Why Your Most Caring Leaders Struggle to Scale Their Empathy

Most organizations, in the face of two managers with similar competencies, will naturally promote their most empathetic—those who excel at building trust, not only understanding individual needs but also embracing different perspectives and creating psychological safety within small teams. But when teams expand, the very skills that made them successful with 10-15 people often fail them when they’re suddenly responsible for 50, 80, or hundreds of employees. According to HBR, in 2023, 70% of newly promoted managers struggle with the transition from managing individuals to managing systems. Whether organizations realize it or not, this reveals a gap in operationalizing empathy, and with never-ending restructuring for strategic and financial considerations, those who do not receive direct care from their manager often fall to the wayside, losing their sense of purpose, engagement, and ultimately performing less well.

Better companies teach managers to be better listeners and emphasize the importance of psychological safety and taking different perspectives into consideration when helping a team move forward, but they don’t show them how to build that at scale. This is why many individual contributors lose a sense of their considerations being taken seriously and therewith, lose a sense of meaning. That’s sad considering there are effective ways to show you care about a group of people without a lot of personal time and it’s exactly that that helps ever-changing teams move forward together.

As you may know by now, at Empathable, we believe leaders learn better when we go beyond teaching them concepts – but rather, through real stories from real professionals. So instead of present you now with a traditional analysis and set of approaches, I’ll take you through a real story from someone who I’m calling Akira Johns to respect their privacy, but this story is illustrative of how one can scale individual empathetic talents to larger teams where you don’t necessarily have direct impact.

When Everything Changes

Imagine Akira Johns, a burgeoning manager at a Fortune 1000 who thought she liked her job, staring at her computer screen this morning, processing the announcement that: ‘due to company restructuring post acquisition, her team of 15 direct reports was about to become 80 people across three departments.’

Akira had built her reputation on being a thoughtful leader—knowing each team member personally, remembering their challenges, and ensuring everyone felt heard in meetings. But 80 people? How could she make the time to maintain those meaningful connections? She’d need three of herself. How would she know when someone was struggling? How could she gather diverse perspectives when she couldn’t possibly meet with everyone regularly? How would she keep everyone engaged?

Somewhat hopefully, she saw the next message in her inbox, which was from Akira’s beloved learning and development director who pinged her to let her know that with these big changes, she’d been selected to be part of a cohort of 100 burgeoning managers would be working with Empathable, an organization that specializes in scaling the weaving of empathy into essential leadership skills—starting with a facilitated kickoff, then a light-touch deep immersion learning experience. Once every two weeks for the next six months, Akira would join cohorts with four other managers to walk in the shoes of other seasoned managers coupled with best in class expert perspectives. People who had already considered deeply how to take into account all aspects of scaling empathy, taking no more than one hour of their time per month.

But this hour wasn’t filled with random perspective and opinion sharing, but rather the sharing of personal stories that help enrich each other, much like people have learned from one another for generations through the power of storytelling.

Akira was aware in advance that she’d learn the following:

• Perspective-gathering protocols that her direct reports could implement with their teams
• Communication templates that maintained her values while allowing for personalization
• Structures for different types of feedback loops that ensured diverse voices reached decision-makers
• Recognition systems that reinforced empathetic behaviors across all levels
• How to leverage AI to condense longer-form shares in ways that still allow everyone to feel represented and give summaries for leaders to make informed decisions

Why Stories Change Everything

But here’s the thing: learning those conceptually doesn’t make the impact that we want it to. Empathable was offering the opportunity to learn that through stories.

Abstract concepts about “scaling empathy” don’t stick. But experiencing the challenge through someone else’s real story? That creates the kind of visceral understanding that drives behavioral change. Through immersive scenarios, Akira didn’t just learn about perspective-gathering systems—she experienced what it felt like to be a manager who had to make decisions affecting hundreds of people without adequate input.

This is the difference between intellectual knowledge and embodied wisdom. Data and facts don’t generally change people’s viewpoints, as stories do. Being able to leverage storytelling at scale is a fundamental starting point for how to bridge the empathy gap.

The First Test: From Theory to Practice

When her first major challenge came—rolling out a strategic initiative across her newly expanded team—Akira applied what she’d learned. Instead of attempting impossible one-on-ones with 80 people, she created structured listening sessions and designed feedback systems that ensured every voice could be heard.

Most importantly, she understood how to help those she did have direct access to impart empathy to their own teams. Making managers capable of building and maintaining empathetic cultures happens through an almost train-the-trainer methodology of allowing them to get better at practicing the deeper meaning of empathy that Empathable believes in—which is the ability to acknowledge the meaningfulness of one another’s stories to be as valuable as our own and get better at being curious about each other’s experiences.