The Trust Notes Blog

Becoming an executor might feel like an honour — and it is — but it’s also a serious responsibility. You’re expected to carry out someone’s final wishes, navigate legal processes, and act as the go-between for grieving family members, institutions, and the courts. It can be overwhelming, especially when emotions are high and instructions are unclear.

It can be overwhelming — and the data backs that up.

According to a survey by EstateExec, the average estate takes over 500 hours to settle, often stretching across 16 months or more.

The biggest delays? Executors feeling unprepared, lacking guidance, or struggling to locate documents and assets.

At Trusty, we’ve spoken with countless families and professionals who agree: executors don’t just need access to documents — they need context, clarity, and structure. That’s why we’ve created this simple checklist to help.

This guide is for anyone who’s been named an executor, whether you’re stepping into the role soon or planning ahead.

✅ Executor Checklist: What to Do When the Time Comes

1. Locate the Will and Supporting Documents

Identify the most recent signed version of the Will. Find supporting documents like powers of attorney, Letters of Wishes, funeral directives, and trust agreements. Confirm where the Will is stored (e.g., lawyer, safe, safety deposit box).

2. Get Official Copies of the Death Certificate

You’ll need multiple copies to deal with banks, insurance, government agencies, etc.

3. Apply for Probate (If Required)

File the Will with the appropriate probate court to validate the Will and receive authority to act.

4. Notify Key Parties

Contact beneficiaries, banks, insurance providers, government agencies, and utilities.

5. Secure and Review All Assets

Take inventory of bank accounts, real estate, valuables, business interests, and digital assets.

6. Pay Outstanding Debts and File Taxes

Settle liabilities and file final personal and estate tax returns.

7. Distribute the Estate

Follow the Will’s instructions and provide transparency throughout the process.

8. Handle Sentimental Guidance with Care

If there’s a Letter of Wishes or video messages, share them thoughtfully to reduce misinterpretation or tension.

Trusty Makes It Easier to Carry It All Out

Trusty isn’t a legal service, but it’s designed to support you through the emotional and logistical complexity of being an executor. Think of it as your digital companion for the moments where clarity matters most.

Here’s how Trusty helps with key parts of the process:

• Step 1 – Locating the Will: The person creating the Will can log where it’s stored and who to contact to retrieve it. No more confusion about which lawyer or what version is valid.
• Step 5 – Tracking Assets: Trusty gives executors a clear, consolidated list of what exists — including homes, accounts, collectibles, and storage locations — often with appraisals and attached documents.
• Step 8 – Understanding Intentions: Trusty goes beyond the legal formality by storing Letters of Wishes and heartfelt video messages that explain decisions and minimize misinterpretation.
• Steps 4, 7 & 8 – Reducing Conflict: When you can show beneficiaries the full picture — not just who gets what, but why — it’s far easier to avoid disputes and delays.

Whether you’re preparing for this role or naming someone else to carry it out, this checklist — and tools like Trusty — help ensure the person in charge can honour your wishes with confidence.

When most people think about estate planning, they focus on what’s in the Will: who gets the house, the jewelry, the investment accounts. But the smooth execution of those wishes hinges almost entirely on one role: the executor.

And yet, the person often given this responsibility—usually a family member—is the least prepared, least informed, and most overwhelmed.

The Forgotten CEO of Your Estate

Think of your executor as the CEO of your estate. They’re tasked with:

• Locating and filing the Will
• Settling debts and final taxes
• Identifying, securing, and distributing all assets
• Communicating with heirs (sometimes with different expectations)
• Working with lawyers, accountants, and the courts

This isn’t a ceremonial role. It’s a job. And it often comes at one of the most emotionally raw moments in a family’s life.

A Familiar Story

After Raj passed away, his daughter Priya was named executor. He’d never told her directly—she only found out through the Will.

She was grieving, raising three kids, working full-time—and now expected to decipher her dad’s finances, gather dozens of documents, calm her uncles, and figure out what he meant by “my coin collection should go to the person who most admired it.”

There was no inventory. No notes. No Letter of Wishes. No hint at what “admired” meant.

Just a family at odds, trying to interpret a sentence that likely came from love—but sowed seeds of tension. A few of these stories is what enlightened Trusty's founder to our company's vision.

“Lack of clarity creates conflict.”
— Randy Frisch, Founder of Trusty

When Families Are Left to Interpret Intentions

When instructions aren’t clear, families fill the gaps with assumptions—and those assumptions quickly turn emotional:

• “Dad always promised me that watch.”
• “She said the cottage was going to be shared.”
• “Why did he name her as executor?”

These moments, however small, can tear families apart. According to a TD Wealth survey, 1 in 4 Canadians report poor planning and communication being the number one cause of family conflict.

In the U.S., LegalShield found that 58% of Americans experienced conflict, or know someone who has, due to the absence of an estate plan or will.

You Don’t Have to Choose a Family Member

While many people instinctively name a child or sibling as executor, it’s important to know that you have another option: appointing a professional executor.

These are individuals or institutions who specialize in handling estate administration—bringing legal, tax, and emotional neutrality to the process.

In Canada, examples include:

• 🏛️ RBC Royal Trust
• 🧾 ClearEstate

In the U.S., similar services are offered by:

• 🏢 Fiduciary Trust International
• 💼 Everplans (partnering with professional fiduciaries in select states)

These services often charge a percentage of the estate’s value (typically 2–5%), or a flat fee depending on complexity. While it may seem expensive, for some families it’s worth the investment to avoid emotional strain, legal missteps, or family conflict.

So… Which Is Better?

There’s no right answer. Some families value the personal connection a loved one brings. Others prefer a neutral third party to ensure no one feels unfairly treated—or overwhelmed.

What matters most is that your executor:

• Understands the responsibilities of the role
• Is equipped with the tools and context to do the job well
• Has access to your true intentions, not just your legal instructions

Trusty: Giving Your Executor a Clearer Path

Trusty was created to support whoever you choose—friend, family, or professional—with clarity and care.

With Trusty, you can:

• Track and catalog key assets with context
• Leave heartfelt video wishes for specific people and items
• Store and locate important documents
• Assign an executor and give them controlled access
• Share relevant data with advisors or institutions helping settle your estate

“One of the reasons I started Trusty,” says founder Randy Frisch, “was to create harmony. I wanted to make it easier for the executor—the person we all turn to—to actually deliver the clarity and peace we intended.”

Clarity Is a Gift. So Is Preparation.

Who you choose as executor may vary based on your family, your wealth, or your personal preferences. But regardless of who takes on the role, the most important thing you can do is equip them—with your documents, your voice, and your true wishes.

Because clarity doesn’t just make things easier. It prevents conflict.

It sounds unthinkable—yet it happens all the time.

Someone passes away, leaving behind what they believed was a carefully planned estate. A Will was drafted, decisions were made, roles assigned. Everything, they thought, was in order.

But when the moment comes, no one knows where the Will actually is.

Maybe they assume it’s with a lawyer, though they can’t recall which one. Maybe it was tucked away in a fireproof safe, but no one has the combination. Sometimes the only copy is in a folder marked “taxes” at the back of a closet no one has touched in years. In those moments, even the best intentions start to unravel.

After her father passed, Emily and her two siblings gathered in his condo to begin settling his affairs. He’d always said his Will was handled—he used that exact phrase: “handled.” But when they went looking for it, nothing turned up. The safe couldn’t be opened. His emails gave no clue. No one could remember which lawyer he’d used, or even if he’d updated it in the last decade.

What followed wasn’t chaos, exactly. It was slower and more corrosive than that. The estate froze. Accounts were locked. They filed court documents and waited for rulings. And slowly, each sibling began to second-guess the others. Was someone hiding something? Was there a version of the Will they hadn’t seen? Had Dad made promises he didn’t write down?

Eventually, they found the Will. It had been sitting in a manila envelope labeled “Dad’s Taxes 2012.” What could have been resolved in a few days took nearly eight months.

That story isn’t unusual. In fact, it’s disturbingly common.

The Canadian Bar Association reports that over half of Canadians don’t have a Will at all, and among those who do, many haven’t updated or properly stored it. In the U.S., a 2024 survey by Caring.com found that 67% of adults don’t have an up-to-date Will. But even having one isn’t enough if no one knows it exists—or where it is.

Wills often end up scattered across disconnected locations: with a lawyer who’s retired, in a bank box no one can access, at a cottage drawer forgotten over the years. Some people never tell anyone they even made one. Others update their Will, but forget to destroy older versions, leaving behind layers of ambiguity. And in today’s mobile world, crossing provinces or states can make tracking documents even more complicated, with local laws and jurisdictions further muddying the waters.

When a Will can’t be found, the law often assumes there wasn’t one. That means the estate is settled according to default rules—which might distribute assets in a way the deceased never intended. Children inherit before spouses. Friends or charities named in conversation are forgotten by the courts. The nuances and wishes that defined someone’s life are reduced to paperwork protocol.

The legal implications are frustrating enough. But it’s the emotional toll that’s often hardest. Loved ones begin to argue. Trust erodes. Executors, who were once confident in their role, are caught between loyalty and legality. Grief becomes tangled in bureaucracy.

It doesn’t have to be this way. Estate planning isn’t just about having documents—it’s about ensuring those documents can be found, understood, and acted upon at the right time. That means naming an executor and letting them know where your Will is kept. It means destroying outdated versions. It means having a way to track not only what you own, but who should be involved when the time comes. And for many, it means going a step further—leaving a Letter of Wishes to explain the meaning behind the decisions and provide the kind of guidance a legal form never could.

Trusty doesn’t replace the legal process. In most jurisdictions, courts still require a physical, signed Will to proceed. But Trusty exists to ensure that when the time comes, the people who need your documents actually know where to find them. It’s a digital companion to your estate plan—one that logs where your Will is stored, who your key contacts are, and how to access related documents when they matter most.

More importantly, it brings humanity back to the process. With Trusty, you can leave video messages, assign heirs, and give your executor the tools and clarity they’ll need to honour your legacy—not just legally, but emotionally too.

Because the best estate plan in the world is only useful if it’s found.

And when it is, it should speak clearly.

When it comes to estate planning, most people assume the Will is the final word. But there’s an important—and often overlooked—companion to the Will that brings heart, clarity, and personal intent to the process: the Letter of Wishes.

Why Wills Fall Short

Wills are legal documents. They’re designed to meet the standards of probate courts, not to hold nuance or emotion. And while they cover the big stuff—like naming guardians or splitting the house—they fall short in the areas that often matter most.

Here’s why certain things shouldn’t go in your Will:

• Wills become public documents once they go through probate—meaning anyone can access them.
• Updating a Will is expensive and time-consuming—involving lawyers and formal processes.
• They lack flexibility and aren’t suited to more fluid or evolving personal instructions.
• They’re written in legal language, not your voice.

So while your Will handles the “what,” a Letter of Wishes explains the “why.”

“It’s often the small stuff—the watch, the wedding ring, the cottage—that causes the biggest fights. The Letter of Wishes is where you prevent that.”
— Tom Deans, author of Willing Wisdom

What Is a Letter of Wishes?

A Letter of Wishes (sometimes called a Memorandum of Wishes or Statement of Intent) is a private, non-binding document that accompanies your Will. It’s meant to guide your executor, family, and advisors on how you want things handled—especially the personal, sentimental, or situational decisions.

Unlike your Will, it:

• Stays private—only seen by those you choose
• Can be updated easily without a lawyer
• Captures your voice—through words or even video
• Fills the emotional and practical gaps your Will can’t

What Belongs in a Letter of Wishes?

Common things people include:

• Personal belongings: Who gets sentimental items and why (e.g. jewelry, heirlooms, collectibles)
• Stories and values: Notes about family traditions, charitable causes, or lessons for future generations
• Explanations: Clarifying decisions that may be emotionally sensitive or unexpected
• Care instructions: For pets, vacation homes, or even family rituals
• Messages: Parting words, notes of gratitude, or personalized video messages

📌 Note: In some jurisdictions, items like personal property can legally be distributed using a separate Memorandum. It’s wise to check with an estate planner in your region.

Letter of Wishes Checklist

Want to start yours? Here’s a quick list to guide you:

✅ List any personal items you want specific people to receive—and explain why

✅ Clarify your intentions behind sensitive decisions (e.g., unequal divisions)

✅ Include notes or stories that add emotional meaning to the items

✅ Provide any special instructions (e.g., how to care for a pet or maintain a cottage)

✅ Add a message for your family—this could be written or recorded as a video

✅ Store your Letter of Wishes in a place your executor can easily find

✅ Review and update it regularly—no lawyer required

The Bottom Line

Your Will is essential, but it was never meant to carry your legacy alone.

A Letter of Wishes helps ensure your voice is heard, your intentions are understood, and your family is supported.

At Trusty, we’ve made it easy to create, store, and share Letters of Wishes—complete with the option to record video messages and attach them to specific assets. Because sometimes, it’s not just about who gets what.

It’s about what it meant to you—and what it could mean to them.

It’s a story we hear all the time.

Different names, different assets, different family dynamics — but the same pattern: someone passes away, and what follows isn’t just grief. It’s uncertainty. Tension. And too often, conflict.

Not because people are greedy. But because no one wrote down the little things — or when they did, they didn’t make them clear.

Sometimes, the things that cause the biggest rifts aren’t mentioned in the Will at all. And even when they are, there’s no explanation behind the choices. That’s where cracks form.

One family we met had a mother who passed away after years of summers spent at the cottage with her three kids. Her Will was perfectly drafted: the house to be sold, the proceeds divided evenly. But it said nothing about the cedar canoe, or her wedding ring, or the cottage table marked with decades of memories. Each sibling had a different memory of what their mother had said. One recalled a promise about the ring. Another believed the boat was supposed to stay in the family. The third said they’d been the one maintaining the property for years. The conversations started civil, but over time turned emotional. Words were said that couldn’t be taken back.

Another story is personal. When my grandmother passed — at 104 years old — she left behind handwritten notes tucked into drawers, journals, and boxes. She had updated them over the years, sometimes every decade or so. But it wasn’t always clear: were the newer ones meant to replace the old ones? Or were they meant to be read together, layered with nuance?

In our case, we were lucky. My siblings, cousins, and I all got along. Maybe too well — because instead of fighting, we politely stalled. No one wanted to be the one to claim anything. We spent months checking in, making sure someone else didn’t want that vase, or picture frame, or brooch. It dragged out what could have been a comforting process. I remember thinking at the time: If only there were an app for this. Something that offered structure but still left room for the human side of it all.

That idea stayed with me.

It helped shape what eventually became Trusty.

And then there are the families where the stakes are even higher.

An executive at RBC Royal Trust once told me about an estate they were settling that included a significant art collection — pieces worth millions. The Will said the art was to be divided between the three children. But once the parents had passed, all three kids agreed: the art should be donated. All of it — except one piece. It was the painting that hung over the dining room table. The one they’d sat in front of every Sunday for decades. That painting, each child felt, belonged to them.

But there was no further instruction. No video. No note. No explanation. Just silence.

The advisor said, “We imagined what it might have been like if there had been a video. Even a short message. Maybe the parents could have added a condition — that whoever received the painting would commit to hosting Sunday dinners. Or maybe they would have said, ‘This one should go somewhere public — so you all can visit it, together.’”

Without that clarity, the piece remained in limbo. The family couldn’t agree. And that one unresolved item cast a shadow over an otherwise generous and well-intentioned estate.

These stories — rings, boats, artwork, family heirlooms — they sound small. But they hold weight. Emotional weight. And when that weight isn’t balanced with guidance, it leads to conflict.

According to the Financial Planning Standards Council, one in four Canadians has experienced family friction over unclear estate planning. In the U.S., 44% of adults say they worry their family will fight over their estate. That fear? It’s not unfounded.

And it’s not inevitable, either.

That’s where Trusty comes in. Not to replace your lawyer. Not to write your Will. But to support everything around it. With Trusty, you can record video messages for specific assets. You can log what you want passed down — and to whom — with context. You can make your intent clear.

You can also prevent your family from having to interpret, debate, or argue over what they think you meant.

Because sometimes what people want most is not just the thing — it’s the feeling that they were remembered. That they were chosen. That they were understood.

Estate planning isn’t just about dividing assets. It’s about leaving behind peace. And that peace rarely lives in legal documents alone.

It lives in clarity.

In compassion.

In stories told — and wishes made — before it’s too late.

For many advisors, guiding a client through their estate planning checklist ends with the Will. And for decades, that was enough. But today’s families are more complex. Assets are more diverse. And expectations — both emotional and legal — have shifted.

Helping a client “get a Will in place” is no longer the finish line. It’s the starting point.

We regularly hear from wealth advisors, estate planners, and lawyers who say: “I didn’t realize how much was missing until I saw the conflict it caused.” From siblings disputing over heirlooms, to executors lost in paperwork, the gaps in most estate plans aren’t just logistical — they’re deeply personal.

If you’re advising clients on how to plan for what comes next, here’s how to take the conversation deeper.

🔍 Go Beyond the Legal Framework: Key Areas to Explore With Clients

Uncover what’s not in the Will

Most Wills are designed to meet legal requirements — but they rarely reflect the nuance of family dynamics, personal values, or sentimental belongings. Encourage clients to reflect on what matters most emotionally, not just financially.

Document specific and sentimental items

Jewelry, collectibles, art, and family heirlooms often hold disproportionate emotional weight. When these aren’t mentioned — or explained — they become flashpoints for conflict.

Ask about pets and who will care for them

Pets are part of the family, yet many Wills omit who will care for them or how that care should be funded. Clarify who’s willing and what’s expected.

Discuss burial and funeral wishes

Clients often assume their loved ones “will just know,” but these moments are fraught with emotion. Encourage clients to document preferences clearly — from cremation to religious traditions to celebration-of-life details.

Explore digital legacies

We now live part of our lives online. Clients may have cryptocurrency holdings, photo libraries, cloud storage, email accounts, and digital subscriptions. They should leave instructions and passwords, and specify what should be archived, deleted, or passed down.

Identify less typical assets

Airline miles, credit card points, loyalty programs — these are often overlooked but can be valuable. Some can be transferred, others may require named beneficiaries. Ask: What have you accumulated that has value — even if it’s not traditional?

Review life insurance and beneficiary alignment

Life insurance isn’t only about coverage — it’s a core part of legacy transfer and liquidity planning. Ensure policies are up to date and that beneficiaries are correctly named and aligned with the rest of the estate plan.

Start conversations around tax strategy

Clients are often unaware of capital gains exposure, estate tax thresholds, or the impact of charitable giving. Collaborate with their accountant or tax advisor to identify planning opportunities early — not when it’s too late.

Clarify the executor’s role and give them tools

The executor isn’t just a name. It’s a job — and often a hard one. Help your client choose someone capable, and ensure that person has access to the information and guidance they’ll need when the time comes.

Encourage personal messages or Letters of Wishes

Sometimes the greatest gift isn’t the asset — it’s the context. A short written or recorded message explaining “why” can prevent years of family friction.

🛠️ How Trusty Helps Advisors Create Real Clarity

Trusty was built to support everything the Will leaves out. It’s a secure digital hub that helps clients capture the human side of their legacy — and gives you, as an advisor, a way to stay connected to the bigger picture.

With Trusty, your clients can:

• Record and store Letters of Wishes and video messages
• Assign heirs for sentimental and digital assets
• Track pets, collectibles, storage locations, and travel points
• Log where their Will and legal documents are kept
• Organize important digital credentials for their executor
• Give you access, so you can support better — and stay top of mind

Clients don’t need more documents. They need clarity.

And when you help provide that, you’re not just planning for death — you’re preserving peace for the people left behind.