June 14, 2021

How to Manage Difficult Employee Conversations: Beginner’s Guide


Performance Issues

Today I’m going to show you how to manage a difficult conversation with an employee effectively.

I remember when I first started managing people how I tried various methods that fell short. Ideas such as ignoring seemingly minor errors led to more significant issues. I avoided telling an employee what to do because I understood that doing so reduces personal motivation and empowerment. I did, however, try selling (convincing them) to do it my way, but they weren’t buying. Even mild veiled threats got ignored. It was frustrating.

In this straightforward guide, I’ll remove all the nonsense so that you can approach any meeting with confidence that your message is received well and change can get started.

Unchecked Issues Lead to Bigger Problems.

Difficult employee conversations address an employee’s undesirable behaviours or actions that require immediate change for the mission and business operations’ wellbeing.

Employees who continue with unchecked behaviours disrupt workplace harmony, negatively impact safety, business operations, customer service and revenue. Change is necessary to continue future employment with the organization.

Now that you understand how meaningful these conversations are let me explain the steps to prepare your discussion so that it is clear and produces the results you both need. 

Analyze the Situation

  1. Name the specific behaviour that needs changing.
  2. How did I contribute to the problem? (e.g. didn’t confront it sooner, wasn't clear before, etc.)
  3. What is the desired behaviour I need from the employee? By when?
  4. What are potential issues that may derail the meeting? How can I avoid them?
  5. What is my commitment going forward?

Book a Meeting with the Employee 

Let the employee know you would like to meet to discuss a recent event. Book a mutually convenient time.

"The best communicators in the world prepare for their conversations." Linda Reddin

Script an Effective & Productive Meeting

Step 1  - Be yourself. Keep your tone calm & familial.

State the purpose of the meeting, process, and what you hope to achieve.

Step 2  - Create a visual of what happened.

Describe the latest scene from an observer perspective: what happened, why the behaviour is detrimental to the company's mission, and what needs to change. 

Step 3- invite the employee to recall the situation.

Ask the employee to recall the situation. Check in for understanding and if there is anything they want to add to the conversation.

Step 4 - make it a team approach. Be solution Focused.

Add in any part you played in contributing to what happened, e.g. not addressing the same behaviour in the past, waiting too long to talk to them about it or combining the issue with other discussion items that its importance was lost.

State how you're going to change going forward should it happen again, eg. "I will talk to you as soon after it happens. Equally, I will also let you know when I notice a positive change."

Step 5 - employee paraphrases what needs to/ will change.

Tell the employee that you want to make sure your communication is clear. To confirm their understanding, ask the employee to rephrase what needs to happen in their own words.

Step 6 - End on a positive Note. reiterate your commitment.

 Reiterate your commitment. Thank the employee for their time and be sure to follow up/through.

Putting it to Work - True Story 

*Names are changed for privacy and confidentiality.

Tom has been a Manager of Rick, his direct supervisor, for the past eighteen months. Tom depends on Rick to oversee the branch’s service operation’s daily management and its 20+ employees. Rick is a competent supervisor but is reluctant or disengaged when asked to take on additional duties when needed. Extra work as required is part of his job description, but Rick is not buying.

When thinking back to previous conversations that failed, Tom realizes that he had included this issue among other topics or waited too long after the fact; thus, the issue was overlooked. 

Tom needs Rick to take on other projects when asked. 

Tom finds Rick at this desk and asks if they can meet tomorrow to discuss the other day’s events. Rick is surprised but agrees. Tom goes away to script an improved discussion. 

The Meeting

Tom opens the discussion in his usual style. He is relaxed; his tone is steady. Tom transitions to the other day’s events and describes what happened from an observer perspective.

Tom acknowledges how much he appreciates his work with the service team and how efficient he is. Tom outlines some extra work that will need his assistance.

Tom admits to previous conversations whereby the same issue was brought to his attention too long after the event occurred and has decided to be prompt in the future. 

Tom checks in and gets Rick’s easy agreement to help out. 

Benefit Highlights from Being Prepared.

  • Tom is relieved that Rick agreed to take on the extra work, he didn’t have to sell the idea to him, and their relationship remains intact. It was easier that he thought possible.
  • Rick felt that his work was acknowledged and was happy to pitch in as part of his regular job. Tom also realized that he never “asked” for a meeting with Rick before but “told” him like a boss. By shifting his approach a collaborative one, Rick was able to participate as a team player.
  • By preparing his discussion, Tom was able to be himself, remain steady, avoid conflict and build trust instead.


Thanks to “Managing Difficult Employee Conversations: Beginner’s Guide,” there is no need to procrastinate or lose sleep over having those difficult employee behaviour conversations anymore.

Whether you are an experienced Manager or brand new, you have everything you need to have an effective meeting and bring an end to behaviours that disrupt harmony and promote a positive workplace culture instead.

As you found in this guide, knowing how to manage difficult employee conversations with ease means you’ll have more time to focus on activities that bring joy and desired results.

Before you move to prepare your next difficult employee conversation, make sure you let me know what you think of “Managing Difficult Employee Conversations: Beginner’s Guide. Please leave a comment below.

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Linda Reddin

About the author

Linda Reddin, CEC, PCC, founder of A Strategic Edge Coaching in Kamloops, BC, helps managers and leaders become excellent communicators and inspiring leaders of successful enterprises. In her free time, Linda enjoys cooking healthy dishes, exploring nature, reading, music, teaching and practicing yoga.

Linda Reddin

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