Difficult Conversations

23.07.2021 |

Episode #9 of the course Mastering your conversations by John Robin


Welcome back to the course!

In yesterday’s lesson, we talked about how to give criticism. That completed our three-lesson tour on assertive conversation tips.

I want you to be fully equipped before I send you on your way, so for that reason, we’re going to turn to some advanced tips in the next two lessons. Arguments, criticism, and being honest, are all great, but there are still some kinds of conversations that are tough in and of themselves.

For that reason, our next stop on the path to conversation mastery is: how to deal with difficult conversations.


Three Degrees of Tough Conversations. Degree One: Detailing Minutiae

I like to think of difficult conversations in terms of degrees of difficulty.

The first degree usually shows up as a wrinkle in a conversation, often with a dominating speaker. I like to call it “detailing minutiae”.

Not everyone is a conversation master like the one you aspire to be. Often, when people talk to you, they might be getting a lot out of you emotionally. If you have a friend who lives in isolation and doesn’t get out much, then your visit with him isn’t just a chance to have a conversation—it’s a lifeline for a desperate connection.

The conversations you’ll have with this kind of person can feel one-sided. They will often go on way too long, in a disordered way, or go into way too much depth in a topic they’re interested in but you’re not. You’ll definitely notice there is a sharing pillow imbalance of some form or other. You might feel you are listening and being a good friend, but halfway in you start to feel like you are trapped.


First Tip of the Day: The “Changing Topic” Trick

You should first and foremost consider the feelings of the other person you’re talking to. Though you might feel trapped and annoyed at how they often wander off into alleyways of minutiae that lose you in the process, if you’re engaged in this conversation, there’s usually something you’re getting out of it as well.

Your goal then isn’t to get out of the conversation. Instead, it’s to change the topic, and get away from those detailed minutiae that don’t need to be there.

When you find yourself in a flood of minutiae and you simply don’t want to continue with this topic anymore—especially if this is the third time you’ve heard the same story—lead with something like, “Sorry to interrupt, but would you mind if I changed the topic? I really wanted to tell you about…” Or, if you’re with them for a defined period of time, try, “Do you mind if we change topics? We don’t have much time left and I really wanted to know…”

This is a great way to throw a bit of a curve ball in the conversation. It’s an assertive redirection, and not too abrupt that the other person will feel any way in the wrong for you butting in.

This goes back to lesson 2 where I described balance in a conversation like a game of tennis. We paid attention to how you could manage to keep the balance by sharing the conversation pillow fairly. Here, with the “changing topic” trick, you’re going a step further by also helping the other person with pillow balance as well.

Imagine, in terms of a tennis game, that you’re noticing they’re continually knocking the ball off into the foul line. What you’re doing when you say “I’d like to change the topic on” is serving them a new ball, getting them to a new part of the court, so they can get back in the conversation game with you.


Degree Two: Complaining and Ranting

The next level of difficult conversation I call “complaining and ranting”. Unlike detailing minutiae, complaining and ranting are tinged with anger and aggressive speaking.

Usually, when you’re on the receiving end of complaints or rants, none of that anger is pointed directly at you. However, by way of the raised voice, the constant negativity, and the whirlpool of verbal onslaught, you can’t help but feel a bit like a punching bag for this person’s general anger at the world and everyone in it.

Often, the natural remedy for this is to simply avoid speaking with this person. However, we all have family, coworkers, and may even have friends who tend to complain or rant. So, often we find we are forced to be confronted with this kind of difficult conversation.


Second Tip of the Day: Becoming a Window, Rather Than a Mirror

You should never feel like you are a volunteer counsellor in a conversation. While it’s tempting to try to cheer up or offer positive suggestions to someone who complains, or to open up alternate views to someone who is on a rant, the reality is this is just going to pull you in more, and exhaust you emotionally more than ever. Don’t let them make you into a mirror where they twist your positive suggestions into negativity so that you are sucked into their image of themselves.

Try to become a window instead. This means you simply do not engage in these conversations. It might seem shallow to simply nod, or agree, or just to listen, but know when you are doing this, you are conserving your energy.

Think of what I’m asking you to do here as asking you to be passive-conservative—you are being passive for the sake of conserving your wellbeing. You know full well the conversation pillow is being hogged, but you know full well that this battle is not worth fighting, so instead of the passive-aggressive reaction, where you want to steal the pillow away, you are willfully forfeiting your interest in the pillow altogether.

Your own self-talk can help. As you are caught in one of these types of conversations, remind yourself, I can’t help this person. I am simply going to listen, and not get involved.

While this might sound defeatist, you’ll see how this rationale stands up in our final lesson on endships.


Degree Three: Elephant in the Room Scenarios

The hardest kinds of conversations are ones where there is something egregious that needs to be said but isn’t. I call these kinds of conversations “elephant in the room scenarios”.

These kinds of situations go something like this example:

Your sales partner always has terrible body odor. It’s been going on for a few weeks now. You’re sure customers notice it too. You’re losing lots of sales pitches, and are starting to fear it’s not a coincidence.

Think of “elephant in the room” scenarios as a type of situation where you find it necessary to criticize another person. They are highly sensitive because there is something unpleasant to address, and however you address it, you run a high risk of embarrassing the other person, or possibly getting them upset.


Last Tip of the Day: “I Have to Tell You Something Difficult”

There are many ways to handle “elephant in the room” situations, but the best way is to be direct, and be respectful.

Using a phrase like, “I have to tell you something difficult,” sets the tone for a conversation that will be uncomfortable no matter how you word your feedback. This wording specifically conveys to the other person that what you’re about to share, you’re also having a difficult time with. It can help de-escalate the defensiveness they might feel if you just came right out with the feedback, since it tells them you’re not simply on the attack.

Also, be private.

In the sales partner example, even though it’s just you and your partner, when you decide to address the “elephant in the room”, make sure you do it somewhere intentionally private shows your respect, and when you lead with, “I have to tell you something difficult,” he will connect the dots and feel more appreciative that you went through the effort to make this conversation easier on him.

This doesn’t make addressing the “elephant in the room” easy, but it helps you make it tactful, and hopefully, effective.

Stay tuned for our final lesson, when we’ll talk about what to do when conversation fails altogether.


Recommended book

Difficult Conversations: How to Discuss What Matters Most by Douglas Stone, Bruce Patton, and Sheila Heen


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