23.07.2021 |

Episode #10 of the course Mastering your conversations by John Robin


Welcome back!

In yesterday’s lesson, we covered the three degrees of difficult conversations. We’ve covered so much ground already in this course!

So far, we’ve learned:

• How to be a good listener, by considering yourself the least interesting person in the room (lesson 1)

• How to read body language, to know if your conversation is moving forward or if you should wrap it up (lesson 2)

• How to achieve balance in a conversation, by way of the conversation pillow technique (lesson 3)

• The substance of a good conversation, by way of making yourself more interesting, telling your stories, being prepared, and how to like, learn, laugh and appreciate (lesson 4)

• The four communication styles, and ways to learn when you’re being too passive, too aggressive, or passive-aggressive (lesson 5)

• How to be authentically assertive, by way of the points of reframing bullet list (lesson 6)

• How to navigate arguments, by enacting the “I might be wrong” negotiator (lesson 7)

• How to give criticism, by recognizing passive-aggressive gossip and instead filtering out objective truths to be delivered respectfully to the other person (lesson 8)

• How to deal with tough conversations, be it changing the topic quickly for those detailed minutiae, becoming passive-conservative for those complaints and rants, or tactfully addressing the elephant in the room (lesson 9)

By now, you’re ready to be a conversation master, and I’m happy to send you on your way. But before we go, there is one topic that completes your tool kit of conversation skills, so let’s dive right in!


No-Win Conversations

Yesterday, when we discussed the “complaining and ranting” degree of difficult conversations, we saw that sometimes there are conversations that are just not worth your emotional energy. While it’s tempting to think that, with the right skills, you can bring around even the most doomed of conversations, the truth is, sometimes, the conversations we have are symptomatic of a deeper problem, such as an unhealthy relationship.

I call these “no-win conversations” because they exhibit a pattern you see time and time again.

This includes one or more of the following:

• The other person is verbally abuse

• The other person is intimidating

• The other person has repeatedly disrespected you in past conversations, even when you try to be assertive

• The other person is emotionally wearing

One goal I’ve returned to throughout this course has been how to develop better assertive communication. But respect is a two-way street.

Being assertive requires that the other person also is assertive. That requires a specific language that helps you prime each other:

• You use “I” words, helping them hear what you think, and how you feel

• They use “I” words back, cued by your willingness to be vulnerable

When the other person uses “I” words back, and shares their feelings, that confirms to you that they are respecting your vulnerability.

This finally takes us back to lesson 4 where I mentioned how to resolve your passive-aggressive weak spot. If you feel yourself continually disrespected, and unable to speak your mind because of the above problems, then you might need to take a tougher tactic, such as what we’re about to cover.

Take a moment right now to think of the relationships you value most. These are relationships with people who you’ve learned to trust over time—over many conversations—who you enjoy spending time with.

Think about the way you communicate with these people. Do you often use “I” words and communicate feelings with them? Do they respect your feelings? Do they listen to you just as avidly as you try to listen to them?

Think of these people as your assertive circle. This is the circle of relationships where you feel most comfortable to be assertive in your conversations.

Now, they’re not perfect. Many relationships in my assertive circle sometimes shift to aggressive, passive, or passive-aggressive moments. That’s because I’m not perfect—and they aren’t either. However, I’ve always found in these relationships that, when I’ve been able to recognize one of my communication weak spots flaring up, it’s not too difficult to shift to an assertive conversation where I feel I’m on the two-way street of respect.

It’s worth taking out a piece of paper and writing down your assertive circle. Who’s in it? Who’s not?

The latter group of people will be the focus of our tip of the day.


Tip of the Day: Creating Endships

Take a look at that assertive circle and you’ll likely see people you consider friends. Even if they are family, the label “friend” simply means this is someone you enjoy spending time with, whether or not they are related to you.

Now, consider those people outside the assertive circle. Now you can create a label for these relationships: Endships. These are friendships you have chosen to end.

If you have found yourself feeling obligated to consider these people your friends, but the relationship is continually disrespectful, and you are always feeling drained, then you are entitled to no longer think of them as friends. If you find your passive-aggressive weak spot is at its worst with these people and you feel like a loaded spring ready to let loose on them, then consider this too when deciding if you should label the relationship an “endship”.

This does not require that you tell them you don’t want to be their friends anymore. It simply requires that you label the relationship with them an “endship”.

When this label goes here, you will now intend to:

• No longer commit yourself to spending time with them

• Absolve yourself of any guilt you may feel for not spending time with them

• Not gossip about them

If you’re worried that this “endship” label might be a mistake, don’t worry. If you’ve made a mistake, you’ll recognize it. Sometimes people do change.

However, it is not your job to change someone, especially when they continually disrespect you. Instead, focus on the richest relationships in your assertive circle, where all the communication tips learned thus far can be put to their best use.

And that’s a good way to wrap up our course. We have covered so much ground on how to master conversations. This course has given you the tools, so now it’s time to put them in action. I hope I’ve inspired you to both realize your power to become more assertive and deepen your assertive circle by way of the conversation skills we’ve shared. I hope you’re feeling encouraged as you try some of the techniques for handling difficult conversations, avoiding arguments, giving criticism, and learning how to handle the conversation pillow like a pro.

I love hearing from my students. If you have any requests for future courses, or questions about this one, please let me know. Many of my best course ideas have come from these email conversations with students!

Reach out to me at:



Recommended book

Never Eat Alone: And Other Secrets To Success, One Relationship At A Time by Keith Ferrazzi


Other courses by John Robin

Browse courses


Share with friends