How to Ask Beautiful Questions

by ISC President Kiran Singh Sirah

This year, I’ve kept my New Year’s resolutions minimal. I used to draft massive personal plans and reports—30 pages of missions and goals. For 2022, I’ve honed it down to just three objectives: to cultivate a more compassionate heart towards other people, to listen better, and to ask better questions.

These goals are all related, I think, in that they’re all part of having good, productive dialogues with the people around us. Personally, I’ve spent a lot of time lately thinking about how to have better conversations with my dad. I’ve long been interested in the work of Anne Basting, a MacArthur “genius” fellow and educator who is an expert in eldercare and creative expression. Her TimeSlips project is focused on supporting better conversations between aging people and their care partners. This work is based on the notion that creative expression is important at every age, and that we all have access to it, regardless of our abilities and limitations.

Basting’s insight is that we all have the ability to ask and answer “beautiful questions”—open-ended queries that allow people to answer in many different ways. Often, people with memory issues feel pressured to remember the “correct” answer to a question about the past, which can lead to disappointment if that answer eludes them. Beautiful questions offer many different ways to respond, providing a more creative and positive experience for everyone involved. It’s a delicate way to probe stories from the past without expectations or pressure to remember all the details.

Asking about the past is a wonderful way to connect with our elders. I always found this to be true in my research with people in homeless shelters, who I worked with as a graduate student. But I also learned that it was useful to ask questions that were somewhat flexible and interpretive, so they could answer in whatever way that suited them best.  Questions like, “Describe your experience living at the homeless shelter” were usually not fruitful prompts, in part because folks were still struggling to make sense of experiences that were traumatic and difficult to talk about. Asking more open-ended questions about their childhoods and other memories (i.e., “Tell me about something you have always loved to do”) helped them connect to their past identities as bakers, writers, or rappers, rather than their current situation of being homeless. Allowing them to respond in their own way made it easier to avoid sensitive or hurtful topics they didn’t want to discuss.

So old stories are a great way to connect with friends, neighbors, loved ones, and even strangers. But we also have to be mindful that when we’re working with older people, especially people with memory problems like dementia and Alzheimer’s, this topic of “the past” can be fraught. It’s important that we ask questions in a way that’s comfortable and healing for the person telling the story. We don’t want them to feel challenged or pressured to form a coherent account that moves in a linear way from past to present. We want them to express the story in whatever way feels best.

To that end, when I was in England with my family over the holidays, I found a little box of notecards in a charity thrift store for one pound. Using the TimeSlips website as inspiration, I made up some of my own beautiful questions to use with my dad. Some of them were:

  • What’s your favorite sound?
  • What’s your favorite smell?
  • What does courage mean to you?
  • Tell me about the best day of your life.
  • What is the greatest gift you have ever received?
  • What makes you laugh?
  • Whose life inspires you? (My father said Barack Obama!)
  • What makes a house feel like a home?
  • What does compassion mean to you?

As you can see, these prompts are designed to be flexible. They’re helpful in revisiting special memories or just providing a new window into a person’s inner life. I noticed that, often, my father’s responses tapped into his sensory experience: the sound of the tide in the seaside town where I grew up; the smell of cooking; or cold walks that we’d take on the beach in the winter.

Elaine Lawless, a former professor of mine, once said, “Storytelling is like a map of the imagination.” When we’re in dialogue with other people, we’re really creating maps together: maps of our lives and experiences that, in places, overlap. We can learn more about our own experiences by seeing the same events through other people’s eyes. We often tend to repeat the same stories, but each time there’s always a chance to go a bit deeper, or discuss a different angle. A detail might be a springboard to new questions or other thoughts.

All my life, my dad has been telling the story of my family’s immigration to England (which happened before I was born). Each time, I learn a little bit more. One time when he told the story I learned that my parents’ plane was diverted to Stanstead Airport because there was a large anti-immigrant demonstration at Luton. He talks about the train to London he took with my uncles to meet his first boss; the first hotel where he stayed (the Bremer); and the first washing machine he ever saw. (He didn’t know what it was because in Africa, everything was washed and dried in the sun.) He describes how strange it was to see white people doing manual labor like picking up trash or cleaning the streets, which was unheard of in Africa. These are stories he revisits over and over and over again, and I never get tired of hearing them.

These days there are many things my dad doesn’t remember, or memories that confuse him. Instead of asking for the full tale, I might ask what he remembers about the day he landed in England. Recently he mentioned how warm it was when he arrived. Everyone had told him to prepare for how cold England would be, but in fact it was a beautiful sunny day. He didn’t even have to change his shirt!

What I’ve come to understand is that when someone’s memory is a little jumbled, the person inside is still the same. By adapting our questions, we can help that person express themselves in ways that build interpersonal connection and help them feel empowered. I have a big family, including 31 first cousins spread out across three continents. I feel that part of my role in my family is to remind my siblings and other family members about how to support our elders. Often, it’s just a matter of showing up and being themselves. Whether you’re calling or video chatting or meeting in person, it’s always possible to share a story and bring your shared map with this person to life.

My advice for anyone who’s recording treasured family stories or even asking informal questions is that it’s critical to remember that we don’t always have to be focused and methodical. We can go off on tangents. We can talk about the present. (The weather always makes for excellent small talk.) We can take breaks, share cups of tea, and then get back to the conversation or save it for another time. One of the things that make our family bonds so rich and special is the way our conversations ebb and flow. We can retrace our steps and tell old stories in new ways.

Anne Bastings, 2016 MacArthur Fellow 

I encourage you to learn more about Anne Basting’s project and maybe even compose your own beautiful questions. They’re great conversation starters with all kinds of people, including kids and strangers at a dinner party. Get experimental with your small talk. As the conversation flows back and forth, make sure you’re doing everything you can to make that person feel safe and comfortable and, above all, heard.

Stay fluid; stay flexible. Set your conversation partner up for success. And really listen. You might even learn something new.