employer speaking with employee

As managers, we’re there with our direct reports through both good times and bad. They’re not always the people we want them to be. Sometimes they have different perspectives, goals, and interests than we might expect.

Many of us dread having difficult conversations with employees. However, those are exactly the conversations that can lead to better relationships, performance, and culture at work—as long as we can learn to handle them well.

What Is a Difficult Conversation?

A difficult conversation is one that contains an element of conflict. A 2008 study found that dealing with conflict in the workplace costs more than 300 billion dollars per year. It can’t be avoided. We’re imperfect human beings. As a result, expect to stumble upon the following types of difficult conversations with employees:

  1. Disappointing an employee because a desired raise or promotion is unavailable
  2. Giving negative performance feedback
  3. Firing an employee
  4. Mediating a feud between employees
  5. Any conversation that may turn emotional

Because we may have had painful experiences with difficult conversations in the past, many of us have learned to avoid them. However, those unpleasant conversations keep coming up, and it’s better to address them head on than to dodge them for so long that they become unmanageable.


To create better outcomes through those conversations, we need to learn some techniques. So how do you prepare for having difficult conversations with employees, conduct the conversations, and learn from them? Start by studying the 20 tips below.

1. Overcome Your Own Anxiety

We avoid difficult conversations because we imagine negative outcomes like employees getting emotional or not liking us. Overcome your fears by understanding that it is just as likely that an employee will respond in a more measured way. They may genuinely need and appreciate your feedback, and having the conversation could lead to a stronger working relationship and open the door for more candid communication in the future.

2. Think More Positively

Frame the upcoming conversation in more positive terms. Instead of thinking of it as “difficult” or “negative,” focus on sharing useful tips, alternative directions, or supportive comments. Plan how your relationship could improve afterward.

3. Consider the Alternatives

Ask yourself what is important about having the conversation. Would it be more difficult for a certain problem to continue or just to have the conversation? Is the status quo good enough? Will the conversation create value?

4. Follow Your Curiosity

At least temporarily, let go of any judgments you are making about the employee. Instead, get curious about the hidden reasons for his or her behavior, the unspoken needs and expectations you both have, and the solutions and agreements you can create together.

5. Prepare to Help

How can you have difficult conversations when you don’t like conflict? Focus on your desire to help rather than being critical. Your body language, facial expressions, and word choice will reflect your intent.

Also, clearly state your desire to help and coach. Give the employee concrete actions to try, as well as solutions, support, and needed resources (even if it’ll be at their next job).

6. Overcome Procrastination

If you’re tempted to put off this conversation until the next time a problem crops up, understand that now is the best time to deal with it. There is no perfect moment. Just choose and schedule a time when you’re prepared to have the conversation and are relatively calm.

7. Write Questions

Instead of just making a speech, prepare some useful questions:

  • How is this project going?
  • How do you feel about being on this team?
  • What ideas do you have to help us reach this goal?

Be prepared to listen and participate in a two-way dialogue.

8. Present the Facts

Carefully prepare the facts of the situation. Never rely on rumors or hearsay. Give concrete metrics and good team feedback, along with specific actions the employee can try. Avoid emotion-laden phrases like “I’m angry,” “The team is disappointed,” and so on.

9. Prepare to Go Off-Script

Don’t plan exactly what you’ll say. Difficult conversations never stick to a script.

10. Recruit a Witness

If the conversation will touch on clear behavioral problems or rule violations, bring in an objective witness, such as another manager or an HR representative. Decide on each of your roles for the upcoming meeting before it happens.

11. Be Fair

Ensure you consistently hold all your direct reports—and yourself—to the same standards. Show that you don’t have a personal agenda or a bone to pick with a certain employee.

12. Listen Carefully and Patiently

Expect the conversation to go longer than you planned. Then, listen. Remove distractions from the room. Make sure you understand your direct report’s point of view and respond to it fairly and directly.

13. Demonstrate Compassion and Empathy

Before and during the conversation, think about what it would be like to be the other person. Show kindness to him or her, especially when stating painful facts.

14. Be Candid

Get to the point. Be open about the challenging details while also being considerate. If the other party doesn’t appear to understand, you might ask what he or she is hearing or how he or she would paraphrase the information you’ve presented.

15. Use THINK (True, Helpful, Inspiring, Necessary, and Kind)

You could organize your ideas around each of the words in the acronym THINK: true, helpful, inspiring, necessary, and kind. To prepare, state your main ideas to another manager and ask if they reflect the intent of the THINK acronym.

16. Don’t Get Defensive

How do you stay calm when you’re having a difficult conversation with an employee? If a direct report places blame or says something in anger, don’t act defensively. Focus on your goal of helping. Maintain a professional, respectful tone, and request that the employee explain his or her perspective in more detail.

17. Encourage Questions

Leave time for your direct report to ask questions. It can help him or her to understand the situation more clearly and give you a chance to explain further. You’ll also get a sense of whether the information has sunk in.

18. Take a Break

Sometimes, a conversation cannot proceed productively because of extreme emotion, misunderstandings, or feeling overwhelmed. Take a break of around 15 minutes to allow you or your employee time to recover.

19. Follow Up

After your first meeting, have a quick follow-up conversation. Ensure your direct report understands you are available to support and coach him or her. This can sometimes be an informal talk on the way to the water cooler.

20. Analyze What You’ve Learned

When you finish having a difficult conversation, think about the techniques you used and those you’d like to try in the future. Think more about your process than about outcomes that are out of your control.

Difficult Conversations with Employees: Common Scenarios

Imagine that you have an employee who is often late to work. Keep a corrective conversation factual, referencing time records and policies. Avoid emotional language. Find out if he or she needs help, and seek a satisfactory agreement.

What about when an employee complains about another employee? You might help him or her file a formal complaint with HR. Then, gather objective facts about the situation. Next, ask another manager or HR rep to help mediate and resolve the conflict. Try to keep the conflict only between those who need to know.

Finally, you may have to talk to an employee about emotion-driven, inappropriate behavior. Kindly ask questions about the behaviors you are seeing, being clear that you want to help. If you learn about a personal, non-work-related problem, bring in an appropriate party who can provide help, such as an HR rep.

Difficult Conversation with Employees: Real-Life Examples

Imagine modeling your ideals after the following examples of difficult conversations with employees:

First, CEO Tabatha Turman realized that a very kind employee was not able to perform at the expected level. After coaching him for six months, she had to fire him.

To prepare, she gathered the plain facts, committed to being candid, and avoided emotional language. She told him in clear terms that he didn’t fit the position and explained the details of the layoff. Although he wasn’t glad about it—why would he be?—he accepted the outcome.

Chief Personnel Officer Betty Thompson was required to lay off an employee that had worked at her company for many years. His position was no longer needed and was located too far away from headquarters.

To prepare, she considered how he’d want to receive the news, and she chose to have several meetings with him over two months. She focused on her good intentions for him and maintained her sense of caring about him in every meeting.

At their first meeting, she asked him how he thought things were going, listened carefully, and then gave her own thoughts on the problems with his position. By the next meeting, he had started to understand these problems. Finally, he decided to resign.

Don’t Avoid Difficult Conversations

With these tips in mind, we hope you won’t put off or avoid having difficult conversations with employees. Since they are going to happen anyway, make sure they go as well as possible by practicing the techniques above.

As you reflect on each conversation and increase your skill, you can learn to achieve better outcomes and reduce pain. To learn more about engaging in difficult conversations constructively, contact CMOE.

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About the Author
CMOE’s Design Team is comprised of individuals with diverse and complementary strengths, talents, education, and experience who have come together to bring a unique service to CMOE’s clients. Our team has a rich depth of knowledge, holding advanced degrees in areas such as business management, psychology, communication, human resource management, organizational development, and sociology.

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