Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change

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LEGACY QUESTIONS

Legacy questions ask about what we’ve done, the people we’ve touched, and the contributions we’ve made. They can be asked every day, at every stage. They help recognize accomplishment, express gratitude, set priorities, or fill a bucket list. They help us recognize what is significant and what matters.

Accomplishments: What are the most important things you’ve done? What are you proud of? Asking what you have accomplished, whom you have helped, what you have created is a powerful way of taking stock and seeing your own footprint. These questions identify accomplishments and contributions.

Appreciation: What do you want your great grandchildren to know about you? Ask yourself this: if a stranger read your biography, what would she say were the significant things you’ve done? Fresh eyes may see more clearly than your own the contributions you’ve made along the way.

Adversity: What is a lesson you’d share from a mistake you made? Ask about adversity, mistakes, and regrets. Most everyone will have a clock they’d turn back, but mistakes can be redemptive. These questions seek meaning in mistakes by asking what we’ve learned from them and how we’ve used them to teach others. Asking about the downside in this way has an upside.

The Bucket List: What’s an adventure you’d like to go on? What do you want to do most? What’s your unfinished business? These questions ask you to daydream. You probably won’t do it all, but your bucket can become a road map, a way to focus on the future, on the things that matter and the story you’re writing.

Ending Questions: How do you want to be remembered? Speaking of story, who is the character you want to be? These questions cut through all the others. Time’s up. Book’s done. What do you want the title to be? What do you want on the inside flap? How do you want the critics to write about you? How do you want the story to unfold?

Listen to Your Own Voice: Listen for nuggets of accomplishment, expressions of pride, gratitude and satisfaction. Pick up on names and ask more about each. Listen for the high notes and pursue them. Listen for regrets and ask what lessons they taught.

Try: Set up a time to speak with a family member, making clear that you want to ask about significant moments, experiences and people. Prepare your questions in “clusters” so you have several that flow from the first. For example: What’s the most significant, yet challenging, relationship you’ve ever had? Ask follow-ups from the cluster, corresponding to what you just heard. Tell me more. Where did you meet? What was this person like? Why significant? How were you similar? How were you different? What was the best day you had together? The toughest? The point here is to ask in series—half a dozen questions or more per cluster—to dig in deliberately and listen intently in search of recollection, meaning and the defining stories of life.