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The Conversation Most Managers Never Have with Employees

What leadership is quietly evaluating — and how the managers who figure this out get to the next level.

When a manager walks into their boss’s office and says, “Johnny is a poor performer,” they think they’re reporting a problem.

What they’re actually doing is signaling one.

Because the first question in that room — spoken or not — is always: ‘What have you done about it?’ And if the answer is ‘I’ve told him a few times, but nothing’s changed’ or ‘I was hoping you could talk to him’ — the conversation has just become about the manager, not the employee. Not because the intent was wrong. Because the work wasn’t there yet.

Leadership evaluates managers on many things. One of the most telling is how they handle underperformers. Not because it’s a test. Because it reveals whether a manager understands their actual job. This is what determines whether a manager will make it to the next level. 

How leadership reads the conversation you’re having with them

Compare these two conversations:

Version 1:

“Johnny is a poor performer. I’m not sure what to do with him.”

Version 2:

“Johnny is struggling. I’ve had direct conversations about expectations, provided access to X training, and connected him with a mentor on the team. We’ve talked specifically about what success looks like. He still isn’t demonstrating the behavior we need, and here’s what I’m seeing.”

Version 1 makes leadership wonder about the manager. Version 2 makes leadership want to support the manager — and respect their final decision.

The difference isn’t the outcome with Johnny. The difference is the work the manager did before arriving at that outcome. Leadership isn’t expecting managers to fix everyone. They are expecting managers to have tried.

Keep your manager informed before it becomes a surprise

Most managers avoid telling their boss about a struggling employee because they see it as an admission of failure. That instinct is understandable and backward.

A short, proactive update — “I’m working with Johnny on some performance gaps and here’s my plan” — is not a complaint. It’s professional management behavior. It signals maturity, not weakness.

Your manager may have context you don’t. They may have ideas, resources, or patience that change your approach. And critically: they don’t want to hear about a separation for the first time on the day you’re ready to pull the trigger. No one wants to be surprised by a personnel decision they had no visibility into.

Keeping your manager informed also protects you. When Johnny’s behavior improves, your manager knows it happened because of your coaching. When it doesn’t, your manager is already up to date and ready to support the next steps. Either way, you look like someone who manages proactively rather than reactively.

The honest conversation — and why it isn’t cruel

Having an honest conversation with an underperforming employee isn’t a confrontation. It’s the information they need to make real decisions about their own career.

It sounds something like:

“I want to be straight with you because I respect you and I want to see you succeed. Here’s what I’m seeing. Here’s what we’ve provided. Here’s what still isn’t changing. I want to ask you directly — is there something we’re missing that would help you succeed here?”

You would be surprised how often that conversation alone turns performance around. Not because Johnny suddenly got more talented. Because Johnny finally understood how his behavior, output, or response to feedback was actually being perceived — and what the desired behavior looked like. Those are two different things, and most employees have never had both explained to them clearly at the same time.

And why would he know? Nobody told him. Not directly. Not clearly. The hints didn’t land. The softened review language didn’t register. Johnny wasn’t being defiant — he was operating on incomplete information. That’s not a character flaw. That’s a communication gap.

Leave the frustration outside the room

This is where most managers stumble, even when they finally decide to have the conversation.

Managers often walk into these meetings carrying six months of frustration.

Johnny walks in carrying six months of incomplete information. Those are not the same thing.

Have this conversation as if it’s the very first time Johnny is hearing honest feedback. Because for all practical purposes, it probably is. It’s easy — and completely understandable — to let accumulated frustration leak into your tone, your word choice, your body language. But it isn’t just what you say. It’s how you say it.

If Johnny feels like he’s walking into an ambush or a verdict, he’ll get defensive. The conversation closes before it starts.

The goal of this conversation isn’t to unload. It’s to inform. You want Johnny to leave that room with clarity he didn’t have before — and with a real choice in front of him. That only happens if you show up without the weight of every frustrating interaction from the past six months.

If nothing changes after that

Sometimes the honest conversation changes everything. Sometimes it doesn’t.

If the answer is still no change — after the direct conversation, after the tools and resources, after the good-faith question about what’s missing — then you have a different situation. An employee who understands what’s expected, has been given what they need to succeed, and is choosing not to engage.

At that point you have a clean, documented, good-faith foundation to have a conversation about fit. And you can do it without cruelty, without drama, and without looking like you didn’t try.

Letting someone linger in a role that isn’t working for them isn’t compassion. It’s avoidance dressed up as patience. And in the eyes of your manager and your peers, it reads as mismanagement. They don’t blame Johnny for that. They blame the manager who let it go on.

The honest conversation — the one most managers are afraid of — is actually the kindest thing you can do. For Johnny. And for yourself.

What this looks like from the top

Executives notice the managers who can do this. Not the ones who push hard and get loud. Not the ones who avoid conflict until it becomes a legal issue. The ones who can have honest conversations cleanly — with clarity, without cruelty, and without drama.

That’s the skill that gets you to the next level. Not because it looks good. Because it’s rare. And because the managers who have it build teams that actually work.

Most poor performers aren’t bad employees. They’re under-informed employees who’ve been managed by people who lacked the courage to tell them the truth. The manager who changes that pattern — even once — understands something most managers never figure out.

So ask yourself: has Johnny really heard it? And if not — what’s that costing both of you?

Go deeper:

If this post resonated, the decisions that shape your career don’t stop here. Behind Closed Doors: Career Decisions covers what HR executives know about how careers are actually built, stalled, and advanced — and what most managers never get told directly.

Available at HRNasty.com/shop

 

This is the third post in a three-part series:

 

See you at the after party,

Ringo “HRNasty” Nishioka

nasty: an unreal maneuver of incredible technique, something that is ridiculously good, tricky, and manipulative but with a result that can’t help but be admired, a phrase used to describe someone good at something. “He has a nasty forkball”.

Ongoing writing and context live on LinkedIn and Bluesky.

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Ringo Nishioka writes about how managers actually make career decisions inside organizations.

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