A Business Owner’s Guide to Navigating Difficult Conversations in the Workplace

A Business Owner's Guide to Navigating Difficult Conversations in the Workplace

Difficult conversations are an inevitable part of any workplace. Whether it’s as small as addressing the coworker who leaves dirty dishes in the breakroom sink or something more significant like addressing performance issues, it can be hard to know what to say, when to say it, and how to say it.

Most people want to avoid difficult conversations, but issues tend to grow larger when they’re avoided. The employee who is regularly late will probably continue to do so if nobody addresses it. Similarly, the administrative assistant who keeps copying all of the leadership team on low-priority emails will only keep cluttering the executive team’s inboxes unless someone is willing to address email etiquette with them.

In this blog, we’ll share practical ways to have challenging conversations and offer frameworks to ensure these discussions are both productive and constructive.


Why Having the Difficult Conversation Matters

When approached thoughtfully, having difficult conversations helps build trust and strengthen relationships over time, even if they are uncomfortable at first. Leaders and managers often need to discuss issues such as:

  • Performance problems or unmet expectations
  • Interpersonal conflicts, like frustrating habits or behaviors
  • Sensitive organizational changes, such as layoffs, restructuring, or downsizing

While discussing these topics is important, the way they are addressed determines whether the message is understood and acted upon or if it leads to more tension.

 

How to Prepare for the Conversation

For a relatable, everyday scenario, imagine you manage an employee named Jack. Jack is intelligent and prides himself on being an ideas guy, which you appreciate; however, he tends to talk over colleagues during team meetings or can come across as condescending when they present ideas he dislikes. As his manager, you know you need to address these behaviors because they affect team morale. Still, you also want to preserve his enthusiasm for contributing since you value his perspective and expertise.

Here are a few ways you could prepare to have this conversation, or any other challenging conversation in your workplace:

  1. Check the timing. If possible, avoid having difficult conversations during highly emotional or stressful times, or right before or after a holiday or vacation.
  2. Clarify your objective. Before you start the conversation, know what you want to accomplish, and make sure the discussion is focused on the action you ultimately want them to take.
  3. Ground yourself. Keep the conversation factual, not overly emotional. Focus on the observed behaviors and their impacts instead of making assumptions or personal judgments.

As you get ready for the conversation, it might be helpful to jot down notes about the specific points you want to discuss or rehearse what you might say during the discussion.

Use the DESC Model for a Productive Conversation

As you have difficult conversations, using the DESC model can transform them into productive discussions that have lasting, positive impacts. Here’s what the DESC model stands for:

  • Describe the dilemma (D): State the observed behavior or issue clearly.
  • Explain the effects (E): Share how the behavior impacts you, the team, or the organization.
  • Specify solutions (S): Collaboratively brainstorm possible solutions or adjustments.
  • Consequences (C): Agree on next steps and mutual accountability.

For the scenario involving the employee, Jack, using the DESC Model to give feedback during a difficult conversation may look like:

  • D: “While we highly appreciate your expertise and opinions, I’ve recently observed you monopolizing team conversations.”
  • E: “Your team members are more hesitant to contribute in conversations because you’re talking over them, and we’re unable to hear other valuable perspectives during our collaborations.”
  • S: “During our next team meeting, I’d love to see you ask others what they think or pause before interjecting with an idea to ensure the rest of the team has time to respond.”
  • C: “You are a valued member of our team, but we have others with valuable insights to offer, too. I want to keep hearing from all of you so our team can be as dynamic as possible. Please keep this in mind for our next meeting.”

Using this framework keeps the conversation objective, structured, and solution-oriented. 

 

Tips for Managing Emotions (Yours and Theirs)

Feedback can be hard to hear, and people can often become defensive even with the most well-intentioned and well-thought-out feedback. It’s important to manage emotions on both sides. 

A great way to do this is to actively listen. Don’t just prepare your response, but take their thoughts, feelings, and feedback into consideration as you have this conversation, without allowing them to dominate. Staying calm and professional is key, even if the other person becomes defensive or emotional during your discussion.

Final Thoughts

Difficult conversations don’t have to be destructive or overwhelming. They can be opportunities for growth, trust, and ultimately, stronger relationships. We encourage you to approach these moments with preparation and structure, yet also with empathy. 

If you are struggling with challenging conversations in your workplace, or if you’re seeking the skills to confidently handle them when they come, we are here to help. Contact us at info@bergerhrsolutions.com or 410-695-9888 to learn more.