Easy Conversation Starters for the Holidays About Estate Organization

Family gatherings are plentiful at this time of year and every family has their traditions. In my family, you could count watching replays of famous golf matches or bringing out a slide projector and carousel upon carousel of photos. You might enjoy making handed-down recipes, going through photo albums or playing games.  These nostalgic moments are the perfect opportunity to have conversations around legacy.

Half of Americans haven’t discussed their estate plans with family. While estate organization (organizing important documents and digital assets when someone dies or becomes incapacitated) is a departure from football and “remember when’s,” discussing legacy plans at the dinner table can pave the way for important transitions in the future.

Try these topics and conversation starters.

1. Using Technology to Keep Memories Safe

Imagine you’re passing around a photo album or scrolling through pictures on your phone from past holidays. Sharing memories is something we all do, but we rarely spend time thinking about how we access or protect photos, files or anything digital. Digital assets are photos, videos, social media accounts and content in apps. One of the biggest challenges when someone passes away is accessing all their digital content.

Conversation Starters:

“Did you know there is a setting called Legacy Contact on your iPhone? If something were to happen to me, my Legacy Contact could access my photos and other apps. Otherwise, Apple will lock the phone down and you might need a court order to access it.”

“Looking at these photos makes me reminds me how important it is to keep our memories safe. “

“I’ve been thinking about how we can make sure these treasures are organized and accessible in the future.”

2. Cutting the Clutter

Does a family member’s living resemble the National Archives? Are there stacks of papers, files, books, financial statements and other documents lying around? Technology has added a whole new layer of complexity because most people don’t keep good digital filing cabinets. If someone you know has a cluttered physical life, just imagine what their digital one must be like.

According to NordPass (2024), an average person has about 255 passwords (168 personal and around 87 business-related). Can you imagine someone trying to navigate all your logins and passwords if something happened to you?

Conversation starters:

“After this year’s big storms, I thought about all those people who lost their homes along with everything in them. If something like that happened to us, would you be able to access all your important documents?”

“I heard about a someone who suddenly lost a family member and couldn’t access their phone, photos or files because no one had access. They lost everything.  It made me think about how much we rely on our phones now, and how important it is to set up something like a legacy contact.”

“There must be years of treasures here. I’d hate for something to get lost.”

“Did you know you can add a section in your will giving someone permission to access all your digital assets?”

3. Talk About Your Goals

Position the conversation as part of a broader, positive goal—creating a legacy, decluttering and organizing. You might say: “I always think about my goals at this time of the year. One of mine is to make sure my affairs are organized so no one has to worry about them later.”

By sharing what you are doing, it creates an opening for others to jump in. Maybe you use an online organizing tool or have a special binder, file or safe with your documents.

Conversation Starters:

• “What’s something you’d want to make sure is preserved or passed down?”
• “There are some online apps for organizing everything from family photos to legal documents. Have you ever heard of Trustworthy or Everplans?”
• “Half of all families have a hard time finding important paperwork after someone dies. Does everyone know where my important documents are if something unexpected happened to me?”

Addressing Key Points

During the discussion, you can touch on three essential areas of estate organizing:

• Digital Legacy: Discuss tools like Apple’s Legacy Contact or Google’s Inactive Account Manager, which ensure access to digital assets like photos and documents. Explain how these tools work and why they’re important.
• Physical Organization: Suggest compiling key documents like wills, deeds, and medical directives in one secure place, and ensuring trusted family members know where to find them.
• Communication: Emphasize the value of openly discussing wishes to avoid confusion or disputes later. Consider mentioning the option of naming a digital or traditional executor in a will to manage assets.

The goal isn’t to have a full-scale estate planning session at the dinner table. Instead, use the opportunity to plant the seed for further discussions. Good luck and make sure to take some time for yourself during this busy time of year!

Be Well!

Andrea Finck and After Loss Professional and the Founder of Lightsome Estate Concierge, helping families with the overwhelming tasks of estate administration and home management after the loss of the loved one.