10 Open-Ended Questions To Ask Your Family Members

Have you ever been to a new restaurant that has pages and pages of options and felt like you couldn’t decide? And then it takes you so freakin’ long to pick something that sounds good (though what if something else is better??!!) that the waiter has completely given up on you and you have to wave your arms over your head like a manic cheerleader giving her final hurrah?

… Just me, then?

Well, the point I’m trying to make is that choosing to embark on a legacy project of your own is a little bit like that. At first you’re excited that you’ve finally decided to ask your parents or grandparents all those burning questions once and for all, until you completely overthink it and fall into analysis paralysis. 

The main problem you’re facing is that you could ask your loved one about literally anything. How do you even freakin’ know where to start or which questions are the most important ones?

The answer, which I know you will not find satisfying in any way, is this →

It doesn’t matter. 

The important thing is starting the conversation in the first place. Trust me. Start with literally any question about their life, and you’ll end up where you need to go.

That said, if you can’t get out of your own head about what to ask, here are ten stellar open-ended questions that are guaranteed to provoke interesting answers from the ones you love most:

1) What are some of the unanswered questions you wish you could have asked your parents or grandparents?

No matter how diligent anyone is about recording their family’s stories (Hey, good job, you!), there will always be a question that gets missed. Your own loved one will have their own regrets about what they never got to ask dearly departed family members too. 

For bonus points, after they’ve answered you, try turning it back on them. For instance, if your dad always regretted never asking his own dad how he felt about working in the family business instead of pursuing some other passion, ask your dad why he stayed (or left) the business.

2) What was one of your most foolish purchases?

This might feel like a silly, throw-away question but it’s great for two reasons. One, it’s going to bring a smile and laughter to your interviewee’s face. And two, depending on their answer, it will really illustrate the change between who they used to be back-in-the-day and who they are now.

3) What do you feel has been your greatest accomplishment to date?

Everyone loves to talk about what they’ve done well. Keeping the question generic (i.e. accomplishment) instead of more specific allows your loved one to choose how to direct the conversation, leading to a more natural and spontaneous answer.

4) If you could only keep one possession, what would it be and why?

Whatever that possession is, there’s a story behind it. And, okay, this is morbid but, wouldn’t you prefer to know now why that thing is important rather than later when you’re going through their items and have no one to ask?

5) What is something you want people to remember about you?

This question is worth-it because the answer is usually a surprise. The way we see people (Hi Grandma!) is often not the way they see themselves (I’m still 29 at heart). Whatever their answer, it’s sure to provoke lots of follow-up questions.

6) What was the most difficult thing you ever had to do?

This is maybe not the question you should open with (Hello, am I being interrogated by the FBI here??!!) but it’s oh-so-worth-it to sneak it into the interview once everyone is comfortable. The difficult decisions people face are the ones that speak directly to the heart of why someone’s life is the way it is.

7) Tell me about someone who has been a friend for most of your life. (Where did you meet? Why did you keep in touch? Etc.)

Some friends are there for one period of life, and others are there for its entirety. Guaranteed that if you’re asking this of your parent or grandparent, you absolutely do not know the full-story behind them and their bosom buddy. 

8) How did you decide on your profession?

Most of us spend the majority of our waking hours working, and yet the people closest to us probably don’t have any idea about what we do in all that time. This question should spark a larger question about your loved one’s career, and what it meant to them.

9) What is one of your dreams that you haven’t realized yet?

Alright, this one might be a bit of a tearjerker depending on the age and ability of the loved one you’re talking to. But you should still ABSOLUTELY ASK IT because nothing speaks louder about who someone is than their dreams. If the dream is still within reach, this may be the catalyst for some future adventure that your loved one may not have thought was possible.

10) During your lifetime, what world event stands out most to you?

For each generation, there is always at least one event where everyone can list where they were and who they were with when X happened. You know what it is for you, so what is it for your older loved ones? A footnote in your history book may be something that completely changed their world as they knew it.

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That’s it! If you still need a little more help figuring out questions, feel free to head on over to my Work with me page.