A View from the Middle

After years of mediating personal injury, insurance, and commercial disputes, estate files stand apart. The legal issues are often narrower. The damages are sometimes easier to quantify. And yet, they are consistently more difficult to resolve.

That is not because the law is unclear. It is because the dispute is, frankly, rarely about the law.

In estate mediations, I am not simply dealing with parties. I am dealing with families, or what is left of them. Siblings who have not spoken in years. Adult children relitigating childhood grievances through a will. Executors who believe they are carrying out a solemn duty, and beneficiaries who believe they are being quietly cut out of their inheritance. The emotional temperature in these files is not incidental. It is the case.

That reality changes everything about how these disputes move and how they ultimately settle.

The Illusion of a Legal Dispute

Most estate files arrive framed in the legal terms of undue influence, lack of capacity, breach of fiduciary duty, unjust enrichment. Pleadings are drafted with precision. Experts are retained. The structure looks familiar.

But early in any mediation, it becomes clear that the legal framing is only part of the story.

A will challenge grounded in alleged undue influence may, at its core, be about perceived favoritism that dates back decades. A passing of accounts dispute may be less about the numbers and more about a breakdown of trust between siblings. Even claims of incapacity often carry an undercurrent of disbelief. “That’s not what mom would have wanted”, which is not strictly a legal argument, but a deeply held personal conviction.

Courts have long recognized that estate litigation operates in a different register. In Tataryn v. Tataryn Estate, 1994 CanLII 51 (SCC), [1994] 2 SCR 807^[1] , the Supreme Court of Canada emphasized that estate disputes often engage not only legal obligations, but moral ones. That observation is not confined to dependants’ relief claims. It reflects a broader truth that any mediator practicing in this area knows well, that estate disputes are rarely resolved by legal analysis alone.

The Evidence Problem: Memory, Narrative, and Credibility

Unlike motor vehicle cases or commercial disputes, estate litigation frequently turns on events that are unwitnessed, undocumented, or reconstructed after the fact. Conversations with the deceased. Changes to longstanding testamentary plans. Subtle shifts in dependency or influence.

The result is that evidence in these cases is often narrative-driven and highly contested.

In Vout v. Hay, 1995 CanLII 105 (SCC), [1995] 2 SCR 876^[2], the Supreme Court set out the framework for suspicious circumstances in will challenges, recognizing that courts must carefully scrutinize the surrounding context where concerns arise about capacity or influence. That framework underscores the inherent uncertainty in many estate cases. Much depends on credibility. Much depends on inference.

From a mediation perspective, that uncertainty cuts both ways. Each party believes their version of events is the truth. Each believes a judge will see it the same way. But beneath that confidence lies real litigation risk, particularly where the key witness, the testator, is no longer available.

That is often the first meaningful opening toward resolution.

The Cost Reality: The Myth of the “Estate Pays”

There remains a persistent belief among litigants that estate disputes are somehow insulated from the usual costs consequences. That the estate will absorb the legal fees, regardless of outcome.

That is no longer the law.

In McDougald Estate v. Gooderham, 2005 CanLII 21091 (ON CA)^[3], the Ontario Court of Appeal made it clear that estate litigation is subject to the same general costs rules as other civil proceedings. The older approach where costs were routinely paid out of the estate has largely given way to a more disciplined, outcome-based analysis.

That shift has practical consequences in mediation. Once parties understand that they may bear their own costs, or worse, pay the other side’s, the risk calculus changes. Positions that once seemed principled begin to look expensive. Litigation strategy gives way to cost containment.

In many estate mediations, it is not the merits that ultimately drive settlement. It is the combined weight of uncertainty and cost.

The Executor’s Dilemma

Executors occupy a uniquely difficult position in these disputes. They are expected to remain neutral while simultaneously defending the validity of a will or their own conduct. They are fiduciaries, but they are often also family members, with their own interests and perspectives.

This tension is well recognized. In Geffen v. Goodman Estate, 1991 CanLII 69 (SCC), [1991] 2 SCR 353^[4], the Supreme Court discussed the nature of fiduciary relationships and the potential for conflict where one party is in a position of influence over another. While not an estate administration case in the strict sense, I believe the principles resonate directly in disputes involving executors accused of overreach, self-dealing, or favouritism.

At mediation, executors often arrive feeling personally attacked. Beneficiaries, in turn, view the executor as obstructive or self-interested. Bridging that divide requires more than legal argument. It requires reframing the executor’s role not as an adversary, but as a fiduciary navigating competing obligations under difficult circumstances.

When that shift happens, resolution becomes possible.

Why Estate Mediations Actually Settle

Estate disputes settle for reasons that are different, and in some ways more human, than other civil cases.

They settle because trials are unpredictable, particularly where credibility is central. They settle because the cost of litigating through discovery, expert evidence, and trial can erode the very estate in dispute. They settle because, at some point, even entrenched parties recognize that a court cannot repair a fractured family.

But most of all, I think they settle because a good mediator creates a space where parties can be heard in a way that the litigation process does not easily allow.

In a courtroom, relevance is narrowly defined. In mediation, it is broader. Parties are able to explain not only what happened, but how it felt, and why it mattered. That does not replace the legal analysis. It complements it. And in estate disputes, that combination is often what unlocks resolution.

The Mediator’s Role in the Estate Context

The mediator’s task in these files is not simply to evaluate legal positions or exchange offers. It is to manage a layered dispute where law, emotion, history, and risk intersect.

That requires a different kind of engagement. Patience where positions are entrenched. Directness where expectations are unrealistic. And a willingness to move beyond the pleadings to understand what is actually driving the conflict.

There is no formula for that. But there is a consistent pattern. Once parties begin to appreciate the limits of what a court can deliver, and the risks inherent in trying to get there, the conversation changes.

And when the conversation changes, settlement often follows.

Estate litigation will never be easy. It is too personal, too rooted in relationships that predate the dispute itself. But it is precisely for that reason that mediation has become such a critical part of the process.

From the middle, where I sit, the goal is not to declare a winner. It is to find a resolution that allows the parties to move forward, even if the past cannot be undone.

And in estate disputes, that is often the best outcome the system can offer.