How to Tell If Someone Is In the Wrong Role

The earlier you catch a role misfit, the better the outcome for everyone. For the associate, because they get redirected before they've lost months or years in something that isn't right. For the team, because you're not carrying someone who isn't performing. And for you, because the conversation is easier when it's about fit rather than failure.

Here's what I look for.

The first thirty to sixty days

When someone first joins your team, they're in an unusual state. They don't know the culture, the dynamics, what's in flight, what the real expectations are. There's a massive amount of context they don't have yet. So you can't judge most things in those early weeks. But you can start to read a few things.

The first thing I look for is curiosity. Are they asking questions? Not just surface questions — "where do I find the shared drive" type questions — but the kind of questions that suggest they're trying to understand the system. The five whys. The "why does this work this way" type of questions. The kind of thing that shows they're pulling at the threads and trying to understand what's actually going on.

New people have a window where they get to ask things that feel obvious or silly that people who've been around for years can't ask anymore without looking out of touch. The ones who use that window — who lean into it and ask the innocent but important questions — are usually the ones who are going to figure things out fast.

The second thing I watch for is cultural fit. Are people forming an opinion about them? A new team member is an investment, and you want to see signals of ROI relatively quickly. If they're getting connected, building relationships, making an impression — good or bad — that's a signal. If nobody has an opinion on them after sixty days, that's a flag.

The third thing is initiative after conversations. If I meet with someone and they come back the next day having synthesized what we talked about and already driving action on some piece of it, that tells me a lot. It shows they're not just receiving — they're processing and moving. That kind of initiative is hard to teach.

The red flags

The biggest red flag I see in new hires is overconfidence that doesn't calibrate.

Everyone who joins a new team goes through some version of the Dunning-Kruger effect. In the first few weeks, they have confidence because they were hired — someone thought they could do this job, so they carry that assumption in. Then as they learn more about the actual complexity, the confidence dips. That dip is healthy. It means they're registering what they're dealing with.

The person who worries me is the one who stays in high-confidence mode too long — who doesn't seem to register the seriousness or complexity of what's in front of them. Who never really asks the hard questions, who's not getting to customers, who's presenting a kind of surface-level certainty that doesn't match what I know about the complexity they're navigating.

That kind of overconfidence, combined with low curiosity and weak relationship-building, is usually a sign that the role isn't clicking.

What I do when I see the flags

I'm pretty direct when I see these things, and I say so upfront.

Within the first few weeks, I'll often tell someone: I need to see your curiosity. I need to see your thinking. I need this to be a conversation, not a monologue. If I'm not seeing that, I'll tell you, and I'll want to understand why. I also tell them that I'm going to be asking their teammates how things are going, so I'd encourage them to go build some relationships because that feedback matters to me.

That's not a threat. It's transparency. These are the things I monitor for, and I want them to know that upfront. It gives them agency.

After I give that kind of direct feedback, I give people room. I'm not making any firm assessments in the first three months. And I'm generally not ready to make a call on fit until we hit a formal review cycle, which could be three months out or six months out depending on timing.

But if by that point I'm still not seeing the curiosity, the engagement, the cultural fit — and I've given clear direct feedback — then I'm ready to start having a different conversation.

The different conversation

Sometimes the issue isn't that someone can't do the work. It's that the work isn't the right work for them.

I had someone on my team who had come over through a reorg. They were in a data analyst role, but over time they'd been doing a lot of product work — owning roadmap decisions, running stakeholder conversations, driving strategy for their product area. They were good at it. And you could tell pretty quickly that the DA role wasn't where their energy was. They were going through the motions on the analyst work but coming alive on the product side.

That person wasn't a problem. They were in the wrong seat.

So over about ninety days, I worked with leadership to shift their role to better reflect what they were actually doing. We moved them into a product-oriented role that matched their skills and their interests. Problem solved — before it became a problem.

That's the best case. You catch the misalignment early, you act on it quickly in one-on-ones, and the person lands somewhere that actually fits. They get to keep doing work they're good at. You get someone fully engaged in the right role. Nobody ends up in a slow-motion exit.

The harder case

Sometimes the role is right and the person genuinely isn't performing at the level required. That's different, and the performance review requires a different conversation.

When I've given someone clear, direct feedback on what I need to see — and I've been specific about it, not vague — and things still aren't shifting, that's information. Either the message isn't landing because I'm not communicating it clearly enough, or the role isn't a fit. Both of those are worth naming directly.

If it's a communication issue, I'll try to be even more concrete. Write it down. What specifically does good look like? In which situations? What would I need to see in the next ninety days to know this is working? If I can't answer those questions clearly, that's on me.

But if I can answer those questions clearly, and the person has those answers, and the gap is still there — that's when the conversation shifts to fit. And the right move then is to help them find something better, inside the organization or out, rather than keeping them in a role that's wrong for them until resentment builds on both sides and the exit gets messy.

People want to do good work. They're not trying to fail. The more clearly you can tell them what good looks like, the more information they have to make real decisions about whether this is the right place for them. That clarity is a gift, even when the news it delivers is hard.

If the performance conversation is part of what's surfacing the mismatch, the feedback framework matters too — see How to Give Feedback That Actually Lands for how to deliver hard observations in a way that opens a door instead of closing one.