“Developing Empathy” Featuring Holly Mandel
We asked 10 successful entrepreneurs to explain their own journey with EMPATHY.
HOLLY MANDEL: iMERGENCE CORPORATE IMPROV, New York City (2011)
Empathy is such an interesting topic. I wouldn’t call myself an authority on it, but I can speak from experience—especially working with people who seemed to have tons of empathy, and others who seemed to have almost none. I’ve also had moments where I really felt my own capacity for empathy expand.
One thing I’ve noticed (in myself and others) is that when empathy seems to be missing, it’s often because we’re focused more on our intention—what we meant to do or say—than the impact we actually had on someone else. That gap between intent and impact can cause a lot of harm, even when we don’t mean to.
Over time, especially when I began managing people or leading teams—whether in training sessions, running events, or directing projects—I started to see how my words or actions could have a negative impact, even if my intentions were good. Sometimes I made people feel like they weren’t doing a good job or had let me down. And while that might have been partly true in some cases, it wasn’t the whole picture. I realized I was focusing on mistakes instead of acknowledging the full context—kind of like throwing the baby out with the bathwater (weird phrase, but you get what I mean!).
Even when mistakes were the big picture, I was still skipping a step. I wasn’t seeing people as whole humans—I was reducing them to a single action or misstep.
So one big condition for developing empathy? Being in a position of leadership. When you’re “in charge,” your words and actions carry more weight. You can either wield that power with care or cause a lot of unintentional damage. If you're only focused on your intentions—trying to clarify an issue, get answers, or address a dropped ball—without also caring deeply about your impact, you can make a real mess of things.
Leadership forced me to get curious about how I communicate, how I manage people, and where I need to slow down and check myself. I learned that just because I know something doesn’t mean others do. And being higher on the org chart doesn’t mean I have the full story either.
Another condition? Growing up and learning about myself. I discovered I’m a gut-driven decision-maker—my instincts lead more than my intellect. When I overthink, I tend to overcomplicate things. So I had to take responsibility for knowing that about myself. Because if empathy is about relating to what another person is feeling, then I have to be genuinely interested in what they’re feeling. And I can’t really do that unless I first know what’s going on with me.
If someone I work with is upset after a meeting, I now pause and ask myself: “Did I show up cleanly there?” “Was I triggered?” “Did I come across more harshly than I realized?” Only once I do that can I honestly connect to what the other person might be going through.
I also had to learn how I behave under stress. And not in a judgmental way—it’s inevitable that stress will happen—but in an honest, self-aware way. Do I get snappy? Do I start mistrusting people? Do I blame others? Recognizing those patterns helps me take ownership and not project them onto others.
Another major teacher of empathy? Screwing up. Big time. The people I’ve met who lack empathy often struggle with accountability. They can’t acknowledge the hurt they’ve caused. But when you’ve been on the other side—when you’ve made real mistakes, felt bad, and had to face yourself—it humbles you. It softens you. It reminds you nothing is black and white. There’s rarely just one story. And when you let yourself be human, you can be more human with others.
I also recently ended a long working relationship with someone who—while friendly—lacked empathy. They couldn’t or wouldn’t see the impact they were having. They defended their intention over and over. Their own feelings mattered more than the feelings they were causing. That taught me a lot. Because empathy starts when you flip that: your impact on others has to matter more than your intention.
And honestly, one of the biggest contributors to developing empathy for me was improv. Improv is the journey and the destination. To be good at it, you have to prioritize the team over yourself. It constantly trains you to serve the group, not your own ego. You learn to read people, adapt to them, and care about what they’re trying to do. You stop performing for yourself and start showing up for the group. Your emotional intelligence gets sharper just by being in the practice.
If anyone reading this worries they don’t express enough empathy—or has been told they don’t—it’s a deeply personal path. But I believe it starts by paying attention, and by being brave enough to ask: “What was the impact of what I just said or did?” That question changed everything for me.