The Role of Empathy in Leadership with Sherrill Kaplan

Leadership feedback loops are what turn empathy from a value statement into something a company can actually measure. Sherrill Kaplan is Chief Revenue Officer at Hand and Stone, where she leads marketing and digital experience, and before that she was Chief Digital Officer at Planet Fitness, with senior roles at Zipcar, Dunkin Brands, American Express, and Citigroup. She joined host Tullio Siragusa to talk about what empathy looks like when it has a mechanism behind it.

In this episode we explore:

• Empathy as solving for the human experience, not the transaction

• Why data without the emotion behind it is only half the puzzle

• What happens when the internal culture contradicts the external promise

• The difference between empathy and sympathy in leadership

• Tying leadership reviews to how direct reports actually feel

• Psychological safety at the executive level

Sherrill starts where every brand marketer should, in the customer’s shoes. At Dunkin the question was how to get a coffee into someone’s hands fast enough to rescue a chaotic morning. At Planet Fitness it was how to make a first timer feel less terrified walking through the door. At Hand and Stone it is how to give a busy person a regular respite. Her point is that a product is rarely just a transaction, it is part of a larger emotional experience.

She is careful not to let technology off the hook. Data and innovation are powerful tools, and features like the Planet Fitness crowd meter or an easier booking flow genuinely remove friction. But she is direct that if you look at the data without the corresponding emotion that lets a customer make their next move, you are only working half the problem.

The hardest part of the conversation is the internal one. Sherrill has seen leadership teams that do not live the ethos their brand sells, and she describes what it does to people: they joined because of the product or the feeling the company claimed to create, then discovered the inside does not match. That gap puts people in distress and conflict, and it costs the company output.

Her mechanism for closing that gap is feedback, and she is specific about it. Early at American Express, part of a leader’s compensation was tied to how their direct reports felt about them, and she assumed that was normal until she found out it was rare. She now solicits 360 reviews on herself and requires them for her leaders, because a manager can look excellent in the room with their boss and be a poor leader to their own team.

She also draws the line between empathy and sympathy cleanly. Sympathy feels badly for someone. Empathy respects that their perspective differs from yours and engages it anyway, which is why she deliberately hires complementary superpowers rather than people who think exactly as she does. For brands trying to make that show up in the market, it is the same discipline Zero Company applies to messaging: the audience can tell when the promise and the experience were built by different teams.

Key Takeaways

• (5:25) On technology and emotion: data and innovation make life easier, but without the feeling that lets a customer make their next move, “you’re only looking at half the puzzle.”

• (8:47) On the internal and external gap, she describes people who joined for the brand promise and then “don’t feel the same way every day,” which “puts people in distress and in conflict.”

• (11:25) Empathy is not sympathy. Empathy means respecting a perspective different from yours, which is why she builds a team of different “superpowers” instead of hiring people who validate her.

• (16:38) At American Express, “part of leaders’ compensation was tied to how their direct reports felt about them.” She now solicits 360 reviews on herself and her leaders for the same reason.

• (21:55) Her answer on executive psychological safety: be the same person in every room. Trust breaks “when you have a different face for the executive team, a different face for the board, than you do for your team.”

• (39:36) Her one step for listeners: “Ask for feedback on how well you’re doing that,” on empathy, on listening, on how connected people feel to you. It might surprise you.

FAQ

How do you know if your team feels heard?
Sherrill Kaplan says the signal is whether a person’s distinct perspective is respected rather than merely tolerated. Leaders do not have to agree with every view, but people can tell whether their input was genuinely considered.

What is the difference between empathy and sympathy in leadership?
Sympathy is feeling badly for someone. Empathy, as Sherrill Kaplan defines it, is putting yourself in their shoes, respecting that their perspective differs from yours, and caring about it enough to engage it seriously.

How do you create psychological safety at the executive level?
Be the same person in every room. Sherrill Kaplan argues that trust breaks when a leader wears one face for the board, another for peers, and another for their team, and that consistency is what makes honesty feel safe.

Empathy is not separate from performance, it is what makes performance last. Hear the full conversation with Sherrill Kaplan, watch it on the video page, and find more on the Bliss Businesses series. Sherrill is on LinkedIn and at handandstone.com.