How to Have Difficult Conversations with Employees—Without the Stress
Nicole MagillHandling Tough Conversations Is Part of Leadership—But It Doesn’t Have to Be Hard
As a small business owner, you wear many hats—leader, strategist, problem solver. But if there’s one role most business owners dread, it’s having difficult conversations with employees.
Whether it’s addressing poor performance, handling a conflict, or letting someone go, these conversations can feel uncomfortable, stressful, and even emotional. The fear of saying the wrong thing—or making the situation worse—often leads to delays, avoidance, or frustration.
💡 The good news? You don’t have to figure this out alone. With the right approach, you can handle tough conversations professionally, confidently, and with minimal stress.
In this post, I’ll walk you through:
✔ Why difficult conversations are necessary (and what happens if you avoid them).
✔ A simple framework to make tough discussions easier.
✔ Word-for-word scripts you can use today.
✔ How My Biz Coach© can help you navigate HR challenges in real time.
Why Avoiding Tough Conversations Hurts Your Business
It’s tempting to push off difficult conversations—after all, no one likes confrontation. But avoiding them only leads to bigger problems down the line, including:
🚨 Lower team morale – When issues aren’t addressed, frustration builds, and team members notice.
🚨 Poor performance continues – Employees can’t fix what they don’t know is a problem.
🚨 Business impact – Unresolved issues affect productivity, customer service, and profitability.
💡 Difficult conversations aren’t just about correction—they’re about clarity. Giving clear feedback helps your employees improve, strengthens your team culture, and keeps your business running smoothly.
How to Handle Difficult Employee Conversations in 4 Steps
Step 1: Prepare Before the Conversation
Before you sit down with your employee, take a moment to:
✅ Clarify the issue – What specific behavior or situation needs to be addressed?
✅ Gather facts – Have examples ready to support your concerns.
✅ Decide on the outcome – What’s the goal of this conversation? Improvement? A warning? A termination?
Example: If an employee is missing deadlines, be ready to discuss:
✔ When and where it happened.
✔ How it has impacted the business/team.
✔ What you expect moving forward.
Step 2: Check In First—Then Decide If You Need to Address the Issue
💡 Before jumping into the issue, start with a general check-in. Performance struggles often have an underlying cause, and taking the time to understand what’s going on can shift how you approach the conversation.
Instead of diving straight into feedback, start with a broader question:
✅ Example:
"Hey [Employee], before we talk about work, I just wanted to check in—how have things been going for you, both inside and outside of work?"
👉 Why this works:
✔ Shows you care about the person, not just their performance.
✔ Gives insight into external challenges that may be affecting work.
✔ Creates a safe space—making the employee more open to feedback.
Step 3: Decide—Do You Still Need to Address the Issue?
After hearing their response, take a moment to assess whether the issue still needs to be addressed or if their explanation makes sense.
🔹 If their struggles are personal (family issues, health concerns, etc.):
- Offer support and flexibility instead of focusing on performance right away.
- Example: “I appreciate you sharing that. Let’s talk about how we can support you through this.”
🔹 If the issue still needs to be discussed:
- Acknowledge what they’ve shared while also setting expectations.
- Example: “I appreciate you opening up about that. I also wanted to discuss [specific issue] because it’s been affecting [team/business]. Let’s talk about how we can improve this moving forward.”
💡 This small but crucial pause allows you to adjust your approach based on what you’ve learned—ensuring you’re leading with both empathy and accountability.
Step 4: Use This Simple Conversation Formula
💡 Here’s a straightforward, 3-part framework to structure your conversation:
1️⃣ State the issue clearly and objectively
"I wanted to talk to you about something important. I’ve noticed that in the last three weeks, your reports have been late, which has delayed projects for the team."
2️⃣ Ask for their perspective
"I’d love to understand what’s going on from your side. Is there anything affecting your ability to meet these deadlines?"
3️⃣ Set expectations & agree on a next step
"Moving forward, we need reports submitted by [deadline] to keep everything on track. How can we work together to make sure that happens?"
✅ Why this works:
- Keeps the conversation calm, professional, and fact-based.
- Encourages dialogue instead of just delivering criticism.
- Provides a clear next step, so there’s no confusion.
Word-for-Word Scripts for Common Difficult Conversations
🔹 Addressing Poor Performance
"I’ve noticed that your recent [task/project] hasn’t met expectations. Let’s talk about what’s happening and how we can get things back on track."
🔹 Handling a Conflict Between Team Members
"I’ve heard some concerns about communication between you and [Employee]. I want to make sure we resolve this so the team can work effectively together. Can we talk through what’s going on?"
💡 Need help navigating these conversations in real time? My Biz Coach© provides instant HR guidance and ready-to-use scripts so you’re never caught off guard.
How My Biz Coach© Helps You Handle HR Challenges with Confidence
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