
Her work sits at the intersection of governance, family dynamics, and leadership development. She is particularly known for helping families and their advisers interpret the underlying patterns—shaped by history, identity, and generational experience—that influence decision-making, trust, and conflict within systems of significant wealth.
Drawing on her own experience as a next-generation leader in a Canadian family enterprise, Jennifer brings both lived and professional insight to the realities of ownership and transition. She also serves, with her husband, as Co-Chair of Class Afloat, a 40-year legacy experiential education school at sea, reflecting her ongoing commitment to developing the rising generation of globally minded leaders.
Based in Malta, Jennifer works internationally with families and is a regular contributor to private forums for family principals and their advisers.
Dr. Kirby Rosplock
Welcome to the Tamarind Learning Podcast. I'm your host, Dr. Kirby Rosplock, and I'm thrilled because Jennifer East is my guest today, and she has a fascinating background, one that I very much relate to because she is both, uh, uh, an, um, senior, more grownup person, but grew up in a family enterprise. So she really understands what it means to be born into a complex business fact pattern and trying to figure it out, find your path. Um, which actually leads her to the work she does today, which using sort of a coaching mindset, she really helps families and individuals navigate these somewhat unclear paths towards adulthood, towards arriving at your purpose and your passion towards building competency. And she also has a fascinating background because she sits in Malta. Wow. Special. And she has that cross-cultural perspective, bringing both sort of an American lens, but also working with a lot of international families and sort of seeing the perspective of family enterprise and individual development, not just from a Western lens, but more broadly. So Jennifer, welcome. I'm so happy you're here with us today.
Jennifer East
Thank you, Kirby. I'm thrilled to be here.
Dr. Kirby Rosplock
So there's so many cool things that you're doing working with families today, but I want to kind of jump into the area that starts with this myth. Let's start with the myth at the center of the conversation. Why doesn't readiness just arrive because someone reaches a certain age?
Jennifer East
Interesting question. I think I like to use the analogy of going to the— running a marathon. So if you want to run a marathon and you haven't done any training, it's it's sort of silly to assume that you're going to be ready for that experience. And so families really don't think that much. I, I, in my experience, they don't think in the kind of detail that they need in order to understand, well, what does readiness really look like? And I would say in some families, sure, if, if like I did grow up around the kitchen table, you're hearing about business and decisions and judgment. Yes, there's a certain readiness that comes by osmosis, but that's really not the same as having serious exposure to business, having opportunities to practice, and then really having real responsibility.
Dr. Kirby Rosplock
And when families say they want the next gen be ready, right? What do they usually mean and what are they often missing?
Jennifer East
I don't actually think they know what they mean. I think it's a vague concept and it's a constantly moving goalpost. The number of families I've worked with where someone will say, well, when this happens, you'll be ready. And then when the young person gets to that point, then the, then there's a new goal. And I would say that one of the things that the leading generation is looking for is for the next generation to be like them. That's what readiness is. And of course, that's not possible because we're all unique individuals. We have a different journey. And that what they're missing, I think, is that the role has to first take into account who that person is. So you can't impose, you know, a business founder, you know, the classic stereotype, but it's often so true of an artist. Child who's an artist, you can't impose an expectation that that person is going to be ready to make business decisions and being entrepreneurial and have a finance mind. That's just not going to happen. So you've got to take into account the individual, and then you've really got to define what the role is that they need to be ready for, or the series of roles, because as you know, in families we all often wear many hats.
Jennifer East
So this frankly takes a lot of work to do that, and, and most families have you know, lots going on and that's something they can think about tomorrow. And then that goes on for years. So there's never a clear sense of what ready means.
Dr. Kirby Rosplock
Well, and it's true because it's like trying to drop a pebble in a moving river, right? And so what are you really ready for? What time of the moment are you catching someone midstream of this life, right? If the river symbolizes living and growing up and you're moving and progressing, the milestones, right, might always be moving as well, the benchmarks. And so, I mean, tell me how you see individuals maybe getting lost in this process or getting stymied, because I can imagine that process without it can create a whole host of problems as well.
Jennifer East
Mm-hmm. I would argue that frankly, every individual, even the founder, kind of gets lost in a very successful family, in the name, in a legacy, in a business. So this large shadow that, that business or that entity casts means that the individual, you know, personalities, needs, hopes, and dreams often get, uh, become secondary to that bigger mission. And so therefore, um, the preservation of that entity, that legacy, really is where everyone emphasizes. And so it's natural for a family to think, well, in order to meet our ultimate goal, which is the legacy and the preservation, then You know, every individual in the family has to find their way to supporting that and fulfilling that. And it simply means that the individual isn't really thought about as much. And it's also, it's like oxygen. There isn't enough oxygen in the room for the individual. There's also an element for some young people of awkwardness in raising it because it may sound, especially if you're receiving a lot that you didn't create, the idea, well, not only am I going to receive it, but I'm going to expect that I have to have some space here for my own needs In once, that's a pretty, it's a daunting question, and often it's just never asked.
Jennifer East
So those individuals just are left to fit in where they must.
Dr. Kirby Rosplock
So I hear the tension, right? I hear the, if the emphasis is all about the business or sustaining the business, and then, you know, you're that rising gen family member who might be coming in or being touched at different points, maybe you're not competent, maybe you're not ready, Maybe you have the interest, but you don't have the skills. Maybe you don't have the interest, but you do have the skills, right? So all of these things, um, talk to us more about what you see when families are so focused on sustaining the enterprise and they don't put enough investment into preparing, right? Those rising gen to find if there's an on-ramp for them or not. What, what does that look like?
Jennifer East
Well, as we were just discussing, the individual tends to, um, the family tends to look for spots where, oh well, that person, you know, seems to have good communication skills, so we'll, we'll put them in HR. Or this family member, you know, started their own business, so they'll be good on the board. So people sometimes get slotted into places that aren't a good fit for them. Then there's also an interesting dynamic with this generation, you know, this this younger cohort. And if you think about older generations, sort of our generation and older, there was— there is still a sense of obligation, a sense of service, acceptance of institutions and authority as a given. So being assigned roles may not have been as challenging. But for this younger generation, it's very demotivating. And that's one of the key things that can happen is because when you— even if you might end up in the same place, by asking the younger family member for their perspective. By not asking, you often create this dynamic where, you know, they want to have a say, they want to feel they have agency, they want to follow their values. A lot of these stereotypes about young— the younger generations, but, but they are impacting families' ability to, um, to really work together and to find the right roles for, for individuals.
Dr. Kirby Rosplock
Yeah, it's so interesting how anointing someone into a role could be demotivating. And I'm— I see a lot of, uh, family members struggle with apathy, right? What do I do? My— I, I thought so-and-so is gonna be the next, um, tracked professional to come into our family enterprise, or I really had aspirations that that cousin would show some moxie and step up. I mean, talk to me a little bit about apathy and what you see happening there.
Jennifer East
Well, some of it does relate to, you know, being told this is what you're going to do. That is not a motivating starting point, even if you again have an opportunity to sort of have input on how it happens, when it happens, you know, over time. But also when you put yourself in the shoes of someone growing up under the shadow of a large tree, it's autumn— there's automatically a fear that, you know, how is success going to be measured for me? Well, if my benchmark is this extraordinary success the success of my parent or my grandparent, then I'm pretty much automatically, I'm assuming I'm not going to live up. So there tends to be sort of a backing away. I mean, I could give you a story if you'd like. Um, again, the idea of, of an artist, youngest family member in a family office. Um, the youngest family member was reluctant to join meetings that she was asked to go to. She was often late. She didn't do the pre-reading. She complained about the financial literacy training that she was expected to attend. And generally speaking, she was perceived as a disappointment by her family.
Jennifer East
Now, after working with her for a while, it became clear that she was looking for some agency. So first of all, no one had ever asked her what role she could see herself in. There were constantly sort of offhand comments about her career, which again was in the arts field, and it made her feel devalued. You know, her and her passions were devalued. Um, she was intimidated because her parents and her older siblings were, were, had a real aptitude for numbers, and so she felt just lost and incompetent. And then the actual staff in the family office sort of sounded frustrated with her every time they dealt with her. And as a result, she really didn't want to spend time with them. So this changed once we expanded the field of vision beyond, you know, finance and financial literacy and started to look at her as a whole person and what she was bringing and what other skills she had. And it really turned the tide for her and the family.
Dr. Kirby Rosplock
Uh, that's such a great anecdote. I'm so glad you brought it to life through story because what I'm hearing you say is you actually pulled back from making it very myopic to like her deficits, right? What she wasn't fulfilling and really creating a process. Maybe you can talk a little bit more about one or more of the tools that you like to use, cuz I know that is a real asset that you bring to your coaching work with clients and I think getting them to have a process and approach to this is also keys to sustainability, to grow and to develop over time.
Jennifer East
Mm-hmm. I mean, I like to think of it as investing in human capital. You know, think about all the work and energy, effort, time, money that we invest in managing financial capital. And somehow we just assume that a young person like this is going to pull up their bootstraps and show up more effectively. So a very simple sort of leadership development process Involves helping that person understand who they are. So what are her strengths? What are the gaps? And really focusing on using the strengths to try to fill those gaps rather than really hammering away at the deficits, as you said. And what are the goals? What are her passions? What is, you know, what are her, what makes her feel like she's going to soar? And then pairing her strengths and goals with a really clear understanding of what are the roles, you know, is, is there a role at the family office board table? Is that appropriate for her? You know, perhaps not in this case. Is she going to be an inheritor, a beneficiary? And so what does that role involve? Um, and, and so defining that and then developing a plan to get you, get her from where she is now to where she'd like to be.
Jennifer East
And that relates not just to the role within the family, but, you know, families who really take this seriously help her be the best version of herself. I mean, one of my favorite examples is a young person who is passionate about trees and trained to be an arborist. So the family leadership development process, yes, prepared him to become an owner at the table, but also enabled him to thrive in this passion that he had and sustain his lifestyle through the family office, one that he couldn't have achieved through, through the career that he chose. Um, a couple of other steps involve getting exposure, getting some practice, you know, attending meetings, participating, maybe is then starting to comment on things, working with a mentor on the board to help understand, well, what just happened at that meeting? I don't understand why did we look to pursue this and then all of a sudden everyone decided not to. I don't really follow. So getting that kind of feedback and then perhaps taking a small project, initiating something where there's not a lot at stake, but giving that young person a chance to pursue, again, with feedback and coaching support.
Jennifer East
So there's actual, real, tangible experience experience happening.
Dr. Kirby Rosplock
That's amazing. Um, couple things I just are, want to key in on. One, I think what I'm also hearing you say is that oftentimes when we talk about readiness, we're like asking people to be operators, maybe of their family office, maybe of their family business. But I'm also hearing you say, no, we genuinely need families to be just good stakeholders and owners or future beneficiaries. And we also need them to know what it means to be a part, right, of an enterprising or wealthy family. Um, and I don't know that we cultivate enough leadership skills just in that capacity, right? We're always so focused on like what's making money, who's gonna be making money, who's doing what in the business or in the office to make money, uh, or sustain or protect wealth. Um, And I think we oftentimes overlook just what does it mean to be a stakeholder in this process. And I need to develop and grow as an individual just to be a good leader in my family around that key item alone.
Jennifer East
Absolutely. And, you know, it's, it's a natural thing because it's much easier to define what does it take to prepare someone to become the CFO. There's a pretty clear path and you can go off and have experience in other organizations. You can come back, you can apprentice with the— that's a clear path. What does it mean to become a good owner? Very few people, you know, at the tips of our fingers can answer that question, nor understand, well, how are we going to get practice at that other than just watching dad be an owner, which, you know, has some benefit, but fairly limited, especially if it doesn't all come naturally to you.
Dr. Kirby Rosplock
Well, and I also think, um, and I'm, I work with a lot of different families like you as well, that when there's one decision maker primarily, right, or a mom and a dad, G1, That's one leadership style. But when we get to that sibling generation or cousin generation, we have to employ a completely different set of leadership skills and we need to have very different abilities to work together. I don't think that is, you know, provided enough support. So how do I use my gifts as a communicator? Or how do I use my gifts as a more introverted listener? Um, what are my gifts in, in, you know, social relationships that can help, um, my sibling group or my cousin group work together. And again, I'm sure that's also part of your process is just helping families understand where they are age and stage and what the family really needs to be focused on. Because again, likely how granddad did it or mom and dad used to do it may not be the working norm when you have more owners, more stakeholders, a flatter, larger, wide tree.
Jennifer East
Well, one of the things you're identifying is just the mere fact that you may or may not know what your strengths are. And again, if you don't go through a process to decide that— there are people who get excited about doing a personality assessment, but a lot of people, I would say probably most people, you know, it's just not part of their normal way of being in the world. And so they're not developing that self-awareness. In addition, not developing awareness about their cousin, their sibling, so that every time they butt heads, they realize, oh, that's why it's because I want precise detail and this person's a strategic thinker and I drive them crazy, and, and vice versa. And so just being able to have these conversations and go through a process where you can practice— okay, let's as a sibling group make some decisions together and let's look at what we've learned. So one of the tools that I like is DiSC, for example. So it gives you not only individual sense but a sense of how do other types of personalities interact, how do you interact with them. And, and it, you know, you can use humor and say, okay, this cousin— this group of the cousins always stays quiet, but that doesn't mean they don't have anything to say.
Jennifer East
So we've got to find ways, like for example, um, we take a couple of minutes where they can write down their thoughts so that we don't rush to the next thing, um, just because all this— the, the real go-getter types want to keep moving and get frustrated by process. We've put in some process, and those quieter cousins have a chance to reflect. We have a coffee break, and then they can come back and share. So that's, and one of the things you and I talked about prior to this is just having like a map. If you literally think about a map where you're getting from A to B, you, you follow a map. And similarly with this quite nebulous thing, what does it mean to be a good owner? I use a competency map for owners and it really helps define what some of the non-financial, non sort of less obvious skills are that young people, and frankly even the leading generation in this new generational transition, that they need to develop.
Dr. Kirby Rosplock
Here's your map. I, I thought I'd just show it because it's so pretty and there's so much good stuff on here. Um, talk to us a little bit about this flow and what you've incorporated here.
Jennifer East
Well, um, there are, as you can see, so we've got the competency on the left and then there are sort of 4 stages. So are, are you at an emerging level? Are you developing? Are you established? Or are you really a steward? So this is really a chance not only for you as the individual but for other people who are supporting you in this process. Maybe it's a coach, maybe it's a, a leading family member, maybe it's a mentor within the organization, can help you think about, uh, different types, different areas, uh, of skill sets that you are developing and want to improve. So if we go back to the example of the, uh, the, the young woman in the family office who wasn't engaged, this process enabled her to identify 3 really strong areas. So judgment and decision-making, collaboration and relationships, and values and ethics. So she had to utilize and had really honed those skills in her art career by— there was a lot of collaboration. She had to make judgment because this was very much a self-reliant career path she'd chosen. It was not— it was a bit of a slog. And she lived very strongly by, by very strong values.
Jennifer East
And so once we started to define her competencies in this much broader sense, it was like a light went on. She realized, oh, I've got a lot to contribute here. And other people in the organization realized, actually, I might go to her when we're having a bit of a values dilemma, because I can see that she's dealt this with this now, obviously in a very different context, but it gave her confidence. It expanded her field of vision of what being prepared to be an owner might look like. And it also helped other people gain confidence in her that this is someone, okay, she may have a lot to learn on the finance side, but she's really got some skills that are, we're going to be able to leverage and it's going to make her a really successful member of this family team. So mapping this out, again, it's really about expanding the field of vision for all the strengths that many different personalities have.
Dr. Kirby Rosplock
I love this, and I love how you help validate in a generative way the potential versus sometimes we look at the glass half empty. And I know families can be so wickedly critical of one another. And so just to be that third-party objective voice to say, let's just find out where your passions, where your interests, and where your strengths are, um, but also help them connect the dots to potential roles and a process that can make it feasible for them to see themselves. I think that's another real reality is that we know we might have to be in, in owner seat, whether we like it or not, if you're in that privileged position. Um, but it's very hard to see themselves sometimes in family leadership roles that might be not directly management-oriented or operations-oriented. And so I love what you've done here because it really makes it more explicit possibility and potential. Um, talk to me more about what are some of the competencies families tend to overlook when they think about preparing future owners. Can you share another story on this front?
Jennifer East
Sure. Well, as you can imagine, a lot of them are more well, as, and as you said, relational rather than technical. And, uh, a story that I, I, I love, 'cause it's a great example, is a group of young, uh, owners who, some of them worked in the operating company and some of them did not. And the, the family business was faced with a PR emergency. And, um, some of the non-working owners, uh, were approached by stakeholders, in some cases even the media, to comment on this situation that the family was dealing with. And what happened was that, of course, some of them who had sort of more experience, you know, handled it well, but others just didn't know how to respond. And it highlighted for the family that some training around something they would never have thought that owners needed, because they weren't involved at the board level, they weren't involved as operators, they were simply owners, essentially mostly silent owners, but they needed training around judgment and around decision-making that had never— had never been made clear to the family, but they found it in a hurry. So again, we go back to the owner's competency map.
Jennifer East
There were some really interesting skills that they lacked because they just hadn't been taken seriously as an important part of this governance group within the family business.
Dr. Kirby Rosplock
Ah, it's such a good example. Again, you're full of stories and I love stories because they always bring these issues to light. And, you know, I love this first assessment that we brought up. I won't bring up the other ones, but you also have an Owner Competency Map, which we just talked about, the Leadership Development Framework, and then you're, um, you have a tracker as well. Talk to us about how using like a tool like this Owner Competency Map, which we just talked about, works so well in conjunction with a document that like helps track or shows the progress. Tell us more about how you use that.
Jennifer East
Well, I always like to think about how we all have to-do lists, but we rarely have accomplished lists. And so our emphasis is always on the lack rather than on the achievement. So having a way of tracking it for the individual, obviously it builds confidence. And that's one of the things that young people in these circumstances often lack. Is they're so intimidated by all of the expectations. So confidence, and it also builds momentum. It also enables transparency because if you're tracking and you're— let's say you're sharing it with your coach and you're sharing it with the family mentor who's been assigned to you and you're sharing it with your cousin because you've paired up and you're sharing each other's tracking so that you have a bit of an accountability structure. This just enables everyone to see Well, this person has really been doing some good work and I can see what they've achieved. It also helps to identify patterns that might happen. So for example, a young person I worked with who had ADHD would start a bunch of projects and always, and the tracker started to show it, they would stop and they would move on to the next project.
Jennifer East
And it was very exciting and they, you know, were great in that initial phase, but it really highlighted that that while there were some great strengths there, there was a need to help teach that person the follow-up. And maybe they needed someone to help them follow it through because they weren't necessarily going to be ever inclined to do that themselves.
Dr. Kirby Rosplock
Well, that's probably like a good segue to a question I had just about what happens when you have that family member who now feels like exposed, right? I've— you're showing that I'm not doing the work or I'm not following through. Do you adjust the tracker? Do you change the approach with the individual? Tell us an example or a story of how you've seen someone sort of come around if they've been feeling like, oh, I'm not measuring up or I'm not making the grade.
Jennifer East
Well, I guess what I would say is that the tracker, first of all, that pattern that was not being tracked before was still evident to the family and probably, you know, in some of the cases I'm thinking about, that was the thing that was being focused on. This person keeps starting— in fact, I, I had some of these tendencies, you know, I, I, you know, lots of enthusiasm for new projects. And when I was working with my family, I, I, you know, was guilty of that. But so that loomed very large. But then once the tracker was implemented, it actually again broadened the scope so that, yes, that was showing up, but people already knew about that. But other things were also showing up, like an incredibly creative approach to problem solving that that even more experienced people in the organization couldn't come up sometimes with these solutions and a really empathetic approach to working with other people. So the positives also showed up. So again, it provided for that individual and for others a more balanced view. So I think that, that's probably the most important part of the tracker is that it's about what has been achieved in terms of how we had to pivot.
Jennifer East
I mean, often someone with these tendencies needs— maybe not a team, but certainly someone around them if they're working on a project who has more of a detail completion orientation. Not the person who's going to come up with the idea, but the person who loves to follow it up and have the Excel spreadsheet to make sure that all the details are followed. So that person, we got them set up on Smartsheet, and they worked with someone who loved that type of thing in order to make sure that they were you know, doing all the final follow-through. So it's instead of becoming about blame and criticism, it's about, okay, here are your strengths, these are some of your gaps, so let's fill in those gaps. And you may be able to do that, but it might take others to support you. Uh, and that self-knowledge is, is golden.
Dr. Kirby Rosplock
Yeah.
Jennifer East
Especially now with AI and other changes in, in the way we work. The more you can know about yourself, the more impactful you're going to be.
Dr. Kirby Rosplock
Yeah, well, you said it when in our pre-call that sometimes this process can be a little bit messy, and that's maybe not a bad thing. Maybe you can speak a little bit about why, um, having thing— everything go to plan or like as expected is probably not the norm. That's the minority. And why is messiness not something that should be discounted or looked as failure?
Jennifer East
That's a good, good observation because human nature is inherently messy. So what I always like to remind people is that yes, we're talking about the younger generation, but this process involves the leading generation making a lot of changes. And that's often where the messiness comes because, you know, sure, Dad may want his son to develop, but then when his son really gets competent, sometimes Dad is the one who struggles to actually make room at the table so that the son can take the next step. So it's often a few steps forward and then a couple steps back. And that, I think, again, you know, these issues are often called, you know, the soft issues, the things that don't fit neatly into a box. And rather than try to put them aside, which a lot of even our industry wants to do because those are the things that don't fit nicely into categories, we, we need to work with that. Because ultimately, what are all— what What is all of this for and what will sustain these legacies? It's the people. It's not the estate planning and it's not the, um, the tax, uh, approach. It is the people and people are inherently messy.
Jennifer East
So the more we can embrace that and see, yes, actually our families learned from that experience that dad protested and then we got dad to embrace it and now we're moving forward again.
Dr. Kirby Rosplock
I love it. Um, another thing I wanna just jump to because I think it's also corollary, which is governance can not just be structure, that you talk about it as a learning tool. What does that look like in practice?
Jennifer East
It looks like, look, first of all, really understanding your governance. And, you know, governance isn't something you put on a shelf and don't look at again. Governance is how you make decisions as a family, how you make decisions at the board table, how you make decisions in operations. And you can look at each of those processes, first of all, understand them better through this process. And provide opportunities for young family members to observe first, and then perhaps to have a specific mandate to make observations and, and ask questions, and then to have another mandate after they've, they've done that for a while to then initiate or go off and research something that the board is interested in pursuing, and then bring it back to the board and get feedback from the board. So not only are they serving an actual role, but they're learning from that process. So when you start to look at, you know, every moment is a teachable moment, and it really is. You know, I have one client who talks about he and his business partner like to have ad hoc meetings. That's how they've always made decisions. But they're now trying to bring in the next generation, even if they can't do it at that moment.
Jennifer East
They bring them in half an hour later and say, okay, this is what we talked about, here's the problem we're dealing with, and this is this is how we handle it. You know, what are your thoughts on how we approached it? So they're even using more ad hoc governance as a way of teaching younger generations.
Dr. Kirby Rosplock
I love it. You also share a lot about how life is really the classroom, right? You may not need to sign up for a program. You might just be looking at what's happening in your own immediate world. Be it in the business or philanthropically or shared decisions. Talk to me a little bit about how you see leveraging, right, where people are, what is in front of them, what's directly in their purview as a great learning tool.
Jennifer East
Well, again, if you— I mean, let's say someone's gone off and taken a course. And then they've learned— maybe they've taken Financials for Non-Financial Managers. You know, it's a common thing. A family wanted me to take that. So that's fine, but it's rarely going to bring it to life or, or, or get someone excited. Whereas if they start, let's say on a monthly basis, reviewing the financials with the CFO, whether it's the family office, the operating company, or even the philanthropic endeavors, that is an opportunity to take that very dry learning that they were forced to do that they feel has no relevance to their own life and start to understand, oh yeah, this is how our family sustains the lifestyle. This is the kind of impact our family is having through our philanthropy. And here's a charity that we chose not to support a second time because of what they did with our money. And okay, now, so it's like it's the synapses are all firing around something that is real for them and impacts them and the family that they're part of.
Dr. Kirby Rosplock
Well, I know you have a busy life and there must be tremendous demand because I can't imagine a lot of complex families trying to do this on their own. Tell us a little bit about why they struggle and how you help. What's your process or how people would find you and work with you?
Jennifer East
Well, sometimes families struggle because a lot of the governance that we've talked about is implicit, is not clearly defined. So, or, and/or, it is evolving whether they realize it or not. And so having an objective person who's not a member of the family, who— a person who's, you know, I'm often saying to Dad or to Mom, you know, do you realize that every time you have a meeting, you know, every— the younger generation sort of waits for your direction to see what your view is. If you really want to know what, you know, what they think, you've got to sit on your hands for a while so that you let them have the stage first. So it's that type of objective feedback. Sometimes it's telling, you know, the difficult things to people to whom, you know, very few truths like that are told. So that's certainly one of my roles. And also, I mean, if you, you're a parent, how objective can you be with your children in terms of their readiness or their ability to step up to a particular role? That's a tough place to be, and it impacts your personal, your family relationship.
Jennifer East
So providing some objectivity and, and a lens through which we can look, um, with less emotion at the readiness of particular family members, that's a really helpful thing. So what I do is I really, um, I like to say I democratize the conversation. That's one of the things I do in, especially in a hierarchical scenario where let's say the business founder is accustomed to leading all conversations. I give voice to those who haven't felt they had a voice. I help to clarify, you know, complex structures and complex language that that's always been spoken way above the level of understanding in the room, but no one's comfortable to admit that they don't understand what's being said. So I try to make things very practical for far more family members than things have historically been practical for. And I help families sort of step out of their comfort zone to achieve things that haven't been possible when sitting around a boardroom table with their lawyer or their accountant because everyone's intimidated. Afraid to speak. So those are some of the ways that I support families. Those are more sort of the bigger picture strategic approach. So a lot of it is in conversation and it's in clarification and it's in believing in people so that they as individuals and as a family collectively can believe in themselves.
Dr. Kirby Rosplock
I love that. It's— I love how you are leveling the playing field. You're also speaking truth to power. And you're really providing the bridge, right, to help one generation rise and be more empowered and more impactful. And you're also helping, you know, an elder generation recognize the potential, the possibility, and a process to help their rising gen, you know, ascend. And that is never, it's never very clear. So I think it's a gift to our industry that you are working tirelessly in it. I wanna, I wanna jump to a speed round really quickly. I'm gonna ask you 3 or 4 ideas, just pop whatever comes to mind. Um, and then we'll close, but this has been just such a fun conversation. So what is one practice to stop doing if to better prepare for the rising generation? What would you recommend?
Jennifer East
Well, it may seem counterintuitive, but I would stop focusing on financial literacy as the litmus test of readiness.
Dr. Kirby Rosplock
I agree. I could talk a lot about that. And oftentimes we get the same question, like, this is where we wanna start. And we're like, yeah, I would probably pivot over here first because you're really gonna alienate them if you start there. But I, I see that too. Um, what is one practice to start doing sooner to prepare the rising gen?
Jennifer East
Uh, invest time, energy, and money in helping them understand their strengths and gaps, who they are.
Dr. Kirby Rosplock
I love that. And what's one experience every rising gen family member should have before taking on responsibility?
Jennifer East
Um, I would say leading, uh, some type of new initiative within their family ecosystem, but not just doing that, but with a mentor who's providing them feedback all along the way, they can learn from.
Dr. Kirby Rosplock
And what's one metric of success to demonstrate leadership readiness?
Jennifer East
I would say the ability to navigate challenging conversations with other family members on about, about the business of, you know, whether that's again, family office, family enterprise, or philanthropy, sort of what we think of as ambidextrous leadership. So being able to have one foot in business and one foot in the family and navigate that conversation.
Dr. Kirby Rosplock
Okay, last question. What's your favorite tool to use and why?
Jennifer East
I mentioned it already, and that's the DiSC assessment because it gives you advice about how you work effectively with, you know, who you are and also how you work effectively with other types of the different types of people.
Dr. Kirby Rosplock
Amazing. Jennifer, this was such a wonderful conversation. What I appreciate about your work is that you make readiness feel both more honest and more hopeful, not as like a check the box, but as a thoughtful process of growth for individuals that feels very fair and real and authentic. So thank you so much for being on the Tamarind Learning podcast today. If you wanna learn more about Jennifer East, you should definitely check out— where, where do they go, Jennifer?
Jennifer East
They find me at my website, onida.ca.
Dr. Kirby Rosplock
Awesome.
Jennifer East
Or on LinkedIn.
Dr. Kirby Rosplock
Yeah. So I know you've been on other podcasts. Um, you're a luminary, you add a lot to the literature, so We're so grateful to have you here today. Please, if you like this podcast, please subscribe, share it with your friends and family. Um, we also are available on Apple, Spotify, Amazon, and YouTube. So we are so grateful. And Jennifer, you'll have to come back again. Thank you so much.
Jennifer East
Thank you. It's been a real pleasure.
