Leading with Empathy: The Overlooked Skill That Builds Better Businesses
May is Mental Health Awareness Month, and inside my business, we're not just recognizing it—we're putting it under a spotlight. Because if you’re leading a team, running a business, or even managing a few contractors, mental health isn’t just a “personal” topic anymore. It’s business-critical.
And this week, I want to talk about one of the most important (and most overlooked) tools you have as a leader: empathy.
Empathy Isn’t Soft. It’s Smart.
For years, I believed work was for work, and personal life stayed out of it. I was efficient. Direct. A little robotic, honestly. And it got me in trouble. A boss once told me, “You’re great at your job, but no one wants to work with you.” That was a turning point.
I had to learn how to show up as a person—not just a performer.
What followed was years of intentional effort. Learning to ask personal questions before diving into the project checklist. Noticing what people shared (and didn’t share). Learning that building trust wasn’t a nice-to-have—it was everything.
Now, I lead with empathy as a non-negotiable. Not just because it’s the right thing to do, but because it works.
Why Empathy Is a Business Strategy
Your people are your greatest asset. Period.
If you take care of them—genuinely, consistently—they take care of your business. But too often, we shy away from connection because we don’t want to “cross a line” or we think it’s not our place.
Here’s the truth: you don’t need to be someone’s therapist. But you do need to create an environment where they feel safe being human. That’s what builds loyalty, trust, and performance.
Especially after the pandemic, employees aren’t hiding their humanity anymore. The lines between work and home have blurred. And younger generations are coming in with an expectation that their leaders will see them, not just their output.
So How Do You Lead with Empathy?
Here are a few tactics that have worked inside my own companies and with the business owners I advise:
1. Check in regularly—before there’s a problem.
Don’t wait for someone to crash. Build in check-ins that aren’t about work. Ask how they’re doing, what’s on their plate, what they need to be successful. It doesn’t have to be formal, but it should be intentional.
2. Watch for pattern interruptions.
Changes in behavior—being late, missing details, seeming short or withdrawn—are often signs something deeper is going on. Don’t ignore them. Instead, create a safe space to check in. Take a walk. Ask what’s going on. And most importantly—listen without judgment.
3. Be a little vulnerable.
I once publicly apologized to a team member for messing up a process I was supposed to manage. It was humbling—but it built more trust in one moment than a hundred flawless spreadsheets ever could.
You don’t need to overshare. But showing your team you’re human makes it safer for them to do the same.
4. Make support easy and accessible.
Flexible schedules, mental health days, Employee Assistance Programs, or even just a few paid therapy visits can make a world of difference. Some of the best support systems cost nothing but make everything better.
5. Respect boundaries—yours and theirs.
Empathy doesn’t mean overstepping. It means creating space and offering support, while respecting what others are willing (and not willing) to share. It also means knowing what you are comfortable sharing.
Empathy Is a Skill. And It’s Worth Building.
Here’s the good news: you don’t have to be born with empathy to be good at it. It’s a muscle. You can train it. You can practice it. And it will transform the way you lead.
If you’re committed to creating a workplace where people thrive—where they want to be—then leading with empathy isn’t optional. It’s essential.
Let’s normalize care. Let’s prioritize people. And let’s build businesses that grow because we treat people like humans first.
What are you doing inside your business to create psychological safety and support mental health? I’d love to hear. Leave a comment or send me a message.
