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Most leaders agree that empathy matters. Putting it into practice can be harder especially when people disagree, performance falls short, or a difficult decision needs to be made.
In this episode, Dr. Kristine Gentry and Monica M. Smith sit down with Rob Volpe, author of Tell Me More About That: Solving the Empathy Crisis One Conversation at a Time, to explore how empathy becomes a practical leadership skill.
From the frozen vegetable aisle of a Walmart to conversations about workplace accountability, Rob shares how curiosity about people’s lives shaped his work and how leaders can bring that same curiosity to their teams.
What we explore:
- Understanding someone’s perspective. Rob distinguishes cognitive empathy from emotional empathy and explains why perspective-taking is especially useful at work.
- Recognizing what gets in the way. How judgment, stereotypes, assumptions, and distraction can prevent us from hearing what someone is actually saying.
- Asking questions that invite conversation. Why Rob encourages open, exploratory questions and phrases such as “Tell me more about that.”
- Finding common ground. An ice cream exercise demonstrates how people with different preferences can work toward a shared decision.
- Combining empathy and accountability. How leaders can approach performance concerns and difficult departures while preserving someone’s dignity.
- Making empathy part of the organization. Rob’s “empathy ecosystem” connects mission and values, leadership behavior, communication, systems and processes, and relationships with the wider community.
- Keeping human development in view. We discuss the role of relationships, intentional connection in remote teams, and our concerns about relying on AI to replace developmental conversations.
Rob’s Five Steps to Empathy
- Dismantle judgment: Notice the assumptions and biases shaping your response.
- Ask good questions: Invite people to explain their experience in their own words.
- Actively listen: Be present and recognize when distraction gets in the way.
- Integrate into understanding: Make room for perspectives different from your own.
- Use solution imagination: Apply what you’ve learned to move the conversation toward a constructive outcome.
Rob explains that these steps are a practice to develop, rather than a rigid sequence. Different situations reveal different barriers.
Episode chapters
00:01 — Welcome and introducing Rob Volpe
02:09 — What consumer research taught Rob about empathy
06:41 — Why “empathy activist”?
12:03 — Cognitive and emotional empathy explained
17:14 — The Five Steps to Empathy
19:42 — The ice cream game: Finding common ground
23:35 — Modeling empathy and establishing team ground rules
27:38 — Difficult feedback, accountability, and dignity
30:23 — Developing people in a workplace shaped by AI
36:05 — Building an organizational empathy ecosystem
39:20 — What gets in the way of connection?
44:16 — How do you want to be remembered as a leader?
46:07 — Rob’s book and where to connect
About our guest
Rob Volpe is an empathy activist, speaker, trainer, and coach who helps people and organizations strengthen connection and understanding. He founded the insights firm Ignite 360.
Connect with Rob and explore his work
- Rob Volpe’s website
- Tell Me More About That — book information and purchasing options
- Rob’s guide to the Five Steps to Empathy
- What Does It Mean to Be Human? — the concluding episode of Rob and Maria Ross’s series on The Empathy Edge
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Thanks for Listening!
We’d love to hear from you.
Kristine Gentry, PhD
kgentry@culturegrove.com
🔗 LinkedIn: Kristine McKenzie Gentry
Monica M. Smith
tradewindscareerconsulting@gmail.com
🌐 www.tradewindscareerconsulting.com
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