The first time I had to terminate a senior staff member, I thought I was prepared. I had read the books. I had taken the HR advice. I had documented the performance issues over six months. I had two warnings on file. I had the script. I had the witness. I had the exit package ready.
I still got it wrong. Not legally — the process held up. Not procedurally — every box was ticked. But humanly, organisationally, and in terms of what it taught the rest of the team about what kind of CEO I was. Wrong in ways I only understood properly two or three years later, when I had done it well enough by then to see the difference.
Here's what I got wrong, and what I learned to do differently in every termination conversation after.
I waited too long
The first sign of underperformance had appeared seven months before the termination conversation. Quiet at first. A missed deadline that was explained away. A piece of work that wasn't quite right but was framed as a misunderstanding. A pattern that I noticed but kept giving the benefit of the doubt to, because that's what good managers do, isn't it?
No. Good managers notice patterns early and name them early. The person I eventually terminated had been told, in soft language, that things weren't quite right. They had not been told, in direct language, that their job was at risk. By the time the conversation happened, they had been operating for months in a fog of mixed signals — small criticisms wrapped in reassurance — that gave them no real chance to recover.
When I finally had to terminate them, they were surprised. They shouldn't have been. The fact that they were surprised was my failure, not theirs.
I confused process with conversation
I had spent so much time getting the process right — documentation, warnings, witness, package — that I had spent almost no time thinking about the conversation itself. What I would say first. How I would frame the decision. What I would do if they cried, or argued, or simply went silent. How I would close the conversation. What I would say to the rest of the team.
The process is necessary. It's not sufficient. The person sitting opposite you doesn't experience your process. They experience your words, your face, your tone, your timing, your specifics. If those land badly, the process becomes the cold shell around an experience the person will carry for years.
What I changed: in every subsequent termination, I spent at least an hour preparing the conversation itself. Not the documentation — the words. I wrote down what I would say first. I planned my response if they pushed back. I planned what I would do if they accepted it quietly. I rehearsed the silence I would hold after they responded.
I made the conversation about them, not about the role
I described their behaviours and their shortfalls as personal failings. They had not met the standard. They had not delivered on commitments. They had not been the person we needed.
That framing put them on the defensive immediately. They felt attacked, because I was effectively attacking them. The conversation became about whether they were a good person or a bad one, rather than about whether the role was working.
The better framing — which I learned later — is about role fit, not personal worth. "This role needs X. You bring Y. They're different. We've tried for several months to bridge that gap, and we haven't been able to. That's not a verdict on you as a person or a professional. It's a recognition that this role isn't right for you, and you're not right for this role."
Same outcome. Completely different conversation. The person leaves with their professional identity intact and the chance to find a role where their actual strengths are valued. The organisation leaves without the toxicity of having told someone they're fundamentally inadequate.
Termination is rarely about whether the person is good or bad. It's about whether the role and the person fit. Saying that clearly is kinder, more accurate, and produces better outcomes for both parties.
I let the conversation drift
The decision had been made before the meeting. The package had been agreed. The transition plan was ready. None of those things were negotiable.
And yet, when the person began to argue and propose alternatives, I let the conversation drift. I felt obliged to engage with their suggestions. I responded to their proposals. I left the room with them believing the decision might still be reversible.
It wasn't. I knew it wasn't. But I had given them, by my willingness to engage, the impression that there was still a discussion to be had. The next 48 hours involved follow-up emails, calls, and renewed proposals that I had to keep rebuffing. Each rebuff made the original conversation worse in retrospect, because they now realised it had been final all along, and I had failed to make that clear when it mattered.
What I changed: in every subsequent conversation, I named clearly at the start that the decision had been made. "I need to be clear that this is not a discussion about whether the role continues. That decision has been made. What we're discussing today is how we end the role in a way that works for both of us."
That sentence is uncomfortable to say. It's much worse to leave it unsaid and have the person discover the truth over 48 hours of false hope.
I didn't think about the team
I thought about the person being terminated. I thought about the legal exposure. I thought about my own performance as a manager. I did not think enough about the rest of the team, who would discover the next morning that a colleague had been let go.
I had no communication plan for them. No clarity about what I would say to questions. No anticipation of the rumour mill that would start within an hour. By the time I addressed the team properly, two days had passed, and the story they had constructed in those two days was substantially worse than the truth.
What I changed: every termination is now planned alongside a team communication. Not the details — those remain confidential. But the framing. "You'll have noticed that [name] is no longer with us. After a period in which the role wasn't working as we needed it to, we've ended the arrangement. I want to thank [name] for their contribution, and I want to support all of you through this transition."
Said within 24 hours. Said clearly. Said once, with the understanding that questions could come privately but that the public statement was the public statement.
What this is really about
Termination is one of the few situations where a CEO can't outsource the human dimension to process. The process is necessary scaffolding. The conversation itself is irreducibly personal. The CEO who treats it as a procedural matter to be executed efficiently produces outcomes that are technically defensible and humanly disastrous.
The conversation matters because the person matters, even at the moment you are letting them go. Especially then. How you handle that conversation will be remembered by them for the rest of their career. It will also be observed, in fragments and through the rumour mill, by everyone else who works for you. They will form a view about what kind of CEO you are based on how you handle the hardest people decisions, not the easy ones.
Get this right, and the rest of the team trusts you more, not less. Get it wrong, and even the people who weren't directly affected lose some of the confidence that makes hard work feel safe.
I learned all of this by doing it badly the first time. If you're approaching your first one, I hope this saves you the cost of that lesson.
