How to Start a Difficult Conversation

You might think that successful, charismatic business leaders who talk to people every day can speak to anyone about anything. They appear to confidently start conversations with their employees about poor performance, their customers about the realities of their complaints, and their spouses about an annoying situation that never seems to change.  

Well, appearances are one thing. Reality is another. 

Many intelligent, communicative, and successful people struggle with finding the right words to start those interactions. They know what they want to talk about, and they have strong opinions on the topic. But getting started? That's a whole other ballgame. 

Why is initiating a difficult conversation so hard?

Many of us struggle to start a difficult conversation because we're afraid of saying the wrong thing. We feel as if we have only one opportunity to get our point across. What if it doesn't go well? Then what? This fear leads many people to avoid difficult conversations altogether. Others want to initiate the conversation but struggle to find the right words. 

In both situations, it's easy for people to get stuck in a negative cycle of delay, avoidance, and silence. Even the most successful among us, those who are articulate and friendly, fear a difficult conversation escalating into a confrontation. But instead of focusing on your fear of conflict, focus on your need for clarification. 

Difficult conversations are essential. If you can't initiate an interaction, you can't fully express your needs, wants, and concerns. You won't resolve any of the problems, issues, or feelings you are having if you don't share what's on your mind. And you certainly won't get the clarification you need to move forward.

The one thing to remember before you start a difficult conversation. 

What is your purpose for initiating this conversation? What do you hope to accomplish? What are your intentions?

Most often, when you are starting an interaction with someone, you are seeking to connect with them, either because you care about them or simply want to be heard. In essence, your goal is to have a productive conversation. By sharing your intentions at the start of the conversation, you can reassure the other person and set the stage for a fruitful discussion. 

In my communication model, the Relationship Protocol, I recommend three phrases you can use to start a potentially difficult conversation:

  1. "I want to get along with you." 
  2. "I don't want to fight with you." 
  3. Or, on a more personal level, "I want to be closer to you."

Once you've shared your intentions, you can set the stage for what comes next. For example:

  • "I have a lot to say, and I'd appreciate it if you could let me finish first, and then I'd be glad to hear what's on your mind."  
  • "I know we both want to get along better. I don't want to argue with you or make you feel defensive." 
  • "I'm not sure how to say this, but I wanted to talk to you about _______. Would you mind?" 

Don't let not knowing how to start a conversation be the reason you remain silent. The examples given above provide you with a good starting place. Modify them to suit your situation and your way of speaking. Be authentic.

If you can't say what's on your mind, then you're not fully taking care of yourself. Your ideas and feelings are as important as the other person's. But unless you find a way to say those words, they will never know what's going on.

And you might mess up. It happens. You can't control the other person's response, but you can control how you approach the conversation. So go in with a good attitude, share your intentions from the beginning, and plan what you want to discuss. You'll have a better chance at a successful outcome. Give it a try!


©Copyright 2022 Debra Roberts, LCSW All rights reserved. No portion of this material may be reproduced without permission from the publisher.

A version of this article was initially published on as: The 1 Thing to Remember Before You Start a Difficult Conversation