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Career Tips

How to have difficult conversations at work

by ACS Careers
January 30, 2021 | A version of this story appeared in Volume 99, Issue 4


An illustration of two people talking, with a speech bubble containing scribbles above them.
Credit: C&EN/Shutterstock
The hardest part of having a difficult conversation is starting it.

Some things are hard to talk about—delivering bad news, coaching an employee on how to improve, or responding to an inquiry from an angry customer. In these situations, there is often an inclination to ignore the problem and hope the situation will resolve itself. But it rarely does; in fact, putting it off usually makes the situation worse. Sometimes you just have to have a difficult conversation. These tips can make it a bit easier.

Be prepared. Decide what information you will share and what information you want to keep private. Do you want to indicate that you have a “family issue” or “medical condition” and keep the details private, or do you want to share more specific information? You want to focus on the conversation, which is hard to do if you are emotionally upset. Think through what concerns or objections the other person may have, and decide how you will address each one. Determine ahead of time what needs to happen by the end of the conversation. Do you need agreement with your plan of action, a choice between several possible plans, or just a plan to make a plan?

Choose the people. Give some thought to who is the right person, or people, to have in the conversation. If there are others who could have the same issue, discussing it with the group might be helpful. If you’re not sure, you may want to speak privately with a few of them first and determine their situations and intentions.

Ask permission. Don’t jump into the conversation; instead, ask for permission to have it. Let the other person know you have something important to discuss, and set a time and place where you will not be disturbed. Make sure you are physically ready (not hungry, tired, or otherwise distracted) and that you are really ready to listen. Enter the conversation with a positive attitude. Use active listening techniques, like paraphrasing their comments, so they know you understand.

Be clear. Deliver your message clearly, simply, and succinctly. Be specific, and don’t assume the other person will understand things you leave unsaid. State the situation and offer possible solutions. You can provide facts and describe how those facts make you feel, but do not assign motives to other people or interpret their actions.

Allow time. While you may have been thinking about this issue for a long time, it may be the first time the other people you’re talking to have considered it. Give them time to assimilate the new information and come to terms with it. They may be angry or defensive or just quiet. You may need to set another time to continue the conversation later. Make sure to follow up, even if it’s not with a scheduled talk. If you had action items, update the other parties on how yours are going. If they had action items, wait a reasonable amount of time, then ask them how they are doing.

No matter how much you want to avoid it, you will always have to have difficult and unpleasant conversations. By planning and making the experience as positive as possible, you can get through the hard times and move on to the better ones.

Get involved in the discussion. The ACS Career Tips column is published the first issue of every month in C&EN. Send your comments and ideas for topics for future columns to


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