Empathy Is the Secret Sauce:
What All Leaders Need to Know

Steve Weiss, ACC
Transformational Leadership Academy

🍽️ A Kitchen, a Vision, and a New Kind of Leadership

In the high-pressure world of professional kitchens—where timing is everything and egos often run hot—Chef Paola Velez chose a different path. As Executive Pastry Chef at Kith/Kin in Washington, D.C., she created not just beautiful desserts, but a culture rooted in empathy and emotional safety.

Instead of leading with fear or fire, Velez led with transparency—openly discussing her own struggles with anxiety and depression. That vulnerability gave her team permission to do the same. Mistakes became teaching moments. Feedback flowed both ways. Staff began to not just show up for shifts—but to show up for each other.

“I want people to understand that you don’t have to break someone down to build them up,” she told Food & Wine. “There’s space in this industry—and in leadership—for love.”

🤝 Empathy: The Most Underrated Leadership Strategy

Empathy in leadership isn’t just “being nice.” It’s a powerful force that improves performance, retention, and innovation.

• A 2021 report from Catalyst found that employees with highly empathetic managers were more than twice as likely to be innovative and more than three times as likely to stay with their organization (Catalyst.org).

• Harvard Business Review called empathy “the most important leadership skill,” noting it helps leaders coach effectively, build loyalty, and navigate crisis with credibility.

Empathy means seeing the world through someone else’s eyes, walking in their shoes, and feeling with their heart—not just offering pity or a solution.

As Brené Brown famously explains, when someone falls into a 20-foot-deep hole, sympathy says, “That’s terrible, I’m sorry you’re down there.” But empathy climbs down into the hole, sits beside them, holds their hand, and says:

“I’m here with you. Let’s figure our way out together.”

That’s leadership.

🔄 Reentry and Empathy: Leadership That Changes Lives

Empathy becomes even more crucial when leading individuals impacted by trauma, incarceration, or social stigma.

When people return from prison, they don’t just need a job—they need a leader who sees their full humanity. A leader who refuses to reduce them to their past. A leader who understands that real accountability comes with compassion, not shame.

This is where empathy becomes transformational.

Programs like The Doe Fund in NYC and Homeboy Industries in LA succeed not just because they offer work training—but because they build community and connection. Leaders greet returning citizens with structure, care, and belief in their potential.

Sharon Richardson, founder of Just Soul Catering and Reentry Rocks, exemplifies this. After 20 years incarcerated for killing her abuser, she rebuilt her life through food—and now helps other women do the same. She mentors formerly incarcerated women, not just as employees, but as people deserving healing and dignity.

“I had to be the leader I never had,” Sharon says. “That starts with empathy.”

This same principle applies well beyond reentry. Whether someone is navigating addiction recovery, single parenthood, grief, or chronic stress—empathetic leadership creates the conditions where growth is possible.

💼 How to Cultivate Empathy in Your Leadership Practice

Empathy can be learned and strengthened, like a muscle. Here’s how to begin:

1. Practice Deep Listening

Put away distractions. Be fully present. Listen not just to words but to body language and emotion. Reflect back what you’ve heard before responding.

2. Ask the Second Question

The first answer is often surface-level. The second question gets to the real story. “How are you really doing?” shows you care enough to stay a little longer.

3. Be Nonjudgmental

Suspend your urge to label, correct, or compare. Focus on understanding. If you find yourself thinking “I’d never do that,” shift to “What might have led them here?”

4. Model Vulnerability

Leaders who show up as whole people—who admit when they’re scared, tired, or unsure—make it safe for others to do the same. It’s the foundation of psychological safety.

5. Adjust for Context

Empathy doesn’t mean avoiding accountability—it means delivering it in a way people can receive. Learn what motivates each team member. Adjust your tone and approach based on who they are, not who you are.

6. Support the Invisible Load

When someone’s performance dips, ask: What else might be going on? Trauma, housing insecurity, depression? Offer to help lighten the load—not to excuse, but to empower.

🌟 Final Word: Leadership Is a Human Practice

Whether you’re managing a kitchen, running a nonprofit, coaching a team, or supporting individuals in reentry—empathy is the throughline.

It’s the skill that allows us to:

• Hold people accountable without shaming them

• Make space for differences without compromising expectations

• Build loyalty, resilience, and innovation—by honoring the full humanity of the people we lead

In a world that often rushes past pain, empathy is the pause that says:

“I see you. I’m with you. Let’s figure this out—together.”

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