The One Employee You’re Terrified to Talk To

You know the employee I’m talking about. When you see them, your stomach tightens. When you think about them, you feel agitated. 

Maybe it’s your top salesperson—the one who brings in 30% of your revenue but treats the rest of the team like dirt. Maybe it’s an amazing developer who demands extra off days all the time. Perhaps it’s someone who has been with you since Day One but has slowly become dead weight.

But you haven’t talked to them yet. Why? Because you’re terrified. You’re afraid they’ll quit, or blow up, or that things will get awkward.

The Cost of Silence

Generally, ignoring the problem won’t make it go away. Here’s why. 

People are emotional, and they are affected by the people around them. When one person’s behavior turns sour, it infects everyone around them. Avoiding conflict can cost you your best people, who eventually get fed up with working in a toxic environment. 

Here are some types of problem employees:

  • The too-pushy team member who dominates meetings.
  • The emotional whirlwind who turns everything into a drama.
  • The incessant demander of perks, raises, and exceptions.
  • The slacker with endless excuses.
  • The employee with hygiene so bad that other employees are complaining about his smell (not theoretical 一 one of my clients actually had to deal with this)

These aren’t just annoyances. If you leave them alone, they can affect everything from hiring to customer service to scaling and even exiting your business.

So you need to address these employee issues. But how?

What to Say, What Not to Say

These conversations are hard, but as a leader, you must lean into them. Here’s a framework:

  1. PREPARE. Break this into a few parts:
  • State the problem (specifically, without generalizing): “On Monday, Tuesday, and Thursday this week, you showed up 30 minutes late”. 
  • Point out the impact: “Your lateness means others have to cover for you.”
  • Say exactly the outcome that you want: “I need you to be here at 9 AM”
  1. BEHAVIOR, NOT THE PERSON. 
  • DO NOT SAY: “You are lazy.” “You have a bad attitude.” 
  • SAY: “Your recent sales numbers are below target.” “The smell in the office is affecting productivity, so we need to make sure everyone is taking care of personal hygiene.” (Yes, even that one. Stick to the observable facts and their impact. You can do this.)
  1. LOWER DEFENSES.
  • Frame the conversation positively: “I want you to succeed here.” 
  • This reduces the chances of their feeling attacked, and counterattacking or shutting down. 
  1. LISTEN
  • Ask open-ended questions. “What’s your perspective on this?” or “What do you think is contributing to this issue?” 
  • Give them space to respond.
  • Be prepared for emotions. You can acknowledge them (“I understand this is tough to hear”), but get the conversation back to solutions.
  1. NEXT STEPS (and Follow Up!)
  • “How do you want to handle this so it doesn’t happen again?” 
  • Set a timeline and a next step. “Let’s check in on this again in two weeks.” 

Tough but Effective

Being straight has a big advantage: it takes care of the problem quickly and decisively. 

A showdown isn’t pleasant, but if it’s done with skill, it works. Here’s an example of someone who is being managed by a former colleague, and he doesn’t like it one bit. 

This is direct and unwavering. It addresses the root issue with finality instead of letting things fester. 

The Payoff: Growth for Everyone

Tough conversations aren’t about being tyrannical or wielding power. They’re about clarity and respect. Pushing yourself out of your comfort zone and having tough conversations builds a stronger team that understands your expectations and trusts you to lead. 

So, next time that knot forms in your stomach, don’t ignore it. Get yourself ready and have that tough conversation. You’re not being a bad guy; you’re building a great business.