Preparing a Will? Stop and Consider These 15 Important Questions First

Most people think estate planning is about documents.

Meeting with a lawyer.
Filling out forms.
Signing documents

In reality, the legal document is the final step.

Before a Will can be written, you have to make a series of decisions about your life, your responsibilities, and the people you trust.

These are the same decisions you will face whether you:

• work with an estate lawyer,
• use an online Will platform, or
• prepare your estate plan on your own.

Understanding these decisions ahead of time makes the process much faster, less intimidating, and more thoughtful.

Below are the fifteen questions that shape almost every Will.

1. Who should administer your estate?

This person is called your executor or your estate trustee (in Ontario).

Your executor is responsible for carrying out the instructions in your Will. That usually involves:

• gathering your assets
• paying debts and taxes
• dealing with financial institutions
• communicating with beneficiaries
• distributing the estate

This process can take a year or more to complete.

You're not choosing the person you love the most.

You're choosing the person who can manage paperwork, deadlines, and communication during a difficult period.

Most people also name an alternate executor in case the first person cannot, or will not, act for your estate.

2. If you have minor children, who should raise them?

If both parents die while the children are minors, someone must become their legal guardian.

This is one of the most personal decisions in estate planning.

Parents often think about:

• values and parenting philosophy
• emotional connection with the children
• geographic location
• stability and capacity to take on the role

Naming a guardian in your Will does not force someone to accept the role, but it provides the court with clear guidance about your wishes.

3. Who should manage money for your children?

If children inherit assets while they are minors, they cannot legally manage those funds themselves.

Someone must act as their trustee.

The trustee is responsible for managing the money and using it for the children's benefit.

Sometimes parents choose the same person as both guardian and trustee.

Other families prefer to separate the roles, appointing someone with stronger financial experience as the trustee.

4. When should children receive their inheritance?

Most parents do not want a large inheritance transferred outright to an 18-year-old.

Instead, assets are often held in trust until certain milestones are reached.

Many Wills use age-based timelines, such as:

• one portion at age 25
• another portion at age 30
• the remainder at age 35

Some families prefer life-event milestones instead of fixed ages.

For example, trustees may be allowed to release funds for purposes such as:

• completing post-secondary education
• purchasing a first home
• starting a business

There is no single correct structure. The key decision is whether you want distributions to follow a timeline or a set of life milestones.

5. How should your estate be divided?

For many families, the plan is simple: equal shares among children.

But equal is not always appropriate.

Different family structures may require more thoughtful planning, including:

• blended families
• children from previous relationships
• dependants with disabilities
• significant differences in financial need

If you do not decide, the government decides for you; provincial intestacy law will apply a default formula instead.

A Will allows you to choose a structure that reflects your family's situation rather than the government's default rules.

6. Are there specific gifts you want to leave?

Many Wills include specific gifts of particular items or amounts.

Examples might include:

• jewelry or heirlooms
• artwork or collectibles
• charitable donations
• a fixed amount of money

These gifts are distributed first.

Everything that remains after debts, taxes, and specific gifts are handled becomes part of what is called the residue of the estate.

The residue is usually distributed according to the main structure of the Will, such as equal shares among children or other beneficiaries.

Because the residue often represents most of the estate, it becomes one of the most important parts of the plan.

7. Who should care for your pets?

Pets are legally treated as property, which means responsibility for them must be assigned.

Many people name a pet guardian and sometimes leave funds to support the animal's care.

Without instructions, responsibility may fall informally to whoever is willing to take the pet.

8. Who are your backup decision-makers?

Circumstances change.

The person you appoint today may move away, become ill, pass away, or simply be unable to act when the time comes.

For this reason, most Wills name alternate executors, trustees, and guardians.

This ensures your plan still functions even if your first choice cannot serve.

9. What happens if a beneficiary dies before you?

Your Will should address what happens if someone you name does not survive you.

Options typically include:

• their share passing to their children
• redistribution among surviving beneficiaries
• a different named recipient

Without instructions, the outcome may not match your intentions.

10. Should any inheritances be protected through trusts?

Some beneficiaries may benefit from receiving assets gradually rather than all at once.

Trusts are often used when:

• beneficiaries are young
• long-term financial support is needed
• there are concerns about creditor exposure
• structured financial oversight is helpful

Trusts allow assets to be managed over time while still benefiting the intended recipient.

11. How should debts and taxes be handled?

Every estate must address:

• outstanding debts
• taxes owing at death
• administrative costs

Your Will can clarify how these obligations should be handled and which assets should be used to satisfy them.

12. What happens to assets that pass outside the Will?

Not everything you own is controlled by your Will.

Some assets transfer automatically to a named beneficiary or surviving owner.

Examples include:

• life insurance with a named beneficiary
• registered accounts such as RRSPs and TFSAs
• pension survivor benefits
• jointly owned property

These instructions operate separately from the Will.

Part of estate planning involves reviewing these designations so they align with your overall intentions.

13. Are there charitable causes you want to support?

Many people include charitable gifts in their estate plan.

These gifts may be structured as:

• a fixed amount
• a percentage of the estate
• a gift of specific assets

For some families, charitable giving becomes an important way to reflect personal values and legacy.

14. How should digital and online assets be handled?

Digital assets increasingly form part of modern estates.

These may include:

• domain names
• online businesses
• cryptocurrency wallets
• digital content accounts
• cloud storage

Your executor may need guidance about what exists and how these assets should be managed or transferred.

15. Have you spoken with the people you appointed?

One of the most important steps in estate planning happens outside the legal document.

Executors, guardians, and trustees should know:

• that they have been appointed
• what the role involves
• where important information is located

These conversations do not need to be heavy or dramatic.

Often they are simple and practical.

But they prevent confusion later.

Now You're Ready to Sign Your Will

Most delays in estate planning are not caused by legal complexity.

Delays happen because people are unsure about the decisions behind the documents.

Once those decisions are clear, drafting the Will becomes straightforward.

Estate planning is ultimately about replacing the government's default rules with your own instructions.

The Will simply gives your instructions legal force.