Strategic Participation Models: Optimizing Multi-Generational Philanthropic Engagement

Welcome to Legacy Builders, strategies for building successful family enterprises. Brought to you by Beacon Family Office at Assante Financial Management Limited. I’m your host, Cory Gagnon, Senior Wealth Advisor. And on this show, we explore global ideas, concepts, and models that help family enterprises better navigate the complexities of family wealth.

Today, we welcome Dr. Sharilyn Hale, President of Watermark Philanthropic Counsel. With over twenty-five years in philanthropy, she has established herself as a trusted advisor helping clients channel wealth and influence for good with confidence and clarity. She is renowned for blending corporate and family governance as an advisor with 21/64, faculty member of the Ultra High Net Worth Institute, and Instructor at Carleton University. As a Chartered Director, her doctoral research produced a governance model that optimizes family giving, earning her recognition with a 2025 Family Wealth Report Award for advancing philanthropy with Ultra High Net-Worth families. Her commitment to excellence in philanthropic governance continues to transform how families create meaningful and sustainable impact across generations.

My goal is to be the most curious person in today’s conversation with Sharilyn Hale, where we explore her innovative work at the intersection of family governance, philanthropy, and multi-generational wealth stewardship. We’ll dive into how intentional giving structures can transform both individuals and family enterprises, challenging conventional wisdom about philanthropic engagement. We will share insights that promise to reshape our understanding of purpose, legacy, and values-based decision-making in high-net-worth families, offering fresh perspectives on building resilient family philanthropy systems that go beyond traditional charitable strategies.

Now, let’s dive in! 

Cory: Alright. Welcome, Sharilyn. We’re excited to have you here today to share your wealth of knowledge and experiences with us. 

Let’s dive in, shall we?

Sharilyn: Alright. Let’s do it.

Cory: Imagine you’re delivering the commencement speech to the graduating class of 2025, and you have the chance to inspire them with your story. How would you begin your speech to convey the incredible lessons and expertise that you’ve gained along your career?

Sharilyn: I will answer that question, but before I do, I just want to tell your listeners that you gave that question to me in advance, along with the link to a video of one of the most iconic, most inspiring, most watched commencement speeches ever delivered by Steve Jobs, which is no pressure at all.

So thanks very much, Corey, for planting that in my, in my Well,

Cory: One of the greatest creative minds of all time. So, no pressure, Sharilyn.

Sharilyn: No pressure at all. So once I kind of distanced myself from that, thinking about my own life experience, life and work, and I don’t know if I’ll ever be in the position of giving a commencement speech or not. But a phrase that has served as a real anchor for me in my life is one that I came across in a book, probably about twenty five years ago, by Parker Palmer, who is a thinker, an educator, an author.

He comes out of the Quaker tradition in the US, and the book is called Let Your Life Speak. And when I came across this book and read it, I felt like the book found me at a moment in my life that I needed to hear those words. He poses a question very early on in the book that says, is the life I am living the same as the life that wants to live in me?

And he goes on to say, before you tell your life what you intend to do with it, listen for what it intends to do with you. And it just flipped on its head, how I was viewing, you know, showing up to that moment in my life. It was kind of early days for me in terms of my professional trajectory.

I was on the path, and I think I was partly worried that I might miss my life, that I might get it wrong, that it might not all come together. And I think what that phrase and what his book really gives is an invitation, to really honor and respect yourself, your story, how it unfolds, the opportunity to reflect, draw on your wisdom, to discern your life in real time. And in the case of the book, it’s very autobiographical in that he shares his experiences of both; opportunity, but also doors closing, things not working out, and how instructive all of those experiences were for him in finding a sense of purpose and his purpose in his life.

And, something that has been very important to me in my journey as my life has spoken to me, is the critical importance of living a life of purpose, how it has evolved for me. And I think there are a lot of takeaways for that in my work with generous people and families. And I know we’re going to talk more about that. But  it takes some of the pressure off  to really believe that our lives will find us if we pay attention. And the world needs us to let our life speak, because I also believe that none of us are incidental, and that we have important things to contribute and to share, and that the world needs of us.

So that’s something that has really served as an anchor for me, and I think it’s relevant whether you’re just starting. But at any point in your life where, as you’ve moved along in your professional career and in your life, you know, life is living, breathing. It’s changing. Our world is changing around us. We’re changing. Our families are changing. Society is changing. And so, that constant attunement, to not just what we’re creating, but sometimes we have to recreate, when way closes.

Cory: That’s amazing! I’m just thinking about that life of purpose. And when you say that, it’s often a phrase “as we think of philanthropy, we think of a purpose and getting to that higher level.” As you mentioned, the getting started or or well established, maybe we look at that from a spectrum. Where have you seen people in tune with that purpose, maybe who are just getting started, and as well, people who are well-established in their journey, when it comes to philanthropy?

Sharilyn: Well, I’ve certainly worked with younger, I mean, age is all relative. I find that the older I get, you know, 50 is suddenly quite young. So it’s all relative. But I have worked with some very purposeful, young people in philanthropy who, from an early age, just had a had a sensitivity and awareness of wanting to be helpers, of wanting to be active, whether it’s a particular issue or, just that that sense of, responsibility, duty, some compulsion to act, to engage, to help, to volunteer. And that’s really beautiful to see.

And certainly in many conversations that I have with parents, often particularly affluent parents, who are thinking about the experiences that their children will be having of wealth, and both the opportunities and challenges that may come along with that. I often hear from parents that they they want to instill these things in in their children, related to a sense of of purpose, but that desire to be engaged, to be grounded, to have a sense of the world around them, to understand that not everyone, has the same life experiences that they may have, and so forth. I’ve certainly observed that in younger people, as well as my older clients, some of whom have been engaged in philanthropy their entire lives. And they’ve made significant contributions, not just in terms of charitable donations, but also in terms of volunteer leadership. Advancing particular charitable priorities or organizations. Our country is really built on those who find ways to serve, in one way or another.

I’ve also worked with people who have kind of gotten to a stage in their life where they realize they’ve spent most of their lives wealth-creating, and focused on work, building businesses, and so forth. They come to a point, maybe they’ve sold the business, and they’re looking around, and they’re like, “okay, now what,” and feeling a great responsibility for the good fortune that they’ve had in that experience. And then, turning around and say, “wow, I can do something really incredible here.” And that’s a lot of fun for me as an adviser, but more importantly, it can also be a very meaningful chapter of someone’s life, a new chapter of someone’s life, where they can engage in the world in a way that they’ve just not had the opportunity to do before, given time constraints, pressures, and so forth.

I think your question reflects the whole gamut of experience in terms of the role that philanthropy can play in someone’s life, as they think about purpose, as they think about meaning, as they think about how to express their values. I think that’s what makes philanthropy such an important topic for discussion among clients who hold wealth, and affluent families, because there are so many conversations that you can have, not just help get funding into communities for example, but that can really be really transformational for an individual and for a family.

Cory: Amazing! I really believe that philanthropy is rooted in values at any level. And so when you’re talking about a family who really wants to instill that in their children, that’s the driver for the conversation and for some of the actions. How does that differ from, there was a catalyst maybe later in life, where some reflection led them, you know, you spoke of the business sale and having that liquidity event that was the, now it’s it’s time to get engaged. So how do you see behaviors differ in families where they’ve been doing this for generations, and it’s really rooted in “let’s do this with our our kids,” and “we’ve been doing this since we were kids,” versus “I’ve created this wealth, and now it’s time to establish this.”

Sharilyn: That’s a very robust question, in that families are all so different.

Cory: They are.

Sharilyn: So one of the questions that I often am asked by parents is how young is too young, how old is too old, to start having conversations about philanthropy with our children or my child. Off the top, I usually say it’s never too young, and they’re never too old. You just have to start, because what I have heard and observed from my career in the philanthropy and charitable spaces now, thirty plus years, is that people engaged in giving often have learned it. They’ve had it modeled to them, by parents, grandparents, other special people in their lives, through their religious traditions if they have, and so forth. And so, to be silent on it with your children, you’re kind of leaving it to chance. And so something I talk a lot about with clients is about intention, and being intentional, relative to giving.

You talked about families that have a legacy of philanthropy in their family. Perhaps they’ve had a foundation in their family for a few generations. The families that are the most effective in that are ones that are very attentive to, I call it governance. How are we going to do this as a family, and how do we build the social infrastructure within our family for this work to happen? And so, they may have systems, processes around, at particular ages, members of the family are going to be invited to observe a decision-making meeting around grants, for example. Or, they may be given an allocation of funding where they can be engaged in identifying potential organizations. Or, as a family foundation that I know, it’s quite a professionalized foundation right now, but a large family. One of the things that they’ve built in terms of process, is that younger members of the family have to volunteer in the foundation office for a particular amount of time before they can participate on the board, or on board committees, for example.

So there’s no one right way, but these are all different ways and strategies that families who have been doing it over time have put into place for that continuity. When I work with families coming from that context, there’s even more conversation about values. Values in terms of the context of the family. And it’s also something that I need to better understand as I’m working with the families. Where did this philanthropy come from? Why is this important to the family? Because you want to carry the threads that you’re inheriting from those who’ve come before, even as you’re moving forward and co-creating something new. And that multigenerational conversation and experience is also something that can be very meaningful for families, and can be a way for younger members in those families to get a deeper appreciation for the family’s wealth, and perhaps, some of the purposeful uses of that wealth as well. So that’s on one end of the spectrum. Three, four generations, for example, in Canada, more common perhaps in Canada, is that first first to second generation, and sometimes to the third, but that first to second generation, because there has been so much wealth creation in Canada, is often where conversations lie.

I think the other thing is modeling. So not just telling the next generation, but showing. Explaining to your kids what donations you’re making, that you don’t have to have a big, you know, a hundred million dollar family foundation. It could just be your own giving practices. What are the issues that are important to you? How am I choosing the organizations that I support? Relaying that decision making process. How did I structure the gift in the case of a larger gift? These are all things that get kids on the inside.

I grew up going to church. Both of my parents were ordained pastors. And so, I had a lot of exposure to giving behavior. The collection plate on Sunday, that was a very thing. I looked around, and everyone was putting money in the collection plate. And there were other things throughout the calendar of the year where it was evident people were contributing and sharing. Those were very powerful influences in me as I was shaping my own views of giving, sharing, and volunteering.

It looks different in every family. Not everyone grows up in a religious context or a faith community, but their families may be very civically engaged. Whatever it is in your context to really be able to highlight and be intentional, point it out so that the younger members of our families are really observing that this is how we show up as a family. These are our values. Our society works because people raise their hand and share. And this is how we care for others that we may not know them well, but we’re sharing this community together. Those messages are so profound, and I know that because conversations that I have with philanthropists, they relay those conversations that they had when they were little. They relay those memories that can often be very visceral to them, and serve as inspiration for their engagement today.

Cory: When you think of families where they have such different objectives, so thinking about where the history of philanthropy has come and where we’re at today. We have direct giving, but then we have community foundations, private foundations, the world, and the fastest growing being donor advised funds. And they’re all created so differently. And some people have this endowment idea, and some people really want to have their money into the community as fast as possible.

So when you’re working with families, and I see it from a financial perspective, some of these large private foundations, they grant a lot of money. If you looked at it relative to how much is in their foundation to what they’re granting, you would say their foundation would wind up in a few years, but they’re constantly replenishing that money. So to set the stage of my question, there’s the financial aspect of it, but then there’s the longevity of here’s what we’re doing and the decisions we’re making for this generation in the teachings and the habits, and those behaviors, and we’ve set up certain structures to allow that to happen, but it’s not always tied to the financial aspect.

If that younger family member came in and said, “why are we granting so much? I can’t see my future here because there’s not going to be much left for me to dictate or to direct when it comes to my turn to really make that difference in the grants that I’m making.” So how have you seen from just that strategic aspect of here’s what we’re doing today versus here’s what our vision is for the family in the future?

Sharilyn: I would start off by observing there’s no one right way, and every family is different. Individuals within families are different. We started this conversation with the phrase, “let your life speak.” I think in the context of my work and how I support families, is giving them an opportunity to let their family speak. Let the family speak. And that very particular methodology of conversation, and then collective feedback, mirroring back what I’ve heard, to then develop priorities and action steps.

Why I think that’s important is because, to grab a strategy off a shelf and put it in front of a family and say, this is what you should do. That is Sharilyn’s strategy. That’s not that family’s strategy. And to your point, there are different ways that philanthropy is funded. There are different structures that generous people and families can use to facilitate their philanthropy. You have values often. There are some shared values often within families, and it’s important to help identify those. But there are also individual values that individuals within the family bring to the table if they’re doing the work collectively. And those values, but also opinions, experiences, perspectives, preferences, all of those things come to bear to make some of those decisions.

You also have some generational dynamics. Some people are more enthusiastic about generational theory than others, but certainly, we all grow up within a historical and social moment that informs how we view the world, our place in it, the role of technology, and so forth. And for those of us who work with families, right, you can often see some of those generational differences, and dynamics that can come out at play as well.

So all of that to say, in the context of families who are giving together, the opportunity for reflection, conversation, getting clear on what are the values that we’re bringing to the table, how are we going to make these decisions, are really critical. Because if you don’t frame that out, you’re going to be talking past each other, or not talking at all. And that can lead to a whole other array of challenges, not just for philanthropy, but for the family and the family system. I think before we even get there, a really fundamental question for generous people, and often it’s the wealth creator, the founder, the patriarch, the matriarch if she’s the wealth creator. Is this going to be my philanthropy, or is this going to be our philanthropy? Or do I aspire for this to be our philanthropy? Because if you’re not clear on that question, it can be very confusing for you and to others who you hope might be able to participate, or might be interested in participating. Wrestling with that question at the beginning is really important.

I work with clients, and they’re very clear. This is our philanthropy in terms of mom and dad. We don’t want the kids involved. We want our children to have their own avenues for generosity, for engagement and community.  We want this just between ourselves, or this is my philanthropy. Women are increasingly creating wealth, inheriting wealth. We know women often inherit twice, first from their parents, then from a partner, so women are increasingly saying, no. I want this to be my philanthropy, and informed by my values, my life experience, the issues that I believe are important.

And so if an adviser, whether you’re a philanthropy adviser or, an adviser from another discipline that is giving some insight or counsel on giving, kind of comes in and says, okay, set up a family foundation and do it all together, and set up a meeting and you all agree on what you’re going to do. That may be the absolutely wrong advice. And it can also be harmful advice, depending on the family and the experiences of those within the family. So being clear on whose philanthropy it is. And many families, many wealth creators, parents, grandparents, they are well intentioned. They want the philanthropy to be something that is special for the family, that gives an anchor to a family as it expands and grows through the branches and the generations. And more often than not, it’s a really beautiful intent to why they aspire to that. So there’s nothing wrong with that. It’s just important to interrogate it a bit and make sure that that model is fit for purpose. And that includes having conversations with those who are invited to participate, because if they don’t want to, then what? You need to be able to be informed by that as well.

Giving should be a joyful act. And for many families, they find it a point of engagement with each other, common ground, something that connects them, often for families who have sold a business. The philanthropy is actually what connects them together after the sale of a business if a family has been deeply engaged. So all of that to say, philanthropy is not just one thing. It’s not just one way, and same for families. And so, for me an adviser, that really means deep discovery in my work with clients not to enter into the engagement, presuming that I’m the clever person and so here’s how you do it, but giving them opportunity to really let their family speak and and see what emerges from within them, individually, collectively, and then see, what that means. They always say purpose before structure and before strategy.

Cory: When you speak of families who decide that it’s best for us to do this separate, they might be making decisions on their own except the whole family is doing it. So they’re collectively doing it. They’re maybe just making decisions on their own. Do you have any examples of families where it’s been a raving success that they decided that siloed model together versus a collective model where they’re, having to to come together to make those decisions? Maybe more of the results of it because they went that route, versus being forced into a structure where they were making decisions together, and it was all done as one.

Sharilyn: I wouldn’t want to cite particular family names, but the worst case scenario is that philanthropy becomes a source of conflict and pain within a family. The ideal scenario is an opportunity for family to come together to learn about each other’s interest, to engage in productive conversation, and to make meaningful decisions together. Those are the two ends of a very long continuum or spectrum. A lot of the work that I do with families is around governance. And when I say governance, I’m not talking specifically about corporate governance, although it includes corporate governance.  But governance, more broadly answering the question, how are we going to do this? How are we going to make decisions together, and be accountable to each other and to others, where it’s appropriate to be accountable. And so governance is really the work that determines where you’re going to land on that continuum.

Cory: And in that governance work, you made mention of people who maybe don’t want to be in the structure, and how that can cause disagreements. How have you seen where people have created that lovely ability to not be involved in the philanthropy where it doesn’t create guilt and shame?

Sharilyn: Participation should be voluntary, absolutely. And not begrudgingly voluntary. Yes, you can say no, but to your point, we’re going to shame you and make you feel like the outsider. No. It has to be a gracious invitation to participate or not. Participate, because what’s the ultimate goal? Ultimate goal is generosity, sharing. And so, that same generosity applied in philanthropy needs to be extended to our family members and to each other, and recognize that people have choices.

And, you know, I often talk about, on ramps and exits. So giving should also not be a life sentence. There are times in life where people are genuinely busy, or they have other priorities and things that are important to them. And so a healthy system has ways for them to engage, but then step back when it’s not possible or desirable for them to engage. And that on that exit, it doesn’t mean they’re gone forever, and that’s it. That was your one chance. You’re 23, and you said no, and that strikes you off the list forever. That there’s a mechanism to come back.

A lovely example that I have seen in a family that talks about some of this, and I did some work with them helping to create those on ramps and exits. It was just a simple newsletter, a family newsletter. It’s an email that they do twice a year that is shared with everyone in the family, whether they’re involved or not. And it gives some examples of “these are the gifts that have been made in the name of the family.” Here’s the, either a press release in some cases, or here’s a summary of the program. This is why we did that. Though that’s a very intentional act to share the information, but then could spark new interest, or renewed interest, or at least allow members of the family to be connected to this good work that is happening, in this case, in the family’s name.

And so that’s done a lot to kind of share it outside just the people who are actively engaged. Because the other thing that can happen is it’s just those on the board, for example, they know everything and everyone else knows nothing, and it becomes a black box. And that can create some challenging dynamics as well within families.

Cory: In that regard, where there are only so many seats on the board, but there’s many members of the family who want to be involved, what are the other roles? You just made it, what a great example of somebody who can take care of that communication to the family is a great role within the family philanthropy. What other sort of roles can families create in that system to allow people to participate at different levels?

Sharilyn: It depends on the size and complexity of the family. Sometimes, if there are multiple branches in a family, there’s some thoughtfulness about adequate participation or representative representation from across the branches of the family. And then other families, they’re not big enough. They almost don’t have enough bums for the seats. That is, that is also something that comes up. I would say in the case of families who give through a foundation, most commonly a private foundation, being on the board can be fun. It can be educational. It’s also a fiduciary responsibility. And so some work needs to happen to make sure that whoever will be serving on the board understands what that role is, and can fulfill it adequately, if not excel in it. Because that has implications, not just for the family, but for our society. Because when money goes into a private foundation, it then becomes a public benefit asset. 

It no longer belongs to the family, but the family has stewardship over those resources and needs to deploy them for the best public interest. And so that’s the function of a board. We add some other stuff onto board function because the family also has to function. So you have the organization and the family who has this stewardship responsibility. So boards actually have a really important role.

But in addition to boards, to your question, depending on the nature of the philanthropy, how the giving and the granting happens, there may be some benefit in having some committees of the board. Boards will typically have a finance and audit committee at the least, so there’s an opportunity. There’s communications that you mentioned. There’s also some engagement in the community. It could be going to visit with grantee partners to understand and learn more about their work, and to get a better sense of what their needs are, where the opportunities are. That’s really important. Organizations that receive donations from generous families, it means a lot to them when you show up, when you go to events that the organization is hosting. For example, to be an ambassador. The support that a philanthropist gives to an organization, to other philanthropists. It’s kind of a third party endorsement that this is a great organization. They’re doing really important work. There’s opportunity there as well.

So the engagement opportunities for those who may not be able or eligible to be on the board, really need to be identified within the context of the family, the context of their giving strategy. But with some thoughtfulness, there’s certainly opportunities there that are meaningful, not just make work. We’re going to put you on this thing, but you don’t really get to do anything. That’s not helpful. Don’t do that. But things that will be really meaningful relative to the goals and objectives of the family. Maybe it’s a next gen planning group. Maybe it’s an education task force on what are all the resources we could find about youth and philanthropy. There are lots of ways to build in engagement and participation, but it really has to speak to the family and what the needs are, what the interests are, and what their objectives are.

Cory: I love that! And that community relation component, that endorsement of here’s the organization that we’re granting to, and a little bit like that collection plate story of, if that if I see that family is giving to this organization, it must be something that that is okay. And maybe I need to be doing that with my family as well. So I think there’s some of that aspect of building for the cause. And you’re not only giving your financial means, but some of that social and relational capital is being given as well.

Sharilyn: Yes, those are really important assets that philanthropists can also bring, in addition to their financial contributions.

Cory: Absolutely! And when you made the comment about that invitation to listen to yourself and your story, and as people become in tune with with themselves, you made comment of of the needs of the community and the world around us, how how do you find that people can really be in tune with themselves, but not take the burden of the world on as as a philanthropist?

Sharilyn: I think your question is so poignant in these days. In this moment, there’s a lot of burden to shoulder. I appreciate your question because I hear it from clients. I know it from my own experience, having spent my career in the charitable, and philanthropy communities and where you’re exposed to tremendous need, but also tremendous potential and opportunity. Often for my clients, they feel that sense of overwhelm, that even if they have a lot of money to deploy, still recognizing that the scale of issues in the world far surpass what they would describe as a measly amount in their $200,000,000 foundation. So I think, how do you not feel overwhelmed? Develop a plan. I have found that clients who develop some focus, some areas of priority to go deep, as opposed to broad, that you can really kind of latch on to some progress, or at least some wins. And sometimes those wins may take time.

We know in community and society, change does often take time. It doesn’t happen overnight, and it doesn’t happen in isolation. So I think another strategy is to develop a good peer network. Who are other people involved in philanthropy, either giving generally, or in this particular issue? So that you have a community of people that you’re strategizing with, collaborating with. Maybe you’re doing a joint funding initiative, whatever the case may be. I think that helps you feel less isolated, less alone in the issues. And I think also really engaging with your charitable partners. And this is also a topic that comes up in my conversations with clients, who are sometimes uncomfortable about, you know, how do I navigate this relationship? There’s an inherent power imbalance because I have money. I can give them money. I can choose not to give them money. And that can be challenging for the leaders of the charitable organization as well, to navigate that, because they are often very stretched for financial resources. And so that dynamic, it’s important to think about, but it’s important to engage in as authentic a way as possible, and within the time constraints that one has for their philanthropy.

I work with some clients who are still incredibly busy. They’re still wealth creating. They’re very generous. They don’t have time to go for lunches and do a lot of site visits and all that goes along with some of that deeper engagement with organizations. But where it’s possible to really listen, because as philanthropists, we work through our charitable partners to accomplish a shared mission. And so our charitable partners are the ones that know it. They know the issues. They’re on the ground. They’re living, breathing it every day. And sometimes they get discouraged as well, but more often than not, they are among the most hopeful, optimistic, people. Very often, they’ve dedicated their lives to these organizations and these causes, and meetings and conversations with them can really restore your faith in humanity.

I think all of those things are strategies to do it. I heard a beautiful quote that nothing worth doing can be completed in a lifetime. So it’s also just recognizing we all have a role to play, and it doesn’t have to be perfect, and it doesn’t have to always get done in the timelines that we’ve imagined. I think those things can take some of the pressure off.

Cory: Absolutely! And a great shout out to the fundraisers of the world because they are such beautiful people and such a great resource. As you mentioned, just leaning on them for, you know, they’re not just there to receive money. They’re also there to give back to the donors and to be great engagement partners in that plan.

Sharilyn: I was a professional fundraiser for a number of years before I started my business, working directly with philanthropists. And, typically, fundraisers are, I often think of that work as they’re translators. They’re translating, and making accessible the mission, the work, the realities of whatever organization they’re representing, and relaying it to those who can help, who can engage, who can participate, and kind of creating that bridge. At the best, a great fundraiser can make the difference between a transformational, really meaningful gift and just a transaction, a financial transaction. And I think, purposeful giving, meaningful giving. And it’s not just fundraisers. It’s executive directors, CEOs, it’s program staff working in organizations. It’s researchers. It’s the whole ecosystem within charitable organizations that allow mission to happen. And the closer that philanthropist can get to the work of that mission, typically, the more inspired you’re going to be, the more informed you’re going to be, so that better giver you can be.

Cory: Absolutely! As we begin to wrap up our conversation today, there’s a few questions I ask each guest before we wrap up. And we’ve modified our questions a little bit in the context of our conversations. But are you ready for the fast round?

Sharilyn: Okay. I see. I’ve forgotten them, but I’ll remember maybe when you say, or I’ll shoot from the hip.

Cory: Awesome! So what is the most essential aspect of building a meaningful giving experience for a family?

Sharilyn: I think we’ve talked about that at length, and I’m going to say, let the family speak. It’s only meaningful if it’s meaningful to them, and to really have opportunity to reflect, engage in conversation, and create something together that’s fit for purpose.

Cory: Awesome! And I think that speaks to the work you do, is also have somebody there to listen. If the family speaks, somebody needs to be listening as well.

Sharilyn: That’s a really good point, because it can be difficult for families to have these conversations on their own. Often, they don’t know where to start, or there can be dynamics, and it doesn’t have to be toxic or anything, but there can just be dynamics about who always speaks, who never speaks. So to have someone that is objective, whose only purpose is to help them collectively, is quite powerful.

Cory: Right! And what is the most common challenge that you see in family philanthropy when it comes to change and continuity?

Sharilyn: A common challenge that I see, or a challenge that I tend to see, is with wealth creators who who enter into philanthropy with high expectations of what they want the philanthropy to make possible for their family, such as cohesion, leadership development, values, extending family values, all of these things. Those are really aspirational objectives for philanthropy, but then are are not either able or willing to invest the time, in the process, to allow those things to happen. Most often evident by not wanting to relinquish control.

We talked a few moments ago about, is this my philanthropy, or is this our philanthropy?

It’s saying it’s our philanthropy, but it’s only me that makes decisions. Or it’s only my interest that will play out at the table. And you can be at the table. I want to see you at the table, but you won’t have a meaningful role, or a voice, or any decision-making power. Of course they don’t say it out loud. But I would say that that’s why I start with the question, is it my philanthropy or is it our philanthropy? Because if you bring people to the table, and it’s not a genuine invitation for engagement, it’s hurtful. It’s uncomfortable. It could be just like what dad does in every other sphere of my life. 

You can see how it has the potential to reinforce perhaps negative experiences within the family and so forth. And that affects continuity because often, part of those aspirations is I want it to last for generations after I’m gone. So if that’s really what you want, let’s deconstruct what you’re doing. Let’s look at what are the things that are required to get that outcome. And then let’s see if that’s still the aspiration, or do we need to modify your goals and objectives in the short term so that we get to the long term. That is also a very useful engagement of an external consultant, to help families navigate those dynamics as well.

Cory: And so on that, when we think of the leaders and the top three qualities that you would say great philanthropists, and the leaders of the family philanthropy, what would be those qualities that they possess, the top three?

Sharilyn: I often talk about emotion. In Buddhism, I think they identify seven emotions that drive our behavior; anger, fear, joy, sadness, love, hate, and desire. I think in philanthropy, the most compelling philanthropists and generous people that I’ve worked with, they connect on their emotions, that drives their generosity. They’re angry about something, an issue, or they’re afraid about something that might happen, or, they have a deep sense of love or compassion for a particular group of people for example. Those philanthropists that really connect with those emotions, it’s such a wellspring for action, for commitment, for drive. It’s people who aren’t that driven by anything that’s hard, the apathy. It’s really hard to be a compelling philanthropist if you have that, because nothing’s going to motivate you, and nothing’s going to be your north star. So emotion, I think, is the first one.

Curiosity about people, about communities, about systems. Because everything is interconnected. How does change over here impact issues over here? I think that sense of curiosity and wonder, it inspires being open, and it inspires a drive for learning. One of the questions I always ask my clients is, how do you learn or absorb new information? Is it through reading? Is it through listening? Is it through practical hands-on engagement experience? Is it first hearing firsthand, like firsthand experiences? How do you get that from the world around you? That’s a really important question because if I just send them a bunch of reports, it may not help to satisfy their curiosity. So that’s the second one.

And then the last one, I think, is humility. There’s so much that we don’t know. And if we have some awareness that there are things that we don’t know, I think we’re better off, because that spurs new learning. It allows us to collaborate with others, to problem solve, whereas if you show up, and this can be a hazard, particularly for very successful people, they’ve dominated a field or an industry. They’ve created a lot of wealth. So you can understand why they may want to enter philanthropy and bring that same kind of gusto. And the gusto is great, with a little bit of humility that will allow them to learn from the very people you and I were talking about, those within, not just the charitable organizations, but the people and issues that they’re in service to. The people who are experiencing poverty and homelessness, the people who may not have the opportunity that we might have. That sense of humility entering the space.

Really fantastic documentary on Netflix about the James Webb Space Telescope that was launched. I think it was just after COVID, and resulted in some really beautiful imagery that is transforming space study and science. I was so struck by that documentary. There was not just one smart person in the room. It was not just an effort of one person. It was over two decades people had been working on it, some longer than others. But everyone in the room was brilliant. Everyone was committed. Everyone understood the purpose and the mission. And so I invite your listeners to check that out. But the comparisons in philanthropy, I think, are quite valid. And so, humility, showing up, recognizing that as brilliant as I may be, change doesn’t happen because of one person. It happens in community, and it happens collaboratively. And so emotion, curiosity, and humility, I think, all lead to great philanthropy.

Cory: Beautiful! And I’d like to highlight where our listeners can engage in more of the conversations you’re having, as well as some of those conversations that you’re maybe listening to, or things that you’re reading. Could you provide our guests with some of that?

Sharilyn: Well, my website, watermarkpc.com, there’s a whole section there on resources, either things that I’ve written, podcasts, webinars, learning experiences, so invite them to go there.

I feel like there’s such an avalanche of resources available these days, on all topics related to philanthropy, family wealth, the interconnection between them. There’s two great colleagues in the UK. One is doctor Beth Breeze. She wrote a book, it’s called In Defence of Philanthropy, and it’s a really insightful book making the case for why philanthropy matters, and, warts and all, there are improvements that we can make, but just why philanthropy is so critical to our well-being in civil society. And another colleague in the UK, Rhodri Davies. He’s quite active on LinkedIn. He has a wonderful newsletter called Why Philanthropy Matters. 

He does a lot of writing around the history of philanthropy, but he finds some really great nuggets that really demonstrate to me that philanthropy has been so instrumental in many of the debates and conversations that we have today about the role of philanthropy, the experiences of affluent families in the context of philanthropy. They seem like new conversations, but they’re not new conversations. They’ve been around for centuries. He has such a compelling way of relaying some great research that I think just helps to reframe where we are today. And certainly in Canada, we have a long heritage of philanthropy since the founding of the country.

Cory: As we talked about two to three generations in Canada, if we look at other countries, we can see more history of that family philanthropy happening in countries that have just more of that history to them as well.

Sharilyn: Some of the families in Europe, they’re on generation 13, 14, 15. And one of the things about philanthropy that I really love, and sometimes we stumble over the word philanthropy. But philanthropy, charity, giving, sharing, whatever the word. It’s a universal experience. It happens in all cultures. It may look different in some parts of the world than others. But since humans have been forming societies, there’s been philanthropy. And so one of the things that I love about working in the philanthropy space, but also being an academic and a scholar in philanthropy, is being able to engage with people in other parts of the world, and meeting families, and advisors to families in other parts of the world.

It’s important for us to recognize, not just the ways that we’re different, but the things that we share. I think there is something very human about coming together, collective action, and helping each other, and I don’t think that will ever go away.

Cory: Amazing! I wanted to make sure that we covered everything today. Is there anything else that we maybe didn’t get a chance to touch on, or maybe any kind of final words for our listeners?

Sharilyn: Sometimes in conversations like this, I think there’s the potential for people to tune out if they’re like, well, my family doesn’t have, you know, a $50,000,000 foundation or the metrics. On one level, the metrics, how much you have to give, they don’t really matter. A lot of the themes and the points that you and I have explored today are really about generosity, and certainly in the context of families. Whether your listeners are kind of well down the road in terms of philanthropy and giving, or whether they’re just starting, it’s not too late to think about what your role is in the world.

We started the conversation with “let your life speak.” What is your life telling you about what you might contribute, how you might be a helper, the ways in which you might be generous in your life, which it may be with wealth, but it could also be with other other capital that you have, your your time, your networks, your resources, and just how you’re going to show up in the world.

So that would be the way that I would end, on a note of inspiration. And maybe after our call today, I’m going to write a commencement speech.

Cory: Amazing, love it! Well, thank you, Sharilyn. What a great way to send our listeners off with, and thank you so much for your time, sharing your expertise and experiences with us. I’ve taken a lot away from our conversation, and I know that our listeners will find the nuggets that you’ve shared incredibly valuable. So thank you for your contribution.

Sharilyn: My pleasure. Really nice to speak with you today.

As we wrap up this episode, we invite you to reflect on Sharilyn’s insights about intentional philanthropy, family governance, and the delicate balance of individual and collective values in family giving.

Whether you are part of a family enterprise or provide consulting to enterprising families, Sharilyn’s approach offers tools for fostering meaningful philanthropic engagement and more effective decision-making across generations.

Throughout our discussion, we explored the pivotal role of governance in family philanthropy. Sharilyn illustrated how addressing these foundational structures can enhance both individual participation and collective impact. We examined practical strategies for improving multi-generational engagement, from creating voluntary on-ramps and exits to developing roles beyond board membership. These insights provide family enterprises with innovative approaches to navigate philanthropic decision-making, foster genuine commitment, and construct enduring legacies that harmonize personal values with meaningful social impact.

For families looking to strengthen their philanthropic journey and navigate the complexities of multi-generational giving, Dr. Sharilyn Hale offers expert guidance and support. You can connect with Dr. Hale through Watermark Philanthropic Counsel, where she provides tailored strategies for developing effective family governance. We’ve included her contact information and additional resources in our show notes to help you begin the process of transforming your family’s approach to giving and creating a more purposeful philanthropic legacy.

Disclaimer:

This program was prepared by Cory Gagnon who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This is not an official program of Assante Financial Management, and the statements and opinions expressed during this podcast are not necessarily those of Assante Financial Management. This show is intended for general information only and may not apply to all listeners or investors; please obtain professional financial advice or contact us at BeaconFamilyOffice@Assante.com or visit BeaconFamilyOffice.com to discuss your particular circumstances before acting on the information presented.