How to Have a Difficult Employee Conversation

Does anyone really like having those difficult employee conversations? You know, the ones where you have to talk to somebody about their performance, a behavior, or something sensitive like body odor or inappropriate dress. Those discussions seem to hang out on the “To Do” list while you hope whatever is going on just magically changes without the need for you to address it.

Well, bad news – it’s not going away on it’s own.

Good news – you’ll feel a lot better once you deal with it and if you handle the conversation properly it won’t be so bad after all. It is possible to have a conversation that is difficult, and still respectful and impactful.

Why it’s important to have the conversation

I’ve definitely had experience at handling things badly. I’ve had people get angry, cry, stomp out of my office and slam the door, or just stare at me blankly and not comment.  But I’ve also had some great experiences where people have appreciated the conversation, thanked me, and moved forward.

I had the benefit of being professionally coached during my career. It’s a terrific (and humbling) learning experience. One of the lessons that really stuck with me was the time that I was observed coaching one of my employees. I was having a conversation with her about commitments that she had made and hadn’t fulfilled, again. She had a few excuses why this had happened, so I let her off the hook. When the session was done, my coach observed that this didn’t sound like the first time I had done this. I admitted that it wasn’t and explained why. Then she said, “So you let her off the hook again?” I nodded, a little embarrassed. Then she asked me, “How is that helping Anna move forward?”

That question really stuck in my head and I remembered it every time I was avoiding a tough conversation. I was a leader. And my role was to help people grow and enable them to meet their full potential. But because I was avoiding having a difficult conversation, I was getting in the way of that employee’s success. I wasn’t letting her know that what she was doing was negatively impacting both herself and her team. So by avoiding a direct and tactful conversation, I was basically saying that her actions were fine, and that was actually preventing her from being successful.

So, while tough conversations can be difficult, they are often the best coaching opportunities and they can help an employee grow the most. If they choose not to, well, at least you’ve given them the opportunity. And when you choose NOT to have a difficult conversation you are sending a message to the employee that what they are currently doing is okay. Essentially, you are endorsing their actions by tolerating them. Read more about this in You Get What You Tolerate.

Tips for Difficult Conversations

Think Before You Act

Sometimes when we leave things off too long something will trigger a quick reaction. Maybe you’ve been putting up with an employee doing a sloppy job filing things, and then one day you lose it on them when you find something misfiled. First thing is to stop and think before you act. Don’t talk to someone when you’re angry. This is a conversation where minimal emotions are involved, unless it is a case that requires some empathy. 

Focus on Behavior and Impact

Plan exactly what you want to say. I suggest writing it down because it’s easier to make sure you focus on saying the right thing and omit words that are negative. Make sure you focus on the specific behavior or requirement and the impact, rather than making it personal.

“I need to talk to you about that strong perfume you’re always wearing. You’re making people sick. Don’t you know this is a scent-free office?”


“I’ve noticed that you are wearing something scented. We have a scent-free office so that all of our employees can work in a comfortable environment. Here’s where the policy is on our website. Let me know if you have any questions about it.”

The first example attacks the person and while it points out the impact of making people sick, it does it in a negative way. When you use phrases like “don’t you know” it assumes the person is stupid not to know something. The second example points out the behavior (wearing a scent), outlines a specific requirement (scent-free environment) and points out the impact (comfortable environment), without attacking the person directly.

Rip Off the Band Aide

Once you’ve taken a BIT of time (not 2 weeks) to think it through and plan what to say, then act. Avoiding it just makes it worse. Obviously the behavior is impacting the workplace and employees can see this.  If they see that you aren’t addressing the issue, it reflects on your credibility as a manager. So don’t procrastinate.  Do what’s called “ripping off the band aide”, you know it’s going to be uncomfortable but it will be over quickly and the anticipation is worse than the actual act.

Express Genuine Intent

For performance related issues, make sure you let the employee know that you’re genuinely interested in helping them, that the point of the conversation is so that they understand your expectations, understand the impact, and are clear on what needs to change. You’re having the conversation with them because they are important and their success is important and you care enough about them as an individual to want to help them reach their full potential.


Let them talk! Sometimes people need a few minutes to digest what you’re saying to them. Don’t jump in and fill the silence. Think about WAIT (Why am I Talking?). You need their input and agreement in order to move forward so make sure you get that. It’s okay if they get a little angry or upset. Hear them out and have a conversation because that’s much better than having someone walk away in silence and you have no idea how they feel.

Difficult employee conversations are, well, difficult. But they also can be some of the most beneficial conversations for your employees. An employee who is focused on self-improvement and success will recognize that your intent is to help them move forward. These are the employees that you want to invest your time in.

Please share if you’ve found this post helpful. I welcome your comments and input, and any experiences you have had with difficult employee conversations.

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