MSP Peer Group Lesson: How to Conduct Difficult Workplace Conversations

I facilitate peer groups for IT operations managers, service delivery managers, and other leaders of managed service providers (MSPs). I help these groups share best practices and collaborate on solving common problems.

Every MSP peer group meeting includes a useful “Lesson of the Day.” One of these valuable lessons is how to have difficult conversations with employees.

To tackle this subject, I use a confrontation model developed by Susan Scott, as described in her book, Fierce Conversations.

As an MSP manager, your leadership will inevitably be tested by difficult situations with employees. Knowing how to hold effective conversations in these challenging moments is crucial to maintaining a collaborative, productive workplace.

A difficult workplace conversation has three main parts: Your initial statement, your interaction with the employee, and your resolution process.

1. Your Initial Statement: Set the Tone

Your initial statement sets the stage for the difficult conversation. You need to be clear, direct, and truthful, but also empathetic, emphasizing that you want to find a solution that benefits the employee as well as the team. Your goal is to create a relaxed atmosphere for constructive communication.

Your initial statement should also be concise—no more than one minute. So rehearse what you’re going to say.

An effective initial statement includes eight elements:

• Thank the employee for meeting.
• Briefly name the issue.
• Provide specific examples of the issue.
• Describe how you feel about the issue.
• Explain why the issue is important to you and the organization.
• Note how you might have contributed to the issue.
• Show that you want to resolve the issue together with the employee.
• Invite the employee to explain how they feel.

Example: “Thanks for sitting down with me today. I just wanted to chat with you about being late for work, which has been happening too often. Like last week, you were more than 15 minutes late to the office on [days], and you were also late to your [day of week] appointment with [client]. When we don’t know if you’ll be on time, it’s stressful for me and the whole team. We don’t know if we’ll need to pick up the slack, and we worry that our client relationships might get damaged. And look, if I’ve contributed to this issue in any way, I apologize. But now I just want to help you address the issue and be the best teammate you can be. Can you help me understand why the lateness is happening, from your perspective? I want to listen and understand.”

2. Your Interaction with the Employee: Use Carefully Framed Questions

How you interact with an employee during a difficult conversations can make the difference between a positive and negative outcome.

Don’t make assumptions or accusations. Instead, ask open-ended questions that encourage the employee to explain their view—and then LISTEN.

This approach will make the employee feel heard and respected, and it will help you gather information to understand the root causes of the issue.

Frame your questions with softening phrases like:

• “I’m wondering…”
• “I’m confused about…”
• “I get the sense that ___; am I off-base here?”
• “Can you share the challenges you’re facing with…?”
• “Can you walk me through your perspective on…?”
• “In your view, what could help us…?”

Be kind. Acknowledge and understand your employee’s perspective. But don’t accept excuses, blame on others, or long, complicated explanations. Focus on the employee’s behavior and accountability.

3. Your Resolution Process: Moving Forward Together

After a thorough give-and-take discussion, look for a mutually agreeable (and beneficial) resolution. Acknowledge the value of the employee’s input, and focus on learning from the situation and devising specific strategies and actions to address the issue.

To reach an effective resolution, you need to answer key questions like:

• What have we learned?
• Do we need to address anything that we haven’t talked about?
• How can we move forward positively from here?
• What do we need to do to address the issue—what can we agree to commit to, specifically?

If the employee is not comfortable with the resolution agreement, give them a day or two to propose a better one.

After agreeing on a path to resolve the issue, set a follow-up meeting to review the employee’s progress. (A two-week interval often works well, with an informal, unscheduled check-in after one week.)

Summary

As an MSP manager, you’re bound to have difficult conversations with employees. But you can use a three-part process to guide you through these conversations and reach a positive outcome.

Part 1 is your brief initial statement. In 60 seconds, lay out the specific issue (with examples), explain your feelings, note the organizational impact, apologize if you contributed in any way, express your desire to work with the employee to resolve the issue, and ask the employee to share how they feel.

Part 2 is your interaction with the employee. Don’t make assumptions or accusations. Ask open-ended questions framed by softening phrases. Then listen carefully to understand the employee’s viewpoint and get to the issue’s root causes. And don’t accept excuses—focus on the employee’s accountability.

Part 3 is your resolution process. By asking key questions in a give-and-take discussion, reach an agreement with the employee on specific strategies and actions to resolve the issue. Then follow up with the employee to help them achieve a favorable outcome.