How To Have Difficult Conversations

How many times have you avoided someone or a topic because you know there is a difficult conversation you have to have? Odds are you can think of at least one difficult conversation in your life that you are currently avoiding.

What makes a conversation difficult? Maybe it makes you feel mildly uncomfortable, maybe it’s something you are sure will start a fight, or maybe it’s something that will make you seem vulnerable to someone else. Whatever the reason, you’re avoiding it. Unfortunately, difficult conversations are often the most needed and they won’t start without a little effort. If you’re struggling to prepare for a difficult conversation or aren’t even sure how to start preparing for one, here’s a list of ten “Dos and Don’ts” for difficult conversations:


Do plan what you’re going to say

Write it out like a script, say it out loud to the mirror, and figure out what wording feels most natural and comfortable for you. This also gives you the chance to write out everything you’re thinking and feeling about the situation and then make heavy edits until you find what you actually want to say to the other person.

Do stay on the same eye level

Watch your body language during the conversation: being at different levels (sitting vs standing) will inevitably make one person feel like they are being loomed over or looked down on. During the conversation you will want to make sure neither person is physically feeling cornered, as that will send signals to their brain to trigger the flight-or-fight response and will make it more difficult for the conversation to be truly productive.

Don’t assume you know what the other person will say

People can surprise you! Keep an open mind and go in both hoping for the best-case result and prepared for the worst. Everyone has different perspectives and motivations, and unless you are a mind-reader (you’re not) you don’t really know what is going on in anyone else’s head.

Don’t blame

Difficult conversations are not the place to point fingers or assign blame. It isn’t productive, and puts everyone on the defensive as they try to explain all the ways the blame belongs to someone else. Leave the blame in the first draft of your conversation script that you end up throwing into the trash.

Do avoid high-emotion language

People begin to shut down or discount arguments or ideas when the speaker becomes emotional, as they no longer appear to be coming from a place of logic at that point. High-emotion language, such as “always,” “attack,” “never,” or “abandoned,” brings emotions to the forefront of the conversation and can easily muddy the water of the conversation. Keep the conversation clear and to the point and avoid using words that are too strongly emotional.

Don’t interrupt

Give the other person the chance to say what they need to say, and make sure they know to give you that same courtesy. Interrupting leads to talking over each other without either person getting heard by the other, which really doesn’t help anyone or resolve anything. Take turns speaking and responding to each other without cutting each other off.

Don’t focus on being “right”

Go into the conversation with the goal of problem solving. There’s a reason you’re having this conversation and not just letting it slide. Whatever the reason, the goal of the difficult conversation is to reduce the need for more difficult conversations in the future. How can you and the other person work together to improve the situation? This may mean compromises need to be made. Know your own limits and what you are and aren’t willing to meet them in the middle on.

Do keep to the topic at hand & be specific

This is not the time to air every grievance you’ve had with the other person over the last 20 years. It also isn’t the time to use sweeping generalities. What specifically are you looking to address with the other person? Name the specific times this issue came to the surface in your interactions. This will give more credibility to your statements and will keep the conversation from becoming a dumping ground of every bad feeling you have.

Don’t walk away without the other person’s agreement

Agree on time outs. Give yourself the chance to say “Can we pause this conversation for five minutes?” when you both are getting too heated or are no longer able to listen to each other effectively. Use those five minutes to use the bathroom, get a drink of water, and take a breath to center yourself again before returning to the conversation. Don’t let the breaks get too long, though, as a long break makes it tough to get back to the conversation.

Do make sure you understand what they said before you respond

Ask for clarification during the conversation if you’re starting to feel lost or confused. Reflect and repeat back what you heard from them to make sure you understood correctly, and then respond to what they said. Fully listen when they speak rather than waiting for them to finish so you can continue on your own thought without considering what they added to the conversation. All of this will make the other person feel heard and help to keep them open to having the difficult conversation. 

If you’re struggling to work up the nerve to have a difficult conversation, having a hard time not letting your strong emotions leak through, or want to practice your side of the conversation before it happens for real, counseling can help! Counseling can also be helpful if you find you always leave a difficult conversation feeling even more upset, disappointed, or dismissed. Counselors can help you figure out where the conversations are going wrong and how to get them back on track while the conversation is happening rather than days later.

Difficult conversations may seem extremely overwhelming and terrifying, but with preparation and practice they become a lot less scary. With a little time, you’ll wonder why you took so long to have the conversations you need to have.

About Michael Hilgers, M.MFT

I’m a Licensed Professional Counselor working remotely with clients around the world. I believe that everyone has the potential to change; to create new paths, to go in new directions. Life is hard. Counseling can help.

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