Before It’s Written Down: Why Estate Planning Is About More Than the Plan

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 Jenna Carvalho, Founder and Principal of Guardian Estate Company. After more than a decade helping families navigate estate planning and administration at BMO Private Wealth, Jenna started Guardian to offer something deeply personal, clear, and grounded to provide support for families facing complex decisions. She has personally managed over 100 estates of varying complexities, as well as acted as trustee for dozens of trusts, foundations, and power of attorney appointments. Her work is driven by a belief that families deserve both guidance and peace of mind.

My goal is to be the most curious person in today’s conversation with Jenna. Where we will explore what really happens when someone steps into the role of executor, often without knowing what lies ahead. We’ll talk about what makes an estate plan practical, not just polished, and how good intentions can fall short without clear communication. We will also consider how the right conversations today can shape not just the transfer of wealth, but the experience of those who carry it forward.

Now, let’s dive in!

Cory: Welcome, Jenna. We’re excited to have you here today to share your wealth of knowledge and experiences with us. Let’s dive in. Shall we?

Jenna: Thank you, Cory. Nice to be here.

Cory: Jenna, 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?

Jenna: Well, Cory, I love this question. It gets really deep really quickly. But for me, it really is about my experience in navigating the complexities of wealth.

So it started about fifteen years ago when I started acting as an executor for several families. I would regularly act as executor, trustee, and attorney under an enduring power of attorney. And through that time, I realized that families are very unique, complex, and they don’t talk enough. And I saw a real opportunity there to help families in a different way. Help them first understand the complexities of passing along wealth, and then two, understand who should be in charge of doing that.

So I think often, there’s all this wonderful planning that happens, but not enough thought that goes into who’s going to activate, who’s going to execute, and who’s going to do the job well. So I saw an opportunity to help clients in a different way, and right now, I navigate and help families choose the best professional executor, a trustee, and attorney for their estate, whether that be a private individual or a corporate entity. Lessons is really about finding the best fit, ensuring that the heirs are well equipped to deal with the finances, and to deal with the inheritances that they’re receiving, but also that the relationships stay intact. That’s the most important thing, to ensure that once mom or dad are gone, that the family is still a cohesive unit and can still have Thanksgiving dinner together.

Cory: Amazing. So, being thrown into acting in these different roles fifteen years ago, tell me, what was that first file like?

Jenna: I’ve never received that question, Cory, and I love it. The first file was overwhelming. First time you’re acting as an executor, you’re learning so much. Different priorities are being thrown at you. Different people are calling you, asking questions, and you have to stay organized, calm, and neutral.

So the first file I was dealing with was a gentleman who passed away, and he was leaving his estate to three beneficiaries who are charities in Canada. So I had to reach out to the beneficiaries, the charities, get their contact information. And then through those conversations, they’re asking me all sorts of questions about when their distributions are coming, what assets they’re receiving, whether it’s cash or marketable securities in kind, and when they’ll receive communication from us. So it’s very basic questions. But as a first-time executor, you really are learning as you go. So there was no conflict in that, luckily. We got more conflict as we went along. But it was a really good estate to learn on, and we achieved a great outcome for the charities.

Cory: Awesome. And so those charities maybe knew the questions to ask because you were engaging with their legal departments. Is that right?

Jenna: Yes. They each have their own departments, and essentially, there’s a few people in each charity who are responsible for the estates, and what they’re receiving from estates in Canada. And so they’re really well equipped with what they’re looking for, what information to seek, and also the timelines that they should be expecting.

Cory: Right. And now that first file may be quite simple. I’m thinking of the listeners and a family member who’s maybe been asked to act in one of these capacities, and maybe we’ll go through.

And, there’s complexities for each of those titles that you mentioned there. Jenna, in your case, you had people behind you. You had people who had a lot of experience, a lot of processes. And if you didn’t, how do you think that, even what now reflecting was probably a pretty simple file, what it felt like?

Jenna: I suppose if I was a family member acting for an individual’s estate and I didn’t have support as you mentioned, one, I think there would be a whole bunch of emotion surrounding the loss of my loved one. Dealing with that at the same time as dealing with financial matters, I think, can be quite overwhelming. Seeking support, I think, is important for any individual acting as an executor. So finding those professionals to be in your corner is crucial. So if I was dealing with a tax return, I’d think the first thing I need is a tax specialist. Maybe there’s a corporate entity. We should probably get a tax lawyer in here to do some restructuring and decide how best to dissolve this business. If there’s a piece of artwork that’s really unique and we don’t know if it’s insured or how much it might be worth, I’d get an appraiser in there, real estate agent to value homes.

So, any asset part of the estate, I would think, who’s the best person to give me advice on this to make sure that I’m maximizing the value? I think the most difficult part of any estate administration though is their interpersonal relationships. The communications that you have with beneficiaries. Sometimes that can’t be taught. Sometimes that’s nature, and how you can take conflict, and how you can resolve conflict, so communicating effectively is crucial for any effective estate administration.

Regular communication, ensuring that you give enough information, but not too much to reveal even more questions and delay the estate administration, but also ensuring that you’re keeping an even hand amongst the beneficiaries. You’re not favoring one over the other. And all of that is really difficult to navigate as a first-time executor, and so having someone to help with those communications is really important. Perhaps a lawyer or even a mediator if it gets to that point.

Cory: Right. And, Jenna, when you talk about the complexities of assets, there is often a plan for the estate. But when we start to peel things back, and now there are these complexities that weren’t anticipated or planned for. I’m sure that there are many situations that you’ve seen that what maybe was intended, and you may or may not have been a part of that, wasn’t exactly what was executed, not because it wasn’t in the documents, but because maybe nobody really knew what those intentions were, or maybe even the person who passed hadn’t even thought of that.

Jenna: Absolutely. When you’re asking this question, one particular estate comes to mind where this well-known Calgarian passed away, and in his will, he wanted to leave a parcel of land that he had to a charity to create a park in his name. Now, he didn’t name a specific charity, so our goal was to find a charity to take that on and to make a park. You think it would be easy to do that, but it’s very difficult.

After searching high and low, contacting different organizations, land preservation organizations, we were unable to find a charity to take it on because there was no cash bequest that came along with that land. So the operating expenses alone would not be prudent for that organization to take on. So we had to go to court to actually vary the will, which was completely different than the deceased intentions. And the outcome was to sell the parcel of land, give the cash to a charity to create a park in his name somewhere else. So it’s as close as possible that we could get to. But if you know that the Calgarian knew that this would be an issue, and he found the charity beforehand and had that communication with them, this could have been avoided, and he could have achieved the outcome he desired.

Cory: Wow. And so in that case where you were a professional executor, acting in the best interest, and really putting in the effort to follow those wishes, how is the family involved, or was there family members that were able to be consulted to help ensure that whatever the outcome was, was as close to maybe what that person wanted?

Jenna: In this case, this gentleman didn’t have close family members that were involved in the discussion. So I think in some ways that probably made it a little bit easier. But I have had circumstances where the family declines or disagrees with the funeral arrangements that the deceased wanted. And so there is some conversation that goes back and forth, of what the deceased wants versus what the family wants, and trying to find a middle ground that everyone can live with and have peace with. But that happens a lot. There’s parts of wills that the family doesn’t agree with. And sometimes it’s difficult to overcome those challenges.

Another estate that I was involved in was related to an operating business, and the deceased child had worked in that business prior to his passing. The child thought that the business would go to him when his dad passed away, and that was not the case. So that just highlights the need to have communication and ensure that everyone’s on the same page before the executor has to deal with these issues, which delays the state administration and likely increases the cost of administering it.

Cory: Right. And so, in that case of having a child working in that business, or maybe having an asset that somebody expected to receive. With that planning, or maybe lack of planning that went on, where do you see families find that ability to not only have those discussions, but carry out those intentions, appropriately?

Jenna: I think it starts with having conversations at an early age so that you normalize these types of conversations. First, when the children are young, have these conversations about what wealth is, how do you make wealth, how do you protect it. And then as they get older, a little more complex conversations of how will this inheritance affect your future outcomes and your goals. So I think just normalizing those conversations throughout life is really crucial. But also when you’re planning your estate to bring your beneficiaries into the conversation, not necessarily sharing the values if individuals aren’t comfortable with that, but more of the themes. Who are the beneficiaries going to be? What percentage of the estate is perhaps going to charity? What’s happening with the business? All of these conversations limit to the disputes on the other end, and litigation, and costs, and all of the above. So it really boils down to communication, and just being open and honest with the people that matter most.

Cory: Right. And, Jenna, in some of the examples that you’ve given us so far, the family wasn’t necessary, or there necessarily wasn’t as many close family members in the picture. As our listeners are contemplating, who is my executor? Have I made that right decision? Is that still the right person to help execute my wishes? Where do we start to see, maybe this person isn’t right for the job anymore, or maybe the complexity of my estate has become to that point. How do you help people understand where that line is for them?

Jenna: Great question. And I think the first thing is the obvious points of choosing an executor that’s local, that’s of the right age, and also the right skills. So if you have people in your corner with those three things, that’s a great start. And then moving on to their temperament, how they handle disagreements. Will they remain calm and neutral with your beneficiaries? How do they get along with your beneficiaries? Are they unbiased? Is there any conflict there? I think often business owners consider their partners as executors and trustees for their will. But if we appoint a partner, that partner could be really negotiating with itself when we’re selling the share of the business the deceased held. And so maybe they’re not the best choice because they need to remain in the estate’s corner, and not in their corner, of course. So that’s another important component of choosing a best executor.

And then I think too, if somebody doesn’t have the time or the willingness to act, maybe they meet all of the criteria, but they’re busy professionals themselves. Maybe they have a young family. Maybe they’re considering moving abroad. All of those factors come into play, and deciding to remove them as an executor isn’t necessarily a bad thing. It’s just revisiting the estate plan and choosing the best person at the current time for the next five or so years.

Cory: Right. And how often do people need to reconsider that? As you mentioned, in that five-year time frame, do you find that people do make this decision quite often as it relates to just the executor, or do you think it’s more “alright, time to revisit the whole will,” and so they’re bringing that up?

Jenna: I would say it’s more often they’re revisiting the whole will every three to five years. I mean, that’s the suggested timeline. I think most people out there probably do it less frequently than that. But it is often an afterthought. Okay, we got to revisit the will. Does this, the distributions, look accurate? Are there any new family members you want to add? And this person can still act. Okay, we’re good to go. But having a conversation with that person every so often is really important, because often, people haven’t been an executor before. They agree to act. They don’t think it’s a big deal, but after they’ve done their first estate, they realize how much work is involved, how much mental energy it takes, and how much time away from their life they have to invest. So if they’ve done an estate and they’re considering a second, maybe they would reconsider that choice and encourage the testator to choose somebody different.

Cory: Right. And speaking to our listeners who have been asked to be an executor, and they’re listening to us, and they’re saying, maybe I shouldn’t have said yes as easily as I did. What could that conversation look like going back to their friend’s loved one, probably parents saying, you know, maybe this wasn’t the best choice?

Jenna: I think open and honest communication, as I mentioned, is important. But to just go back to that individual who asked you and to say to ensure I fully understand what I’m committing to, can we have a conversation about what assets you own, what your will looks like, who your beneficiaries are? Once you fully understand that, I think it makes the decision easier. As an executor, am I equipped to deal with this level of complexity? Do I feel prepared, or does it scare me? Do I have the necessary professionals that I know who to call to help me through this? And am I prepared to take on that liability?

Because often people don’t realize that being an executor, you do assume personal liability.

So any mistakes you make could come back to your personal affairs, and you’d have to reimburse the estate. So all of those factors come into play in the discussion. And I think it’s much better to have the conversation while your friend or family member is still alive saying, I can’t agree to act. Please remove me. Then after they pass away, that executor still has a choice. Do they want to act or not? So if they don’t want to act, all they do is sign a simple piece of paper shortly after the deceased passes away, and they remove themselves, leaving the estate perhaps in an uncomfortable position. Who’s going to be acting? Is there an alternate named? Do they have the skills that the testator intended? So the conversation during life is really the best bet to ensure a smooth administration in the end.

Cory: And, Jenna, I want to go back to the conflict of interest component, because when working with family enterprises, as you were mentioning, that conflict of interest, I was thinking about a third-party partner, somebody who’s arm’s length, who’s outside of the family. But if the family members are shareholders, and now we’re, we’re putting on more than one hat. We’re a brother or sister, maybe we’re still a child of somebody who’s surviving. Maybe that spouse of the deceased wasn’t acting. And so we have to be in the family as well as in the business, because we’re an owner, and we’ve got this new role that we’re assuming as, as executor. What are all those complexities that maybe we should consider, because it’s not now just a business partner who’s outside of the family, but somebody who’s wearing all these hats?

Jenna: Definitely puts them in an uncomfortable position. The first obviously is the relationships that they’re having with the other shareholders, which are likely their siblings. How do the siblings feel about their brother or sister being in charge of perhaps the dad’s shares of the family business, and how does that affect their relationship? So that’s one aspect.

The second is doing what’s in the best interest of the estate. It’s really hard to take off your hat as a shareholder and negotiate or decide on the outcome of the business. Is it going to be sold or transitioned, or perhaps sold to some of the surviving shareholders? It’s hard not to be self-interested in that if you’re also a shareholder. You don’t want to lose money. You don’t want to do something that’s bad for yourself or your family. So removing that conflict of interest is a great idea.

Otherwise, I think another option in that situation is perhaps to put, if there’s two shareholders, two siblings, perhaps put both of them on so that they have equal decision-making power, that there’s no issue in terms of conflict of interest because they’re both conflicted.

Cory: Right. And how about the complexity of now two people acting as executor? What does that add?

Jenna: It adds a lot. If you’ve ever been an executor, working by yourself is often a lot easier than working with somebody else with different decision-making abilities, different work process, different skills. So yes, I think when you have two executors, both have equal decision-making power. So if you can’t come to a decision on a discretionary item, it’s really difficult to pass that.

you can seek advice, obviously. As a last resort, you could go to the court, but nobody wants to do that. That’s an uncomfortable position.

So if you are appointing two or more executors, it’s great to have them be able to work together really well. And even if they disagree, have a method of moving forward and finding even ground to make a decision that would be really helpful. Any more than three, I think is chaotic. I’ve seen an estate with five siblings on there. And that is really challenging. Everyone has to make the decision. Everyone has to sign off and nobody wants to go down.

Cory: Absolutely. And thinking of alternatives, you mentioned that bringing and and selecting a professional executor is an option. What does that look like to begin exploring if that’s right?

Jenna: I think the first thing to explore is just understanding the market out there. I think the professional market is the trust industry’s best-kept secret. The trust companies, I don’t know between you and I and their listeners, you don’t see ads for them on TV. You don’t see ads for them in the newspaper. They’re really only word-of-mouth. Or if you work with an advisor, the advisor shares that information. So one, finding out what’s out there is important, and then two, looking for the best fit.

In Canada, there’s 18 trust companies that can act. So they’re corporate entities that can be appointed as executor, attorney, and trustee, in various provinces across the country. And then there’s also a number of private fiduciaries. So these could be lawyers, accountants, professional trust and estate practitioners, who take this on as part of their business. That market is obviously less regulated than you would expect from a trust company. But I think they serve well. They serve well for certain families who need an unbiased approach, who need someone that they can see eye to eye with, and know who’s going to be acting for their estate. And often, they may know them prior to passing too in other business dealings. So the market is actually quite big out there in terms of options. It’s about finding the one that can handle it most prudently, efficiently, and cost-effectively.

Cory: Okay. And so the 18, we know what that looks like because there’s a certain number.

But when you think of these fiduciaries who are acting as a professional, but as an individual versus a corporate entity, what are those considerations? And then we’ll head over to those 18 and how they differ or are the same.

Jenna: Absolutely. So the decision between a corporate entity and an individual is really unique. So first I counsel my clients on what is important to you. Do you want a company that’s always going to be there? They’re not going to die. There are several people within the organization that could help, and they have a lot of support. Or do you want an individual who may be better equipped or more well aware of your individual affairs because they’ve been working with you through life? Maybe they have special skills that you need. Maybe they’re well-accustomed to your business. Perhaps they’re a real estate professional who understands the market.

So those I would say, the major decision is what type of fiduciary feels best. An individual, I think, has to be the right age, obviously, the right location, and then also to make sure that they have the right qualifications, as well as a plan for insurance. Insurance is really actually quite difficult to get as a private fiduciary, over a certain value. So if they have a plan or perhaps some ways to mitigate any risk, then that’s ideal.

Cory: And thinking of conflicts of interest as it relates to them acting, what do you see in that area?

Jenna: I mean, if they’re a third party who don’t know the family, who aren’t involved in the family, I think the conflict of interest is low. If they’re well aware of the family dynamics, and if they’re involved in the business, and if they’re shareholders of the business, obviously there’s really a big conflict of interest there to decide if it’s worth appointing that individual.

Cory: Right. And making that decision versus a corporate entity, thinking of the corporate entity, the insurance, and things are maybe not as much of a barrier, or how they act. And that regulation, I think, is one of the things that you mentioned that was quite different. So how is that positioned?

Jenna: They are quite highly regulated. And I think they are held to a higher standard than the average professional fiduciary because they are a trust company. They have to provide regular accounting and have policies and procedures in place. So when you go to a trust company, you can expect similar service across the country because they have their policies. They have the way they need to administer in a state, and they have the same support system, whether that be a discretionary committee to make big decisions, whether that be an accounting team to help with the tax returns. So I think you get a similar outcome.

And they’re also, obviously, as you’ve touched on, they’re neutral. They follow the letter of the law, and they follow your will. They don’t care about hurting feelings. They don’t care about who’s not having dinner together, because their sole job is to do what’s in the best interest of the estate. They’re not also beneficiaries, so there’s definitely no conflict there. And this is what they do each and every day. They’re well-accustomed to doing that job, and there’s a business for it. There’s a need, and there’s a big industry.

Cory: Right. And, Jenna, we started off talking about the importance of families communicating and talking about conflict. Having one of these professional entities acting, how can that help or hinder in that area?

Jenna: It does remove the emotion from decision-making. So in theory, the estate should be administered more cleanly, with less delay, because you don’t have these ongoing conversations about what mom or dad said, or hurt my feelings. And, you know, this is what happened when I was five years old. Let’s make it right now. So I think that’s an important component of having a trusted company in place. When you have an individual, obviously, there’s more emotion that comes into account, and different factors that shouldn’t matter come into the decision-making process.

Cory: Right. And so somebody is contemplating the pros and cons here. What are some of the factors that maybe we haven’t talked about that people ask about or are concerned with?

Jenna: I think there is some hesitancy in appointing a corporate entity because it’s a business. It’s not a person. You lose some of that hand-holding and some of that eye-to-eye conversation. Although all trust companies are great at meeting with people and having those conversations, but ultimately, when that person passes away, it could be a different individual acting. So some people are uncomfortable with that. They’re also, if they want their executor to be a little more flexible and maybe distribute all personal items in the home a little bit loosely, I would say a person would be better suited, because they’re going to be a little more flexible and perhaps not as stringent on policy.

The other component, of course, is age, and if that person’s going to be available when the time comes. So I think we’ve hit on the major ones, but it’s really the person’s preference. Some people don’t like corporations for certain reasons, and some people don’t want to appoint an individual for other reasons. Just placing that liability on the individual alone can be burdensome, and they don’t want to do that to a family member or a friend.

Cory: Right. And if somebody’s listening and saying, I’m really not sure what mom and dad have done, maybe I’m a shareholder in the business. We own some assets jointly, and we haven’t had these conversations yet. Not that I want to promote fear tactics, but what are some of the things that maybe, as they’re thinking, there’s a lot here to consider, what can they bring forward to the family to say, this is important now, because as you mentioned, there’s there’s a lot more complexity and cost that could come about if we we don’t get on this.

Jenna: I think an important thing to talk about is stories. If you share stories of what you heard, that really opens up a conversation. So if you have a friend, perhaps who lost their parent, and they were completely overwhelmed and shocked about the estate plan, bringing that up, I think, opens a conversation with your own parents.

The older generations some of them are hesitant to share information about their estate. It’s a very private thing for a lot of people. So starting that conversation can be quite difficult, but I think it’s an important thing to do because the contrary is way worse. Contrary is full of questions, hurt feelings, disputes. So starting with a story of something you heard, and then communicating that, you know, I listened to Cory’s podcast, and they were talking about how it’s so important to have this conversation so that the beneficiaries or the heirs are well-equipped to deal with member dad’s estate. And we were just wondering if you can share with us who the executor is so we know and can ask questions if it’s one of us, what your plan is in terms of distributing your wealth, so that if we are unsure, or have questions with that plan, we can ask you while you’re alive. It’s way more difficult to ask you when you’re dead, and by that point, the hurt feelings just can never be resolved.

Cory: Jenna, what’s the best-planned estate that you’ve seen?

Jenna: I think there’s always room for improvement, Cory.

Cory: Of course. Yes.

Jenna: The best-planned estate is the one that gets updated frequently. The one that is well-documented so that the individual writing the will, which is called a testator, writes down all their assets, writes down how to find them, writes down the people to contact. Without that, it can be difficult to find the assets, especially at the age we live in with a lot of online accounts.

so documenting those.

And then the last is communicating with the people that it affects, the executor, the trustee, the beneficiaries, making sure that everyone has an opportunity to absorb the information, take it back, think about questions, and then bring it forward. Family meetings are key, and I’m sure you’ve had many discussions with your families about this. But having a regular occurrence of the opportunity to ask questions brings out so many conversations that are, one, benefiting the family today, building those relationships, and then reducing surprises in the end. So those are my three things that I would say in general. And as I’m communicating them, I’m thinking, I need to go do what I’m saying and go update my documents. I go tell my family members, because it’s always easier said than done.

Cory: It is. And so that for me is, is really if somebody is thinking, if I did this right, and thinking those three items. And of course, I think there’s a spectrum within those, of what could be the most detailed documented, versus just what is the most essential? What is that level of conversation that you’ve had with those people? And I think for everybody, it’s their own, you know, what are they comfortable with? What do they think is appropriate? But I think having that list of three is great, Jenna, because now our listeners can take that back and say, have I done this? Is it time for a refresh? What does that refresh look like?

Jenna: Absolutely. I can’t stress it enough how beneficial it is for an estate and for family harmony to have those conversations. I’ve administered over 100 estates, and the ones that are the most successful, or the beneficiaries that become the most successful in the end, are the ones that knew what was going to happen. The other ones lived in stress, and perhaps, substance abuse issues, and they didn’t have the skills to take on that level of wealth.

Cory: Absolutely. Being prepared is key, and we’ve covered that a few times.

Now, Jenna, as we near the end of our conversation today, there’s a few questions that I ask each guest before we wrap up. Are you ready for the tough ones?

Jenna:  I’m ready.

Cory: What is one key strategy you believe is most essential for building a successful family enterprise?

Jenna: The key strategy for me is getting everyone on the same page. Assuming that people believe the same way you do and understand things in the same context is a mistake. So being purposeful about having those conversations to ensure that people know where they stand and understand the situation in the same way, is the best strategy in my opinion.

Cory: And what is the most common challenge that you see family enterprises encountering when it comes to wealth transition and generational continuity?

Jenna: So I think it’s the opposite. But I think the challenge really boils down to being uncomfortable with the uncomfortable conversations to the point where you avoid them altogether. Avoiding is not a solution. It is a recipe to create too much trouble. So communicating and having those tough conversations is essential.

Cory: I love that. Becoming comfortable with the uncomfortable is a great one.

And in your experience, what are the top three key qualities that successful family enterprise leaders possess?

Jenna: I think being direct and honest is one. Being kind is also being direct and honest, because if you are leading someone along thinking that they’re going to inherit, or thinking that they’re going to take over the family business, knowing full well that that’s not the plan, I think that’s unkind. So having those difficult conversations and being honest is a great quality of a successful family enterprise leader.

Second is knowing the skills and attributes of the key stakeholders, knowing if they can take on the leadership role, knowing what they want to do, being honest with yourself and with others with respect to those skills and attributes.

And then third, focusing on the important things, which I think for most people is the relationships that you built. You’re building this family business. You’re building this enterprise. What is it for? It’s for the people you’re leaving behind. So just having that as a priority in all of your decision-making, I think, is another great quality.

Cory: Great. And before we conclude our discussion, I’d like to highlight where our listeners can engage in more of the conversations you’re having, as well as any materials, or items that you want to point out for our listeners, where they can find you or resources relative to our conversation?

Jenna: Well, thanks, Cory. I’ll take the opportunity to sell myself a little bit, please. So I’m from Guardian Estate Company, the founder of Guardian, and we are the only estate service brokerage in Canada. So that means connecting Canadians to the best professional executor, attorney, and trustee according to their unique estate. So we value what we provide to the Canadian marketplace, and we try to find the best fit for clients, at the best price. You can find us at guardianestate.ca, and feel free to reach out to us with questions. We’re always happy to have a chat.

Cory: You also co-host a podcast. Can you plug that for me?

Jenna: We cohost a podcast, yes. I co-host with a lawyer, Gordon Vanderleek. Our podcast is called Estates Made Simple, and we really highlight estate administration issues and, just providing information on how to act prudently in an estate for the executor listener.

Cory: Great. And I wanted to make sure that we covered everything today. Is there anything else that you’d like to share with our audience that maybe we didn’t get a chance to touch on?

Jenna: No. Thank you so much, Cory. Great to be here.

Cory: Well, thank you, Jenna. Thank you for taking your time. Thank you for sharing all of the stories, your experiences, expertise with us today. Your insights have been incredibly valuable to me, and I know that our listeners will be grateful for your contribution as well.

Jenna: Thank you.

As we wrap up this episode, we invite you to reflect on Jenna’s reminder that estate planning is personal, built through clear decisions, steady guidance, and the kind of conversations that families remember long after the paperwork is done.

Whether you’re part of a family enterprise or work alongside enterprising families, Jenna’s perspective offers a grounded view of the decisions, roles, and conversations that make estate planning work lived, not just something on paper.

Throughout our conversation, Jenna shared what it means to take on the role of executor with confidence and care. She walked us through real situations, unexpected conflicts, unclear intentions, and emotionally charged decisions that many families face. And she offered a path forward: start the conversations early, choose the right people for the right roles, document what matters, and revisit it all as life evolves. These are the steps that turn intention into preparation and help families move through transition with greater trust and less regret.

If Jenna’s work has sparked something for you, if you’re revisiting your estate plan or rethinking the role you’ve agreed to take on, Guardian Estate Company offers a thoughtful way forward. You’ll find more about their work, along with Jenna’s contact details, in the show notes.

Disclaimer: 

This program was prepared by Cory Gagnon, who is a Senior Wealth Advisor with Beacon Family Office at Assante Financial Management Ltd. This not an official program how Assante Financial Management and the statements and opinions expressed during this podcast are not necessarily those how 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.