Here's How to Have a Difficult Conversation with an Employee

No employer looks forward to having a tough talk with an employee. These conversations are rarely easy, whether it's about poor performance, behavior issues, or interpersonal conflict. However, avoiding them only worsens matters for the employee, team, and workplace culture.

In fact, a study by Bravely found that 70% of employees avoid difficult conversations with their boss, colleagues, or direct reports. Workplace health is suffering as a result. When feedback is withheld, misunderstandings multiply, morale drops, and performance problems go unaddressed.

So, how can employers and supervisors navigate these conversations effectively? Below are key steps on how to have a difficult conversation with an employee at work with professionalism, empathy, and clarity.

Step 1: Prepare with Purpose

Before initiating a conversation, clarify your intention. Are you trying to correct a performance issue? Address a complaint? Resolve a conflict? Write down the key points you want to communicate and focus on facts, not assumptions or emotions.

Ask yourself:

• What behavior or outcome needs to change?
• What examples can I provide?
• What does success look like moving forward?

Example: Instead of saying, "You're always late and that's disrespectful," say, "Over the past two weeks, I've noticed you've arrived 10–15 minutes late on five occasions. Let's discuss what's going on and how we can address it."

Step 2: Set the Right Environment

Create a private, neutral space where both parties can speak openly without distractions. Give the employee notice so they aren't blindsided. This also allows them to prepare emotionally and mentally.

Avoid delivering difficult feedback over email or in a public setting. A face-to-face (or virtual) meeting promotes respectful dialogue and gives space for questions and reflection.

Step 3: Start with Empathy and Openness

Opening the conversation with empathy sets the tone. You're not there to attack. You're there to find a solution together. Here are examples of how to start a difficult conversation with an employee:

• "I wanted to meet with you today because something important has come up."
• "I value your role on this team, and I want to talk about something that's been impacting our work."
• "Let's have an open conversation. I'm here to listen as well as share."

Avoid sugarcoating or delaying the message, but also avoid being harsh. You can be direct and kind at the same time.

Step 4: Focus on the Issue, Not the Person

Use specific examples and observable behaviors. Stay away from blanket statements like "you always" or "you never." Instead, describe what happened, how it affects others or the organization, and why it matters. Framing the issue around shared goals, such as team success, client satisfaction, and workplace culture, shows that the conversation is meant to support, not punish.

Example:

Good: "In yesterday's client meeting, I noticed that you interrupted your teammate several times. That made it difficult for us to present a united front."

vs.

Bad: "You're not a team player."

Step 5: Listen and Collaborate

After sharing your perspective, allow the employee to respond. They may have context you're unaware of, such as personal challenges, misunderstandings, or unclear expectations.

When they're speaking, it's essential to use active listening skills, like maintaining eye contact, not interrupting, and reflecting back what you hear. Then, collectively collaborate on next steps. What actions will be taken? What support is needed? When will you follow up?

Step 6: Document and Follow Up

After the conversation, document what was discussed and any agreed-upon actions. This protects both the employer and the employee and ensures clarity moving forward.

Set a follow-up meeting or check-in to review progress. Difficult conversations are rarely one-and-done. They're part of an ongoing dialogue.

Remember: Difficult Conversations Are a Leadership Skill

Done right, these conversations build trust, accountability, and stronger working relationships. Employees want clarity. They want feedback. And they also respect leaders who are willing to have uncomfortable conversations in a respectful, constructive way.

Have questions about how to have a difficult conversation with an employee? Reach out to EANJ for a consultation—we're here to help.

Ready to Further Build Your Communication Skills?

Join us on Thursday, September 18, 2025, from 10 AM to 11 AM for EANJ's webinar, How to Conduct Difficult Conversations with Employees, led by Andree Laney, Esq. This one-hour session will explore the legal, business, and interpersonal elements of managing workplace conflict. You'll learn practical strategies for navigating tough conversations, improving communication, and resolving issues effectively. Registration is $65 for EANJ Members and $125 for Non-Members. Register today!