difficult conversations at work

Difficult conversations  at work are an inevitable part of professional life. As a business coach we focus on the importance of soliciting and providing feedback to be a successful leader.

Whether giving feedback to a team member, addressing inappropriate behavior, or discussing poor performance, these conversations can be uncomfortable and challenging. However, avoiding them only leads to more significant problems in the future. 

Having a successful conversation depends on how prepared you are to identify the key message you want to deliver. Visualize the conversation in your mind and think about the outcome you want to achieve. 

During the conversation it is important to do the following:

  • Maintain a calm and empathetic tone.
  • Be direct and specific about your concerns. 
  • Listen actively to the other person’s perspective and be open-minded toward finding solutions. 
  • Avoid making assumptions or accusations and instead focus on describing behaviors and their impact.
  • Following up after the conversation is crucial for ensuring that both parties are on the same page.

The Importance of Difficult Conversations at Work

It may feel uncomfortable, but having difficult conversations can lead to:

  • Improved communication
  • Greater trust between colleagues
  • Better outcomes for everyone involved.

What is a Difficult Conversation?

A difficult conversation is any dialogue that tackles sensitive or uncomfortable issues, such as: 

  • Conflicts with colleagues 
  • Change in roles 
  • Cynicism
  • Firing an employee 
  • Discussing performance

Here are the five tips for having a successful conversation (even when you don’t want to have it.)

    1. Being with Empathy– Empathy is important for connecting with the other person’s viewpoint.
    2. Have a Clear Agenda- Visualize the conversation in your mind and think about the outcome you want to achieve. 
    3. Choose the right time and place- Make sure you are having conversations at a time and place that doesn’t distract focus from the rest of the team.
    4. Manage emotions- It’s important to maintain a calm and empathetic tone throughout the conversation. Avoid making assumptions or accusations and instead focus on describing behaviors and their impact.
    5. End on a positive note- Be respectful. This person was hired for a reason and deserves your best effort. Make them feel significant.

Always being with Empathy

When having a difficult conversation, staying calm and collected while communicating clearly and respectfully is essential. Being empathetic towards the other person’s feelings will help them feel heard and understood. 

Another way to set the tone is by acknowledging any emotions that may be present in both yourself and the other person. Emotions play a significant role in how we perceive and respond to situations, so it’s essential to address them before discussing them. Try using empathetic statements such as “I understand this may be difficult for you” or “I can see why you’re upset.” Acknowledging emotions shows that you respect the other person’s feelings and create an atmosphere of empathy.

Have a Clear Agenda

It’s crucial to prepare for the discussion adequately by identifying what needs to be addressed beforehand. Having a clear agenda ensures that both parties stay on track while maintaining focus on finding solutions rather than dwelling on the problem itself. A successful outcome also involves active listening from both sides while acknowledging each other’s perspectives without judgment or criticism.

How to Prepare:

  • Consider what you want to say and how you want to say it
  • Identify the issues that need to be addressed
  • Outline specific examples
  • Consider any potential objections
  • Anticipate reactions

Choose an Appropriate Time and Place

Find a quiet space where you won’t be interrupted or distracted, and ensure that both parties have enough time set aside so that the discussion isn’t rushed or cut short. Be mindful of your tone of voice and body language during the conversation; while expressing yourself is necessary, try not to be overly aggressive or confrontational.

Telling an employee that he or she did not get a promotion is a delicate situation. Learn more about Communicating a Promotion Denial.

Managing Your Emotions

When it comes to having difficult conversations at work, managing emotions is key. Recognizing and acknowledging your emotions before engaging in any conversation is important. Take a moment to breathe and calm down if angry or upset.

One way to set the tone is by being mindful of your body language and communication style as they convey important messages that can encourage or discourage open dialogue.

  • Tone of voice
  • Facial Expressions
  • Gestures

During the conversation, try to remain calm and composed. Listen actively to the other person’s perspective without interrupting or becoming defensive. If necessary, take breaks throughout the conversation to prevent emotions from escalating.

It is also important to remember that emotions are not always destructive – they can help us express ourselves authentically and connect with others on a deeper level. However, managing them appropriately is crucial for productive conversations and maintaining positive colleague relationships.

Remember, it’s not about winning the argument but finding a solution.

Maintaining a respectful attitude throughout challenging conversations sets a positive tone for everyone involved. Avoid making assumptions about what someone else thinks or feels; ask questions and listen actively to their responses. Doing so demonstrates that you value their perspective and are open-minded about finding solutions together. Above all else, keep in mind that setting a positive tone creates an environment where people feel comfortable sharing their thoughts without fear of judgment or retaliation – leading to more productive outcomes from difficult conversations at work.

Close on a Postive Note

When having a difficult conversation at work, it is essential to close on a positive note. This will help ensure that the other party feels respected and valued. By positively ending difficult conversations, you can build stronger relationships with your colleagues while fostering a more productive and positive work environment.

  • Express gratitude for their time and willingness to have the conversation.
  • Summarize any agreements or action items discussed during the conversation. This will demonstrate that progress has been made and show that both parties are committed to finding solutions.
  • A smile, gentle nod, or handshake can convey respect and appreciation in ways words alone cannot.


Don’t forget to follow up after the conversation. It is crucial for ensuring that both parties are on the same page.  

Handling difficult conversations at work can be challenging, but it is essential for effective communication and a healthy work environment. It may feel uncomfortable, but having difficult conversations can lead to improved communication, greater trust between colleagues, and ultimately better outcomes for everyone involved.

About the Author Ben Shaver

For over a decade, I've guided growing dental practices and groups on how to use leadership and communication to build referable teams and memorable brands.

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