Jessica Jackley interviewed entrepreneurs over coffee, UCI students explored small farmers’ experiences in online conversations, and IDEO designers walked hospital rounds with nurses. How might you connect with your community partners to gain empathy insights?
We know why empathy interviews are crucial for social entrepreneurs (as we covered in Part 1), so now let’s turn your knowledge into action. Whether you’re planning to start a food security initiative or design a community education program, here’s your practical guide to conducting these interviews.
Before the Interview
Start with a clear purpose. What do you need to learn at this stage of your project? Are you exploring needs, checking assumptions, or testing ideas?
Once you know your goal, decide who to talk to. Community partners, people with lived experience, and those with expertise in your area are great starting points. For example, if you’re working on food insecurity, you might talk with a local food pantry volunteer or a teacher who notices when kids arrive at school hungry.
Next, develop open-ended questions. Open-ended questions, such as ‘What does a typical morning look like for you?’ lead to stories and insights you wouldn’t get otherwise. They invite conversation and nudge your partner to think specifically and concretely about what the community needs.
Closed-ended questions like ‘Do you eat breakfast every day?’ often just get yes-no answers and shut down conversation. Avoid leading questions (‘Don’t you agree that this community needs a food bank?’) and double questions that confuse your partner.
Use a mind map to brainstorm many potential questions, then select the best ones for a rich conversation. Tools like Google and AI chatbots can help you find and generate effective questions. Review and edit to ensure clarity and focus.
Finally, prepare but stay flexible. Bring a short list of must-ask questions, but don’t treat it like a script. A good interview feels more like a conversation than a cross-examination. Surprises and the new information they spark are indicators of a dynamic interview.
Also, when scheduling, let participants know how you will use their ideas and stories, and ask permission if you’d like to record the conversation.
During the Interview
“When I do empathy interviews, I often abandon those questions and follow the person in front of me. I’m not interested in their biography. I want the stories people tell about themselves.” — Kara Imm
Set the stage for comfort and trust. A coffee shop, library room, or quiet park corner can help people open up. Video calls work too but may take longer for you both to relax and enjoy the conversation.
Whether in person or online, start by building rapport. Listen actively and pay attention to words, tone, pauses, and body language. Follow up on surprises and unexpected comments with ‘Can you tell me more about that?’
The best interviews naturally draw out stories, with the interviewer gently guiding but never interrupting the flow of conversation. For example, if someone mentions struggling to access fresh produce, don’t immediately jump to your solution. Instead, ask: “Could you tell me more about what that’s like?”
Respect time. If you said 20 minutes, wrap up then. People appreciate it when you keep promises.
As you close, ask two key questions: 1. ‘What else should I be asking?’ 2. ‘Who else should I be talking to?’ These often lead to new insights or contacts.
After the Interview
The conversation doesn’t end when you leave. Reflect on what you heard and synthesize your notes. Add your notes to a project journal while ideas are fresh. Look for themes, patterns, and surprises. Focus also on adding in your own reactions, feeling, opinions, and ideas. Usually, it seems there is no time to journal afterward, but these immediate reflections often prove invaluable later on.
Remember gratitude. A handwritten note is best, but an email works too. Send it the next day and your community partner will remember you, and you will build goodwill.
Finally, plan your next step. Who else do you need to talk to? What new questions have come up? Let each interview lead you forward. Pay attention to when stories or names repeat in your interviews. When this saturation occurs, you’ve talked to enough people to see the bigger picture. You can move on.
The Takeaway
Each interview gives you more than information. It builds your skills, strengthens your network, and deepens your understanding of the people you want to serve. This understanding sets successful social enterprises apart from initiatives that miss their mark.
By combining digital research with empathy interviews, you’ll have both the facts and the human insights you need to create solutions that truly resonate with your community. Remember: the most effective social enterprises start with listening.
Sources & Further Reading
- Estes, F. (2022). Design Thinking: A Guide to Innovation.
- Jackley, J. (2010). Clay Water Brick: Finding Inspiration from Entrepreneurs Who Do the Most with the Least.
- Stanford d.school. (n.d.). Empathy Interview Guidelines. https://dschool.stanford.edu/resources
- Imm, K. (2023). Empathy Interviews for Deeper Learning. The Math Learning Center Blog.
- Startup Grind / Medium. Demian Borba. (2017). Build Customer Empathy by Listening to Their Stories.
- Andrés, J. (2020). Without Empathy, Nothing Works. TIME Magazine.
- University of California, Irvine (UCI) ANTrepreneur Center. (2022). Interview with Leprendo founders Dan Ta and Dylan Riffle.
- IDEO. (n.d.). Empathy in Practice: Observing and Listening to Healthcare Workers. IDEO.com.
- Photo by Christina @ wocintechchat.com on Unsplash