Guilt, Grief, and Growing a Team

By VICKY BROWN

Nobody warns you about this part of leadership

You’ll hear a lot about how to scale. How to delegate. How to write job descriptions, set up payroll, use the latest software. But what rarely makes it into the business playbooks is this: leadership is emotional.

Especially when you’re a founder or small business owner. Especially when it’s your name on the lease, your money on the line, your dream you’re trying to build. Team-building isn’t just tactical—it’s personal. These aren’t just employees. They’re people you hired, trained, encouraged. People you’ve shared victories with. And that’s what makes it so painful when it’s time to make a hard call.

Letting someone go. Replacing someone you’ve outgrown. Downsizing to survive. These are the parts of leadership no one prepares you for. They’re quiet. They’re heavy. And if you’re not careful, they can erode your confidence and your heart in ways that no spreadsheet ever will.

Why these decisions cut deeper than you expect

When you have to let someone go, it’s more than a business decision. It’s the end of a version of the story you were hoping to write. Maybe you saw promise in them. Maybe you pictured them growing with the business. Maybe they were with you in the early, scrappy days, and it feels like a betrayal to say, “This isn’t working anymore.”

Even when your head knows it’s the right call, your heart doesn’t always follow. You feel guilt: Did I train them enough? Did I give them enough chances? Was I too impatient? Too accommodating?

You feel grief, too—real grief—for what could have been. It’s the loss of potential, the death of a shared vision, the unraveling of a bond you may have worked hard to build.

And when the person you’re letting go isn’t toxic—when they’re kind, decent, well-meaning—it’s even harder. Because now the decision doesn’t just feel hard. It feels wrong, even when it isn’t.

The quiet guilt of being a good person in a hard role

This is where emotional leadership truly shows up. It’s not about whether you care – of course you do. It’s about what you do because you care.

Founders often carry a deep sense of responsibility. You want to give second chances. You want to believe in people. And when you can’t make it work, it feels like a personal failure. But here’s the truth: sometimes being a good leader means choosing what’s right for the business even when it hurts.

You’re not just managing people. You’re managing your own humanity. And that’s what makes leadership so complex.

Real-life moments that test your emotional leadership

Let’s talk about a few situations that tend to stir up these emotions:

  • The “nice but not a fit” team member. They’re loyal, they try, the team likes them. But their performance just isn’t cutting it – and you’ve tried everything. You feel cruel even thinking about letting them go.
  • The early hire who helped build the business. They were there when no one else was. But now the business has grown, and they haven’t kept pace. You know they’re not the right person anymore – but your loyalty runs deep.
  • The forced restructure. Maybe cash flow is tight, or you’ve lost a big client, and now layoffs are on the table. It’s not just numbers – it’s people’s lives. People you know. People you’ve worked beside.
  • The inherited mess. You didn’t hire this person, but now it’s your responsibility to fix what’s broken. The performance isn’t there, the dynamic is off, and it falls to you to clean it up.

These aren’t hypothetical scenarios. These are the crossroads every leader faces eventually. And they don’t come with a guidebook.

… When you have to let someone go, it’s more than a business decision. It’s the end of a version of the story you were hoping to write.

How to navigate these moments without losing yourself

So what do you do when you’re in the middle of it – when you’ve made the call, or you’re about to, and everything inside you feels shaky?

You lead with integrity. You lead like the kind of leader you’d want to work for – even in hard moments.

  • Be clear and kind. That means no long, vague intros. Don’t try to soften the blow with confusing language. Say what’s true, with empathy. Clarity is kindness.
  • Own your decision. Don’t blame the budget. Don’t say “they made me do it.” If it’s your business, own the call. That honesty matters – even if it stings.
  • Support the exit. Offer a reference if you can. Share resources. Preserve dignity. Because how someone leaves matters as much as how they came in.
  • Care for yourself. This one’s big. Talk to someone you trust – a mentor, a peer, a coach. Don’t carry this alone. Don’t pretend it didn’t affect you. Because it does. And that’s not weakness – that’s proof you’re leading with heart.

Whether you’re an entrepreneur jumping into a leadership role, a seasoned business pro with new HR responsibilities, or just starting your HR career – we’ve got the right path to guide you through your HR hurdles.

Check out the Leaders Journey Experience.  This online education platform holds the LJE Masterclass, HR SimpleStart Academy and HR FuturePro Academy.

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This is what growth really looks like

Letting someone go doesn’t mean you’re ruthless. It doesn’t mean you failed. It means you’re growing. It means you’re choosing alignment over comfort. And that’s the real work of leadership.

The highlight reels don’t show these moments. But they’re the moments that shape you.

Every difficult decision you face builds your resilience. Sharpens your instincts. Strengthens your boundaries. And – if you let it – deepens your compassion.

Emotional leadership isn’t about being soft. It’s about being strong enough to feel everything – and still move forward.

So if you’re in one of those hard moments right now, remember: you’re not broken. You’re becoming. And that’s what leadership is all about.

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