Difficult conversations usually mean bad news for at least one person, and they affect both the teller and the receiver of the news. Both people in the person the conversation experience a variety of emotions, including regret at having to speak, relief at getting the conversation over, and unhappiness at the result. How do you start a difficult conversation, how do you get through it, and what do you do if it doesn’t go as you expected?

How Do You Start a Difficult Conversation?

Before you begin a difficult conversation, make sure you are clear in your own mind why the conversation is necessary and what you hope to accomplish. In the midst of the conversation, your emotions may get in the way of obtaining a result that actually matches your goals. 

For example, if you speak to your boss about getting a raise, you should make the case based on your contribution to the company, not on your need for money. If your emotions side-track you into the reasons why you need money, you may find the conversation devolves to a lecture on money management and alternative sources for cash, not on the possibility of a raise.

Hedging around a difficult conversation makes it more difficult. A direct, specific statement is best, one that you can deliver without putting your own emotions first. You may need to rehearse the words, as well as your gestures and facial expressions. 

For example, if you need to fire someone, do not begin with a list of all the errors they made or with all the reasons you wish you could keep them on. Begin with the statement that they are being laid off and go from there. If you feel the need to apologize, do so once with a simple “I’m sorry”; the rest of the conversation belongs to the person being laid off.

Be self-aware enough to understand that you may have contributed to the situation that led to the difficult conversation or that the other person may feel that way. You cannot take responsibility for the other person’s feelings but do not assume you are blameless and beyond reproach.

How Do You Get Through a Difficult Conversation?

Difficult conversations are best held face-to-face, in person or if necessary through video conferencing. When the conversation affects an entire group, the group should be broken up into as small units as possible to allow time for the group to react to the news together. Buried, simmering resentment or unhappiness quickly saps morale and resiliency.

Active listening helps a difficult conversation end as well as it can. Each person allows the other(s) to speak and truly listens, with focus and concentration on what the other(s) are saying. 

Active listening may not reduce tension between the parties—bad news is bad news—but it conveys respect for the other person and a willingness to find a mutual solution, if one is possible. Further important information may emerge, and misunderstandings about the conversation or the circumstances that prompted it can be corrected.

When practicing active listening, be careful of avoiding merely parroting back what has just been said or riding over the other person with platitudes like “I see” and “I understand.” Some conversations cannot go beyond the listening stage, but others can move on to action: now that the situation is understood by both parties, what happens next?

What Do You Do If the Conversation Doesn’t Go as Expected?

Sometimes one or more persons in a difficult conversation may have difficulty expressing their reaction in the moment or at all. They may feel a need to revisit the conversation and that should be allowed when appropriate.

At some point, a conversation cannot be re-adjudicated. If you are the person who received the bad news, you might want to purge your emotions and thoughts in writing, without necessarily sharing what you write. Be careful of any language you use, crossing over into harassment, bullying, or stalking either in person or online. If you cannot recover from a difficult conversation, you may need to ask for help in conflict resolution and managing your feelings.