In my 20 year career in tech, I've had to fire a lot of people. And there's a script that plays out every time someone needs to be let go.
I've seen it dozens of times. Whether it's a senior manager or a junior employee, the management team always goes through a familiar bargaining process. A process in which you'll hear one (or a couple) of these statements...
"Maybe they're just in the wrong role."
"We can't afford to lose them right now."
"We've let them down somehow—they deserve another shot."
“They need more time to settle in.”
Even when everyone at the table universally agrees the person is a bad fit, we still try to talk ourselves out of the inevitable. This stage is natural.
But here's the hard truth I've learned from two decades running agencies and helping agency owners through this exact situation: you have to push beyond it.
What seems like an impassable crisis now might not just be an inevitability, but an opportunity.
As much as it might torment you, you have to get really good at firing.
Accept It Now: Letting People Go Is Inevitable
If you're reading this and thinking, "Yeah, but if I hire the right people, I won't have to fire them"… I'm sorry, but you're wrong.
No matter how confident you are in each hire you make, having to occasionally fire someone is a universal reality.
When I was at Metalab—starting as employee #2 and watching the company grow from a tiny startup to hundreds of people—I saw every type of termination scenario you can imagine. Great people in the wrong roles. Wrong people in any role. Performance issues. Culture misfits. Budget cuts. Strategic pivots.
It never gets easier. But you can get better at it, if you want to.
Here's what you need to understand: The best outcome for everyone is to move on as quickly as possible when it's clearly not working.
Because here's what actually happens when you don't:
…The person stays in a role where they're failing
…Your team compensates for their weaknesses
…Resentment builds on all sides
…The inevitable conversation gets harder
…Everyone suffers longer than necessary
As the person in charge, you have the privilege—and the responsibility—of releasing everyone from this situation. So let's get you started.
The Bargaining Stage: Why We Try to Talk Ourselves Out of It
Let's briefly go back to the bargaining process I mentioned earlier, because that's usually where the saga begins.
I want to tell you about a termination I was part of about a decade ago.
We had a project manager who was clearly struggling. Missed deadlines. Clients were unhappy. The team was frustrated. In our leadership meeting, everyone agreed that it wasn't working.
But then the bargaining began.
"What if we moved them to a different type of project?"
"Maybe they just need more training."
"We're about to enter a project blitz—we can't afford to be short-staffed."
People in this meeting were actually starting to feel excited about how they could rescue this person's job... even though 5 minutes earlier we had all agreed they were terrible at what we'd hired them for.
Sound familiar?
This bargaining happens even when the decision is obvious to everyone in the room. It's not about logic. It's about the fact that we're about to do something that feels, on some deep level, like we're harming another person.
We're about to mess with someone's livelihood. Their identity. Their sense of security. And on some level, we're going to humiliate them by saying "You're not good enough."
That's heavy, and it should be.
But your job as a leader isn't to avoid difficult conversations. In fact, you're usually the one who can be encouraging them. And beyond that, it's your job to make the right decisions for everyone involved—including the person you're letting go.
Because here's what most people don't realize: Keeping someone in the wrong role is cruel, too.
They know they're struggling. They feel the team's frustration. They sense your disappointment. Most people are very emotionally intelligent, and when people are struggling, every day they come to work is another day of failure and stress.
Sounds crazy, but letting them go—done right—can actually be the kindest thing you can do.
Common Bargaining Statements (And Why They're Wrong)
Let me address the most common things I hear during the bargaining stage:
"That person is just in the wrong role."
Maybe. But probably not.
In my experience, "wrong role" is usually code for "we don't want to admit we made a hiring mistake."
Yes, sometimes people are genuinely talented but misplaced. But more often, the core issues—work ethic, communication, judgment, cultural fit—don't change with a different title.
Ask yourself honestly: Is this a role problem or a performance problem?
If you moved them to a different role tomorrow, would you be confident in the outcome? Or would you just be delaying the inevitable?
"We can't afford to lose them right now."
This is fear talking, not strategy.
You know what you actually can't afford? Keeping someone who's:
- Doing subpar work that you have to redo
- Frustrating your clients
- Demotivating your team
- Taking up management bandwidth that should go to productive team members
The cost of keeping the wrong person is always higher than the short-term pain of replacing them.
I've seen agencies limp along with underperformers for months, even years. Sometimes even elevating within the company during periods where they succeeded. Without exception, when they finally made the move, they said the same thing: "We should have done this six months ago."
"We've let them down—they deserve another shot."
Unless you've truly failed to give them the tools, training, or support they need, this is misplaced guilt.
Yes, as a manager, you're responsible for setting people up for success. But you're not responsible for doing their job for them.
If you've:
- Communicated clear expectations
- Provided necessary resources
- Given honest feedback
- Offered coaching or support
- Allowed reasonable time for improvement
...then you've done your job. If they're still not performing, that's on them, not you.
"They need more time to settle in."
Here’s another quick scenario for you.
About 5 years ago, I was at a small and fairly rapidly growing company. We were going through a period where we had more work than we could handle, and a lot of the pressure was on the senior management team.
We hired a mid-level designer who seemed to check all the boxes. But when he started, it was clear within a few days that they weren’t the designer they said they were. Their work was slow, they were uncommunicative, and the quality just wasn’t quite there.
Talking to my creative director, we agreed that it would suck to have to re-open the hiring process, and go through the motions again: sharing a job posting, reviewing portfolios, conducting interviews, test projects. But we also agreed that giving ourselves a future that involved this employee would be much more painful than going back and finding a better person.
And maybe more importantly, we didn’t have the time to spend on someone who our instincts were telling us was a dead-end. Most small agencies don’t.
So we made the call, even though they’d only been with the company for a couple weeks — it wasn’t working out, and we had to part ways.
It may seem like a situation where you could make a rash decision, but it’s also an important opportunity to trust your instincts.
How to Actually Fire Someone (The Right Way)
Okay, you've pushed past the bargaining stage, and you’ve realized there’s no way out of doing what you need to do next. You've made the decision. The hard part is done.
Oh, actually, no. Wait. Now comes the hard part: the actual conversation. You have to sit someone down and fire them.
Here's the best advice I ever received: Keep it under two minutes.
I know that sounds cold. But trust me on this. Once you deliver the news, the person you're letting go will want to get out of there as fast as possible. So will you, most likely, so give everyone involved a break and keep this fast.
1) Before the Conversation: Prepare These Details
Don't wing this. Have your answers ready for:
Severance:
- How much are you offering?
- When will they receive it?
- Are there any conditions?
Benefits:
- How long will their health insurance remain active?
- What happens to unused vacation time?
- Any RSP/401k considerations?
Logistics:
- When is their last day?
- How will you handle the announcement to the team?
- What happens to their company equipment?
- Will they work out a notice period or leave immediately?
Support:
- Will you provide a reference?
- Can you connect them with resources (recruiters, job boards)?
- Are you willing to write a LinkedIn recommendation?
Having your shit together makes the situation clear. This is a final decision you made thoughtfully. You're standing by it. There's a plan. This is not a conversation.
Again, sounds cold. But professionalism and a clear gameplan actually helps soften the blow.
2) During the Conversation: Be Direct and Compassionate
Here's the structure that works:
1. Get to the point immediately (30 seconds)
"Thanks for meeting with me. I need to let you know that we've made the decision to end your employment with [Company]. Today will be your last day."
Don't bury the lede. Don't make small talk. Don't ease into it. Rip the band-aid off.
2. Give a brief, honest reason (30 seconds)
"We've talked about the performance issues over the past few months, and unfortunately, we haven't seen the improvement we needed. This decision is final."
Keep it factual. Don't over-explain. Don't list every mistake they've made. Don't get defensive.
3. Explain the details (30 seconds)
"Here's what happens next: We're offering [X] weeks severance. Your benefits will continue through [date]. We'll need your laptop and keys today. HR will send you the paperwork tomorrow."
Clear. Professional. Complete. In some cases, the ‘what happens next’ can happen with someone other than the person doing the firing (i.e. someone from HR/People Ops) — but that’s a luxury that most small businesses don’t have.
4. Acknowledge their contributions (30 seconds)
"I want to say that your work on [specific project] was really valuable, and we appreciate what you brought to the team."
This isn't bullshit. Find something genuine to acknowledge. They're still a person. They did some things right. It wouldn’t be fair for them to believe that their time with you was a complete write-off.
5. Offer support (if genuine)
"If you'd like, I'm happy to serve as a reference for your job search. I can also connect you with [recruiter/resource] if that would be helpful."
Only offer what you're genuinely willing to provide.
Total time: Under 2 minutes.
Then stop talking. Let them respond. They may have questions, but I would say in 90% of scenarios, they don’t. If you’ve been as clear as you should have been, then there’s nothing else to say.
What Might Happen (And How to Handle It)
People react to termination in different ways:
Shock/Silence:
Just sit with it. Don't fill the silence with more explanation.
Anger:
Stay calm. Don't argue. "I understand you're upset. This is a difficult situation."
Bargaining:
Hold firm. "I know this is hard, but the decision is final."
Questions about details:
Answer them. This is fine.
Tears:
It's okay to show empathy: "I know this is really hard."
What you DON'T do:
- Apologize profusely (you made a business decision)
- Rehash their failures (you already decided)
- Give false hope ("Maybe in the future...")
- Get emotional yourself (stay professional)
3) Immediately After the Conversation: Taking Care of Business
1. Secure access:
If this is a contentious termination, you may need to:
- Disable their email/systems access immediately
- Collect company property (laptop, keys, phone)
- Escort them out (only if necessary—this is rare and feels terrible, but sometimes required)
Most terminations aren't contentious. Most people just want to leave with dignity.
2. Notify the team:
Don't wait. The rumour mill is vicious.
Send a brief, professional message:"I wanted to let you know that [Name] is no longer with the company as of today. We wish them well in their next role. [Name of person] will be taking over their responsibilities."
Don't trash-talk. Don't over-explain. Keep it simple and respectful. If anyone asks you about it, your response should be, “It was a really tough decision. I wish it had gone differently.”
4) In the Following Weeks
1. Check in with the team:
Some people will be upset. Some will be relieved. Some will be worried they're next.
Address it directly: "I know this is a change. If anyone has concerns or questions, send me a DM."
2. Document everything:
Keep records of the termination conversation, the severance agreement, and any follow-up.
You hope you never need it, but if there's a lawsuit or unemployment claim, you'll be glad you have it.
3. Learn from it:
Why did this hire not work out?
- Did you miss red flags in the interview?
- Did you set clear expectations?
- Did you provide adequate support?
- Was this a role problem or a hiring problem?
Use this to improve your hiring process for next time.
The Hardest Part: Living With the Decision
Here's what nobody tells you: Even when you make the right decision, it can still feel bad.
I've terminated people where I was 100% confident it was the right call. Where the team was relieved. Where the person's performance was clearly unacceptable. And I still felt terrible afterwards.
That's normal. It means you're human. It means you care about people.
But don't let that guilt make you avoid necessary decisions in the future.
The best leaders I know—and I've worked with some exceptional ones at Metalab and elsewhere—are the ones who can make hard people decisions quickly and compassionately.
They don't drag it out. They don't avoid the conversation. They don't let poor performers linger and poison the culture.
They make the call, they do it with dignity, and they move forward.
When Firing Becomes Easier (And Why That's Okay)
I'm not going to lie to you, the first time you fire someone is awful. The second time is still pretty bad.
By the fifth time, you have a process. You know what to say. You can keep your composure, even if you still feel like a complete scumbag.
By the tenth time, it feels almost routine. Some people worry about this. "Am I becoming cold? Am I losing my humanity?"
No. You're becoming competent.
Firing people is a skill like any other leadership skill. The more you do it, the better you get at it. That's not callousness. That’s just sharpening a skill like any other.
It feels really, really icky to look at firing as a skill, but you know what? Someone’s gotta do it. Unfortunately, it’s probably going to be you. As I said earlier, firing is simply a reality, a tightly interrelated part of hiring, scaling, and growth.
Sorry to say it, but if you want to sit in the big boy/girl chair, this is part of the job description.
At the end of the day, you can care about people AND make tough decisions. In fact, the best leaders do both.
