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As a recovering toxic boss, one of the cruelest contradictions of leadership is this: Sometimes, you have to let go of someone you genuinely care about. Not because they did something wrong. Not because they weren’t loyal. But because the business — your business — just needs something else, something they’re not providing in their role.
I’ve had to let go of people I’ve liked. Really, really liked. People I mentored, advocated for and rooted for. People who reminded me of a younger version of myself. And I’ve got to tell you, it doesn’t get easier with experience. But it can get cleaner, kinder and more purposeful — if you do it the right way.
Here’s what I’ve learned about firing a hire you love and how to do it with empathy, clarity and integrity.
Recognize that a good vibe doesn’t always mean a good fit
As a leader, you’re constantly hiring for potential — for what you see in job candidates, their attitude, their energy, their fit with your culture. You’re not just filling roles; you’re building a team to call your own that you can be proud of. So when someone’s vibe feels right, it’s easy to want to invest in their potential.
But potential doesn’t always translate to performance. Or the needs of your company evolve in such a way that what seemed like a great fit is no longer aligning with the direction in which you’re heading. In other words, appreciating someone’s spirit doesn’t always equate to them being the right person for the job anymore.
And this is where things get cloudy, because you start rationalizing in your mind. You think, “But they’ve been with us so long” … “But they’re trying so hard” … “But I like them so much.” All of that may be true, but if your business instincts are whispering (or yelling) that the relationship just isn’t working, you owe it to both yourself and your employee to listen to your internal sensibilities.
Heed your gut
What does it mean to listen to that inner voice that tells you something is off? It means not waiting too long to make the decision. Most leaders do; I’ve done it myself. I’ve dragged my feet, silently hoping the situation would resolve itself through performance changes or through the employee resigning.
But effective leaders know that, almost always, things don’t fix themselves. Rather, leaders need to acknowledge the gap between what needs to be done and what’s actually getting done … and then take action to narrow or fully close that gap.
When determining if it’s time to let someone go, I evaluate three specific factors:
- Performance: Is this person sufficiently and consistently delivering what’s needed?
- Potential: Are they growing in a way that aligns with your company’s objectives?
- Impact: What effect are they having on your overall team, your culture and your outcomes?
If someone you love isn’t measuring up in these areas — after you’ve provided guidance and support to them — it might be time to make the hard call.
Related: Terminating an Employee? Don’t Make These Legal Mistakes
Prepare for the conversation
The most compassionate firings I’ve been a part of were those where the boss came to the meeting well prepared. When you’re vague or overly emotional, the employee doesn’t get the right message. Instead, clarity translates to kindness — the more intentional and on point you can be, the clearer the employee will be on where you stand and what’s happening.
Here are some ways to prepare:
- Document instances when performance didn’t meet business goals
- Create a transition plan that clearly explains the employee’s termination date and what their responsibilities will be until then
- Offer support in all ways you can: severance pay, a letter of recommendation, introductions to others in your industry
In terms of what to actually say, you want to stay focused but also thoughtful, professional but also gracious. To lessen the sting, you can say things like, “This isn’t about you as a person at all — it’s about what the business needs right now” and “I’ll continue to support you in your next steps because I know what you bring to the table, even if this is no longer the right table for you.”
Related: I Fired an Employee After Finding Their Secret Second Job
Display your humanity
Letting someone go is a very difficult thing to do. And as much as you want to be direct to minimize the discomfort, you want to remain empathetic and generous-minded; you’re dealing with a person’s self-esteem and livelihood, after all, so do your best to treat them the way you’d want to be treated if the roles were reversed.
Avoid making the encounter seem transactional by:
- Allowing space for emotions (without taking them on as your own)
- Letting the employee respond to you — don’t make it a one-way discourse on how they fell short; grant them a real person-to-person conversation so they can get closure (with a reasonable time limit to not elongate the awkwardness for both parties)
- Offering to be a reference or a source of networking, if appropriate
- Showing genuine appreciation and gratitude for the contributions they did make
It’s not your responsibility to secure the next step for them, but you can handle their exit with grace and magnanimity.
Let yourself grieve
A firing isn’t just a loss for the employee; it’s a loss for you too. And some losses are truly worthy of grieving. Don’t deny your feelings of sadness, but don’t confuse them with regret or second-guess your decision either.
You can wallow in feelings of guilt, self-blame, playing the bad guy. Or you can choose to let the experience be a valuable lesson in leadership. Ask yourself: “What did I learn here about my hiring process?” “Why did I wait so long to act on my inner knowing?” “How can I become a better leader from this?”
You can’t escape the pain of letting someone go, but you can expand your leadership skills and increase your emotional intelligence as a result of it.
Love and let go
You can be someone’s fan and still release them from a fit that wasn’t right for either of you. You can believe in someone’s future and still recognize that the future isn’t with your company. And you can like someone tremendously — even love them — and still realize you can’t keep them on your team just for personal reasons.
When you make the purely professional assessment that it’s time to let someone go, it can be the most loving thing you can do for all involved. Doing so for the right reasons maintains your integrity and their dignity. Most of all, it sets them farther down the path of finding where they truly belong. And that’s something that everybody deserves.
As a recovering toxic boss, one of the cruelest contradictions of leadership is this: Sometimes, you have to let go of someone you genuinely care about. Not because they did something wrong. Not because they weren’t loyal. But because the business — your business — just needs something else, something they’re not providing in their role.
I’ve had to let go of people I’ve liked. Really, really liked. People I mentored, advocated for and rooted for. People who reminded me of a younger version of myself. And I’ve got to tell you, it doesn’t get easier with experience. But it can get cleaner, kinder and more purposeful — if you do it the right way.
Here’s what I’ve learned about firing a hire you love and how to do it with empathy, clarity and integrity.
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