Empathy Enterprise: Leading with Heart in the Modern Workplace

There’s a quiet shift that happens when the work stops being about people—and starts being about attention. Kevin Riley has spent a lifetime noticing that shift, and what it costs.In this conversation, Scott creates space for Kevin to reflect on what journalism used to hold, and what it’s slowly losing. Through decades in newsrooms, Kevin brings a grounded view of empathy—not as a soft idea, but as something that shapes trust, decisions, and the way we show up for one another in our work.Kevin speaks from lived experience inside high-pressure environments where speed often wins. But he keeps returning to a simpler question: who are we really serving?Kevin Riley brings a lifetime inside American newsrooms, shaped by moments where decisions carried real human weight. His perspective is rooted in experience—leading people, navigating mistakes, and staying close to the impact of the work.You’ll HearWhy the best organizations behave like a good friendHow speed and competition can quietly erode empathyThe leadership choice that stayed with someone for yearsWhat it means to trust people, especially when they get it wrongLeaders trying to hold onto humanity while navigating pressure, pace, and responsibility.If this conversation resonated with you, share it with someone who leads with heart — or is learning how to.

Sometimes success comes with a cost you can’t ignore.And sometimes the hardest shift is not in your work—but in how you see yourself.In this conversation, Scott sits with Patrick Davis to explore what happens when performance stops feeling like purpose. Patrick reflects on a career built on pressure, fear, and results—and the quiet, difficult work of choosing a different way to lead. Together, they move beyond the idea of empathy as a concept, and into what it asks of us in real decisions, real relationships, and real workplaces.Patrick brings a perspective shaped by both success and reckoning. His voice is grounded in lived experience—learning, unlearning, and choosing to lead people with care, even when it would be easier not to.You’ll hear:Why empathy begins with how we treat ourselves—not othersThe difference between intention and impact in leadershipHow fear and shame can quietly shape workplace cultureWhat changes when curiosity replaces controlFor leaders who are achieving on the outside, but questioning what it’s costing them—and others—on the inside.If this conversation resonated with you, share it with someone who leads with heart — or is learning how to.

Sometimes it takes a pause we didn’t choose to see what we’ve been missing all along.In this conversation, Scott sits with Danielle Berg to explore what happens when success stops being about output and starts becoming about wholeness. Danielle brings a deeply personal lens to empathy, leadership, and workplace culture—one shaped by lived experience, hard-earned self-awareness, and a willingness to change how she leads.Danielle is someone who has lived the pressure of high performance and the cost that can come with it. What she offers now is a different way forward—one rooted in trust, curiosity, and the kind of leadership that begins from within.You’ll hear:Why empathy starts with seeing the person, not the roleHow curiosity can unlock better thinking than control ever couldThe quiet ways limiting beliefs shape culture—and how to rewrite themWhat it means to build a “well workplace,” not just a wellness programLeaders who feel the weight of performance and are ready to lead in a way that sustains both people and results.If this conversation resonated with you, share it with someone who leads with heart — or is learning how to.

Most people think empathy means agreeing with someone. But often, it simply means understanding what they’re feeling — and why.Scott Annan sits down with psychologist Dr. Dana Ackley for a grounded conversation about what empathy actually is — and what it isn’t. Drawing on decades at the intersection of psychology and leadership, Dana explores how emotional intelligence shapes the way leaders listen, make decisions, navigate conflict, and build trust.The discussion moves from brain science to everyday leadership moments, showing how empathy can transform not only workplace culture, but the way we relate to people across differences.Dr. Dana Ackley is a psychologist who has spent more than five decades helping people understand themselves and each other. Through his work with leaders and organizations, he focuses on the practical skills of emotional intelligence — and how empathy can turn human connection into a real advantage.You’ll HearWhy empathy is understanding someone — not agreeing with themHow other people’s emotions function as data for better leadership decisionsThe balance between empathy and assertiveness in creating true win-win outcomesHow “conflict entrepreneurs” manipulate emotions — and why empathy helps us see through itLeaders who want to build stronger relationships, navigate disagreement with clarity, and lead people with empathy without losing their voice.If this conversation resonated with you, share it with someone who leads with heart — or is learning how to.

Some businesses begin with a pitch deck. This one began with two parents trying to feed their child — and sitting inside the fear of not knowing how.Scott creates space for a conversation about empathy as something lived, not branded. Alex shares how personal need, grief, care, and love shaped not just a product, but the way he leads people, builds trust, and makes decisions when the stakes feel real.Alex Abelin is a founder, a partner, and a father who builds from lived experience. His voice carries the perspective of someone who has felt vulnerability firsthand — and let it guide how he shows up in business, family, and leadership.How a moment of parental fear became the foundation for a companyWhy empathy starts with listening — not convincingWhat leading with heart looks like when pressure and uncertainty riseHow care, presence, and long-term thinking shape workplace cultureWhy inclusion matters more than being “right”For leaders, founders, and parents who want to build something meaningful without leaving their humanity behind.If this conversation resonated with you, share it with someone who leads with heart — or is learning how to.

Some of the most meaningful lessons about leadership don’t come from boardrooms. They come from how we’re raised, how we listen, and how we choose to care when it would be easier not to.In this opening episode, Scott creates space for a deeply personal conversation about empathy as a lived practice, not a concept. Scott and Lois explore how empathy shapes culture, trust, and long-term success — in business and in life — when it’s treated as something personal, intentional, and real.Lois Krasilovsky brings a lifetime of lived empathy — shaped by family, work, and relationships — into how she leads people and serves customers. Her perspective is grounded, human, and earned through years of paying attention to what people actually need.You’ll HearWhy empathy is learned through example, not instructionHow listening — real listening — changes how people work togetherWhat it looks like to build trust through care, honesty, and attention to detailWhy love, joy, and customer loyalty are not separate from business resultsFor leaders, founders, and team builders who want to create workplaces rooted in empathy, trust, and human-centered leadership — and who believe culture is personal.If this conversation resonated with you, share it with someone who leads with heart — or is learning how to.

The Empathy Enterprise is the podcast for leaders who believe empathy is more than just a buzzword. Join host Scott Annan as he explores how leading with heart creates teams that perform, cultures that thrive, and businesses that matter.