Asking an Empathetic Question

Illustration by Kris Russell. Learn more about our illustrators.

Asking an Empathetic Question

Embracing empathy when interacting directly with other people often involves being able to ask questions that open up the conversation, building a bridge rather than creating a barrier. We have some principles for asking these questions that we practice when we’re interacting with clients, stakeholders, and even friends. 

How can this question build on the expertise of this person? 
It can be tempting to ask everyone you’re talking to the same standard set of questions, but this does not always reflect the specifics of someone’s expertise and experience. Questions that are mismatched to the person (at best) make your conversation partner strain to spin the question into something they can answer, or (at worst) convince them that you don’t value their actual experience. Think about the different kinds of expertise someone might have and what they will likely feel most comfortable sharing about. For example, a community member who has experienced something directly is going to be able to talk about their own experience, but they may not be able to talk about their neighbors’ experience with the same thing. An academic who studies a specific issue may be able to share a big picture view that describes how a population of people behaves, but they may not know at a detail level what specific tools or workarounds someone is actually using. 

To address these concerns, we direct questions to people’s specific sets of expertise. For example, if we want to learn about how teachers communicate with each other, we may ask a set of teachers to tell us different stories about how they have communicated with their colleagues. We might also ask principals to tell us about their observations of teachers, or about the ways they have supported teacher communications. But we wouldn’t ask teachers or principals to extrapolate or share broad assumptions, such as , “What do you think is the most common way all teachers communicate with each other?” Keeping a question grounded in the person’s actual experience both gets more accurate responses and builds trust that you value their lived expertise. 

How can we ask something that is open-ended, but with focus and scaffolding? 
Open-ended questions are a valuable tool to broaden the conversation while focusing on someone’s expertise. An open-ended question is one that cannot be answered with a single word, like yes, no, or a number. 

Open-ended questions or prompts Tell me a story about… Walk me through the process of… What works well for you about…?  Why?

Close-ended questions or prompts How often do you do…? Did you enjoy…? Were you successful?

But asking too broad an open-ended question can lead to conversation paralysis, where someone may not know where to begin or how to respond. We are careful to focus our open-ended questions, frequently ordering them in a way that allows our conversation partner to build up to the big question, like “If you could wave a magic wand and change anything, what would you do?” We start instead with specific areas to ask open-ended questions within, so the metaphorical conversation space feels like an approachable size. During the UMSL campus planning process, we asked student and employee workshop participants to tell stories and imagine changes within specific categories, before following-up with broader questions about the kinds of big changes they’d like to see. 

How can we ask in a non-judgemental and non-leading way? 
It can be easy for our own judgment or biases to slip into questions in subtle ways, like the tone of our question or how we phrase it. The difference between “Your experience was good, wasn’t it?” and “What was positive about your experience? What was a challenge?” is small, but the second set of questions opens up the possibility of people more honestly sharing their own experiences. We frequently practice asking our questions beforehand, and reading them outloud to help us hear where there’s subtle judgment in the way we’re asking questions. Since our goal is to learn what’s really true for our conversation partner, we want to keep our questions neutral to express that we’re open to what they want to share, even if it may surprise us or upset assumptions. 

How can we ask using shared language?
Finally, we want to make sure that the language we’re using is something our conversation partner would understand and use, and that clearly communicates what we’re intending. We might start with the words that people actually use, and then practice our questions with others (out loud!) to be sure that the phrasing is as clear as it can be. We may also change language on the fly — for example, if we learn there’s a different term that a conversation partner uses, we may ask them to define that term and then immediately start using it while talking to them. This demonstrates that we have listened to them and brings us closer to their experience. 

One of our go-to open-ended question prompts is “Say more about…,” which encourages people to elaborate further on the points they’ve just brought up. Tell us some of your favorite prompts in the comments below, or send them along to hello@publicdesignbureau.com.