Judgment Is the Enemy of Empathy: How Humility Builds Stronger, More Connected Teams

I used to think that being a strong leader meant having all the answers. That success required always being right, staying in control, and being the smartest person in the room.

But over time—and with plenty of experience, reflection, and tough lessons—I realized that what I thought made me a great leader was actually keeping me disconnected from others.

In Episode 66 of the Connected Teamwork Podcast, my co-host Hylke Faber and I unpacked one of the most powerful practices for leadership and life: letting go of judgment and stepping into humility.

What emerged was one of the most honest, vulnerable, and transformative conversations I’ve had in my career.

“Judging less equals leading better.”

That was one of the most important lessons I’ve learned. When I began to step away from judgment—of others and of myself—I started to lead with curiosity instead of control, and with compassion instead of comparison. And that changed everything.

The Trap of Being “Right”

For a long time, I believed that being seen as successful meant always having to be right. I needed to prove myself, to show that I was capable. But that belief system was actually masking my own insecurities.

“I always thought success was about being right or having all the answers. But when that pressure fades, you realize it was actually a challenge you had with yourself.”

That realization hit hard. I started asking myself—why am I judging this person? What story am I telling myself about them, and where is that story coming from?

Most of the time, it wasn’t about them at all. It was about me.

Humility Isn’t Weakness—It’s a Superpower

There’s a false narrative that humility means thinking less of yourself. But that’s not true.

“Humility isn’t thinking less of yourself—it’s thinking of yourself less so you can truly see the people you’re working with.”

That’s a game-changer. As leaders, we’re not here to tower over others. We’re here to walk with them, to create safety, to foster growth. That starts with humility.

It takes real strength to say, “I don’t know.” It takes courage to admit you were wrong. It takes leadership to prioritize understanding over being understood.

From Flat Judgment to Full Humanity

Hylke offered a powerful metaphor in our conversation:

“When I’m in judgment, my mind becomes very square. I almost liken it to thinking the Earth is flat. I don’t see the other person anymore—I just see my judgment.”

That resonated deeply. Because judgment flattens people. We stop seeing their full humanity. We label them based on one behavior, one disagreement, one perspective.

And when we do that, we’re not just cutting them off—we’re cutting ourselves off from growth, from connection, and from truth.

The Inner Work of Letting Go

This practice of humility and releasing judgment isn’t some lofty concept. It’s practical. It’s uncomfortable. And it requires inner work.

Hylke shared a simple yet powerful process:

Of course – Of course I have judgment. It’s natural.How do I feel? – Notice the anxiety, impatience, or tightness that comes with judgment.What’s the thought? – Find the “should” in your judgment. (“They shouldn’t act this way…”)Is it true? – Ask yourself if that thought is absolutely true. It rarely is.Get curious – What else is true about this person? What do I appreciate?

That’s how we start to unravel the grip judgment has on us.

Leadership from a Place of Love

This might sound radical in corporate culture, but I believe it deeply:

“If I’m not grounded in love, I’ve lost the plot.”

The most connected teams aren’t built by the loudest voices or the smartest strategies. They’re built by people who listen deeply, who seek to understand, who stay when things get uncomfortable.

When I stopped leading from ego and started leading from empathy, I saw my relationships improve—at work, at home, with my kids, and with myself.

Practical Ways to Apply This Today

Here are some simple but transformative ways to put this into practice starting right now:

Challenge your stories – When you catch yourself judging someone, pause and ask: “What story am I telling myself right now?”

Sit in the tension – Disagreement doesn’t mean disconnection. You don’t have to resolve every difference. Sometimes, just being with someone is enough.

Shrink your bubble – Look inward before reacting. Why is being right so important to you in this moment?

Listen without needing to respond – Instead of formulating your rebuttal, focus fully on what the other person is saying.

Validate the other person’s experience – Even if you disagree, their experience is real and deserves to be acknowledged.

Get curious about others’ perspectives – Ask open-ended questions like “What matters most to you about this?” or “Help me understand your point of view.”

Own your part – Whether it’s defensiveness, impatience, or fear—own it, name it, and choose differently.

[image error] Practice the 1% principle – Focus on the small inner shift you can make. That’s where transformation begins.

Lead with love, not ego – Remember: leadership isn’t about control—it’s about connection.

Final Thought

Letting go of judgment isn’t just a better way to lead—it’s a better way to live. We don’t need to agree on everything to walk together. We just need to stay in the room, remain curious, and honor the full humanity in ourselves and others.

“The most connected teams are not built by the loudest leaders. They’re built by those who listen deeply, serve selflessly, and never stop learning.”

If you want to be that kind of leader—the kind who changes culture, creates safety, and elevates everyone around you—it starts with humility.

Let’s build more connected teams—together.

Drop a comment and let me know: What’s one judgment you’re letting go of today?

#LeadershipDevelopment #EmpathyInAction #HumilityInLeadership #ConnectedTeams #EmotionalIntelligence #JudgmentFreeZone #PsychologicalSafety #SelfAwareLeadership #TeamCulture