Preparing for Tough Conversations

14.02.2019 |

Episode #11 of the course Mastering your conversations by Jordan Thibodeau


“I have several times made a poor choice by avoiding a necessary confrontation.” —John Cleese

Welcome to our final lesson!

You will come across situations in your life where you need to provide someone with feedback that you might not necessarily want to give and they might not want to hear. But if you hold back on having this conversation, you both will suffer for avoiding the problem. The ability to challenge someone and express your good intention is called Radical Candor. Unfortunately, people are too afraid to engage in Radical Candor because if the conversation goes wrong, you could ruin the relationship.


How to Be Radically Candid

First, you need to establish in the other person’s mind that you actually care about them and want what’s best for them. There is no way that you can quickly establish your caring right away: You need to build trust and demonstrate care over several interactions, covering a relatively long time period (as we learned in Lesson 8).

Second, you need to be honest and direct with this person. This could easily backfire, especially if you haven’t really established the caring aspect well in advance. Most people are too worried about that bad reaction, so they water down their feedback. You need to do the exact opposite: Trust in the relationship that you have already built with this person, and prepare to be completely honest in what you are about to say to them. Even if they get upset and don’t want to hear what you are saying, if they believe that you care about them, they will absorb what you are saying. They might need a day or two to cool down, depending on just how shocking your conversation is, so be prepared for that.


Why Does This Work?

It works because you actually tell the person what they need to hear in order to do what they need to do. The reason they haven’t done it already is because they either don’t know they need to do it or some other belief is holding them back from making necessary changes. Unlike most people, you actually care enough to take the risk, and their knowing that you care is why they will actually appreciate what you have to say. This is crucial: If they don’t think you care about them, then they will not absorb a difficult message from you.

Let’s imagine a combination of different possibilities—caring or not caring, honest or dishonest—as they play out in a conversation. These four possibilities are represented in the chart:



The vertical axis tells us how you feel about the person you are talking to. In the upward direction, you care about the person and want the best for them. In the downward direction, you don’t care about them and don’t mind if things don’t work out for them. The horizontal axis tells us how much you are committed to an honest dialog with the other person. To the right, you will tell the truth even if it’s hard. To the left, you will say whatever is easiest or whatever is best for you. Moving along those axes, up and down and left to right, gives us the four quadrants: four possible ways that you can relate to the other person in the conversation.

In the top left quadrant, you care about the person you are talking to, but you are not honest enough to tell the truth. This is Ruinous Empathy. You might be worried about how they will react, or you might want them to like you. Whatever the reason, you chicken out and water down the message. It’s easy to see why this won’t work: The person you are talking with will never know the truth, so they will never be able to take the right action, to make the right changes, etc.

Moving down to the bottom left quadrant, you no longer care about the person and you are willing to say whatever is best for you. That’s certainly not honest! This is Manipulative Insincerity. Because you are not worried about the other person and you are free to say any evil thing you like, you can tell this person whatever is necessary to get them to do what you want. Most people are going to see through this: They will sense that you don’t care about them and are not acting in their interest. They will ignore what you have to say or try to manipulate you in return.

Moving to the right but staying at the bottom of the chart, we enter Obnoxious Aggression. In this quadrant, you still don’t care about the other person, but at least you are being honest. Here, you tell the person everything they really need to hear, but there is no way they are going to take it well. They know you don’t care about them, so they can’t trust you. You might be saying things to manipulate them, or you might be saying things just to hurt them. In fact, whatever you are saying probably will hurt them, but that’s not the worst part. The worst part is that they won’t take what you say to heart, so they won’t benefit from it, even if what you are saying is actually what they most need to hear.


Run a Simulation

Before you engage in radical candor, you should run a simulation in your head to imagine the possible scenarios for how the other person could react to your conversation. Imagine you’re having a conversation with them. Visualize where you both are and what you’re saying to them.

• What is their body language expressing?

• How are they responding to your message? What’s the pitch of their voice?

• How will they react? What would be a positive reaction? What would be a negative one?

• How would you respond to either scenario?

By running the simulation, you are now prepared to engage in radical candor.


To Do:

1. Think of a tough conversation you have been avoiding that could benefit from radical candor.

2. Run a simulation in your head where you imagine how the conversation will transpire.

3. Set up a time to speak to the person to engage in radical candor.

4. Special To-Do: At the beginning of this class, I asked you to start a Conversation Journal. Based on what you learned from this entire class, review your past conversations that were bad, and see which tools from the class you could have used to make them better.



If you enjoyed this course, consider enrolling in another! Here are two of my courses that will expand upon the conversational skills you have just developed in this class:

Building a network for success

Bouncing back from failure

Finally, if you would like to give me feedback on this course, be added to my newsletter for supplemental course material, or be notified about my upcoming courses, please visit

Jordan Thibodeau

Conversation Mentor


Recommended book

Radical Candor: Be a Kick-Ass Boss without Losing Your Humanity by Kim Scott


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