Empathy in Leadership Starts With How People Feel Around You

Leadership is often judged by output, execution, and growth. Yet the deeper test is simpler. How do people feel when they work with you. Do they feel seen. Do they feel respected. Do they feel like their perspective matters.

That is where empathy moves from theory into practice. It is not just a soft skill. It is a measurable leadership advantage that shapes morale, trust, retention, and the quality of work people produce.

On The Bliss Business Podcast, we sat down with Sherrill Kaplan, Chief Revenue Officer at Hand and Stone, where she leads marketing and digital experience. Prior to joining Hand and Stone in 2024, Sherrill served as Chief Digital Officer at Planet Fitness and held senior leadership roles at brands including Zipcar, Dunkin’, American Express, and Citigroup. Her perspective is especially valuable because she sits at the intersection of leadership, brand strategy, digital experience, and customer growth. What came through clearly in the conversation is that empathy is not separate from performance. It is one of the forces that strengthens it.

Empathy Is About Solving for the Human Experience

Sherrill defines empathy in a practical way. It is putting yourself in someone else’s shoes. In leadership, that means understanding how other people experience work, change, stress, and decision making. In brand building, it means understanding what customers are actually feeling, not just what they are buying.

That lens has shaped her work across very different businesses. At Dunkin’, the question was how to help someone start a chaotic morning well and get coffee in their hands quickly. At Planet Fitness, the challenge was how to make a first-time gym visitor feel less intimidated walking through the door. At Hand and Stone, the focus is helping busy people find a regular moment of relief and restoration in lives that are often overloaded.

This is what strong leaders understand. A product, service, or process is rarely just a transaction. It is part of a larger emotional experience. Empathy helps leaders and brands solve for that experience instead of only optimizing for efficiency.

Digital Tools Only Work When They Protect the Human Element

One of the most useful parts of the conversation was Sherrill’s point that data and innovation are powerful, but incomplete on their own. Technology can make life easier. It can remove friction, surface useful information, and give customers more control. Yet if leaders think only about the data without understanding the emotion behind the data, they are solving only half the problem.

She used examples like Planet Fitness’ crowd meter and Hand and Stone’s booking improvements. These features matter not because they are clever, but because they reduce stress, intimidation, and inconvenience. The goal is not innovation for its own sake. The goal is to make people feel more comfortable, more capable, and more supported in what they are trying to do.

That is an important reminder in a digital economy. Human-centered design is not about adding warmth on top of technology. It is about making sure technology stays grounded in what real people need and feel.

The Internal Experience Has to Match the External Promise

One of the strongest moments in the episode came when Tullio raised the disconnect many companies create between the empathy they promise externally and the culture they build internally. Sherrill did not hesitate. She said she has seen both sides of it, and when leadership teams do not embody the same ethos they are selling to customers, the gap becomes costly.

People join brands because they believe in the product, the mission, or the feeling the company says it creates. Then they get inside and discover that the way employees are treated does not match the story. That creates distress and conflict. Employees want to do great work, but they are stuck inside a system that does not reflect the values it markets so confidently.

This is one of the clearest leadership lessons in the transcript. Empathy cannot just live in advertising language or brand messaging. It has to show up in the way leaders listen, evaluate, support, and reward people internally. Otherwise the company creates emotional dissonance, and that always leaks into performance.

The Best Signal of Empathy Is Whether People Feel Heard

When asked what tells her a team feels heard, Sherrill offered a nuanced answer. It is part art and part science. She drew a distinction between empathy and sympathy. Sympathy feels bad for someone. Empathy respects where they are coming from, understands that their perspective may differ from yours, and still cares about it enough to engage it seriously.

That mindset changes how leaders build teams. Instead of hiring people who think exactly like them, she intentionally looks for different superpowers and different ways of seeing. She wants people who will pressure test ideas, bring new angles, and expand the quality of thinking around the table.

The key insight here is that people feel heard when their distinct perspective is not just tolerated, but respected. Leaders do not have to agree with every opinion. They do have to listen well enough that others know their input was genuinely considered.

Feedback Cultures Make Empathy Real

One of the most practical sections of the conversation centered on systems. Tullio asked what structures help keep empathy embedded in decision making, especially in a digital world. Sherrill immediately pointed to her experience at American Express, where part of leaders’ compensation was tied to how their direct reports felt about them. That early lesson shaped her own leadership model in a profound way.

Since then, she has carried those values with her by building strong feedback loops into how she leads. She asks her team for feedback on her own leadership. She incorporates three hundred and sixty reviews for her leaders. She wants to know not only how people perform in front of her, but how they lead their own teams when she is not in the room.

This matters because many leaders do not know how they are landing. They may be unintentionally blocking, intimidating, or frustrating people and never hear the truth because no system invites it. Feedback is what turns empathy from an aspiration into a practice. If leaders want to become more empathetic, they cannot rely on instinct alone. They need to ask.

Psychological Safety Starts With Consistency

A question from the audience asked how leaders create psychological safety at the executive level where the stakes are high. Sherrill’s answer was simple and powerful. Be the same person in every room.

She encouraged leaders to stand for the same values and show up with the same integrity whether they are with their team, peers, or the board. When leaders wear different masks in different environments, people feel it. Trust erodes. Psychological safety breaks down because no one is quite sure which version of the leader they are dealing with.

Consistency is underrated as a leadership strength. It helps people relax. It makes honesty feel safer. It creates clarity about what you really stand for. Leaders who can be candid, grounded, and human in every room make it easier for others to do the same.

Purpose Makes Empathy Sustainable

The conversation also moved into purpose, and Sherrill drew a direct connection between empathy and mission. At Hand and Stone, the company’s mission is to make it the best hour of a client’s month. That statement only works if people inside the company actually understand what modern stress feels like and what it means to offer real relief.

She made a similar point about Planet Fitness’ judgment-free positioning. Great mission statements work because they begin with the emotional reality of the customer and then organize the brand around solving for that feeling.

On a personal level, Sherrill said her own purpose has evolved. While she of course works to contribute to her family, she now feels increasingly driven by helping the people around her succeed, especially her three daughters, her team, and those she has built trust with over time. That is not cheesy, as she put it. It is clarifying. It gives leadership its emotional center.

Love Shows Up When Leaders Remember Their Why

When the discussion turned to love as a leadership practice, Sherrill brought a grounded answer. She said that daily pressure, board meetings, deadlines, and deliverables can easily crowd out empathy and connection. Leaders can become so focused on getting through the day that they forget why they are doing the work in the first place.

What resets her is stepping back and reconnecting with the people who matter most. Family, purpose, and perspective bring her back to center. That re-centering is what helps the softer qualities, empathy, presence, connection, love, remain active instead of being swallowed by urgency.

There is a practical lesson in that. Love in leadership is not sentimental. It is the discipline of remembering what matters enough to keep your humanity intact when the pace of work tries to strip it away.

Key Takeaways

• Empathy is putting yourself in someone else’s shoes and solving for the human experience, not just the transaction.

• Digital innovation works best when it reduces stress, friction, and intimidation for real people.

• A company’s internal culture has to match the empathy it promises externally, or trust breaks down.

• People feel heard when their perspective is respected, even when leaders do not fully agree with it.

• Feedback systems, especially three hundred and sixty reviews and upward feedback, make empathy measurable and scalable.

• Psychological safety grows when leaders are consistent and show up as the same person in every room.

• Purpose helps leaders sustain empathy by reconnecting them to why the work matters in the first place.

Final Thoughts

Empathy in leadership is not just about kindness. It is about alignment. Alignment between what a company promises and how it behaves. Alignment between what leaders say and how they show up. Alignment between digital strategy and human need.

Sherrill Kaplan’s perspective makes one thing very clear. The strongest brands and the healthiest teams are built by leaders who understand that empathy is not separate from performance. It is one of the things that makes performance sustainable.

Check out our full conversation with Sherrill Kaplan on The Bliss Business Podcast.