This panel discussion is part of our special report, “Women in Family Offices.” To see more content in the series, click here.
On March 25, 2025, Canadian Family Offices and PBY Capital hosted an online panel discussing how women are increasingly taking a bigger seat at the table in family offices and what this means for the industry. It was an engaging conversation that also dug into the generational wealth transfer, women being wealth creators and opportunities within the family office ecosystem.
The panel featured:
Carolyn J. Cole, Founder & CEO, Cole & Associates
Martha Simmons, Co-chief Operating Officer, Forthlane Partners
Anna Dayan, Head of TD Wealth Family Office
Patricia Saputo, Co-founder, Crysalia
Here is the full *transcript of the engaging panel discussion:
*This transcript is provided for convenience and is based on the audio recording of the video. While efforts have been made to ensure accuracy, minor errors are possible.
Ashley Redmond: Hello, and thank you for joining our panel discussion today, Women and Family Offices. I’m Ashley Redmond, content producer at Canadian Family Offices.
We will hear from four women today with deep experience in the family office ecosystem who graciously accepted our invitation to share their wisdom with you. As many of you watching know, this month’s special report on our website is Women and Family Offices in Alignment with International Women’s Day held March 8th.
There is a lot to dig into with this topic — from female colleagues interacting in a specific way with clients, to women controlling 40 per cent of the wealth by 2030, and of course, the Great Wealth Transfer. What does this all mean for family offices? How are they adapting? And what are the new and emerging opportunities for women in the field?
Before we get into the discussion, one order of business. Canadian Family Offices would like to thank PBY Capital for their generous financial support, both as sponsor of today’s panel and as title sponsor of CanadianFamilyOffices.com. PBY Capital is committed to delivering exceptional investment solutions to family offices, institutional investors, and high-net-worth individuals across diverse asset classes, guided by a process centered on partnerships, education, and sophisticated service. To learn more about PBY Capital, visit pbycapital.com.
Now over to the panelists. I would like each panelist to introduce themselves and tell us who you are and what you do today. We’ll go in alphabetical order. So, Anna, let’s start with you.
Anna Dayan: Thank you so much, Ashley. My name is Anna Dayan. I am the region head of our GTA region at TD Private Wealth Management, which is comprised of a talented team of investment professionals, private bankers, trust, tax, estate, business succession, and insurance specialists that support high-net-worth and ultra-high-net-worth clients. I also head up our TD Wealth Family Office, a multidisciplinary offering supporting ultra-high-net-worth clients and family offices with holistic wealth management.
I’ve been with TD Private Wealth Management for about 12 years and was previously a tax lawyer at a national law firm.
Ashley Redmond: Fantastic. Carolyn?
Carolyn Cole: Hi everyone. My name is Carolyn Cole, and thank you to Canadian Family Offices for hosting this. I’m very excited about the conversation.
I spent about 25 years in the wealth management sector — three Canadian banks and an accounting firm — and subsequently founded my own firm to help families either design their own family office from scratch or work with the family office structure they have set up. I really wanted to come at it from a lens of no product, really collaborating, and making sure that no one had to break up with any providers in order to have a better system.
We focus on family office strategy and design, inheritor education, and helping families with communication.
Ashley Redmond: Thank you.Martha?
Martha Simmons: Morning everyone. I’m Martha Simmons. I’m Co-COO at Forthlane Partners. We’re an independent wealth and asset management firm located in Toronto. We’re focused on curating well-diversified global portfolios for our clients and providing a sophisticated client service model to support their diverse needs.
I’m a lawyer by training and have a Master’s and PhD in Law with a specialization in dispute resolution, which definitely comes in handy when working with families — my own and my clients. I’m happy to be here today and I’m looking forward to the discussion. I’m sure it’ll be broad and interesting.
Ashley Redmond: Great. Thank you, Martha. Patricia?
Patricia Saputo: Yes. Hi Ashley. Thank you for having me here today. My name is Patricia Saputo. I come here today wearing two hats.
My first hat is as CEO of my family’s family office. I’m a professional tax accountant and estate planner by trade. I’ve pioneered the single-family office space since 1998, when Saputo Inc. went public. I came in to help my father with the dividends that were being paid out on a quarterly basis, to look at the investments and all that came with it. That was at a time when the terminology “family office” wasn’t even existing.
Today, we’re transitioning our office to version 3.0, where we’re bringing in the next generation of decision makers.
My second hat is as a strategic advisor and co-founder of Crysalia. We are a Chief Learning and Development Office, and we help enterprising families and their individual members harness the full potential of their human capital — in every aspect of the enterprising family space.
Ashley Redmond: Fantastic. Thank you, Patricia.
Okay, let’s get started with the discussion. Today I’d like to begin with the Great Wealth Transfer, which in broad strokes is a transition of wealth from baby boomers to their children. But the reality is that the first step in the Great Wealth Transfer isn’t necessarily matriarch to kids. It can be matriarch to patriarch, patriarch to matriarch, and then to the kids.
So, are you seeing this in the family office space, and what are some of the impacts? Patricia, why don’t you start us off?
Patricia Saputo: Sure. I’ll bring my tax hat on for this question, because that’s actually the reason why you do see that more often than not. The Income Tax Act allows a transfer from one spouse to another on a tax-free basis. A lot of people will say, “Why would you want to pay your taxes in advance and transfer directly to the children,” when you can take advantage of deferring that tax and the time value of money? The more you have in your pocket today, the better it is, because it gets to accumulate.
Although, we are starting to see a change, because more people don’t remain in the same marriage. And in order to protect from other spouses and other children coming in to inherit the assets someone might have built up, you’ll see more trusts being created. These trusts will then give the income to the spouse and the capital to the children.
So to me, it’s all about tax planning — what is possible, and how you control the outcome to ensure that the assets remain in the family branch you intended.
Ashley Redmond: And Carolyn, I know you see this a lot in your family office work. Do you want to weigh in?
Carolyn Cole: Yeah, I’d love to. I think this really goes back to some of my earlier years, career-wise as well. Go back 20 or 30 years, and it was all about financial planning.
Then, in the early 2000s, everyone was teaching business succession planning — that’s where a lot of the Family Enterprise Advisor foundations came from. But we realized people weren’t necessarily transitioning their businesses to the next generation. That led to a wave of business exit strategies.
Now, what we see as the mainstream is the family office space. When you’re doing business succession planning, there’s usually one family member — often male — taking the lead. But in the family office space, there’s room for many people at the table. There’s space for collaborative decision-making, and that’s where women in families are far more likely to have a seat, be heard, and offer their advice.
And as Patricia just said earlier, there’s more than one type of capital. So it’s not just the financial capital that the women are having a conversation around. There’s definitely a big transition happening in the decision-making process, and women are increasingly taking the lead when it comes to managing wealth.
Ashley Redmond: Right now, we hear a lot about equal representation.
Martha, I’m going to throw this question to you. We were talking previously about why equal representation matters — and why it matters when a client walks through the door and sees themselves in the person offering them financial advice and guidance. Martha?
Martha Simmons: One of the most important things in the family office space and in wealth management is that clients trust you. There’s research that shows people generally tend to trust others who are like them more than those who are not. People gravitate toward others who share their interests, values, and beliefs.
I don’t think it’s exclusive to gender — it’s important to have lots of diverse people around the table. But it’s not only about who you are. You also need to show confidence, consistency, integrity, and all those really important qualities.
That said, having something in common with your clients helps take you one step closer to building that trust. It creates space for deeper conversations, where clients may feel comfortable sharing their most personal secrets and priorities — things that could be crucial for estate and legacy planning.
Ashley Redmond: That makes sense. And not to lean on stereotypes, but if a client wanted to talk about motherhood, that might come easier with you than with a male colleague.
Martha Simmons: Yes, exactly. We have both men and women in our office, and clients talk about many things with all of us. But I do find that many women open up to me more about parenting, schooling of children — topics that might not be the first thing that comes up with a male colleague.
Ashley Redmond: Patricia, what do you see in your office?
Patricia Saputo: When you raise the topic of equal representation, the words that come to my mind are connectivity, understanding, relationships, credibility, shared values, legitimacy.
Everyone wants to be represented. Everyone wants to feel their voice is heard — even if they don’t have a vote at the table. Sometimes younger voices may be muffled, and someone needs to help them feel confident enough to speak up and spread their wings.
Often, when clients come in, it’s about being understood — not judged. It’s about feeling like someone “gets” them, like they can trust that person, and that the person genuinely cares. Many say, “I don’t know what I don’t know. Can you help guide and advise me?”
Some clients want comfort, a sense of assurance. They might not trust themselves to do a good job, so they trust their advisors. And sometimes they’re honest — “I don’t know this stuff, I don’t understand it, I don’t like it. I’m expected to, but I don’t care to — can you help me?”
They’re just trying to find someone who can help them figure out their position.
Especially with younger women, financial literacy is often still assumed to fall to the male counterpart — even when the female counterpart might know more. So we work to help those women open up, realize they know what they’re doing, and feel more confident with their knowledge, so they can have a voice — and eventually a vote — at the table.
Ashley Redmond: I loved your line: “younger voices may be muffled.” That would be a great headline for a next-gen article. But the point is, we still need to make room for those voices.
I’m curious about female colleagues you see in action. Anna, I’ll throw this question to you. Do you find that female colleagues at your office approach clients differently?
Anna Dayan: Yes, absolutely. There are certain common characteristics we see in highly effective wealth advisors — and that’s regardless of gender. Obviously, you need strong wealth management expertise — that’s the baseline.
But effective advisors often have strong emotional intelligence. They’re good at active listening and excellent at building trusting relationships with clients.
In the family office space specifically, managing family dynamics and bringing empathy into conversations are critical. Women, on average, tend to excel in these areas. They build trust, listen actively, and communicate effectively.
On a practical level — and I think Patricia was alluding to this earlier — effective advisors read the room in meetings. They don’t overload clients with industry jargon. They pause, check in to see if participants have questions, and make sure clients are following and understanding.
It’s important not to assume that because someone has wealth or has had a successful career that they automatically understand the nuances of wealth management. Great advisors take the time to explain, and they make space for questions.
Ashley Redmond: Carolyn, anything to add to that?
Carolyn Cole: Yes, it’s interesting. I work with a lot of women, and a lot of the families I’m working with now include female wealth creators at very significant levels. I’ve noticed a certain nuance.
First, what I’ve had to learn is that sometimes women — whether they’re clients or advisors — can feel less comfortable when there’s a group of men in the room.
Because I worked in a male-oriented workspace for quite a number of years in the wealth management space, I do see quite a difference in how open female clients are with female advisors compared to male advisors. There’s just a different level of comfort there.
I also think that women in this space are often able to challenge or have more difficult conversations with strong, confident men in a different way. I might be generalizing, but in my experience, when a male colleague challenges a male client, it can become a kerfuffle. Whereas when I say the same thing, it might be received differently — with less conflict. That sometimes gives women an advantage in advisory roles, especially when tough conversations are required.
There’s also a clear distinction in how women are perceived — assertive versus aggressive. This language matters. Can you be assertive with your clients, have those necessary conversations, and not be deemed aggressive? I think we’ve come a long way in the past 20 years, and I think women in the family office space hold themselves to a high standard and are doing really well with it.
Ashley Redmond: Carolyn, I want to stay with you for a moment because this next question builds on what you were saying. I read a stat recently that says 80 per cent of women change their financial advisor after their husband passes away. Do you see this happening in the family office ecosystem?
Carolyn Cole: I’m really passionate about this topic because I spent 23 years in the wealth management space, licensed and working closely with clients. I remember this exact stat emerging in the early 2000s — that 80 per cent of women were moving their money within 18 months of their husband’s passing.
Fast-forward to 2024, and I was reading the same stat again. Nothing has changed. Why haven’t we evolved?
I looked into it, and part of the reason might be representation. In 2002, around 12 per cent of wealth managers in Canada were women. In 2024, it’s 11 per cent. We’ve actually decreased. If you factor in the United States, the decline is even bigger. So fewer women are in that space today.
So are women moving their money because they lack a relationship with the advisor, or because the advisor is male? We don’t have the data to say. But what we do know is that women today have more decision-making power than ever before.
In the U.S., 70–80 per cent of purchases are made by women. In Canada, women make 80 per cent of household purchasing decisions. We’re ahead in that sense. But it still brings us back to the key question: why do women move their money?
This is my personal opinion, not backed by specific stats, but I think they move for a few reasons.
First, as you alluded to earlier, this is a relationship-based business. If a client had a close relationship with her husband’s advisor — but not with the advisor herself — she’s likely to move on. It’s not necessarily about gender. It’s about connection.
Second, I would love to see stats comparing the performance of portfolios managed by women versus men. Are female-managed portfolios growing faster? I haven’t seen those numbers, but I’d love to.
This issue still feels unresolved after 20 years, and it’s a mystery why more progress hasn’t been made.
Ashley Redmond: Martha, anything you’d like to add?
Martha Simmons: Yes — I think it’s a real shame. It reflects on the advisor-client relationship if that’s what’s happening.
In this space, it should be about building a relationship with the whole family, not just with the financial decision maker. If you’re only focused on one person, you’re missing the bigger picture.
Early on, we prioritize the entire family. We spend time with the spouse who may be less financially literate and offer financial education to make them comfortable participating in the discussions. When it comes time for portfolio reviews, everyone’s on the same page — everyone understands the language we’re using.
If you make the whole family feel welcome — the spouse, the children — you’re planting seeds for a relationship that can span generations. There are similar stats about children switching wealth managers once they gain access to family money. That’s also unfortunate because continuity matters. A long-term advisor learns so much about the family, and keeping that relationship intact is a huge asset when transitioning between generations.
If people are constantly switching advisors because they don’t feel seen or understood, there’s something fundamentally wrong with the system.
Carolyn Cole: Let me jump in again — I think this is such an important point. There’s a real distinction between choosing a financial decision maker and a relationship decision maker.
You might have a strong financial relationship between a patriarch and an advisor, but the relationship driver in the family could be the spouse. And if that relationship isn’t there — no matter how great the returns are — it may not matter in the end.
You know, I cite my late mother-in-law, who unfortunately passed away. She had said to my father-in-law, “The second you die, I’m firing that guy.” Now, the reality is she passed away first, which is unusual. But she was very clear — “He may get us great returns, but I’m done with him.”
Again, relationship versus financial returns are not equal.
Ashley Redmond: Patricia, anything to add?
Patricia Saputo: Yes. I saw this even in the 1990s when I was working at Deloitte as a tax professional. Clients would come in alone, without their spouses, and I’d wonder — why aren’t the spouses here?
As we were doing succession and estate planning, it felt like a missed opportunity. Shouldn’t the spouse understand what’s happening? If they’re left with the assets and the responsibility to manage things, it puts them at a disadvantage.
And sometimes the professionals themselves don’t think to ask: “Wouldn’t you want your spouse involved in these meetings?” These are the people raising your children, your grandchildren. Then you have the layer of in-laws — who you don’t want to become “outlaws.” So how do you keep them as in-laws and make sure they feel included?
It’s about setting a narrative, clearly explaining your wishes, and removing assumptions. That way, misunderstandings are minimized and communication is stronger — and that narrative can be passed down from generation to generation.
In a family office, you have a team of professionals who really get to know the family. Not every personality will click, but the team is there for the benefit of the whole family — and that includes every individual member.
You want everyone to feel safe, like they can ask questions — whether one-on-one or in family meetings — and get the services they need, wherever they are in life.
Ashley Redmond: From your perspective, have you seen improvement in this since the ’90s?
Patricia Saputo: Yes, because of the family office space. And I hope that continues. There’s also a big difference between single-family offices and multi-family offices. In single-family offices, the entire setup is for that specific family. Multi-family offices vary — not all are created equally, and each handles their clients differently.
Ashley Redmond: Interesting. Okay. I want to go back to that stat I mentioned at the beginning: women will control 40 per cent of the wealth by 2030. And with the risk of sounding too stereotypical, Martha and I did a video last month where we lightly touched on this — but do women invest differently? And how? Are there specific assets they gravitate toward?
Patricia, let’s start with you.
Patricia Saputo: In general, women aren’t just about the numbers — it’s more than that.
Return on investment matters, because that gives you liquidity, and liquidity allows for spending. But it’s also about the return on the means. The relationships you build, the impact you have on others or in your community, the knowledge you gain — these all matter.
So when a woman makes an investment, she might ask: “What else do I get out of this?” Maybe she’s meeting the people behind a private equity deal. Maybe she’s investing in something that supports her community or the environment. If the returns are the same, but the investment aligns with her values, it just feels better.
That kind of empathy and caring is something I see more in women investors. With men, I often see more focus on: “What’s the return? How much am I getting?” But women often ask, “How does this feel?”
Ashley Redmond: Anna, do you want to chime in?
Anna Dayan: Absolutely. We’ve talked a lot about women as wealth inheritors, but I think more and more, women are becoming wealth creators. In my experience, especially in the last five years, women clients have become more actively involved in wealth management conversations.
Of course, women are not a monolithic group. But studies show women actually tend to outperform men as investors. That might be tied to behavioral finance — they may be less reactive.
Women often focus on personal goals: financial security, philanthropy, sustaining wealth for future generations, creating a legacy. And on average, they prioritize capital preservation over maximum returns.
As Patricia mentioned, women often want their investments aligned with their values — that’s where ESG (Environmental, Social, and Governance) conversations come into play. Women also tend to engage deeply in areas like estate planning, legacy planning, philanthropy, and family dynamics.
They’re often very detail-oriented and ask great questions. When you create a safe, open environment for women to ask questions, you get incredible engagement.
Ashley Redmond: Martha, anything to add?
Martha Simmons: A lot has been said, but yes — there’s a lot of research out there suggesting that women are more conservative investors. They tend to take a longer-term view and are more comfortable riding out market fluctuations rather than reacting quickly.
That focus on long-term goals — thinking about the next generation — often fuels their investment behaviors.
But it’s important not to generalize. Not all women are the same. As we see more female wealth creators, especially in fast-paced sectors like tech, we’ll see more women who are risk-seeking too.
Still, the research has been consistent over time, and we should take it seriously.
Ashley Redmond: Looking at the questions we received from the audience beforehand, several of them were from younger women interested in joining the family office space or financial services more broadly.
How do they get in? What advice would you offer?
Anna, can we start with you?
Anna Dayan: From my perspective, this is an incredible time for women to enter the family office or financial services industry. Women clients are playing a more active role in managing their wealth, and there’s a real push to have more women represented on advisory teams.
We’re seeing more traditionally male-dominated teams actively seeking out women to join them — not just for diversity, but because of the unique capabilities women bring to the table.
In terms of advice, I would say take the time to hone your skillset, be curious, and make time in your schedule to network as much as possible.
Patricia Saputo: Yeah, so for me, I would maybe start with defining the family office space, because there’s many different versions and varieties of that. There used to be the single family office that really looked at one family or different branches of a family. Then there was a multi-family office space, which were offices spun out from financial institutions. Now, in the financial institutions where Anna’s coming from, it has its own type of family office. They’re not all created equally, they’re all very different. Some of them are mainly just financial capital oriented, and there’s others that look at the other sources of capital—whether it’s the intellectual capital, the social capital, the human capital, the cultural capital, the symbolic capital.
There are many different sources and they’re all intertwined somehow. You’ll see more of that being intertwined in a single family office space because you’re really there to service the entire family. Compared to, as you get further away from that, it could be just certain parts of the family. So it’s to understand really what’s that cross world between that financial world you want to be involved with, but also building the bridges and bringing together that financial skill and knowledge to the intuition, the empathy, and the ability to build the relationships with the clients.
This is a lot of what I see in the single family office space, but it’s also growing in other environments. So it’s just to understand that they’re not created equally and ask the questions—what is it you’re getting involved with? If you’re going into the family office space, what kind of family office environment are you getting involved with?
Martha Simmons: I think feeding off of what Patricia is saying, I think you have to follow what you’re passionate about first. As you’re coming up and getting your education and early working roles, whatever you’re passionate about, you’re likely to be more successful at.
The family office space is very diverse. There’s lots of roles to have and lots of jobs to do and lots of angles that you can look at it from. A lot of the young adults growing up now are going to have more than one career in their lifetime, and maybe more than our generation has. So follow your passion and then there’s going to be a place for you somewhere if this is ultimately where you want to wind up.
And I agree 100 per cent with Anna—networking is key. Meet as many people as you possibly can and stay in touch. Also make sure your reputation stays intact. That’s the one thing that you never get back. Always make sure to remain honest, be good to other people, and pay it forward, and it will all come back.
Carolyn Cole: First of all, I think that each of the women that have just spoken have nailed it—absolutely articulated it. There are tons of technical elements that go into a multidisciplinary service called family office. So really understanding what you’re curious about, what you’re good at, and get your skill. There’s a technical skill that’s going to be required.
Then step back and ask yourself, why this industry? Is it because it’s suddenly new? It’s interesting because there’s cachet attached to it? Why are you wanting to work with the families that are in this space? It’s hard work. It’s not easy to be able to balance the multidisciplinary service providers as well as the nuance of the family dynamics. When you’re in that space, you have to bring all of that together.
So I think it’s really understanding why you want to do it, what area you want to be in, and then be clear that this isn’t a rosy job. This is just as hard as anything else in the industry and you’ll have to work for it and earn it. And just because you’re great at your technical skill doesn’t mean you’re going to be great at applying that technical skill in the family office space. So ask a lot of questions.
Patricia Saputo: Yeah, that in itself, it’s not really new. It’s actually bringing under one roof all the service providers—the lawyers, the accountants, the investment people. So everybody’s under one roof now to service whoever the family is.
Whereas before you would go to a law firm for the legal stuff, accounting firm for the accounting stuff, your investment advisor, the banks for the investment—you know, and everybody kind of just did things independently. Now it’s everybody coming under one roof to give full service, as Carolyn mentioned—that multidisciplinary team approach to their clients to be able to service them in all the aspects of what they need.
Ashley Redmond: Yeah. It’s funny you mention that because a lot of the questions we get are, what exactly is a family office? What’s the definition of a family office? That seems to be pretty popular in the past few years. Do you get that as well, Patricia?
Patricia Saputo: All the time. The terminology—it’s a bad word. It’s been bastardized over the years. Everybody’s creating their own definition and just making it their own. Some say, “Well, don’t call me a family office. I’m not. I just do the investment arm for the family.” So they’ll go back to that old way of the financial institution—do the investment arm and that’s it.
Don’t call me a family office. I’m not that, but people think I am because I just do the service of investments. So yeah, everybody just thinks it’s everything and nothing. It is very confusing out there for those coming up the ranks. And over the past 20 years, it’s changed quite a bit because there’s more and more people calling themselves that. What you provide as a service is everybody’s option of what they want to do for their clients—or not do for their clients.
Ashley Redmond: Anna, do you get that at TD as well—just people asking about the terminology “family office”?
Anna Dayan: Yeah, absolutely. And I would agree that different people have different definitions. At TD, we’re truly a multidisciplinary team. We do the investment management, the tax and estate planning, private banking, family governance planning. We have a family governance specialist on our team.
In terms of our actual family office team, it’s all-encompassing. Unlike some other family office offerings, we don’t refer to investment advisors or portfolio managers—we do the investment management. We have an external CIO-type role working with our wealth investment office.
So it’s a little bit differentiated. But again, it’s interesting to see all the different makeups of family offices across the industry. It truly is different in every case. So do your homework when you are seeing something that’s called a family office.
Ashley Redmond: I actually wanted to add one thing that I missed on the question of younger females that are looking into the space. Do you encourage them to look for a mentor? I know Martha mentioned networking—so maybe network first and then mentor? Or what do you think?
Anna Dayan: I think a mentor is always helpful. It doesn’t have to be a female mentor—some of my best mentors have been male. It also doesn’t have to be formal. It can just be taking someone out for coffee and coming prepared with questions, so that you’re not wasting their time, as opposed to just showing up and expecting them to do the work.
I always give that kind of advice—if you’re a mentee or asking someone for guidance, make sure you’re coming prepared to the meeting. It doesn’t have to be a multi-year mentorship. Those kinds of relationships happen more naturally. But just getting to know people and picking their brains in the industry—it goes back to the advice around networking and meeting as many people as possible.
Martha Simmons: Yeah, and if I could jump in, it’s great to have a champion too. If those mentors can turn into champions for you in advancing your career, that’s extremely helpful. It’s also valuable to have someone you feel comfortable having more intimate conversations with.
There are certain things we’re not supposed to talk about in the workplace. You’re not allowed to ask a woman if she’s going to have a child, for example. But if you can have someone you’re close enough with to say, “Hey, I’m thinking of becoming a parent—male or female—what do I do? How does the workplace deal with that?” and get the actual details, it makes a big difference.
If you just go to HR, you’re going to get one level of answer. But if you have someone you trust and you can be open with, you can get a deeper understanding so that you can have a fulfilled life the way you want to have it. You can make sure that your career goals align with your family goals.
Carolyn Cole: Ashley, I’m just going to jump in—can you guys hear me? I had a bit of a headset issue. Okay, just making sure.
I think it’s not just about having a mentor. I really like that we’re talking about this, because I think it’s about having your own counsel. If you think about the family office space, you have a series of individuals with technical expertise that are brought together and unified for the service of a family.
Now think about that in your own world. Do you have someone to go to when you’re balancing your professional life with your personal goals? Do you have someone to go to when you’re dealing with a financial challenge or anything else?
So, not just mentorship in the career sense, but find a really good, dynamic group of people—who may not even know each other—that you can call on for advice and support through different parts of your life. Life throws a lot at us, and having that group matters just as much as having a specific career mentor.
And whether they’re male or female, it doesn’t matter. Building that circle is just as important as building one single mentor relationship.
Patricia Saputo: Yeah, and just to add—when you talk about a mentor, it’s important to understand the difference between a mentor, a coach, and an advisor. There are different people you can reach out to, and it’s important to know what you’re looking for from each of them.
Is it to get a job? Is it just to listen? Is it to get advice or to be held accountable? Is it to have someone who will check in with you and make sure you’re progressing? Everyone has a different position in your journey.
Whether it’s a formal or informal relationship, you need to be clear on your expectations. And the person you’re speaking with needs to understand what they’re being asked to do, too. That way, both parties know what to expect, and the relationship can actually serve a purpose in this stage of your life.
Carolyn Cole: Patricia, take that and apply it right back into the family office space. When you’re at the table as a professional—let’s say you’re building a team around the family—being able to clearly define the role and relationship of each team member is essential. It helps both the professionals and the family understand what’s expected.
Whether it’s through quarterly meetings or biweekly check-ins, setting that clarity allows everyone to shine in their expertise. And I think that’s what I’m really enjoying about the family office space: helping people define how they can best support the families, bring clarity, and truly do their best work.
So when you’re bringing that tax accountant in, you can facilitate helping them understand the nuances of the different adult children and how they think about money. Or when you’re bringing a team of wealth professionals together that might be doing different things, you can facilitate what is expected from them.
And I think that’s what makes women really good at this. We do well by bringing people together. We do well collaborating. We do well with that abundance theory—that there’s enough for everyone. Having more advisors at the table doesn’t take away from anyone. It actually makes things so much better.
I do feel that we have a female advantage in the family office space because of those natural instincts we have for building a good team.
Ashley Redmond (Moderator):
That’s great. Thank you. We actually have time for audience questions. And due to Martha’s background and her PhD, I’m going to send this first question to her.
This question was from Daniel via Gmail. Thank you, Daniel.
Martha, do you see a role for conflict resolution experts, advisors, and coaches to help navigate the opportunities and transitions that are coming in the family office space?
Martha Simmons: Obviously, my answer is yes. I think it’s absolutely essential. I love when people think ahead of time that there’s going to be conflict and bring in experts—whether they’re coaches, mediators, governance experts, or others—before a conflict happens, because they’re bound to happen.
People hesitate to engage help ahead of time because they might worry about digging up old issues. But really, having deep conversations, and knowing how to have those conversations—often with the help of an outside facilitator—is really helpful to avoid long-term damage in a family.
Whether the expert is internal to a family office or brought in from the outside, there are many capable people out there who specialize in mediation, dispute resolution, and conflict management. And it’s wonderful when families think ahead and engage those kinds of people to support them and avoid challenges.
Even if you’ve already missed that boat and are in the middle of conflict, it’s still worth it to bring in external help—before it gets worse or ends up in court. Keep things confidential. Keep things within the family. Outside neutrals can be incredibly valuable in supporting that process.
Ashley Redmond: Patricia, due to your experience in this field, I’m sure you have some stories you can’t share with us today—but what’s your opinion on the role of conflict resolution experts in this space?
Patricia Saputo: This is exactly what Crysalia does as an independent consultant. Because we deal with families and all the family members, there are obviously old relationships that started in childhood. “You took my doll and never gave it back,” or “You stole my boyfriend. I still haven’t forgiven you.” These underlying currents exist in families all the time.
So, we actually start by helping each family member understand their own “winning conditions” and what the winning conditions of their family counterparts are. That way, when they’re having a conversation and people start to feel anxious, and the anxiety builds up, we can help defuse that before it escalates.
You can be one person in your natural state, but when you start getting poked, you become someone else. Then the organizational psychology kicks in—fight, flight, or freeze.
Einstein said the definition of insanity is doing the same thing over and over expecting different results. If each family member understands that when they feel that anxiety, what they’re really trying to do is regain control—not take control from someone else—it changes the tone.
They’re not trying to get one up on you. They’re trying to feel safe enough to keep having the conversation. That’s where we come in and say, “Do you need a break? Do you need five minutes?” Or we create a safe word, so someone can say, “You’re stepping on my toes—we need to stop.”
We also look at how the environment impacts things. If you’re having a meeting at Dad’s office where all his people are, it’s not neutral. But if it’s at a neutral place—maybe at home—everyone feels more comfortable. Once you’ve set that kind of table, nobody feels blindsided or controlled. Everyone feels they have a seat, they can contribute to the conversation and the decision-making.
Because when families don’t share the same North Star—when they don’t have aligned goals and values—it will fall apart, no matter what. You cannot force everyone to follow the same direction if the objective isn’t shared.
I strongly recommend looking at pruning the family tree and considering the best way to divide assets or go your different ways in a manner that doesn’t make everybody feel like they’ve lost something. That way, the reputation of the family and the wealth don’t just dissipate. You can do it in a controlled fashion where everybody comes out positive. It might ruin some family relationships—but so be it. At least everyone can do what they need to do and follow their own North Star. You can’t force people to follow yours.
Ashley Redmond: It was interesting what you said too—even changing the location can change the dynamics in the family.
Patricia Saputo: Oh, absolutely. Even having water at the table—or not. Some families say, “Clear the table. No water, no nothing. This is serious.” Others don’t want to meet around a boardroom table; they’d rather meet in the living room, with coffee, water, and pastries. Make it feel natural. For some, the boardroom is too severe. So let the setting be more natural.
Ashley Redmond: Anna or Carolyn, anything to add to this one?
Carolyn Cole: I think Patricia and Martha made great points. I’ll just add that a skilled advisor knows when to bring in an outside facilitator, because this is such a critical piece of the family office offering and how we work with ultra-high-net-worth families. Conflict can destroy families, so it’s essential to set things up properly from the start—and to recognize when you don’t have the skillset to manage a particularly nuanced family situation. That’s when it’s time to refer out.
Martha Simmons: Yes, and I think it’s fantastic to be able to say, “This isn’t my area of expertise—let me bring someone in who can help better than I can.” We don’t have to pretend we’re all things to all families all the time. It’s better to be upfront and say: this is a team sport.
Ashley Redmond: Great. Okay. I think we can squeeze one more question in, and then I’ll have a final one to wrap things up. Let’s go to this next audience question.
Anna, why don’t you take this one? We often hear about the trade-off between protecting capital for future generations and taking risks to grow it. How does your family office think about striking that balance, and has that thinking changed over time?
Anna Dayan: We spend a lot of time with our families explaining what risk really entails. From our perspective, not growing your capital is itself a risk. So, a lot of our conversations focus on ensuring that purchasing power and capital growth for future generations are outpacing taxes and inflation. That doesn’t necessarily mean you’re making risky investments. It means having a well-thought-out investment plan. We detail cash flow exercises, proper asset allocation, and match short-term requirements while still leaving room to take advantage of long-term opportunities. It’s not an either-or situation. We sit down with families to figure out what their priorities are and then work toward those goals.
Patricia Saputo: I definitely want to add something here. In the past, you always had a tension between the owners of the business, who wanted dividends, and the operators, who wanted to reinvest in the business to keep it growing. Today, the conversation is different. I truly believe individual family members are assets themselves. If I could add another line item on the balance sheet called “human capital,” it would be the family members.
If you don’t invest in them—if you don’t educate them, communicate with them, and help them understand that life is more than just financial assets—you’re missing out. The human capital is just as important.
I once heard someone say, “I won’t give my children anything, but I’ll invest everything in them.” That says a lot. If you don’t treat them as a resource, you’ll either deplete them or make them obsolete. Family members are resources we should be tapping into. We should be doing so much more.
People who say, “We need to put more money into investments and not into our children or other family members,” are missing a huge opportunity.
Carolyn Cole: Well said. Love that. And to add to that, I think every generation needs to understand that they are either a net wealth creator generation or a net wealth consumer generation. Just because there’s a lot of wealth at the table doesn’t mean they shouldn’t have responsibility to continue creating something. Depending on the human capital at the table, who’s doing it and how they’re doing it may vary—but if you’re spending your way through wealth without continuous creation, there’s a challenge. It may not happen in this generation, but if it continues, it becomes a problem. It’s hard to tell families that, but that’s why you have to be impartial and straightforward.
Ashley Redmond: Okay, onto the last question. This can be more general. When you think of your younger self—originally I said one line of advice, but we have seven minutes, so if you want to tell a story or add something behind it, feel free. One line of advice you’d give your younger self. Let’s start with Martha.
Martha Simmons: I would just say, and I think I alluded to it earlier, stay open to opportunities. Get educated, follow your passions, but stay open—because you never know where you’re going to end up. I didn’t expect to be in the wealth management space. I was a lawyer, then a law professor, and I thought that would be my whole career. But opportunities present themselves in strange ways, so stay open, say yes, and see where it takes you.
Ashley Redmond: You said something to me last time we spoke—that men’s careers typically go like this (straight trajectory), and women’s go like this (more curved). I wish someone had told me that earlier in my career, especially when it comes to raising a family.
Martha Simmons: Yes, someone gave me great advice when my kids were little—and I had them early in my career. They said, “Never leave work. Figure out how to stay in, in a way that works for you.” It’s easier to dip back in if you’re still connected, rather than stepping completely away. I was teaching, consulting, writing—I always found a way to stay involved. There’s no such thing as perfect work-life balance or having it all at once, but you can make it work. And going back to mentorship, find people with similar values and goals—you can use that support system.
Ashley Redmond: Great. Anna, over to you.
Anna Dayan: I would echo Martha’s comments. I’d also add: be an advocate for your own career. Don’t wait to be asked. If you don’t check all the boxes for an opportunity but you check seven out of ten—or even six—go for it. We tend to hold ourselves back, thinking we need to be 100 per cent ready. Most of the time, you’re more than capable. So, be open to opportunities and advocate for yourself.
Ashley Redmond: Carolyn?
Carolyn Cole: This is directed at myself. I would say: get comfortable with being uncomfortable. My younger self didn’t do well in uncomfortable situations. I would also say: get comfortable with other people being uncomfortable. That’s a trick, especially in the family office space. And understand—it’s okay that I’m not everyone’s cup of tea. That’s something I wish I had realized earlier. If I had, my confidence would’ve come much earlier in my life. I still keep that reminder on my wall: it’s okay if not everyone’s comfortable, that’s part of growth. I use the elastic band analogy—throw it across the room and it doesn’t go far. Add some tension, it goes further. Add too much, it snaps. It’s all about balance.
Ashley Redmond: I think that “cup of tea” thing is especially hard for women.
Carolyn Cole: Absolutely. We want to make everyone happy—we’re pleasers by nature. I once got career advice from a man who told me, “If you don’t do this, this, and this, it will be a career-limiting move.” I look back now at where his career ended up and where mine went… not so much. At the time, I took it to heart, but now I see it was ridiculous advice. It made me uncomfortable, yes, but I pushed through and followed what felt true to me. And I don’t think it hurt me at all.
Patricia Saputo: Mine is actually very similar to Carolyn’s: keep extending outside of your comfort zone, because that’s where you grow the most.
If anyone knew me in high school, I was extremely introverted. I never spoke to anyone. There’s no way my younger self would’ve imagined doing this today. But the more you stretch outside that comfort zone, the more you realize, “I can do this, I can do that”—and eventually, no one can tell you otherwise. And don’t let them.
If I had listened to the man who interviewed me for my first job at a CA firm—when he saw that I had a scholarship to the Grand Ballet and said, “Why don’t you become a ballerina? Why are you going into chartered accounting?”—I wouldn’t be here today. He implied I didn’t belong in business because that was a space for men.
At the end of the day, it’s about what you’re comfortable with. Step out of your comfort zone and grow, grow, grow. You never know who you’ll become when you look back.
I also believe that you’ll never regret a decision you’ve made if it was based on your true values—those values you were raised with. If you make decisions rooted in what you believe in, you’ll never regret them.
Ashley Redmond: Stick to your values—so important. Thank you, Patricia. And I can’t picture you as introverted at this point, so you’ve clearly done a great job.
Okay, time is up. I want to thank all the panelists, and for everyone watching at home, the full transcript and video will be up on our website later this week. Check back on Friday for that.
Otherwise, have a lovely day, and thank you all!
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