How to Have Difficult Conversations with Employees: A 6-Step Framework for New Managers
Most managers avoid difficult conversations until they become impossible to ignore. Here's your map for navigating them with clarity and confidence.
Every manager faces that moment—when you know a conversation needs to happen, but you keep putting it off. Maybe it's addressing missed deadlines, performance issues, or team conflicts. The conversation feels heavy, unpredictable, and frankly, easier to avoid.
But here's what most leadership training gets wrong: difficult conversations aren't about being tough or confrontational. They're about having a clear map when the territory gets messy.
Why Most Managers Struggle with Difficult Conversations
The problem isn't that you don't care about your team—it's that you don't have a framework. Without structure, these conversations become emotional minefields where good intentions turn into defensiveness, blame, and damaged relationships.
The cost of avoidance is real:
Small issues become big problems
Team performance suffers
Trust erodes when problems go unaddressed
You lose credibility as a leader
The solution isn't to avoid these conversations—it's to approach them with a proven framework that keeps you focused on facts, solutions, and positive outcomes.
The Difficult Conversations Framework: Your 6-Step Map
This isn't another "just be direct" approach. It's a structured method that separates facts from feelings and creates space for real solutions.
Step 1: Set the Stage (Open the Conversation)
Purpose: Create a neutral, safe space for discussion.
Don't ambush someone or start with accusations. Instead, frame the conversation around your shared goals.
What to say: "I'd like to talk about [issue] because I value our working relationship and want to find the best way forward."
Step 2: Share Your Observations (Fact-Based Approach)
Purpose: State what you've observed without blame or judgment.
This is where most managers go wrong—they lead with feelings instead of facts.
Instead of: "I feel like you don't care about your work." Say this: "I noticed that three of your last five assignments were submitted past deadline."
What to say: "I've noticed that deadlines on our team have been slipping, and I wanted to check in with you on what's been happening."
Step 3: Express the Impact (Why It Matters)
Purpose: Explain why the situation is important and how it affects others.
Help them understand the bigger picture without making them feel attacked.
What to say: "When deadlines aren't met, it creates additional stress for the rest of the team and impacts our ability to deliver results."
Step 4: Invite Their Perspective (Encourage Dialogue)
Purpose: Give the other person space to share their side.
This is the moment that transforms a confrontation into a conversation.
What to say: "I'd love to hear your thoughts—what challenges are you facing that might be contributing to this?"
Step 5: Explore Solutions Together (Collaborate on Next Steps)
Purpose: Shift from problem identification to problem-solving.
What to say: "What do you think would help improve this situation? Let's explore ways we can work together to find a solution."
Step 6: Confirm Next Steps (Ensure Alignment)
Purpose: Summarize and confirm what was discussed.
What to say: "So, moving forward, we've agreed that you'll provide a status update every Friday. I'll check in with you next week to see how it's going. Does that sound good to you?"
Essential Do's and Don'ts for Difficult Conversations
✅ Do:
Prepare your key points in advance
Keep a calm, neutral tone
Listen without interrupting
Stay solution-focused
Define your desired outcome before the conversation
❌ Don't:
Use accusatory language ("You always..." or "You never...")
Let emotions take over
Make assumptions about intent
End the conversation without a clear resolution
Troubleshooting Common Challenges
What if they become defensive? Stay calm and reiterate your intent: "I understand this may be difficult to discuss, but my goal is to work together to find a solution."
What if they refuse to engage? Keep the door open: "I can see this might not be the best time to talk. Let's revisit this when you're ready."
What if emotions escalate? Take a break: "I want us to have a productive conversation. Let's take a moment and come back to this."
Your Framework in Action: A Real Example
The Situation: Sarah, one of your team members, has missed three project deadlines in the past month.
Step 1: "Sarah, I'd like to talk about our recent project deadlines because I want to make sure you have the support you need to succeed."
Step 2: "I've noticed that the last three projects were submitted past their due dates. Can you help me understand what's been happening?"
Step 3: "When deadlines shift, it impacts our client commitments and puts additional pressure on the rest of the team."
Step 4: "What challenges are you facing that might be contributing to these delays?"
Step 5: "What support or adjustments would help you meet deadlines moving forward?"
Step 6: "Great, so we've agreed you'll send me a progress update every Wednesday, and I'll check in with you next week to see how the new system is working."
The Leadership Map You Need
Difficult conversations don't have to be confrontational. With the right framework, they become opportunities to strengthen relationships, solve problems, and build trust with your team.
Most leadership advice tells you to "just have the conversation." But you need more than encouragement—you need a map for when the territory gets challenging.
Ready to transform how you handle difficult conversations? Discover your leadership identity and get practical tools designed for real management moments. Take the free Leadership Pathway Explorer to uncover your natural leadership style and get personalized tools that actually fit how you lead.
Looking for more practical management tools? The Manager's Map Drawer delivers three new leadership maps every month—including conversation scripts, one-on-one templates, and situation guides. Learn more about monthly management tools here.
