How to Manage Difficult Work Conversations

It’s a part of the job many of us dread. Having a difficult conversation at work can be, well, intimidating. Whether it’s about delegating a problem between a manager and employee, addressing performance issues, or even letting someone go, these conversations can be the most taxing and stressful tasks for HR professionals. While there’s no way to make them pleasant, we have a few ways to make these conversations productive and respectful.

1. Organize Your Thoughts Before You Request the Meeting

Knowing the points you want to make before any conversation begins can keep a difficult conversation from becoming too emotional. Plan out, in writing, what you want to say before you even reach out to the person or people. This will give you a handle on the situation from the beginning.

2. Plan for Possible Responses

While planning the conversation, consider what responses the other parties may have. What questions might they ask? What would your reaction be if someone cries or flies off the handle? Even though more extreme reactions are unlikely, you’ll feel more confident going into the meeting when you know you’re prepared for anything.

3. Offer Choices When Possible

In other words, don’t ambush the individual or people in question.1 Ask when a good time would be to talk about the feedback you would like to share if not now. This way, employees have a chance to control the setting and are less likely to feel put on the spot. Also, by keeping the current time available, employees can address the issue now if they would prefer, so they don’t have to agonize over it.

4. Get to the Point

During the meeting, it can be tempting to walk around the bad news or negative feedback, but when you stretch out a hard conversation with small talk or empty praise, you’re making the news more painful.2 As Ashira Prossack at Forbes points out, people usually know when they’re about to receive distressing news, so you’re not doing anyone any favors by not getting to the point. The longer you go on, the more anxious and defensive your audience becomes.

5. End the Conversation Carefully

Make sure to give others in the conversation a chance to ask questions. Be explicit about what the next steps are and how you will follow up, if applicable. (Later, make sure you follow through on what you said you would do.)

By preparing and being candid, you can make a tough talk productive.

In the comment section below, please let us know what has helped you manage a tricky conversation with your employees.


1. Susan M. Heathfield, “How to Hold a Difficult Conversation with an Employee,” Balance Careers, January 15, 2019, https://www.thebalancecareers.com/holding-difficult-conversation-employees-1918468.

2. Ashira Prossack, “How to Have Difficult Conversations at Work,” Forbes, October 28, 2018, https://www.forbes.com/sites/ashiraprossack1/2018/10/28/how-to-have-difficult-conversations-at-work/#5b57efdd10b7.

Stop dreading and start planning: Here’s how to manage difficult work conversationsAre you prepared for any reaction?Here’s what to do when you’re the bearer of bad news.We can’t make it fun, but we can make it productive: Here’s how to handle a difficult work conversation.