A Tech Executive's First Will Had to Cross Two Borders

The situation

Herman was 42, a technology executive living in North York, and he had never made a will. He had moved to Canada from Singapore in his late twenties, built a career at a software company, bought a condo, and settled into the kind of life that made estate planning feel like a problem for later. Later arrived sooner than he expected. His father died the previous year, and Herman inherited a family apartment in Singapore outright, along with a modest investment account held at a bank there. He was single, with no children, and his closest relationships were his brother Raymond, who owned and operated several franchise locations across the GTA, and a longtime friend and former business partner, Arjun, who still held a passive interest in a technology venture Herman had co-founded years earlier.

The inherited apartment forced the question Herman had been avoiding. He now had meaningful assets in two countries with two different legal systems, and no instructions anywhere for what should happen to any of it. He came to Treadstone Law wanting a straightforward first will. What he got was a plan that had to work in Ontario and stay out of the way of a second estate process eight thousand kilometres away.

What the review found

The first step was an inventory of everything Herman owned, in every currency. In Ontario, that meant the North York condo, worth roughly $950,000, a portfolio of vested and unvested stock options and RRSP holdings worth close to $1,100,000, and a further $750,000 in non-registered investment accounts. In Singapore, the inherited apartment was worth roughly $1,200,000 in Canadian-dollar terms, plus a smaller investment account. Altogether, Herman's estate sat at around $4,000,000.

Without a will, Ontario's Succession Law Reform Act would decide who inherited the Canadian assets. That statute sets out a fixed order of relatives entitled to an intestate estate, and for someone without a spouse or children, it generally flows to parents, then siblings. Herman assumed that meant Raymond would simply inherit everything, and in Ontario that assumption was roughly right. But it left no role at all for Arjun, no instructions about who should manage the estate, and no say for Herman over how or when Raymond received it. An intestate estate also needs a court-appointed estate trustee before anyone can act, which adds delay at exactly the moment family members are least equipped to handle it.

The Singapore apartment raised a separate issue entirely. Property located outside Canada is generally governed by the succession law of the country where it sits, not by an Ontario will's general language. A will drafted in Ontario that purported to gift "all my property, wherever situated" could still leave the Singapore apartment tied up, because a Canadian grant of probate is not automatically recognized by authorities or land registries overseas. Worse, if Herman later signed a separate will in Singapore to deal with the apartment, a poorly worded Ontario will could unintentionally revoke it, or vice versa, since a new will generally revokes any earlier one covering the same property unless it is drafted to expressly carve out what it does not touch. Herman needed two wills that were aware of each other, not two wills that quietly cancelled each other out.

What we did

1. Mapped the estate by jurisdiction, not by asset type. We separated Herman's holdings into a Canadian estate and a foreign estate, because each would eventually be administered under different rules, by different professionals, using different documents.
2. Drafted an Ontario will limited to Canadian assets. The will was written to expressly apply only to property located in Canada, so it would not touch, and could not accidentally revoke, a separate will made to deal with the Singapore apartment. This is the same drafting approach used when someone holds Canadian assets that should pass without probate alongside other assets that require it — the wills are drafted to coexist rather than overlap.
3. Talked through executor choice honestly. Herman's instinct was to name Raymond as estate trustee because he was family. We walked through what the role actually involves — locating assets, paying debts and taxes, filing the estate's final tax returns, distributing to beneficiaries — and how that workload sits alongside running several franchise locations. Herman ultimately named Raymond as primary estate trustee with Arjun as an alternate, giving the estate a backup if Raymond was unable or unwilling to act when the time came.
4. Set out specific and residual gifts. Rather than one gift to one person, the will named Raymond as the primary beneficiary of the Canadian estate but included a specific bequest to Arjun reflecting their history together, along with a contingency plan naming a charitable beneficiary if both Raymond and Arjun predeceased Herman with no other named beneficiary alive.
5. Flagged the deemed disposition on death. Under the Income Tax Act, a person is treated as having disposed of most capital property immediately before death, which can trigger tax on accrued gains in non-registered investments. Employee stock options carry their own separate tax rules that also needed a specialist's attention on death. We did not attempt to solve this inside the will itself, but made sure Herman's estate trustee would know to obtain tax advice promptly rather than distributing assets before the estate's final tax position was clear.
6. Referred Herman to counsel in Singapore for the foreign will. We are not licensed to advise on Singapore succession law, and said so plainly. What we could do was draft the Ontario will to leave room for a Singapore will to operate independently, and give Herman a clear written summary of what the foreign will needed to state — most importantly, that it applied only to Singapore assets — so the lawyer he engaged there could draft with the Ontario document already accounted for.
7. Added powers of attorney for property and personal care. Since Herman had no will at all, he also had no documents naming anyone to manage his affairs or make health decisions if he became incapable. We prepared both at the same time, naming Raymond with Arjun as alternate, so the planning gap did not stay half-closed.

The outcome

Herman signed a completed Ontario will, along with powers of attorney for property and personal care, within a few weeks of his first meeting with our team. The will named Raymond as estate trustee, set out clear gifts to both Raymond and Arjun, and was drafted narrowly enough to sit alongside a future Singapore will without conflict. Herman engaged a lawyer in Singapore several weeks later to draft a will covering the apartment and the local investment account, using the summary we had prepared to make sure the two documents lined up rather than overlapped.

The practical difference is significant. If Herman dies today, his Canadian estate passes according to his actual wishes rather than a fixed statutory formula that would have written Arjun out entirely. His estate trustee does not need to apply to a court simply to get authority to act, because a validly signed will and a named estate trustee, once probated, is a far more direct process than an intestacy. And the Singapore apartment is governed by a will drafted specifically for that jurisdiction, by a lawyer qualified to draft it, rather than by an Ontario document reaching for a country it was never built to reach.

None of this changed how much Herman is worth or how much tax his estate will eventually owe. What it changed is who decides what happens to it, and how much friction his executor and beneficiaries face when that day comes. For a first will, that was the whole point.

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