5 Questions Your Grandchildren Will Wish They Had Asked

Your grandchildren won't know what to ask.

They'll sit across from you someday, years from now, wanting to understand who you were before you became their grandparent. They'll want to know your story, your struggles, the moments that shaped you. But they won't know which questions unlock those stories.

That's where you come in.

The questions to ask grandparents that reveal the most aren't the obvious ones. They're not "where were you born?" or "what year did you graduate?" Those facts are easy to find. The meaningful questions dig deeper. They uncover the wisdom, the context, the humanity behind the dates and places.

Here's what we've learned after guiding hundreds of families through legacy film interviews: most people ask the wrong questions. They focus on facts when they should focus on feelings. They ask about events when they should ask about meaning.

Your grandchildren will wish they had asked these five questions. So ask them now, while your parents and grandparents can still answer.

Why Should I Interview My Grandparents?

Interviewing your grandparents preserves stories that can't be found anywhere else. Their memories, perspectives, and wisdom exist only in their minds, and when they're gone, those stories disappear forever unless someone asks the right questions and records the answers.

Beyond preservation, these conversations deepen your connection with your family's history. Research shows that children who know their family stories are more resilient, more confident, and have a stronger sense of identity. Family history isn't just interesting—it's foundational.

The urgency is real. Memory fades. Health declines. The window to capture your grandparents' stories closes a little more each day. Don't wait until a crisis forces the conversation. Start now, while they're still here and able to share.

Question 1: "What's the hardest decision you ever had to make?"

This question cuts straight to character.

Everyone makes hard decisions. Career changes. Moving across the country. Ending relationships. Financial sacrifices. Your grandparents have decades of these moments, and each one reveals something about their values and priorities.

When you ask about their hardest decision, you're not just collecting a story. You're learning what they chose when the choice mattered most. You're seeing who they were when life forced them to pick between competing goods or lesser evils.

The answer shows you how they think. How they weigh options. What they're willing to sacrifice. What they're not willing to compromise on.

Follow-up questions that go deeper:

• What made that decision so difficult?

• Looking back, would you make the same choice today?

• How did that decision change your life?

• What did you learn about yourself from making that choice?

These follow-ups transform a single answer into a conversation about identity, regret, wisdom, and growth. Your grandchildren will want to know not just what their great-grandparents decided, but why, and what came after.

Question 2: "What do you wish you had known at my age?"

This question creates direct connection across generations.

Your grandparents have lived the life stage you're in now. They've been 25, 40, 60. They've navigated the same universal challenges—relationships, career uncertainty, parenting, aging parents, financial stress—in different contexts.

When they answer what they wish they'd known, they're offering hard-earned wisdom that can't be taught any other way. They're giving you the benefit of their hindsight. They're pointing out the mistakes they made so you might avoid them.

And here's what makes this question powerful for legacy films: it's inherently forward-looking. Your grandparents aren't just recounting the past. They're actively trying to help future generations.

The answers reveal regrets without dwelling on them. They show growth without being preachy. They connect lived experience to practical guidance in a way that feels personal, not prescriptive.

What this question reveals:

• Their biggest regrets (framed constructively)

• What they value most now

• How their perspective changed with age

• What they consider truly important versus what seemed important at the time

Your grandchildren will ask themselves the same question someday. Having your answer preserved gives them a roadmap through life's complexity.

Question 3: "Tell me about a time you failed at something important."

Nobody wants to talk about failure. That's why this question matters.

The stories we remember aren't always the victories. Often, the most formative experiences are the ones where everything fell apart. The business that failed. The relationship that ended. The opportunity that slipped away.

Your grandparents have survived failures you'll never know about unless you ask. And in surviving them, they learned resilience, adaptability, and perspective that success never teaches.

When you ask about failure, you're giving them permission to be honest about struggle. You're showing that perfection isn't the goal—truth is. You're creating space for the messy, complicated reality of a life fully lived.

This question also combats the Instagram version of family history. Too many legacy projects become highlight reels. They show only the accomplishments, the happy moments, the proud memories. But that's not a complete story. Your grandchildren need to know that their great-grandparents struggled, failed, got back up, and kept going.

The insights this reveals:

• How they handle adversity

• Their definition of failure (which often evolves)

• The role of failure in their success

• How they rebuilt after loss

These stories give your grandchildren permission to fail, to struggle, to be human. They need that permission more than they need another story about someone's achievements.

Question 4: "What's something you've never told anyone?"

This is the question that transforms an interview into intimacy.

Everyone has untold stories. Moments they've carried alone. Experiences they never found the right time to share. Thoughts they kept private because no one asked.

When you ask what they've never told anyone, you're not prying. You're offering them the chance to be fully known. You're creating a moment where secrets can become stories, where private experiences can become shared wisdom.

Not every grandparent will answer this question immediately. Some need time. Some need trust. Some need assurance that the answer won't be judged. But when they do answer, what emerges is often the most meaningful part of the entire interview.

These are the stories your grandchildren will treasure most—not because they're dramatic or shocking, but because they're real and vulnerable in a way that rare in family conversations.

How to ask this question:

Make it safe. Frame it as an opportunity, not an interrogation. Let them know they can pass if they want. Give them time to think.

Say something like: "Is there something about your life that you've never really told anyone? Something you'd like someone to know?"

Then wait. Let the silence do its work. Don't rush to fill it. The most powerful answers often come after a long pause.

Question 5: "How do you want to be remembered?"

This question looks forward by looking back.

Everyone thinks about legacy, whether they articulate it or not. Your grandparents have lived long enough to see how their choices rippled outward. They've seen what lasted and what didn't. They know what they hope people remember when they're gone.

When you ask how they want to be remembered, you're asking them to distill their values into a few key ideas. You're asking what matters most when everything else falls away. You're giving them a chance to state their legacy on their own terms.

The answer reveals their priorities. Not what they said was important, but what they demonstrated through how they lived. Not what society valued, but what they personally held dear.

And for your grandchildren, this question provides a north star. When they face their own choices, their own crossroads, they'll have their great-grandparents' stated values as a guide. They'll know what your family has always stood for.

The layers this question uncovers:

• Their core values

• What they're most proud of

• What they wish they'd done differently

• How they define a life well-lived

• Their hopes for future generations

This isn't morbid. It's clarifying. It's giving your grandparents the chance to write their own story's conclusion while they're still here to tell it.

How to Actually Ask These Questions

Having good questions matters. But how you ask them matters more.

These aren't questions for a quick phone call or a distracted conversation over holiday dinner. They require time, attention, and trust. Here's how to create the right environment:

Pick the right time. When your grandparents are rested, not stressed, and have hours available. Not squeezed between other obligations.

Set the scene. Quiet space. No interruptions. Phones off. This conversation deserves full attention from everyone involved.

Record everything. Don't rely on memory. Use video if possible, audio at minimum. Your grandchildren need to hear their voices, see their expressions.

Listen more than you talk. Your job isn't to share your own stories or offer commentary. It's to create space for theirs.

Ask follow-up questions. The first answer is rarely the whole story. Dig deeper. Ask "why?" Ask "how did that feel?" Ask "what happened next?"

Don't rush. Some questions take time to answer. Some stories take multiple sessions to tell. That's okay. The goal isn't efficiency—it's truth.

What Happens If You Don't Ask

Here's the hard truth: if you don't ask these questions, no one will.

Your grandchildren won't know to ask them. They won't have the context, the life experience, or the understanding of what matters until it's too late. By the time they're old enough to appreciate these conversations, your grandparents may be gone.

You're the bridge. You're the generation that still has access to these stories and the wisdom to know which questions reveal them. If you don't capture them now, they disappear.

Every family gathering where you don't ask is a missed opportunity. Every phone call that stays surface-level is a lost chance. Every time you think "I'll ask them next time," you're gambling that next time will come.

These Questions Are Just the Beginning

Five questions won't capture a complete life. They're starting points, not endpoints.

But they're the right starting points. They open doors to deeper conversations. They signal that you're interested in more than small talk. They show that you value your grandparents' experiences and wisdom.

The real gift isn't the answers themselves. It's the conversation. It's sitting together and talking about what matters. It's your grandparents feeling heard and valued. It's you learning who they really are beyond their role in your life.

At DocuFamily, our guided interview process is built around questions like these—thoughtful prompts that reveal character, wisdom, and truth. We help families have the conversations that matter and preserve them in beautifully crafted legacy films. If you're ready to capture these stories before it's too late, we're here to help.

Don't wait for your grandchildren to wish they'd asked. Ask now, while you still can.