When to Let Go: The Hard Lessons of Leadership and Loyalty

Leadership requires balancing loyalty, accountability, and compassion, with hard decisions like letting someone go often being necessary for the health of your team, your business, and even them.

Leadership is tough. It’s a delicate balancing act of motivating your team, driving results, and making the hard decisions that no one wants to make. One of those hard decisions is knowing when to let someone go. How many chances are too many? When does loyalty turn into liability? And how do you balance compassion with the responsibility of running a successful business?

These questions have haunted me for years, and I’ll admit it: letting people go has been one of my biggest weaknesses as a leader. I’m a perfectionist, but I’m also a loyalist, and sometimes that loyalty has come at a steep cost. Let me walk you through the lessons I’ve learned (and am still learning) about leadership, loyalty, and the fine line between giving chances and protecting your business.

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Lesson #1: Loyalty Can Be a Double-Edged Sword

Loyalty is a beautiful thing—until it’s not. In business, loyalty can lead to blind spots. When you work with someone for a long time, you tend to trust them implicitly. You stop checking in as much. You assume things are running smoothly because they’ve always been reliable. But here’s the hard truth: no one is immune to complacency.

I once had a senior leader who I trusted completely. They did an amazing job for three years—or so I thought. I stopped micromanaging and gave them full autonomy. But then, little cracks started to show. Deadlines were missed. Mistakes were made. Projects were delayed. I chalked it up to stress or a busy season. But when the cracks turned into chasms, I flew this person out to St. Augustine for an in-person meeting. That’s when they admitted it: they hadn’t been doing their job for months.

At that moment, I realized I had failed as a leader—not because I gave them autonomy, but because I gave them too much without oversight. I kept them around for six months longer than I should have, hoping they’d turn things around. They didn’t. The cost? Hundreds of thousands of dollars, a frustrated team, and a burned bridge when I finally let them go.

Takeaway: Trust, but verify. Loyalty doesn’t mean ignoring issues. Regular check-ins and accountability measures are non-negotiable, even for your most trusted team members.

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Lesson #2: Keeping Someone Too Long Hurts Everyone

One of the best pieces of advice I ever received came from a mentor who said, “If you don’t fire them, you’re hurting yourself, your company, and them.” Let’s break this down:

1. You’re hurting yourself because you’re carrying the weight of someone else’s shortcomings. When someone isn’t doing their job, it inevitably falls back on you. You work harder to cover for them, leading to burnout and frustration.

2. You’re hurting the company because a weak link in the chain affects everyone. Your team feels the ripple effects of someone underperforming. Morale dips, productivity slows, and your bottom line takes a hit.

3. You’re hurting them because you’re keeping them in a role they’re not thriving in. Letting someone go isn’t just about protecting your business; it’s about allowing them to find a role where they can excel.

I’ve made the mistake of keeping people around too long more times than I care to admit. I’ve seen the damage it causes—to me, my team, and the person in question. It’s never easy to let someone go, but I’ve learned that the longer you wait, the worse it gets.

Takeaway: Firing someone isn’t cruel—it’s necessary. Doing so allows them to find a successful role while protecting your business and your team.

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Lesson #3: Sometimes a Second Chance Works

Here’s where things get tricky. While I’ve learned the importance of cutting ties when necessary, I’ve also seen the power of second chances. I fired two people, only to bring them back later. Why? Because they showed me they were ready to make changes.

Both of these individuals needed time away to grow. They left, learned new skills, gained fresh perspectives, and returned stronger. One even told me that being let go was the wake-up call they needed. Both are thriving in their roles today, and I couldn’t be prouder of their progress.

But here’s the key: second chances aren’t for everyone. These two individuals demonstrated clear growth and a willingness to change. They earned their way back, and I made sure to set clear expectations upon their return.

Takeaway: Second chances can work only if the person shows real growth. Set clear expectations, and don’t hesitate to pull the plug again if things don’t improve.

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Lesson #4: Letting Go Can Be the Most Compassionate Choice

I used to think firing someone was the cruelest thing I could do. I’d agonize over it, thinking about how it would impact their life and family. But then I realized something: keeping them in a role they’re not suited for is far worse.

Imagine this: you’re struggling in your job. You’re overwhelmed, unhappy, and underperforming. Deep down, you know you’re not doing well but are too scared to quit. That’s the situation many underperforming employees find themselves in. Letting them go gives them a chance to reset, regroup, and find something that aligns with their strengths and passions.

Takeaway: Letting someone go isn’t a punishment—it’s an opportunity for them to find the right path.

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Lesson #5: Know When It’s Time to Move On

One of the hardest parts of leadership is recognizing when it’s time to move on. As leaders, we often see potential in people and want to give them every chance to succeed. But potential doesn’t pay the bills, and it doesn’t drive results. If someone isn’t meeting expectations despite multiple chances and clear feedback, it’s time to make a change.

I’ve learned to trust my gut. If you’re constantly frustrated by someone’s performance, it’s a sign that something isn’t working. And the longer you wait, the more damage you do—to yourself, your team, and your company.

Takeaway: Trust your instincts. If someone isn’t meeting expectations after multiple chances, it’s time to part ways.

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Building a Culture of Accountability

Letting someone go is never easy, but it’s necessary to build a strong, high-performing team. It starts with setting clear expectations from day one. Your team should know what’s expected of them, how their performance will be measured, and the consequences if they don’t meet those expectations.

Accountability isn’t about micromanaging—it’s about creating a culture where everyone knows their role and takes ownership of their work. When you combine accountability with compassion, you create a motivated, productive, and resilient team.

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Final Thoughts: The Balancing Act of Leadership

Leadership is a balancing act. It involves knowing when to push and when to pull back, when to give chances, and when to cut ties. It also involves balancing loyalty with accountability and compassion with responsibility.

If you’re struggling to let someone go, remember that you’re protecting your business and allowing them to find a role where they can thrive. It’s never easy, but it’s always worth it.

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