Executor Secrets: What Every Canadian Needs to Know About Settling an Estate – with Shelley Essery

Hosted by Glory Gray of Glory Gray Wealth Solutions

Being named as an executor can feel overwhelming — but it doesn’t have to be.

In this episode, Glory speaks with Shelley Essery, Estate Specialist, about what every Canadian needs to know before and after a loved one passes away. Together they share insights that can save you time, stress, and unnecessary conflict when settling an estate.

You’ll learn:

• The first steps to take when you become an executor
• Common mistakes that delay the process — and how to avoid them
• How to stay organized and keep family communication clear

Thanks for listening, and we look forward to sharing more empowering stories with you. Don't forget to subscribe and leave a review!

Hosted by Glory Gray, BSc Finance, MFA

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Settling the Estate: What Every Executor Should Know with Shelley Essery

Announcer:

You're listening to the Women's Wealth Canada podcast with Glory Gray. Be sure to download and subscribe using your favourite podcast app and like us on Facebook.

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Glory Gray: Hi, everyone, I’m Glory Gray and welcome to the Women’s Wealth Canada Podcast.

Today, we’re sitting down with Shelley Essery — Certified Executor Advisor, author, and co-founder of The Empowered Estate. With over 20 years of experience in wills, estates, and real estate, Shelley knows exactly how overwhelming it can be to manage someone’s estate after they’ve passed.

In this episode, we’re breaking it all down. Shelley shares practical advice from her book, The Executor’s Survival Guide, and walks us through what really goes into settling an estate — from applying for probate to handling taxes and keeping beneficiaries in the loop.

If you’ve ever been named an executor or just want to make things easier for your loved ones down the road, this episode is for you. You’ll learn how the right preparation can save time, reduce stress, and give everyone peace of mind.

Let’s get into it.

Glory Gray: What sparked you to write the Executor's Survival Guide? 

Shelley Essery: What actually sparked me was I wanted to create a guide that felt comforting and approachable that could help simplify and break down the executor's journey so that it was easier to manage. I found oftentimes executors just didn't really understand the role, or giving them all the information upfront was just overwhelming.

So by producing this, it is short, it's sweet, it's simple, and written in, a simple language and a little bit more user friendly to hopefully guide and be more of a comfort, like a hand on the shoulder to the executor. 

I work with the executors or oftentimes the will makers, because honestly the will makers can do half the work in advance to relieve a lot of the burden on their executors. So in part of the process, I just  want to guide through what is the executor's role.

What can we do in advance? What's the information that they're going to need? How can we be helpful and get that all set up so that it just relieves a little bit of that burden as well? So I prefer to call myself a guide rather than a coach. 

Glory Gray: Yeah, that it makes sense. And it's wonderful to be able to help people think about this in advance instead of, “Oh, my gosh, I have to think about this now, at a time when my brain is barely functioning because I'm going through a grieving process or what have you.

Shelley Essery: It really does make such a huge difference when we can do a lot of the prep work in advance. Because even like in the lawyer's office, oftentimes you'd see, death can really bring up the worst in people, and it's awful.

You've got one sibling who's “no, Mom wanted this,” and the other sibling thinks Mom wanted that, but with advanced work, Mom gets her wishes known. Then it's easier and it creates that little bit more harmony at that time because grief affects people differently. We don't always know how or when it's going to affect us.

It might come out in anger, it might come out in sadness. It can come out in a million different emotions. And with that clarity and that guidance, it can help really relieve a lot of the burden to let family members and loved ones go through that grieving process without maybe taking it out on each other or feeling the combat of energy around what did Mom really want? 

Glory Gray: What or who has inspired you the most to do what you do and why? 

Shelley Essery: Honestly, it's the families that I've worked with that are just trying to do the right thing and are just feeling so overwhelmed. Everybody's looking for guidance.

They really, genuinely want to do the right thing. And I've heard so many parents that are just like, my children just don't  want to be the executor. I just can't find anybody who's wanting to be the executor. And I get it. It's a big responsibility. I never want to diminish that.

But also it is a gift, a last gift to honor somebody who's passed. This is their legacy. This is their life story. So as an executor, you get to step into that role and honor the wishes and just continue that legacy for that person. It's almost like they're still there guiding your hand.

So it's a big responsibility. I never want to diminish how much time, effort, and energy is going into the role of executor, but also it can be a gift. A gift to the deceased, a gift to the other family members, a gift itself to just know, oh my gosh, I really just carried on the legacy for this person that I loved so much.

So it was really wanting to support that role and know that there's always a method to the madness. There's always a system. You're never alone as the executor. I feel like oftentimes executors would feel like they just didn't know where to start. They didn't know who to ask for support. It  wasn't there. 

The government is great at laying out all the rules for us. So there is a method to the madness. And as executors, you are allowed to seek support. Oftentimes, lawyers are great resources, even if you just  want to work with them to help with the probate process. You can work with Certified Executor Advisors like myself to give you that information, that guidance to help you along the way.

So I always  want to make sure that people know there is support. And by saying yes, that doesn't mean you're going to have to go it alone. 

Glory Gray: As you said, it's a gift that they're giving us, but we also need to go in pretty clear-eyed into the role of the executor.

So what is the role of the executor? What are we getting ourselves into? 

Shelley Essery: A lot actually! So it's true. And again, I know I really don't ever want to minimize it, but your executor is responsible for carrying out the final wishes, managing all the paperwork, gathering the assets.

Paying out the debts, distributing what's left to the beneficiaries. And all those tasks they have to apply for probate. They also need to be great at communication because they're the one that's going to be communicating with the beneficiaries, the banks, the financial people, insurance companies.

So you do want to make sure that the person, first and foremost, is trustworthy. That's going to be able to administer your estate and also have some good communication skills so that they're able to handle that. And also be able to maybe have some tact or some grace with people that are in the grieving process as well.

So it's a big role, but if it's broken down into steps and you're guided through it, it doesn't have to be as overwhelming. And in, in my role as legal administration, that was how I approached it when somebody would come into the law firm, and they were the executor for the estate.

It was really just a case of, okay, this is where we're starting. This is just what I need from you right now, but this is what you need to be looking forward to. Here's the next step. So it was just holding their hand and guiding them through at a pace where I wasn't downloading everything and just saying, okay, I need it all right now, because the truth is I don't need it all right now. This is the first step. This is what we want to focus on right now. Once you have that together, then we're going to talk and move on to the next phase. 

Glory Gray: So they don't have to feel overwhelmed when they're working with you. Things will be given to them in the proper order when it's needed.

Shelley Essery: Exactly. Exactly. And oftentimes, most executors are working with lawyers, at least for the probate process. So that's really tremendously helpful because the lawyers know exactly what needs to be done. They know how to fill out the forms. They know what information has to happen, and so they're a really great resource for that executor to rely on that important piece of the puzzle.

Glory Gray: You mentioned probate and I know that also our executors need to take care of the tax returns of the deceased as well. But what is probate? 

Shelley Essery: Yeah, and probate is actually just the court process that validates that the will is in fact the legal will and gives the executor the authority to act.

It's the official green light to put it in simple terms. So the executors have to provide, have filled out the probate application, provided everything to the court so the court can verify that yes, the person is deceased. Here's the supporting document. Yes, this is the original last will and testament. It's signed, this is their wishes, and this is the executor accepting the role officially and signed, sealed, and delivered.

The executor has now got the green light to go ahead and start doing all the administration process, managing the estate the way that they need to in order to fulfill that rule. It's actually quite simple. It really is just the court saying ‘here's your green light.’

Glory Gray: Okay, so we talked about probate and of course in some provinces there's a probate tax. Is there anything you want to add about that particular one? Because I think people get confused between probate tax and the income tax. 

Shelley Essery: Yes, they're two completely different taxes.

So the probate tax is payable when you apply for probate to the courts, and that's a percentage of the value of the estate. The income tax is the traditional income tax that's essentially paid to the government. The CRA's coming in, knocking on your door, and it's really important for the executor to note that the probate fees are completely separate.

Both fees are payable by the estate, but when it comes to the income tax, sometimes there are several different income tax filings that can also be done that might help with that as well. So again, that might be another place where an executor might want to get some professional support. And also, I really recommend getting that clearance certificate once all the taxes have been filed. Any penalty has been paid. It's really important that they get that clearance certificate, which is essentially something from CRA saying, yes, the taxes have been paid. You are now clear to go ahead and pay out the residue of that estate. 

Glory Gray: That can really avoid any bad surprises down the pike for sure.

Shelley Essery: Oh. A hundred percent. It's like a little bit of butt coverage for the executor.

Without that, if it's later determined that there are actually taxes owing that didn't get paid out, the executor has now closed out the estate, the executor will be on the hook to pay those taxes for not ensuring it was done at that time.

So it really is a really key, important thing to get is that clearance certificate. You just want the government to sign off. 

Glory Gray: That brings me to another question then, as an executor, am I personally liable for paying the debts of the deceased 

Shelley Essery: Generally? No. And that is actually one of the biggest questions that I always get as well.

So you are not liable, but you do have a duty to pay those debts from the estate and distribute anything to the beneficiaries after the debts have been paid. So again, I'll go back to that CRA example. If you have paid out the beneficiary and it's later determined that there are debts that are owing to the estate, you are on the hook for those.

So it's really knowing in advance, what are the rules, what are my responsibilities and how do I cover my butt? And that's one of those cases to make sure that the debts are paid and that includes any interest and penalties. We want to make sure accounts are closed as well. That's a great little indication to make sure that yes, the account has been closed, everything is paid.

I've got my zero at the bottom of this statement. So we  want to make sure that's all handled first. Otherwise, if something's determined later and there's no money left in the estate, then you would be  responsible for paying up those debts. As a general answer, no, but let's make sure that we've covered everything off in advance.

Glory Gray: I had somebody tell me at one point that when someone passes away, don't turn off their cell phone really quickly because to get into a lot of those accounts, we're all using two-factor authentication. They need to text you and if you've closed that cell phone down.

Shelley Essery: Absolutely. Oh my gosh, that is so true. I've already told my husband that if I predecease you gotta keep this phone going because I have so many accounts that are, oh, you get a text to your phone and type that number in, like you, without it you're in trouble. Really great point to make.

Glory Gray: So, we've cleared off the CRA. Now we've received a certificate that says, okay, there's no more tax owing. We've closed out those accounts. So how did I properly value and dispose of the assets of the estate? 

Shelley Essery: Yeah, so actually valuing the assets of the estate is something, a step that's going to happen before you apply to probate because the government wants to know what is the value of that estate.

So in order to properly value oftentimes, like if there's property involved, we like to apply the rule of three. So maybe get three real estate agents in to get an appraisal. If there were paintings, jewelry, anything like that, you might need to get a professional in to verify the amount of that as well.

So it is really important before you even apply to probate that you've actually determined the actual value of all of those assets. And same with the debts. You're going to  want to reach out to all of the debt holders and get the valuations of those debts. 

And when you're looking at the debts, it's important to also check to see if any of them have life insurance. A lot of people will have insurance on their debts, which means that's covered and you aren't responsible for paying it, but you are responsible for making sure that the steps are happening with the debt holder to make sure that it is actually paid and closed as well.

So that's all part of the probate process.  Once you have the probate and you've actually determined all the value of all the assets and the debts, you've paid everything out, you've got your clearance certificate. Typically what you'll do is you'll do a final statement of accounts, which will show the value of all the assets, what you sold them for.

You're going to  want to make sure to get fair market value. What's really important to remember as an executor is you are acting for the benefit of those beneficiaries. So any asset you sell you  want to make sure that you are selling it for fair market value. You're not underselling it. Or selling it to yourself for some kind of a really low amount.

These are really important things to remember. So as long as you're cashing them in and selling all of those assets for an amount that maximizes the value of the asset or the benefit of the beneficiaries, you're covered. Typically, once you've got all of the assets and the debts are paid, then you'll  want to do a final accounting, which will include any professional fees.

Yeah, lawyers, accountants, any of those. If you're taking executor fees, which you are entitled to, make sure to include that in, I would recommend sending that to the residual beneficiaries, sending all of that out. It's a full statement, really a full accounting, and get them to sign off on it to get them to release and indemnify the executor that, yes, we agree, these accounts look good. This all makes sense, and that's the amount I'm expected to receive. That's great. And then once you've got that back, you can just finalize paying out all those professional fees, paying out the beneficiaries. Once everything has then cleared the bank account, then you can close that estate bank account and your job is essentially done.

Glory Gray: Wow. That's really helpful. What has surprised you maybe in the past with this? 

Shelley Essery: I'll share this story. What really drew me into this area of law was a family who had lost a child. Which is probably the worst thing that can happen as a parent to anybody. And just helping them through the administration, their grief process. They started a not-for-profit charity in honor of their child.

And so out of their grief and out of this whole entire process–which…I mean it was a child. There wasn't a lot of estate administration to do, but there was still, death certificate, that type of thing. We started to work on this not-for-profit, which, to watch it grow…I'm not going to name the not-for-profit, but it is still, it's still active, it's still growing, and that just so touched my heart so much because I…I was a young mom and I just could not imagine.

How would you even remotely start to get through that? And so to see this couple come together in their grief and do something so amazing that is helping so many other people in that child's name, I'm just like, this is where I need to be. Like it was just so heartfelt and not always the experience you get in a law office.

Most people are not coming into a lawyer's office for a good reason. Sometimes they are. But it was just so heartfelt and so touching that it just really drew me to the wills and estates area of law. 

Glory Gray: That must have been such a reward of the heart for you.

Shelley Essery: It was just I still think of them. I still just, I'm in awe of how they were able to get through that and I felt so honored to just be a teeny, tiny part of that. And it was such a learning curve for me because I had no idea how to do this. The lawyer I was working for at the time was phenomenal.

She was so good, which really helped the process as well. But it just, to be able to have a teeny tiny piece in this story was, I just felt so honored to be part of that. 

Glory Gray: So can you clarify then for our listeners…Let's say that they have just been faced with the fact that they're going to be an executor.

They, I'm assuming, will be dealing with a law office, maybe an accountant, but when can they bring in you to help them be their guide? 

Shelley Essery: Absolutely. My goal is to meet them wherever they're at. Ideally, before death. But if a death has occurred and they're just like deer in headlights, I just want to sit down with them. We can do a discovery call. I have a little package where we'll talk for up to an hour if need be, and I can go over the estate with them. I have specific questions that I'll ask them, and give them some guidance on next steps. Give them some butt coverage pointers to make sure that they're covering their butts, and doing things legally and ethically, the way that it's meant to be.

Help them set up accounts, get the accounting system set up so that they're already in a good place to start recording income of funds and outgoing of money so that everything is transparent about what's happening and where the funds are going. 

So, it’s really a case of just meeting with them. Where are you at? What does the estate look like? And if there is an area where I feel they really do need some more support or some professional guidance, then I do have some vetted professionals that I will then refer them to. I'm not a lawyer, I don't give legal advice. I know where the line is, but I have some really great lawyers that I can refer them to as well.

Or accountants, financial advisors, insurance people as well. I  do have a great network of professionals, but my whole thing is heart centered and I just  want to be a comfort, that guide, like, where are you? Let's talk about next steps. And then here's some guidance for you to move forward.

And if you need more support, great, let's have another call. If not, great. I'm glad that you got set up and you know exactly what you're doing now and you've got the right support, the right people in place to help you get there. 

Glory Gray: And if someone is a will maker, how can they work with you on that? 

Shelley Essery: Ah, this is my favorite. I so tremendously respect Will makers who are helping get everything set up in advance for their executor. They're literally taking half of the burden off their executor's shoulder. 

What I'd like to do is sit down with the will maker and make sure that they have everything in place. We can fill out all the information, talk about all the contact information, passwords, literally the entire thing that the executor is going to need. We're going to sit down, make sure that's all recorded, and if it's an option, I then like to have a meeting with the will maker and the executor together, so the executor has an opportunity to just get clear and understand what the will maker's intentions really are. What do they really want? And ask questions in advance so that they're already not deer in headlights. When they get into that role, they already know. Here's the answers, here's the contact person. Here's the questions I'm concerned about. And now before I even get into the role, I have a little bit of guidance on where to start.

And this is where it's so brilliant with Will Makers doing this, not even just with me, of course, this is like my happy place and this is where I  want to be to really facilitate that. But if a will maker has a financial advisor, lawyer, accountant–those relationships are tremendously important and valuable to the executor.

So it, if there's any ability there to bring an executor in in advance to then meet with your financial advisor that way they've got that nice, warm, friendly feeling already. It's already like having a friend when they really need it most. And this  is something that will makers don't often think of, especially in my experience in the law. In the law, it's like a box we tick, right? Oh, I've got my will, I've got my power of attorney. 

My business partner and I did a trade show recently and so many people would walk by our booth and they're like, oh, I've got a will. I've got my power of attorney. And our line is always “That's a great start!”

There's so much more prep work. So much more. But it's so rewarding too and the will Makers just don't know. They just don't know. So it's really rewarding to be able to sit down and just have those conversations and it is overwhelming, but we can start with one small task.

Let's just start with this and tick this box and get that done and move on to the next thing when you're ready. So it's really building those relationships in advance, which just release a lot of burden on the executor at the time. 

Glory Gray: And what's the best way that our listeners can get ahold of you, Shelley?

Shelley Essery: I have a website, so the best way is to fill out the contact form on the website, send me a quick message and leave your telephone number. I'd be happy to give you a call. We can jump on a discovery call and see how I can help you talk you through whatever your needs are. We can start there.

Glory Gray: That's perfect. Thank you so much for being on the Women's Wealth Canada podcast with us today, Shelley. 

Shelley Essery: Thank you. It's been my pleasure. Thank you so much for hosting me. 

Glory Gray: I wanted to let you know that our office is accepting new clients. So, if you live in Canada and want to get serious about getting your financial house in order, go to GloryGray.com and get in touch with me. 

If this podcast helped you, please subscribe, leave us a positive review and tell others about it so we can help them too.

I'm Glory Gray, your personal trainer for financial fitness telling you to take charge of your finances, plan for the future but most of all, enjoy today. Bye for now.

Announcer:

This podcast is for informational purposes only and should not be construed as investment, tax or legal advice. It is not an offer to sell or buy or an endorsement, recommendation or sponsorship of any entity or security cited. Mutual funds offered through Portfolio Strategies Corporation. Other products and services provided through Glory Gray Wealth Solutions. 

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Links for episode notes:

The Empowered Executor: The Executor’s Survival Guide by Shelley Essery

Meet Shelley Essery