🤔 Dear Lewis, should I fire a difficult employee?
In today’s edition, a VP wrestles with whether to fire a defiant employee after a blatant act of insubordination during a team crisis.
Welcome back, friends. Last time, we left Jolene standing at the edge of a leadership cliff. On one side? The hope that trust could somehow be rebuilt. On the other? The cold, hard reality that sometimes, the only way forward is to let someone go.
And in the middle? Dave. Senior engineer. Crisis refuser. Team abandoner. Ego with legs.
Jolene’s question was simple: “Should I fire him?”
The answer? Not so simple.
Firing someone isn’t just a decision—it’s a declaration. It says something about your leadership, your values, and the kind of culture you’re building. So, how do you know when it’s time to pull the trigger? How do you balance accountability with empathy? And how do you make the call without second-guessing yourself into oblivion?
Let’s break it down.
Step 1: Call It What It Is – Insubordination
First things first: let’s not sugarcoat what happened. Dave didn’t just “decline to help” during the crisis. He didn’t “misunderstand” Jolene’s request. He straight-up refused to do his job, then strutted out of the war room like a peacock in a power suit.
This wasn’t a lapse in judgment. It was insubordination—the workplace equivalent of flipping the table and saying, “Not my problem.” And in the leadership world, insubordination is a flashing neon sign that says: “This cannot stand.”
But not all insubordination is created equal. Before Jolene could decide whether to fire Dave, she had to ask herself three questions:
Was the directive clear?
Yes. Jolene told Dave, in no uncertain terms, to step in and help fix the crisis. No room for ambiguity there.Was the directive reasonable?
Absolutely. This wasn’t a “fetch me coffee” kind of request. It was a “help save the Titanic” situation, and Dave was the most qualified person in the room.Was the refusal deliberate?
Oh, it was deliberate. Dave didn’t just say no—he said it with flair. In front of the team. During a crisis. If there were an Olympic event for workplace defiance, Dave would’ve taken gold.
Verdict? This wasn’t a misunderstanding. It was a power play. And it left Jolene with a big decision to make.
Step 2: Assess the Fallout – What’s the Damage?
Firing someone isn’t just about their behavior—it’s about the ripple effects. Jolene had to ask herself: What’s the cost of keeping Dave?
Here’s what she found:
Team morale:
Dave’s walkout wasn’t just a refusal to help—it was a giant middle finger to the team. It sent the message that he was above the work, and by extension, above them. That kind of toxicity spreads faster than bad office coffee.Trust in leadership:
By refusing Jolene’s directive, Dave didn’t just disrespect her—he undermined her authority. If she let it slide, what message would that send? That you can ignore your boss as long as you’re good at your job? That ego trumps accountability?Cultural integrity:
Every team has unwritten rules about what’s acceptable. Dave broke those rules. And if Jolene didn’t hold him accountable, it would set a dangerous precedent: that talent excuses bad behavior. Spoiler alert: it doesn’t.
The damage was clear. Keeping Dave wasn’t just risky—it was radioactive.
Step 3: Spot the Pattern – Is This a One-Off or a Personality Problem?
One bad day doesn’t define a person. But a pattern? That’s a different story. Jolene had to figure out if Dave’s behavior was a one-time fluke or part of a larger trend.
Here’s what she uncovered:
Dave had a history of dismissing others’ ideas in meetings.
He regularly refused tasks he deemed “beneath him.”
He was quick to criticize teammates but slow to offer help.
In other words, the crisis didn’t create Dave’s ego—it just put it on full display. The walkout wasn’t an isolated incident; it was the natural conclusion of months (maybe years) of unchecked arrogance.
Step 4: Consider Redemption – Can This Be Fixed?
This is where things get tricky. Jolene wasn’t just deciding whether to fire Dave—she was deciding whether he could change. Because firing should never be the first option. If there’s a chance to repair the relationship, you owe it to yourself—and the team—to try.
So, Jolene sat down with Dave for one last conversation. She laid it all out: the crisis, the walkout, the impact on the team. Then she asked him the million-dollar question:
“Do you understand how your actions affected the team?”
His response?
“I’m not here to fix other people’s mistakes. That’s not my job.”
No apology. No self-awareness. No willingness to change. Just ego, sitting there like an uninvited guest at a dinner party.
That was the moment Jolene knew. Dave wasn’t just unwilling to change—he didn’t even see the problem. And you can’t fix what someone refuses to acknowledge.
Step 5: Weigh the Costs – Keep or Let Go?
Finally, Jolene had to weigh the costs. Because firing someone isn’t just about what you lose—it’s about what you gain.
Here’s how she broke it down:
The cost of keeping Dave:
Continued damage to team morale and trust.
The risk of losing other team members who were fed up with his behavior.
A culture where ego goes unchecked and accountability is optional.
The cost of letting him go:
Temporary disruption.
The challenge of finding a replacement.
The emotional toll of firing someone she once relied on.
The scales weren’t even close. Keeping Dave would cost Jolene her team’s trust, her culture’s integrity, and her own credibility as a leader. Letting him go wasn’t just the right decision—it was the only decision.
The Leadership Takeaway: When to Fire Someone
Firing someone is never easy. It’s messy. It’s emotional. And it forces you to confront your own values as a leader. But sometimes, it’s the only way to protect your team and your culture.
Here’s the framework Jolene used to make her decision. If you’re ever in her shoes, ask yourself these five questions:
Was the behavior insubordination? Did they deliberately refuse a clear, reasonable directive?
What’s the impact? Is their behavior damaging the team, the culture, or trust in leadership?
Is there a pattern? Is this a one-time mistake or part of a larger trend?
Can it be fixed? Are they willing and able to take accountability and change?
What’s the cost? Will keeping them do more harm than letting them go?
If the answers point toward firing, don’t hesitate. Leadership isn’t about avoiding tough decisions—it’s about making them with clarity, courage, and compassion.
For Jolene, firing Dave wasn’t just about removing a problem. It was about sending a message: that ego doesn’t excuse bad behavior. That respect and accountability are non-negotiable. And that leadership means making the hard calls, even when it hurts.
Keep striving for greatness,
Lewis C. Lin
CEO, ManageBetter
Simple, right? Well, not always
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