How to Master the Art of Having Uncomfortable Conversations

“A person’s success in life can be measured by the number of uncomfortable conversations he or she is willing to have.”   – Tim Ferris

I bet you have something in you that needs saying. There’s an issue that’s been going on for years and you’ve dealt with it because you can’t bear to have the conversation that would make it stop.

I understand that apprehension, but I’m here to tell you that that isn’t the way. What goes unsaid can drag you down your whole life. Here are some examples of what I’m talking about:

• Someone is treating you poorly and you want them to stop.
• Your partner is doing something you don’t like and you can’t express how you feel.
• You feel like you’ve earned a raise at your job but you still haven’t gotten it.
• You feel that your friend is destroying their life but you don’t have the heart to tell them.
• You want to admit that you love someone, but you don’t know if they’ll feel the same.

All these scenarios involve confrontation, and that can be scary for an empathic person. I’m going to lay out some strategies you can use to make these conversations easier, have them more often, and get the things you want. But first…

Why Uncomfortable Conversations Are So Uncomfortable

Every uncomfortable conversation you have will involve vulnerability.

As in, you are making yourself vulnerable to rejection, ridicule, anger, and harm by speaking what you believe to be true, and stating exactly what it is you want. This can make even the toughest people shudder.

There is as much potential for pain in vulnerability as there is for victory and deeper connections with other people. It’s a bold risk, and it always will be. Risking your body or health is one thing, but vulnerability is risking your soul.

Most uncomfortable conversations are, at their core, a negotiation. According to FBI hostage negotiation expert Chris Voss:

Everything in life is negotiation. … If you want somebody to say yes to anything, you’re in a negotiation. If somebody is trying to get you to say yes to something, you’re in a negotiation. If you say, I want or you think I need, you’re in a negotiation.

This isn’t about brutally convincing someone to do what you want either. It’s about collaboration:

The person across the table is a counterpart that’s struggling with some aspect of the same problem that you are. You work with them and solve that problem together, and you’re both better off.

The better you get at being vulnerable, and at negotiating, the more you will get what you want out of life. You will be able to say what you need to say when you need to say it. Sometimes that’s all you have to do.

When you do finally speak your truth, it might get ugly. But you know what? You can handle ugly.

Strategies For Successfully Having Uncomfortable Conversations

Sometimes it’s about getting what you want. Other times it’s about helping someone out. Either way, you need to take the leap. Here are some tips:

Plan Out Exactly What You Want to Say

You need to be clear about what you want. You need to back up what you have to say with concrete reasons. You need to be able to tell someone exactly how you feel, and why. Draft out what you want to say beforehand.

Plan Out the Worst Case Scenario

What’s the worst that could happen? Does she reject you? Do they get mad at you? Do they judge you? Will any of these experiences kill you? Going in knowing what the worst outcome could be, and knowing how you’ll respond, will give you an edge.

Do It In Person

Ideally, these conversations wouldn’t be had through text, email, or voicemail. You would carve out some time to sit down with someone and look them in their eyes. You want it to be as real as possible. That will have the most impact.

Be Straight Up; Don’t Hesitate

This is tough, but when you’re in the conversation, don’t waste time. Don’t give too much preamble. State your case honestly, and directly. Try to maintain confident body language, and wait for their response.

To Start the Conversation, Say, “Hey [Name], I need to talk to you about something.”

It’s simple and direct. It conveys how serious you are. This conversation matters to you, so you need to be the one who makes it happen.

Empathy Wins

You can learn everything about body language cues, conversational tells, eye contact, or anything else, but the only way people will listen to you is if you listen to them.

Hear them out, understand their perspective and acknowledge it. It’s the only way to get through to anyone.

The more uncomfortable conversations you have, the better you get at being honest about what you want. You need to negotiate to be satisfied in life. If you run, you end up nowhere. The goal is to get as good as possible at making your needs known, no matter how uncomfortable it feels.

The Potential Benefits

One uncomfortable conversation can change your whole world. It can lift burdens you’ve been carrying for years off your shoulders. You can find solace, acceptance, and peace knowing that you’ve expressed what was burning up inside you.

You could find love. You could find respect. You could stop wasting time. You could make someone realize how badly they’ve been fucking up, and they change their lives for the better.

You could earn more money. You could reconnect with old friends. Your relationships could become richer and more transparent. You could talk to anyone about anything.

What you hide will fester. What’s pushed to the background could quietly damage everything, but usually, it’s just you who suffers. You’re the one whose needs go unfulfilled. You’re the one who gets the short end of the stick. And before you know it, your life is over.

So please, for the love of God, say what you need to say, and say it as soon as you can.