The hardest part of a performance conversation isn’t the conversation. It’s the six weeks before it, when you know you need to have it and keep finding reasons not to.
Someone in your reporting chain is not performing — not dramatically, not in a way that’s creating a crisis yet, but in a way that you can see and that people around them are starting to notice. Their direct reports, their peer managers, the cross-functional partners they work with. Every week you don’t address it is a week the broader team watches you not address it, which is its own signal about what gets tolerated.
What I’ve learned, after many of these conversations over the years, is that the fear is usually worse than the conversation. Not because the conversation is easy — it isn’t — but because the fear is often about something that doesn’t actually happen. You’re afraid the person will become defensive or angry, that the relationship will be permanently damaged, that you’ll handle it wrong and create a worse problem. These things occasionally happen. Much more often, the person knows something is off and is actually relieved that someone is naming it directly rather than signaling it through omission.
The first thing I try to do before any performance conversation is get clear on what I’m actually observing, separate from what I’m interpreting. Observations are factual: missed commitments, a team that’s chronically struggling without clear direction from their manager, a pattern of being absent from conversations where their leadership is needed. Interpretations are the layer on top: “they don’t care,” “they’re not cut out for the role,” “this isn’t working.” The interpretations might turn out to be correct, but walking into a conversation with the interpretation as your premise is how you create defensiveness. Walking in with observations and genuine curiosity about what’s behind them is how you have a conversation that might actually go somewhere.
The distinction I’ve found most important in practice is between someone who lacks capability and someone who lacks direction. They can look very similar from the outside, but they call for completely different responses. The manager who doesn’t have the skills the role requires — even with support and clear expectations — needs a different kind of conversation than the manager who has the skills but is operating without clear enough context about what they’re supposed to be doing or why. I’ve seen too many people treated as performance problems when they were actually direction problems, and it’s one of the things that makes me most careful about diagnosing before responding.
In a first performance conversation, I’m not coming in with a plan for the person. I’m coming in to have an honest reckoning together. My opening is usually something like: “I want to share what I’m seeing and understand what’s happening from your side, because I think we’re not where we need to be and I want to understand why.” Then I say what I’m observing, specifically and without softening it so much that the message disappears. I’ve seen leaders bury the real concern under so many qualifications that the person leaves the meeting not fully understanding that a problem was identified. That’s not kindness; it’s a failure of clarity.
What I’m watching for in the first conversation: Does the person recognize what I’m describing? Are they engaging with it genuinely — asking clarifying questions, reflecting on it — or are they dismissing it, or only defending themselves? Is there something I learn that changes my read on the situation — a misunderstanding about expectations, a personal situation I didn’t know about, a skill gap that surfaced because they were never clear on what was required? The conversation that goes well is usually one where we both come out of it with a shared picture of what’s happening, even if we haven’t yet figured out what to do about it. Shared diagnosis is prerequisite to shared response.
I tell people things directly in these conversations. Not harshly, not punitively, but directly. I say things like: “The way this is going, if nothing changes, this becomes a real problem for your career here. I don’t want that, and I don’t think you want that. So I want us to figure out together what needs to change.” That’s a real statement of stakes. Not a threat — it’s not meant to be frightening, it’s meant to be honest — but real. People deserve to understand the actual stakes of the situation they’re in. Managing someone through a performance problem without telling them clearly what’s at stake isn’t protecting them. It’s leaving them to find out the hard way.
The signal I watch for after the conversation is whether the person’s behavior changes in the following two or three weeks — not a transformation, but something. Engagement in conversations, responsiveness to feedback, a question about whether they’re on track. The absence of any signal is itself a signal.
In either case, the next conversation comes sooner than it would have otherwise.