Wills, Executors and Powers of Attorney: What I Learned Sitting Down With a Local Estates Lawyer

I asked Ben Poole of HGR Graham Partners the questions I'd want answered for my own family. Here's what he told me, in plain English.

Let's be real for a second. Nobody wants to talk about wills. It feels a little like planning your own funeral, and most of us would rather talk about almost anything else.

But here's why I wanted to have this conversation. I've helped more than 500 families around Georgian Bay buy and sell homes, and a lot of those sales happen after a parent passes. When the paperwork is in order, the family gets space to grieve. When it isn't, they spend months untangling things nobody wrote down, usually while trying to sell the house they grew up in.

Ben is an associate lawyer at HGR Graham Partners in Penetanguishene. He works in real estate and wills and estates, so he sees both sides of this. I went in with the questions I hear from clients, friends and my own family. Here's what he said.

You're Never Too Young to Write a Will

I figured there was a right age to start thinking about this. According to Ben, there isn't.

"You're never too early. There's no harm in putting something together and being prepared. If something were to happen, it makes settling your estate so much easier for your loved ones."

Most people finally get around to it after a big life moment: getting married, having a baby, buying a house.

You Can Write Your Own Will, but Here's Why Most People Shouldn't

I didn't know this, but in Ontario you can write a will entirely by hand and it can be valid. It's called a holographic will.

The catch is everything you don't know you don't know. Ben sees it all the time. Someone comes in wanting to leave everything to one person, or name a certain executor, and he has to gently tell them it's going to trigger a tax bill or start a family fight down the road.

His advice is simple. Walk in knowing two things: who you want in charge, and who you want to leave things to. Let the lawyer poke holes in it. "It'll be much smoother," he said, "and it can save your loved ones and your estate a lot of money in the long run."

How Your Name Is on Title to Your Home Matters More Than You Think

This is where my world and Ben's overlap. If you and your spouse are both on title as joint tenants and one of you passes, the house generally goes to the other automatically. That's the right of survivorship.

If you bought your place years ago and can't remember how title was set up, it's worth a quick look. Your lawyer can tell you in minutes, and so can I.

Picking an Executor Isn't a Favour, It's a Job

This one hit home. A lot of parents want to name all their kids as executors so nobody feels left out. It feels fair. Ben says it often isn't.

"Being an executor is not an easy job," he told me. "You're not doing anybody a favour by appointing them." Your executor has to track down every account, pay every bill and carry out your wishes, and that can take many months.

Here's what he looks for in a good one:

1. Someone you trust completely with money that isn't theirs
2. Someone organized who won't let deadlines slide
3. Someone who's comfortable working with a lawyer
4. For most people, someone who lives in Canada

That last one surprised me. If your executor lives outside Canada, your whole estate can be treated as non-resident for tax purposes, and suddenly the CRA is involved and everything gets more complicated.

And if you do name more than one person, they have to make every decision together. "They have to get along," Ben said. "Otherwise, things come to a grinding halt." If you've got two kids who can't agree on where to go for dinner, think carefully.

Always Name a Backup, and Maybe a Backup for the Backup

Life happens. People move away, get sick or pass before we do. Ben builds alternates into every will so if your first pick can't do it, the next person steps in. Some of his clients name three levels deep.

Should You Hire a Law Firm or a Bank to Be Your Executor?

Some of Ben's older clients ask the law firm to act as executor so their kids don't have to deal with it. He usually talks them out of it. Lawyers are busy, and it tends to cost the estate more.

If there truly isn't anyone in your life who fits, a trust company or a bank's estate service can do it. Just know it usually costs more than what a family member would take.

Make Sure Your Family Can Actually Find Your Will

This is something I'd never thought about. Say your dad always told you he had a will, but never told you where. He passes, you call the lawyer you think he used, and they can't tell you a thing.

That's not them being difficult. It's lawyer and client confidentiality. "If somebody calls in and asks, did you do work for so and so, it's not like I can openly talk about that," Ben explained.

His firm gets around it with a permission form signed at the same meeting as the will. It lists who the firm is allowed to talk to later, usually your executors. It also works the other way. If there's a relative you don't want getting any information, you can say so, and they won't.

Whatever lawyer you use, ask if they do something similar. And at the very least, tell your executor where the original is kept.

If You Have Young Kids, Your Will Should Say Who Raises Them

Nobody wants to picture this one, but it matters. Your will can name who you'd want to raise your children, plus a backup. A court still has to make it official afterward, but your will makes your wishes clear.

Pull Your Will Out Every Three Years

Ben suggests giving your will a read at least every three years, and anytime something big changes: a new baby, a marriage, a separation, a death in the family, a new property.

Even if nothing in your life has changed, the law has. He sees wills from 20 or 25 years ago that still roughly work but use old language. A refresh never hurts.

One more tip. People used to tack changes onto an old will with a separate document called a codicil. Ben's firm now prints a brand new will instead, so there's never more than one document floating around to get lost.

How to Pick the Right Lawyer

I loved Ben's answer to this one. He compared lawyers to restaurants. "If the menu says they do pizza and steak and sushi and tacos and everything in between, that should raise some red flags."

A firm can do lots of things, but the lawyer sitting across from you should ideally practise in one or two areas of law, rather than dabble in many. A few ways to check:

1. Look them up online and make sure wills and estates is actually one of their areas
2. Ask how often they do wills, and whether it's a big part of their work
3. Trust your gut on whether it feels like a good fit

At Ben's firm, you meet the lawyer at least twice. The first time is to talk through what you want. The second is the signing, where he walks you through the finished will "in plain English." And with about 30 lawyers across five offices, the tricky files get vetted through the firm's senior partners.

Why You Should Wait in the Lobby When Mom or Dad Makes Their Will

This is the question I get most from friends with aging parents. Should you go in with them?

Ben's answer: if your parents need help getting to the office, then yes, give them a hand. Then wait outside. When it's time to talk about what goes where, it's just the lawyer and your parent in the room.

It isn't about trust. It's about protecting your parent's wishes later. Estate fights happen more than you'd think, usually from someone unhappy with their share. Ben takes careful notes showing your parent met with him alone, made their own choices and explained why. That makes it much harder for anyone to challenge the will down the road.

No, You Probably Don't Need a Trust

I asked Ben for the one myth he wishes would go away. He didn't even pause. "Every other client comes in and says, I want to put everything in trust."

A lot of it comes from American videos on TikTok and Facebook. In Canada, trusts cost money to set up, need an accountant every year, and make things more complicated. "Unless you've got millions and millions of dollars or a big family business," he said, "it doesn't usually warrant it."

I hear this in real estate too. People ask about buying a cottage in trust without knowing the ongoing costs. Chat with your accountant and lawyer before you go down that road.

Dodging Probate Is Often More Trouble Than It's Worth

Probate is the court step that confirms your executor is allowed to act. The bank and the land registry want to see it before they release money or transfer a house. In Ontario it comes with a tax, and people will go to great lengths to avoid paying it.

"No tax is better than tax, obviously," Ben said. "But in the grand scheme of things, probate tax is on the lower end."

Some things skip probate on their own. A TFSA or RRSP with a named beneficiary usually goes straight to that person. A house owned jointly goes to the surviving owner.

That's why some parents add their kids to the title of the family home. Ben says that's usually a bad idea. It opens up risks and tax consequences that often cost more than the probate you were trying to avoid. There are situations where it makes sense, which is exactly why you talk to a lawyer, and often your accountant, before anyone signs anything.

Be Careful Adding Your Kids to Your Bank Account

Same idea with bank accounts. Adding a son or daughter can make it easier to pay bills and keep property taxes current as you get older. It can also go sideways.

Ben sees a pattern: one child is on the account, the parent passes, and that child says the money was meant for them alone, not split with their siblings. "A lot of this boils down to trust," he said. "Is this someone you trust to look out for your best interest?"

The Document That Might Matter Even More Than Your Will

At the end, I asked Ben what we'd missed. His answer changed how I think about all of this.

"There's a big focus on wills. But almost more important are your power of attorney documents."

Here's why. Your will only matters after you're gone. Your powers of attorney decide who handles your health and your money while you're still here but can't make decisions yourself. After a stroke, say, or as dementia sets in.

There are usually two:

1. Power of attorney for personal care covers medical decisions, where you live and your day to day care
2. Power of attorney for property covers your money and assets, though that person can't write a new will for you or change who you've named on accounts like your TFSA

As long as you're of sound mind, you can change them anytime. Ben pointed out that capacity isn't always black and white. Someone living with dementia might be sharp in the morning and foggy by afternoon. When he meets with someone, he has to be sure they understand what they're signing in that moment.

Ben offered to come back and do a whole conversation just on powers of attorney. I'm taking him up on it.

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All answers are current as of October 2026.