Legal

Executor Survival: Navigating Legal, Emotional Turbulence – Lawyers And Family

Phillippa Cranston Baran August 21, 2025

Executor Survival: Navigating Legal, Emotional Turbulence – Lawyers And Family

The emotional and financial costs of handling estate-related litigation can be severe, and not always fully understood. In the second article in a series, the author looks at important considerations for people going through such ordeals, or about to do so.

This is the second article in a three-part series that examines how the human and emotional realities of steering an estate through ugly, litigious waters are not well understood. This article deals with how an executor can tippy-toe through the minefields of the hot dynamics of family and the cold, impersonal world of lawyers and billable hours. The author is Phillippa Cranston Baran (pictured below), president, Toller International. See here first article here.
 

Phillippa Cranston Baran

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The financial, human, and emotional costs of steering an estate through ugly, litigious waters are huge – not only the dollars burned, but also the intangibles of lost time, massive stress, blown reputations, damaged goodwill, and irreparable relationships. 

How does an executor tippy-toe their way through the minefields of the hot dynamics of family and the cold, impersonal world of lawyers and billable hours? 

For a short while, I thought of starting this piece with a lawyer joke. Ha, ha. I actually looked for a good one, but you know what, after nine years and a horrifying amount of money, it is no laughing matter, and the jokes aren’t funny. 

Think about this. The average legal and accounting costs for settling a Canadian estate vary widely but are typically in the $12,000-$13,000 range (1), higher with a larger estate. With my brother’s estate, the legal fees and associated costs to deal with the lack of a valid will, confirm the heirs, and sever and sell properties in Mexico amounted to roughly $20,000 on a $6.5 million dollar estate. That should have been the end of it, but my administration was challenged by the heirs. The ensuing litigation dragged on for almost a decade, and more than a million bucks went up in smoke, out the window, down the drain – choose your metaphor. You can read about it here (2). 

There were hearings, undertakings, responses, appeals, mediations, discoveries, and trials in English and Spanish. There were brilliant sharks performing at the top of their game, bullies doing what bullies do, and a lot of wind-baggery, arrogance, and stupidity. Let’s just say that I saw a lot of lawyering and a lot of family, and I can confirm that in a contested estate, the only ones who walk away unscathed are the lawyers.

This is what I have learned.

The lawyer is the lawyer. Don’t expect a friend
As executor, you want a lawyer with wills and estates experience, someone with whom you feel comfortable, but understand it’s business. Expect the lawyer to be experienced and knowledgeable, but don’t expect them to care. Some do, for sure. But for many you are just another file – a source of billable hours which, I can tell you, is seriously not a good feeling. 

Get an understanding about costs
Try to be clear right from the get-go about costs and billings. You might pre-negotiate for an agreed amount, a percentage of the estate, or go by the hour. Expect value for money but don’t waste time, yours or the lawyers, micro-managing, or scrutinizing every item. It will make you nuts. And don’t get sucked down the rabbit hole of defending and explaining every half-truth, and insinuation in the filings even though it is beyond exasperating to suffer the endless BS. If you fall into a trap of always being responsive, it can get very expensive very quickly. Stick to the what, why, how much, and when of your decisions. Ensure that your lawyer tells the story and makes it easy for the court to “see” the whole picture. The law, the evidence, and your story, well told, is the key.

Be involved. Be informed
Lawyers are valued partners on the team but you, the executor, are the captain. Get involved.

The more you understand about the law and the process, the more confident you will be and the better able you will be to participate, contribute, clarify, and give proper instructions. 

Be alert for waste and redundancy
You: Hey, Mr/Ms Lawyer, I have a few executor questions. Can we talk?
Lawyer: Yes, when would you like to speak?
You: I’m flexible.
Lawyer: How about Monday?
You: Monday is good. What time?
Lawyer: Between 2.00 and 3.00 pm?
You: Great. Will I call you, or will you call me?
Lawyer: I will call you.

These back-and-forth emails are needlessly fussy, but more galling is when you get dinged for every exchange. In this situation, there could be multiple items billed as “communication with client.” Pay attention to the itemized billing and resolve any concerns early on. Listen to your spidey-sense.

Family 
What if you have a loving family? 
Good. Lucky you.

What if you don’t? 
Buckle up.

Ahhhh, families…complicated at the best of times. In an estate situation when strong emotions (love, loss, grief, anger, jealousy, resentment) collide with complex relationships, reason can fly out the window. Battles may not escalate to all-out litigation, but almost 70 per cent of families lose a portion of their inheritance due to disputes (3). The fights might be over the dog, the farm, or the diamond ring, but the result is the same. Blood on the floor. Scars that don’t heal. Trust, respect, affection, goodwill – all shot to hell. Don’t expect the heirs to be grateful. They won’t be.

And understand that Ozzie and Harriet families don’t exist. Never did. Somewhere in most families there is a holier-than-thou know-it all, a greedy sister-in-law, and usually some over-zealous control freak. In an estate situation, misunderstandings, insecurities, resentments, and old jealousies can lead to problems. A smooth estate administration depends largely on how relationships are managed. (4) 

Communications
Executor communications should be calm, respectful, and well-documented. Keeping the heirs fully in the loop makes infinite sense. But sometimes, even with regular communications, heirs think they know better, come to believe that they are being cheated, or are convinced that they have some final say over whether or not the artworks are liquidated, how the jewelry is distributed, or what is an appropriate list price on the family home. They are incorrect. They don’t have the authority. An executor may listen to the heirs’ concerns, but ultimately the decisions belong to the executor. 

Investing in relationships 
A clear and unambiguous will is immensely helpful for an executor and can go a long way to preventing acrimonious and expensive disputes. Dr Tom Deans (5) is a proponent of in-person meetings between a testator and the heirs.. Evidence shows that engaging in conversation with intended beneficiaries about one’s wishes can save time, money, and misunderstandings. Consider, for example, the family cottage. What if one beneficiary wants the cottage, one has no interest, and another lives too far away to enjoy it? It is sensible to speak with the heirs to gauge interest and then make decisions on who actually wants the cottage, and who can maintain it and use it? Bottom line, it may be impossible to make everyone happy but explaining reasons for certain decisions can at least help beneficiaries understand. When wishes are clearly communicated to the heirs, the will is less likely to be challenged down the road. 

No evidence. No facts. Just conflict
Why do families drag an estate through the muck without a smidgeon of evidence of any kind of wrongdoing? Damned if I know. It’s damaging. It’s costly. It wastes time. It makes absolutely no sense. And it happens way too often. 

When an executor understands their role and the extent of their authority, they can better lead the way, make judgements, referee, facilitate, soothe, explain and hold the line when necessary. If things go south, an executor must strive to remain as calm and as clear as possible, document their decisions, and stay focused on the finish line.

It is an honour to serve as an executor. It is an achievement to survive unscathed. It’s a triumph to emerge with intact relationships.

Breathe. Good luck.
 

Footnotes:

(1) https://www.estateexec.com/ca/Docs/General_Statistics

(2) The case was widely covered. The following are good summaries.
Losers in Toller Cranston estate litigation ordered to pay $325,000 in costs
Posted by Lynne Butler, BA LLB, Monday, May 31, 2021

Toller James Montague Cranston (Estate of): Lose Big, Pay Big
By Hull & Hull LLP | June 1, 2021 

(3) Seventy Percent of Families Fight over Inheritance
 https://www.dupagelawyers.com/wheaton-family-law-estate-planning/families-fight-over-inheritance

(4) https://deerlakelaw.ca/how-to-resolve-family-disputes-over-wills-and-inheritance/
according to a Deer Lake Law Group article. 

(5) D. Tom Deans, https://www.thomaswilliamdeans.com/

About the author
Phillippa Cranston Baran is the sister of Toller Cranston (picture of Cranston below), a two-time Olympian, international artist, Order of Canada, Honorary Doctorate, and member of multiple Halls of Fame.
 


Toller Cranston

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