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13 Tips On How To Have Difficult Conversations With Employees

7 min read   |  
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Worried about how to have difficult conversations with your employees? You are in the right place!

Difficult conversations with employees are hard. However, you must consider them if you see:

  • Your team is underperforming or unproductive.
  • There are recurring issues like tardiness or misconduct.
  • Your employees need constant supervision.
  • Mistakes happen frequently.
  • There are teamwork or collaboration issues.

And many other issues that need quick resolution.

Get ready to explore why these conversations are crucial and get 13 essential tips for navigating them effectively. Let's dive in!

Key Takeaways

  1. What is meant by difficult conversations with employees?
  2. Why should you not avoid the difficult conversation with your employees?
  3. 13 brilliant tips on how you can prepare for difficult conversations with employees.

Understanding What Difficult Conversations With Employees Are


Conversations are a great way to understand people and are considered as an essential communication skill. And they are even more important in the workplace. And as a manager or leader, one must be ready for clear talks with the employees.

Difficult conversations with employees involve addressing sensitive workplace issues that require careful handling. These talks may cover performance problems, misconduct violations, denied requests like promotions or raises, or policy breaches. Handled constructively, difficult conversations can improve employee relations, performance, and alignment with company goals.

One known issue in dealing with such employee-related concerns is to sweep it under the rug, ignore it, and hope it goes away. That may be a simple choice, but it is far from profitable. Such ignorance could make things even worse. And in no time, it will affect the overall environment in the workplace.

Here are a few tips on preparing for difficult conversations with employees.

13 Tips On How To Have Difficult Conversations With Employees

1. Gather Your Guts And Take The Initiative.

Managers are reluctant to participate in uncomfortable discussions because they are unsure how to handle them. They also fear that the debate won't go as planned and that the employees will get upset. That is an obvious concern. Some employees don't like being told they are playing poorly or failing.

If you're gearing up for a conversation you've labeled "difficult," you're more likely to feel nervous and upset about it beforehand. Instead, try framing it in a positive, less binary way," suggests Jean Francois Manzoni. Consider you are not giving negative feedback; you are just having a constructive conversation for betterment.

It will change your mindset and make it easy for you. "The key is to learn how to handle them in a way that produces a better outcome: less pain for you and less pain for the person you're talking to," added Manzoni.

So remember, preparation is the key.

Gather concrete facts, data, and specific examples to support your concerns. This will help you deliver clear and objective feedback.

2. Decide On The Right Time And Situation.

It will worsen if you pick up one employee and complain to the team members. You must demonstrate empathy and find the right stage for a difficult conversation.

Also, choose the right setting.

Find a private space free from distractions where you can have a confidential conversation. It could be the conference room or the meeting room or even a casual discussion over a cup of coffee. You have to find an atmosphere that makes everyone feel relaxed and comfortable.

3. Keep Your Emotions In Check.

Your conversation should be fact-based and not filled with emotions. Feelings or emotions might dominate the conversation and deteriorate any progress being made.

In case you are overly emotional or unprepared for the conversation, you have to postpone and reschedule the meeting. Avoid saying, "I'm upset" or, "I thought." It will add negative emotional factors to the discussion.

At the same time, Don't rush the conversation. Allow ample time for the employee to ask questions and express their perspective. It will energize the conversation and develop a better employer-employee relationship practically.

4. Set the right tone

Be empathetic and professional. Let the employee know you care about them and their well-being while maintaining a respectful and constructive demeanor. This approach fosters trust and understanding, leading to more effective communication and problem-solving.

5. Keep It Private

Employees generally expect employers to maintain confidentiality whenever they come up with a complaint. However, ensure they understand that you cannot fully guarantee the same. You will have a duty to take action or to speak to others, depending on what they say.

Such circumstances often have three sides: the employee who complained, the employee who protested, and the facts. You have to take a step back and know the truth. Depending on the situation, you should schedule a private conversation.

However, you can consider having a witness with the experience and the ability to handle tough conversations. Know more about this in the next point.

6. Start With Positive Reinforcement

Begin by acknowledging the employee's strengths and contributions. This helps to affirm their value to the team and creates a positive atmosphere. After that, you can address the specific issue, maintaining a supportive tone throughout the conversation.

7. Focus On Behavior, Not Personality

Discuss specific actions needing improvement, avoiding personal attacks. Stick to observable behaviors for effective resolution. This approach fosters a constructive dialogue and promotes a positive work environment.

8. Use "I" Statements

Say, "I noticed deadlines aren't consistently met, and I'm concerned about the project's impact," instead of "You haven't met deadlines." This approach avoids blame and defensiveness.

9. Don't Make It Scripted.

According to Holly Weeks, the author of Failure to Communicate:

It's very unlikely that it will go according to your plan. Your counterpart doesn't know his lines, so when he goes off-script, you have no forward motion, and the exchange becomes weirdly artificial. Your strategy for the conversation should be flexible and contain a repertoire of possible responses. Your language should be simple, clear, direct, and neutral.

And rightly so. You must do your homework and prepare for the meeting with proofs and cold facts. Noting down points can help you to say what you want. However, drafting a foolproof script can waste time and effort.

10. Remain Objective and Be Mindful Of Cultural Differences

Avoid personal biases or emotions influencing judgment.

Be sensitive to cultural norms while in conversation with employees from diverse backgrounds.

11. Keep A Witness To The Conversation.

You should almost always find a witness to be present unless this is a short conversation. A witness is even more important for dealing with issues like policy and behavioral problems. Usually, a witness is a supervisor or HR representative and never another employee. They should be informed about the situation in advance, too.

12. Help The Other Person See A Way Out.

Remember, as a business leader, you are a coach too. It is up to you to deliver everything your staff needs to succeed.

So, the other person should be able to learn something from the conversation. You can write a strong recommendation or ask how to help him or her.

Like you don't want problems, your employees hate it too. Just don't tell them that they're doing wrong. Give examples of positive things they should do to change. Please provide them with the required instruments and tools for development. Giving them options and a helping hand can solve many problems and restore respect in the workplace.

Also read: Master the art of respect in the workplace with these 8 tips

13. Take Time To Review

Keep a record of the key points discussed, decisions made, and action items. Carefully review what has been debated. Let the employee know when the problem is fixed or improved. Take them for a brief and informal discussion, or reaffirm your guidance. It will boost their confidence.

Also, make sure that you pre-schedule a follow-up plan if necessary.

Frankly, no one looks forward to difficult conversations at work. However, adopting a systematic approach will help such challenging conversations to be successful. Strategies might be different for all, but understanding how to have a difficult conversation with employees ahead of time enables you to communicate effectively.

The Consequences Of Avoiding Difficult Conversations


Ignoring issues or concerns can cause team members to grow resentful and distrustful of one another, creating a toxic work atmosphere. If unattended, unresolved concerns might become more serious, harming the relationship. Avoiding these discussions can also lead to lost possibilities for development and progress and lower productivity over time.

That is why, when you know that a discussion is required around a topic, take the initiative to open the conversation immediately.

How Do You Soften The Message In Tough Conversations With Employees?

Softening tough conversations with employees is like sweetening bitter medicine. It makes it easier to swallow without losing its effectiveness.

One cool trick?

Sprinkle in some storytelling! Sharing personal anecdotes or examples helps them connect and grasp the message better. Ultimately, it's about crafting a narrative that resonates deeply, fostering emotional understanding.

FAQs on Difficult Conversations With Employees

FAQ about difficult conversation with employees

Q: How do I prepare for a difficult conversation with an employee?

A: Prepare by understanding the specific issue, gathering the relevant information, and thinking about the possible solutions. It would be great to plan the conversation in a private and comfortable setting.

Q: How do I deliver feedback without demotivating the employee?

A: Focus on the behavior or performance, not the person. Be constructive and use specific examples and offer solutions for improvement.

Q: What if the employee becomes defensive during the conversation?

A: Be calm and empathetic. Allow them to express themselves but bring the conversation back to the original issue. Listen actively and acknowledge their feelings.

Q: How can I ensure a positive outcome after a difficult conversation?

A: Follow up with the employee to show support and offer any necessary resources. Set clear expectations and a plan for improvement, and be open to ongoing communication. Reward and recognize the employees for their efforts.

This article is written by Susmita Sarma, a digital marketer at Vantage Circle. She was involved with media relations before shifting her interest to research and creative writing. Apart from being a classical music buff, she keeps a keen interest in anchoring and cooking. For any related queries, contact editor@vantagecircle.com

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