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Having Difficult Conversations

Coworkers having a serious conversation

Communication Series: Part 3

Management Topic: Having Difficult Conversations

Dear Colleagues,

In April, we began our three part series on communication. This month marks the completion of our communication series for 2021. We hope you have found these topics helpful and feel confident communicating with your team members, regardless of where they are working.

This month, we will be discussing one of the most challenging and daunting tasks for people: having difficult conversations. The first thing that comes to mind for most when imagining difficult conversations is relaying negative feedback. However, we have difficult conversations more often than we realize. Managing up, communicating with a difficult coworker, dealing with upset clients and customers are just a few examples of conversations we have on a regular basis. This month, we will focus on how to prepare for these conversations, what to do during these conversations and best practices for following up.

What Makes the Conversation Difficult?

Conversations can be difficult for a variety of reasons, including feeling uncertain how the person will react, discussing difficult and/or sensitive subject matter, being perceived as uncooperative, and more. However, just because the conversation is difficult does not mean it should not occur. The following are some tips to help you feel more prepared and confident in your conversation.

How Can You Prepare?

  • Prepare key points to discuss with the recipient, as well as responses to anticipated questions. Use your emotional intelligence to ask yourself the following questions.
  • Are you in a good frame of mind to have this conversation with this individual? Difficult conversations should not occur when emotions are high or otherwise out of check.
  • Have you cleared your calendar and workspace of distractions to ensure you can provide your undivided attention? Show that you respect the other person’s time and that the conversation is important. Find a time that allows you to avoid interruptions.
  • Have you secured a private location for the conversation? Avoid having difficult conversations in the presence of others.
  • If taking place virtually, is your camera and microphone working?
  • If the anticipated results of the conversation will impact a larger group, have you informed your management of the issue and the anticipated outcome?
  • Have you sought advice from a trusted colleague or supervisor who may have experience with similar issues?

Holding Difficult Conversations

Coworkers having a serious conversation

Be as transparent as you can in your explanation of both the “what” and “why” when communicating changes or other difficult subject matter. Individuals respect and appreciate honesty in responses. Be direct, specific and sincere. Focus on the facts to avoid making the issue personal.

Make sure the other person feels empowered and safe to provide an initial response, even if the reaction is more negative than anticipated. Your job is to find a balance between creating a safe space, allowing employees to be heard, while also clearly defining boundaries and ensuring the conversation remains professional, respectful, and that all parties leave the conversation with an understanding of their role and expectations.

As managers and supervisors, your experiences during recent years of ever-changing pandemic guidance, continuing process improvement initiatives and a myriad of other changes have shown that flexibility is essential. Engage staff to discuss their concerns and ask questions, while reminding them of this fact: Change can be hard, but is essential.

Be empathetic to an individual’s concerns and feelings and respect their point of view. Demonstrate hope and optimism in the individual’s abilities and the future. If applicable, be honest about your own concerns and what actions you are taking to find solutions for you both. Commit your support through time, training, and resources, without removing responsibility from the other person.

Remember, the more trust and rapport you have with this individual, the better this conversation will be. If concerns are valid, commit to share them with decision makers.

Difficult conversations can cause various reactions in others, as well as yourself. Be cognizant of your own reactions and subsequent verbal and non-verbal communication.

  • Control your emotions and behavior before responding.
  • Do your best to remain calm and self-assured, even if you feel uncertain.
  • Use active listening to clarify and paraphrase the other individual’s statements and concerns. Acknowledgement is not agreement but allows the other person to feel heard.
  • Pace questions you may have, and allow time for the person to think and then respond. Silence is helpful and allowing it signals you are serious about listening to what the person has to say.

Follow Up and Other Considerations

Check in approximately one week later to see how the person feels after processing the conversation. Provide specific, timely and balanced feedback about any changes made since the conversation. Inquire if any questions have arisen throughout the week or if there are any new concerns you should be aware of. Acknowledge and express appreciation for their flexibility, professionalism, work and commitment.

Helpful Tools to Learn More About This Topic:


COVID has caused significant operational interruptions for your department and you need to modify your employee’s role, removing some tasks and adding others. In addition, their role will now require they work alongside another team member with whom they have a poor working relationship. You anticipate resistance to these changes from your team member.

  1. What questions do you anticipate getting from your employee and how will you respond?
  2. If the conversation is unproductive, how will you correct and/or de-escalate it?
  3. How can you support the working relationship between your employee and their teammate?
  4. What resources are available to you? What resources can you offer to your employee?

Interested in reviewing prior months’ topics? Visit our Monthly Management Tips website.

Stay Safe!

Leadership 2029

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