Estate Planning Conversations During the Holidays

For Canadian families, holidays are often the only time everyone is together — providing rare opportunity for estate planning conversations. Approached thoughtfully, these discussions can deepen family connection rather than disrupt the celebration.

Why holidays work #

Family togetherness. Most extended families gather at holidays — sometimes the only time all year.

Reflective atmosphere. End-of-year reflection naturally extends to bigger life questions.

Trigger events. Recent deaths in the family circle, health updates, or major life changes often prompt awareness.

Time available. Holidays often have longer time blocks than typical family visits.

Why holidays don't work #

Atmosphere mismatch. Celebratory atmosphere doesn't always lend to serious topics.

Family conflicts. Holiday tensions can amplify disputes.

Busy schedules. Meals, gifts, traditions, other guests compete for attention.

Some family members travel: Limited time per visit.

Stress: Many people feel stressed at holidays; adding heavy topics can backfire.

The 'scheduled conversation' approach #

Rather than free-form bringing it up:

Schedule specifically:

• "Tomorrow morning before brunch, can we have a family talk about estate planning?"
• 30-45 minutes, specific topic
• Coffee or tea, comfortable setting
• Limited audience (immediate family, not all extended family)

Specific topic:

• One question (not everything)
• Concrete deliverable (decision, document update, follow-up commitment)

Outside main festivities:

• Morning walk
• Afternoon coffee
• Quiet hour before dinner
• Day-after-the-celebration reflection

Topics that work for holiday discussions #

Confirm Wills exist #

Quick check-in:

• "Do you have a current Will?"
• "When was it last updated?"
• "Do you know where it is?"

Often surprises emerge — Will exists but is 15 years old; Will exists but spouse hasn't updated after major life event; Will doesn't exist at all.

Executor check-in #

For parents whose Will is current:

• "Is [named executor] still the right choice?"
• "Have you talked to them about it?"
• "Do they know where the Will is?"

Executors named years ago may have moved, lost touch, or become inappropriate (estranged sibling, distant cousin).

Beneficiary designations #

For accounts with named beneficiaries (RRSP, TFSA, life insurance, pension):

• "Are your beneficiaries still correct?"
• "Have you updated after [marriage, divorce, birth, death]?"

Beneficiary forms outdated by life events are extremely common.

Aging parents' care planning #

For adult children of aging parents:

• "How are mom and dad doing?"
• "What's the plan if [health change]?"
• "Who's the point person for medical decisions?"
• "Do you have Power of Attorney set up?"

Often these conversations only happen during health crises; pre-crisis discussion is much better.

Funeral wishes #

Particularly with parents:

• "Have you thought about what you'd want when the time comes?"
• See talking to a loved one about their funeral wishes

Family business or cottage #

For families with shared assets:

• "What happens to the cottage when [parents] aren't around?"
• "How does the business succession work?"
• These often have buried disputes that only surface at the worst moment

What to avoid #

Don't blindside: Don't bring up serious topics at the dinner table with extended family.

Don't lecture: Don't bring extensive materials and lecture the family on what to do.

Don't fight: Don't try to resolve family conflicts during holiday gathering.

Don't push: If someone clearly doesn't want to engage, respect that. Try later.

Don't make it about money: Frame as 'making sure we honour your wishes' not 'figuring out what we get'.

Handling resistance #

If a parent doesn't want to discuss:

• "I understand it's not a fun topic. We don't have to right now."
• Try a single specific question: "Just one thing — do you have a Will?"
• Offer specific help: "If you'd like to update it, I'd be happy to help find a lawyer or use an online service."
• Leave the door open: "Let me know if you ever want to talk about it."

If a sibling resists:

• "I just want to make sure we're aligned in case something happens."
• "If you don't want to discuss specifics, that's fine. But I want you to know that [I've done my Will, named executor, etc.]."

If a family conflict surfaces:

• "It sounds like there's something to discuss. Let's set a time when we're not all in one room — it deserves its own conversation."

Multi-year approach #

Some families address estate planning topics gradually over multiple holiday seasons:

Year 1: Confirm everyone has Wills.

Year 2: Discuss executor choices and ensure executors know what they're doing.

Year 3: Address beneficiary designations.

Year 4: Discuss aging parents care planning.

Year 5: Funeral wishes.

Spread out, each conversation is manageable. Together over years, family has comprehensive picture.

After the conversation #

Document immediately:

• Notes during or after conversation
• Confirm understanding before holidays end
• Share with relevant family members

Make follow-up commitments:

• "Will you call your lawyer in January about updating?"
• "I'll send you the link to that online service."
• "Let's check in next month."

Schedule the next:

• "Should we plan to discuss [next topic] next time we're together?"

What we focus on at It's Simple Will #

The Will Creator provides an easy way to get a Will done — often the first concrete step out of holiday conversations. Pre-Planner and Life Discovery Kit (post-payment) extend the planning.

Related guides #

• Talking to a loved one about their funeral wishes
• How often review estate plan
• Estate planning after a major health diagnosis
• Funeral pre-planning Canada