Bennett: 10 Actionable Tips for Mastering Tough Conversations with An Employee

April 28, 2023
Facing difficult conversations with employees is an inevitable part of any managerial role. How you handle them is what matters most.

Imagine this scenario: As an owner or manager, you’ve noticed one of your team members has been underperforming, causing delays and impacting the overall productivity of the team. The thought of addressing the issue weighs heavily on your mind, and you find yourself losing sleep over it. Yet, the fear of confrontation or losing an employee and being short-handed holds you back, and you delay the conversation hoping that the problem somehow resolves itself. Unfortunately, avoiding difficult conversations only leads to mounting tensions, unresolved issues and declining morale within the team. The statement “the fastest way to lose good employees is to tolerate a bad one” is never truer than in the employee-centric climate we now operate in.  

Facing difficult conversations with employees is an inevitable part of any managerial role. While these discussions may cause anxiety for you, it's crucial to tackle them head-on to foster a healthy and productive work environment. Here are 10 actionable tips to help you overcome anxiety when approaching a challenging conversation with an employee. 

1. Be Prepared 

Gather all relevant information, consider different perspectives and anticipate the employee's possible reactions. Being well-prepared helps you feel more confident and ensures a smoother conversation. Take time to: 

  • Write down the main talking points you want to address. 
  • Practice your delivery for clarity and empathy. 
  • Anticipate pushback or disagreements but be prepared to bring it back on topic by focusing on ideal outcomes. 
  • Consult with HR or a trusted colleague if necessary to make sure what you intend to communicate comes across clearly. 

The key point here is to not be de-skilled in the conversation. Not every tough conversation will escalate. However, preparation and practice will give you the tools and confidence to bring the conversation back on task should emotions become heightened and the conversation de-evolve. 

2. Choose the Right Time and Place 

Find a quiet, private space free from interruptions, distractions, customers and other employees. Ensure the timing is appropriate to help both you and the employee feel more at ease for an open and honest conversation.  

3. Focus on the Issue, Not the Person 

Concentrate on the issue at hand, rather than the individual, to prevent emotional reactions. The appearance of personal attacks can trigger a full-on self-defense reaction. Use "I" statements to express your concerns. Avoid accusatory phrases like “you did X..” or “you’ve failed to...”. Instead, state what you yourself have observed or noted- “it appears to me...” or “by missing our promised time…”. Focus on the situation and its impact NOT on the person or personal failures.   

4. Listen Actively 

Give the employee your full attention, maintain eye contact and avoid interrupting. Demonstrating that you're genuinely interested in their perspective establishes trust and fosters open communication. Keep the conversation focused on facts and solutions. Avoid listening simply to formulate your response/argument. Genuinely listen to your employee. You might be surprised by what you learn when you commit to listening. 

5. Offer Support and Solutions 

Be prepared to provide resources, tools, or additional training to help the employee improve. Discuss potential solutions and work together to create a plan of action, focusing on growth and improvement. Make sure that you have a strong mutual agreement on what improvement and success will look like. Set a timetable for action and improvement.  

6. Maintain a Calm and Composed Demeanor 

Throughout the conversation, remain calm and composed to set the tone for a productive discussion. Take deep breaths if needed and remind yourself that addressing these issues is essential for the well-being of both the employee and the team. 

7. Emphasize the Importance of Open Communication 

Encourage the employee to share their thoughts and feelings openly. Make it clear that you value their input, and that open communication is crucial for resolving issues and fostering a healthy work environment. 

8. Follow Up After the Conversation 

After the conversation, track the employee's progress and offer extra support as needed. Schedule a follow-up meeting to discuss their progress and address any lingering concerns. This ongoing engagement demonstrates your commitment to their success and helps to build a strong working relationship. 

9. Avoid Procrastination and Delaying the Conversation  

I have always believed the statement, “that which you fail to confront, you validate.” Procrastination and delay can only exacerbate anxiety and allow the issue to worsen over time. Putting off a difficult conversation may lead to misunderstandings and further complications in the workplace. You may lose your best employees if they lose faith in your ability to protect the team from bad behavior or poor performance. Addressing concerns promptly demonstrates that you are proactive and committed to resolving problems before they escalate. To avoid procrastination: 

  • Set a deadline for yourself to start the conversation. 
  • Remind yourself of the potential benefits of resolving the issue sooner rather than later. 
  • Break the conversation preparation into smaller tasks to make it feel more manageable. 

By taking timely action, you show your employees that you value their well-being and are dedicated to fostering a positive work environment. In turn, this can help build trust and respect between you and your employees, making future difficult conversations less daunting. 

10. Learn From Your Experiences 

After each tough conversation, take time to reflect on the outcomes and identify areas for improvement in yourself as a manager and leader. Consider seeking feedback from a trusted colleague or mentor to gain insights into your approach. By improving your communication skills and confidence, you can become more effective at navigating challenging conversations with employees. 

I encourage you to embrace the role of being a proactive leader, even in difficult situations. Learning to tackle tough conversations with difficult employees quicker fosters a more transparent, supportive, and high-performing work environment. By addressing issues promptly and constructively, you show your dedication to your team’s growth and well-being, while also building trust and respect in the process.  

As you refine your communication skills and face tough conversations with confidence, you will build a culture of open and honest conversation and continuous improvement. This approach not only contributes to the success of your team but also enhances your own personal and professional confidence and quality of life.  

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