Thanksgiving Gatherings: Starting Important Family Conversations

Thanksgiving brings families together around dinner tables across Manitoba, creating one of the few times when multiple generations gather in one place. While these conversations often focus on sports scores and holiday plans, Thanksgiving also presents a unique opportunity to discuss topics that families typically avoid – but shouldn’t.

Why Thanksgiving Is the Right Time for Serious Conversations

Family gatherings feel warm and connected, making them ideal for broaching sensitive topics. When everyone’s relaxed and in good spirits, discussions about wills, powers of attorney, and family wishes feel less clinical and more like caring conversations about the future.

The challenge is that these topics can quickly become uncomfortable or overwhelming, especially when family members have different expectations or concerns they’ve never voiced.

Common conversation roadblocks include:

• Parents who feel discussing wills is “morbid” or premature
• Adult children unsure how to bring up caregiving concerns
• Siblings with different ideas about family property or businesses
• Assumptions about who wants what without actual confirmation

The key is starting small and focusing on understanding rather than decision-making.

Conversation Starters That Actually Work

Begin with Care, Not Paperwork: Instead of diving into legal documents, start with expressions of care: “We want to make sure we’re prepared to help if anything happens” or “We’ve been thinking about how to honour what’s important to you.”

This approach opens dialogue without immediately triggering defensive responses about death or incapacity.

Ask About Values, Not Just Assets: Rather than asking “Who gets the cottage?” try “What does the cottage mean to you, and what would make you feel good about its future?” These conversations often reveal that families care more about preserving memories and relationships than specific ownership arrangements.

Understanding values first makes the practical decisions much clearer and less contentious.

Focus on One Topic Per Gathering: Trying to cover wills, powers of attorney, healthcare wishes, and property distribution in one conversation guarantees overwhelm. Pick one area that feels most pressing – perhaps starting with healthcare wishes or powers of attorney – and save other topics for future conversations.

This approach allows families to process information and emotions without feeling rushed into decisions.

Creating Safe Space for Difficult Topics

Acknowledge the Awkwardness: Starting with “This feels awkward to bring up, but…” gives everyone permission to feel uncomfortable while still engaging in important discussions.

Listen More Than You Plan: These conversations often reveal assumptions that were completely wrong. The child who everyone assumed wanted the family business might prefer a different path, or parents might have concerns no one realized.

Respect Different Comfort Levels: Some family members need time to think before discussing major decisions. Offering to continue conversations later removes pressure and shows respect for different processing styles.

Moving from Conversation to Action

Once families start talking, the next step is translating wishes into proper legal documentation. Conversations reveal preferences and concerns, but wills and powers of attorney ensure those wishes are legally protected and enforceable.

Many families discover that their assumptions about each other’s wishes were incorrect, making these conversations invaluable for creating plans that actually reflect everyone’s values and goals.

Taking the Next Step

Thanksgiving conversations plant important seeds, but they need follow-up to become meaningful protection for your family’s future. If your family is ready to move from conversations to creating proper wills and powers of attorney, or if you need help facilitating the next round of these discussions and working them into a concrete plan, we’re here to guide you through the process. Call us.