Difficult Conversations at Work: A Guide for Supervisors

Management can have great rewards and great challenges. Handling a difficult conversation—delivering bad news or discussing an uncomfortable subject—is definitely one of the toughest parts of the job. It must be, or else why would so many supervisors go out of their way to avoid doing it?

Yet try as they might, the truth is that difficult conversations are inevitable in every workplace. However great your employees may be, as a supervisor you will eventually have to remind someone of the dress code or rules for tardiness, discuss a hygiene issue, deny a promotion or raise, or let someone go.

Evading these tough topics is not going to solve the problem.

The good news is that careful preparation can go a long way toward helping any supervisor master a challenging conversation.

Start by asking yourself a few questions:

  • What is the purpose of the conversation and the nature of the problem you’ll be addressing? Make sure you stay focused during the conversation. It’s often tempting to stray from the subject at hand as a way of lightening the mood, but that risks failing to ensure your message is heard.
  • What behavior changes are you hoping will occur because of this talk? It’s vital to make sure your employee understands exactly what he or she needs to do (or stop doing) going forward.
  • How would you like the recipient to feel about the message—and about you, the messenger? You can’t control someone else’s feelings, but how you deliver the message can have an emotional impact.
  • What facts do you have to support your position? Gather any relevant documents, such as a copy of the company handbook, and specific examples – dates, times, and emails.
  • What is the history of the problem? What has been done in the past to address it?

Answering the questions above before your meeting will help clarify your purpose, keep you on subject, and focus on the facts—all vital elements of managing tough talks successfully.

That said, there are several other do’s and don’ts to be aware of for handling these conversations. Keep these in mind:

  • Do consider the best time and place to have the conversation. There’s no magic formula—when and where depends on the specific circumstances. For example, letting someone go on a Monday may be insensitive, but waiting until closing time on Friday may not be much better. The point is, while there’s no perfect choice for your tough conversation, the options available should be carefully pondered beforehand.
  • Do conduct the meeting face-to-face. Difficult conversations should be in person whenever possible. Face to face is more humane, and it allows the supervisor to see important nonverbal cues. For example, a frown or roll of the eyes can tell you how the employee is processing the information and whether follow-up questions, such as “It doesn’t seem you agree with my last statement, do you?” or “Do you have anything to add?” are appropriate.
  • Don’t try to handle certain conversations alone. If the employee has a history of outbursts, for example, don’t hesitate to invite a witness to the meeting. Also seek support if the problem at hand is highly sensitive and/or could be pertinent to current or future legal action.
  • Don’t get into a debate. Addressing the issue shouldn’t entail arguing the facts with the employee. It’s entirely possible to be a good and respectful listener without participating in an unproductive back and forth.
  • Do be direct. Tact is a must, but there’s nothing good to be gained by beating around the bush. If an employee has a hygiene problem, be specific. They may be unaware and it might be the sign of a serious health issue. Use phrases such as “This is going to be a difficult conversation.” The goal of the conversation is to make the employee aware of the problem so that he or she can be a part of the solution.
  • Do keep it professional. Restrict the conversation to the employee’s performance and stay away from conjecturing about the employee’s motivations, beliefs, thoughts, etc., which you typically can’t know. For instance, if the employee won’t be getting a pay increase because she hasn’t met her annual goals, there’s no need to mention that you think the employee is disorganized. For this conversation, focus on the “what” and not the “why.” That said, it’s okay to ask the employee how you can help.
  • Do remind the employee of available resources, such as your EAP. Remember, the EAP is there as a resource for you and your employees. Use your EAP to prepare for these difficult conversations.
  • Do be compassionate. Tough conversations are difficult for the supervisor, sure, but they’re even harder for the employee. Don’t ignore emotional responses by the employee; acknowledge them. For example, if an employee starts to cry, yell, etc., saying things such as, “Let’s take a break.” “Let’s push the pause button for a moment.” This gives everyone time to collect themselves and allows for the message to be shared and delivered.
  • Don’t forget to follow up. Be sure to check in with the employee a few days or so after the conversation to ensure he’s feeling okay and that whatever actions were decided at the meeting are being initiated.

Some conversations are always difficult, but if you prepare thoughtfully and focus on specific outcomes, while maintaining compassion for your employees, you’ll find the discussions going more smoothly and predictably over time. Having a successful difficult conversation help you to become a better supervisor. The final result should be a win-win leaving everyone feeling better. For more help or a deeper conversation, get in touch.

Post Written by

Senior Clinical Liaison

Meghan Stokes is an experienced licensed clinical social worker. A native of Washington County, MD, Meghan graduated from Western Maryland College (now McDaniel College) and earned a master’s degree from the University of Maryland School of Social Work in Employee Assistance Programs. In addition to holding the highest social work licensure, Meghan is also certified as a Clinical Supervisor and Field Instructor for undergraduate and graduate programs and has a certification in Critical Incident Stress Management.