How To Manage Difficult Conversations At Work

Difficult conversations, from poor performance reviews, to reprimands, to terminations are an inevitable part of running a business. These conversations aren’t just hard for the employee, they’re hard for management and HR alike! Preparing in advance is the best way to help make sure that a difficult conversation goes as smoothly as possible. Sharing their best tips on handling difficult conversations are HR Business Partner, Belinda Dantin, and HR Generalist, Danielle Duvigneaud. 

Difficult Conversation Preparation

Preparing for a difficult conversation is key to making the process run smoothly, and can help you be more calm during the actual conversation. Making sure you are ready for the conversation ahead of time helps to take the pressure off of the day, and makes sure you have all of the tools and documentation necessary to have the discussion go smoothly.

Questions You Should Ask Before The Conversation

To ensure that you’re going into the conversation with the right intentions, that you’re not being reactionary, and to ensure that the conversation ends appropriately it is important to ask yourself the following questions.

  • What are the facts that lead us to needing this conversation?

  • What is my objective in this conversation?

  • Does the other person have a different objective?

  • Do I have any assumptions about this person or problem?

  • Am I being fair and consistent? Would I have the same conversation with another person if they made the same mistake?

  • What may the other person’s reaction be? Will they be surprised?

  • How would I want to be treated, if someone were having this conversation with me?

  • What outcome am I hoping for? And what other outcomes may arise?

  • What solutions can help solve the problem, or help to arrive at the desired outcome?

  • Do I need to call in a witness for this conversation?

Documents And Procedures To Prepare In Advance

To prepare the appropriate documentation, you need to know the purpose of the conversation: is this a termination after previous warnings? Or is this a formal reprimand? 

For a formal reprimand, or other non-termination discussions, make sure to prepare yourself with talking points, the offence that occurred, any previous offences, and any other relevant information regarding the problem like emails, text messages, and so on. It’s also important to have a copy of the policy that has been violated. 

You should have duplicates of all of your paperwork, one for you, and one for the employee to review. Danielle recommends that “you should present the employee document for their review at the beginning of the discussion to digest the information. The document should contain the people present for the conversation, a description of the matter, the action being taken against the employee, preferred goals/corrective behavior, and a space for employee comments. Everyone present for the discussion should sign the document, as well.”

A termination discussion will require the same information regarding the offence. In addition you will need to work through a termination checklist. Belinda says “Information that should be provided at the point of termination include expectations of final pay, benefit timelines and COBRA notice. A separation notice or letter should have all of the pertinent information mentioned above on it as well as an area for the employee to sign and acknowledge the termination.”

How To Emotionally Prepare For A Difficult Conversation

There is no denying that difficult conversations are emotionally draining for both parties. Acknowledging in advance that this conversation could bring up feelings of disappointment, anger, frustration, fear, and more is important! Danielle says “It’s important to acknowledge your emotions prior to the discussion and ensure you leave them at the door.”

Before the conversation, have a check in with where you are emotionally and mentally. Danielle recommends practicing being mindful: having an open mind will help you to remain receptive and empathetic. 

It’s also important to remember that you set the tone for the meeting, so bringing in a calm, respectful, but serious presence is key. Belinda tells us to “be cognizant of your body language and how you present yourself to the other person, and ensure you set boundaries for the discussion.” At the end of the day, it’s not personal. Make sure you stick to the facts and avoid assumptions to help you get to the bottom of the situation.

Do I Need A Witness?

Not every difficult conversation will require a witness. However a manager or direct supervisor, and HR Professional should always be present when the discussion is regarding policy violations, behavioral issues, or disciplinary action.

Ending Your Difficult Conversation

Throughout a conversation it’s important that you are listening with the intent to understand the issue. Make sure to acknowledge that the person has been seen and heard, and take pauses in the conversation when appropriate. Although pauses may feel uncomfortable, it’s important to give both parties time to process the conversation, and review paperwork if necessary. 

When you are ending a conversation with an employee who is not being terminated, you should share your takeaways to make sure you have a common understanding of what happened, and the process moving forward. At this point you and the employee should sign off on any necessary paperwork, or if this was a timely verbal reprimand an email should be sent recapping the discussion. 

After The Conversation

For employees that have been reprimanded, the conversation can’t simply be over at the end of your meeting. Continuing the conversation is necessary to ensure that the problem is resolved or the behavior rectified.

Managers should check back in with the employee within a week after the reprimand. Use this time to ask open-ended questions that can allow the employee to expand upon what they said in the previous conversation. Danielle says “This aids the employee in feeling supported and typically contributes to a higher chance of improved behavior.”


Navigating difficult conversations isn’t easy! An HR professional is highly equipped to work through challenging conversations, and ensure they’re done appropriately and legally. HR NOLA can help your business work through difficult conversations, and can help train management for handling difficult conversations. Contact us today to set up a consultation and find out how HR can boost your business!

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