How to Have Difficult Conversations

See also: Communicating in Difficult Situations

Most of us have difficult conversations from time to time.

Negotiating a raise or telling your boss you’re quitting are both difficult, as is firing an employee.

Asking someone to repay money they owe you or asking to borrow money are both difficult.

Talking about illness, politics, and divorce can all be hard too. Sometimes a conversation is difficult because you’re disappointed in the other person, the outcome, or yourself.

No matter what difficult conversation you need to have, there are some ways to make it easier.

1. Don’t Put it Off

Most people are conflict avoidant. It makes sense, who wants to fight? However, when you put off having a difficult conversation you actually make it much worse. For one thing, your own stress and discomfort grows. This means you’re more likely to say something you don’t mean, or say it in an uncomfortable way. It’s also possible that the situation could get worse while you’re waiting to say something. Imagine you have an employee who isn’t doing well. By not telling the employee that there are problems, you are taking away their ability to improve. They may assume everything is fine and continue making the same mistakes. If you must have a difficult conversation, take the time you need to make sure you know what you want to say, but don’t put it off too long.

Keep in mind that what you see as one difficult conversation may actually need to be a series of conversations. The longer you put off starting the conversation, the longer it will last.

2. Practice

One of the reasons difficult conversations are so difficult is because they’re unusual. Doctors have a much easier time giving bad health news than lay people because they do it so often. If you have to have a difficult conversation, take a little time to think about what you want to say. You can even make notes or role play with a friend. You don’t want the conversation to sound too rehearsed or stiff, but taking the time to think about what you’re going to say, and how you’ll say it, will make the conversation easier on you and the listener.

Of course, many difficult conversations come as a surprise. For example, an upset customer might call with a serious complaint that you can’t fix. You can’t rehearse for these kinds of conversations, but you can prepare for them.

3. Be Clear

Standard management advice used to be to first give a compliment, then give the criticism. Unfortunately, this leads to a lot of misunderstandings. If you’re having a performance review, you should absolutely tell your employee what’s going well and what’s not going well. However, if you’re trying to tell an employee that their job is in jeopardy, you need to be clear. State what you need to say clearly, and ask questions to make sure the other person understands. Do not try and soften the blow with extraneous information.

4. Focus

Multi-tasking has become a way of life for most of us. But the last thing you want when you’re having a difficult conversation is for the other person to feel like you’re too busy for them. Set time aside to have the conversation and make sure you aren’t looking at your phone or checking your email. Focusing can be especially difficult when you’re having a conversation over the phone and cannot see the other person. It’s natural to not want to see someone get upset, but if possible, try and have difficult conversations in person, over Zoom or other video conferencing. If you’re meeting in person, find a quiet, secluded place where the person won’t feel like they’re on display. If you have to meet over the phone, do what you can to stay focused on the conversation. If you feel like the other person may not be fully listening, make sure to ask questions.

5. Practice Active Listening

A conversation isn’t just about talking, it’s also about listening to the other person. Active listening is often used in solving disputes or conflicts. The idea is that the listener fully concentrates on, understands, responds and remembers what the other person is saying. It sounds easy, but too often when we have difficult conversations, we spend our time focusing on what we’re going to say. As this article describes, active listening can be very helpful in processes like salary negotiation. If you’re trying to negotiate for a higher salary and your boss explains that the organization is losing money, you’ll want to use arguments about your productivity and the ways in which you save the company money. On the other hand, if your boss rejects your request because you’re new to the company, you may want to make a different argument.

How someone feels about a difficult conversation often depends on whether or not the person feels heard. If you can repeat back to someone what they’re upset about, it can help them feel heard. It’s important to remember that while you’ve had time to think about what you want to say, the conversation may be a surprise for the other person. Give them time to react and ask questions. Everyone processes difficult news differently. Some people may have a lot of thoughts as you’re talking. Others may want to wait and discuss the issue with you again later.

6. Be Empathetic

Empathy is the act of putting yourself in someone else’s shoes. At the end of the day, the only real rule for giving someone bad or unwelcome news is to be empathetic. To try and see the situation from their point of view. Approaching a difficult conversation not just as something that you have to get through, but as something that’s difficult for both parties will keep you respectful.

There’s an old saying that people don’t remember what you do, they remember how you make them feel. It’s easy to make someone feel good, respected, and heard when you’re sharing positive news. Making people feel respected and heard when sharing difficult news is a more important, and much less common skill.

Further Reading from Skills You Need

The Skills You Need Guide to Interpersonal Skills eBooks.

The Skills You Need Guide to Interpersonal Skills

Develop your interpersonal skills with our series of eBooks. Learn about and improve your communication skills, tackle conflict resolution, mediate in difficult situations, and develop your emotional intelligence.

About the Author

Boris Dzhingarov is a passionate blogger. He is the founder of