What happens to your estate after you’re gone may depend less on your lifetime planning than on what your Will actually allows others to do in your absence. Even the most thoughtful estate plan can fall apart if the Will isn’t drafted with flexibility, tax efficiency, and post-mortem strategies in mind. The result? Missed opportunities, excess tax, and unintended outcomes for your heirs.

This article is the first in a series exploring how Canadian families, executors, and advisors can navigate post-mortem planning in an increasingly complex legal and tax environment. We will analyse recent case law and legislative changes, and unpack best practices to ensure your Will does more than express your wishes – it empowers action.  

Defining with clarity: Post-mortem estate planning

Post-mortem estate planning refers to legal and tax strategies that can be implemented after a person’s death, aimed at minimizing total tax obligations, avoiding double or even triple taxation, and ensuring a smooth, effective transfer of wealth to beneficiaries. Typically, the focus is on how the transfer of low-cost, high-value assets – often private corporation shares –  is managed in a tax-efficient manner.

Why a strong Will is the key to post-mortem flexibility

Post-mortem estate planning, by definition, happens after death – but its success often hinges on choices made well before that point. The Will is not just a legal formality; it is the document that empowers your personal representatives, beneficiaries, and their professional advisors to act. Without the right tools embedded in it, even the best advisors may be unable to fix poor asset structures, navigate tax pitfalls, or carry out your intentions effectively.

Common roadblocks include:

  • assets held in ways that restrict flexibility or tax planning;
  • unanticipated transfer restrictions on private company shares; and
  • Wills that lack language to authorize post-mortem tax elections or asset reallocations.

The result? Higher tax, increased complexity, and potentially unfair or unintended outcomes for your beneficiaries.

This article will explore key considerations that Will-makers and their advisors should address during the Will drafting process.

Appointment of executors and trustees

Too often, the default choice for executors and trustees is the Will-maker’s spouse, children, or other immediate family members. More often than not, such choices are driven by emotion rather than practicality. A surviving spouse may have deep knowledge and experience with the individual’s assets and affairs, which could place them in an ideal position to serve as executor. However, just as often, the spouse (or children) may lack the knowledge, wisdom, poise, expertise, and skills necessary to manage a complex estate administration process.

The choice of executors and trustees should involve a discussion of these factors – and that discussion must include the intended appointee. They may not wish to take on the responsibility involved, and the option of appointing a trust company or professional trustee should almost always be considered.

Maintaining GRE status

Electing for an estate to be a “graduated rate estate” (“GRE”) can provide significant tax advantages for beneficiaries. A Will that grants executors and trustees broad direction to elect for and maintain GRE status can be a powerful planning tool.

For example, the Will might prohibit executors and trustees from taking any action that would compromise the estate’s status as a testamentary trust. Additionally, if the executors and trustees are directed to maintain GRE status, this can help manage beneficiaries’ expectations regarding the early or premature disposition of estate assets.

Trustee powers: Why the standard clauses often fall short

Executors and trustees have certain inherent powers granted by legislation, but their authority is only as strong as the Will allows. While some powers are granted by provincial law, many of the actions required to carry out a post-mortem plan demand express authorization in the Will itself.

This makes it essential that the Will-drafter carefully craft the scope of trustee powers. On one hand, trustees must be given sufficiently broad powers to ensure they are not prevented from performing essential acts. On the other hand, those powers should not so be broad as to permit a trustee to act contrary to the Will-maker’s intentions.

Most Will-drafters understand that executors and trustees must be expressly granted a power of sale. However, it is also generally necessary to provide them with extended powers, such as:

  • the power to carry on businesses; and
  • the power to exercise all rights and satisfy all liabilities incidental to the ownership of private corporation shares.

A Will-drafter experienced in tax law, property law, corporate law, corporate reorganizations, capital loss and pipeline planning can provide a great service to their client by: (1) anticipating the powers executors and trustees will need; and (2) drafting comprehensive powers clauses to ensure that the scope and extent of the authority of executors and trustees cannot be challenged.

For example, it may be necessary to consider relieving executors and trustees from statutory investment restrictions. It can be difficult for an executor and trustee to comply with the prudent investor rule – and the related requirement to diversify investments – if the only significant asset under administration consists of illiquid, non-income producing private corporation shares. It may also be necessary to relieve executors and trustees of their duties to sell wasting or hazardous assets, as those requirements could severely limit their ability to manage or dispose of certain assets as part of an overall estate plan.

Bequests – Specific and residual

Where the use of specific rollover provisions in income tax legislation is a deliberate intention of the Will-maker, it may be appropriate to identify and bequeath specific properties and assets to a particular qualifying individual – for example, a surviving spouse. Outside of this exception, however, a Will-maker must carefully consider whether making gifts of specific properties or assets could lead to a mismatch between the asset and its associated tax liability, or restrict the ability of executors and trustees to manage those assets as part of an overall post-mortem reorganization plan.

The Will-maker must also contemplate whether the terms of the Will comply with any transfer restrictions –  such as those found in a shareholders’ agreement to which the Will-maker is a party.

If the Will-maker intends for assets to be transferred to a qualifying spousal trust, the terms of the Will must be carefully drafted to ensure that all conditions for qualification are met, that the trust is not tainted, and that the actions of the executors and trustees in administering the trust conform with those qualifying conditions.

Key takeaways: How to future-proof your estate plan through a well-drafted Will

  • A Will is more than a document — it’s your executor’s toolkit. Without the right provisions, even the best estate plan can fail to achieve its objectives.
  • Post-mortem planning starts during your lifetime. The choices you make today – from how assets are held to the powers granted in your Will – determine what’s possible after death.
  • Trustee powers must be tailored, not templated. Standard clauses may not permit the business, tax, or reorganization actions needed to minimize tax and preserve estate value.
  • Choosing executors is a strategic decision. Emotional choices can lead to administrative headaches. Consider professional or institutional trustees for complex estates.
  • Preserve GRE status. Proper drafting helps maintain tax advantages and manage beneficiary expectations around asset distribution timing.
  • Avoid unintended tax burdens through careful bequests. Specific gifts must be aligned with associated liabilities, transfer restrictions, and rollover opportunities –particularly for spousal or testamentary trusts.
  • Legal nuance matters. From corporate share structures to capital loss planning, your Will should reflect an integrated legal and tax strategy – not a one-size-fits-all approach.

It should be clear from the foregoing that crafting an effective Will requires the assistance of a professional with deep knowledge and experience – not only of your individual situation and wishes, but also of the wide range of strategies necessary to create and implement an effective post-mortem estate plan. Contact one of our experienced Private Client Services lawyers to discuss your specific needs.