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Week 1 Topic: Empathy in Support 

Empathy gets a lot of airtime in support, but too often it stops at the job description. We sit down with customer experience leader Jenny Dempsey to unpack what empathy really looks like on the front line—and why leadership modeling, team culture, and practical guardrails determine whether agents can truly use it. From the first hello to the closing summary, we map the specific behaviors that show customers they’ve been heard while still moving the conversation toward resolution. 

Jenny walks us through building a shared definition of empathy that fits your channels, your product, and your customers. We compare high-stakes roles like dispatch with day-to-day SaaS troubleshooting to show how the same fundamentals—listen, validate, clarify, act—scale across contexts. You’ll hear concrete ways to hire for the right signals using scenario-based prompts and writing samples, then score them with consistent rubrics that prioritize curiosity, respectful tone, and clear next steps. 

We also tackle empathy fatigue. High-empathy teammates can burn out when volume surges and autonomy vanishes, so we outline safeguards that keep care sustainable: time buffers for complex cases, channel rotations, debrief moments after tough interactions, and coaching that favors cognitive empathy over emotional overreach. Finally, we address the biggest blocker of all—policy. If you measure only speed, you’ll get speed; if you reward thoughtful acknowledgment and precise solutions, you’ll get loyal customers. Tune in for a practical, people-first framework that lets empathy thrive without sacrificing efficiency. 

I grabbed Jenny just as she'd moved into a new home and was waiting on her soft furnishings, which is why this episode is a little echo-ey!