How to Prepare for a Dreaded Conversation

Do you have a dreaded conversation in your future?

By “dreaded conversation,” I’m talking about one that you’ve been procrastinating because you don’t want to experience it. 

Maybe you’re worried about making them feel bad by telling them some not-so-nice things.

Maybe you’re worried about getting frustrated and losing your cool.

Maybe you’re worried about saying the wrong thing and making the situation or relationship worse.

And yet, you know that putting off the conversation until tomorrow and tomorrow and tomorrow isn’t going to help. 

The issue isn’t going to resolve itself. 

It might even fester and get worse.

And you might become more and more upset and resentful, until you explode in a flurry of highly unskilled (read "apeshit crazy") speech that might destroy the relationship.

"Just Tell Me What to Say"

When I coach or train people to have what they think of as “dreaded conversations,” what they’re mostly looking for is techniques.

Basically, they want me to tell them what to say. The magic words that will compel the other person to listen, agree, and change.

They want to know things like:

• What's the best way to start?
• What do I say to disarm their defensiveness?
• What words do I utter to convince them that they need to change?

I get it.

When I’m at a loss, I also just want someone to tell me exactly what to do.

I don't want a deep dive into underlying principles, just a set of instructions I can follow.

Instructions can be helpful — in certain situations. When things are static, memorizing and mastering technique may be all you need. 

You Can Memorize Chess Openings

Take, for example, the first three moves in a chess game. If you memorize a dozen classic chess openings, you can probably hold your own against most grandmasters through move number three. 

(And maybe even up to move seven if you employ a pro tip that I learned from high school chess team: learn how to insult your opponent under your breath in Russian.)

That’s because chess openings are predictable.

Once you get into the mid-game, though, knowing a bunch of techniques isn’t going to help you. There are too many variables, and every move can completely change the dynamics on the board.

When things get complex, mastery of technique and tactics loses relevance.

At that point, you have to based your actions on an understanding of fundamental principles.

In chess, those include things like piece activity, king safety, control of the center, pawn structure, and so on. (Also, if your opponent is muttering in Russian, protecting against an immanent attack.)

The Principles of Dreaded Conversations

Dreaded conversations are another place where memorizing and mastering techniques won't help you.

Like in chess, you can memorize a few openings. My favorite is the OCP (outcome/confidence/permission) formula that I teach in my book and in workshops. But there are others, and they aren't hard to master.

Once the other person responds, however, you're firmly in the world of principles, not memorized responses.

To be clear, you will still be using techniques and tactics. But they'll "work" (ie achieve their purpose) only when they're based on underlying principles.

So what are the principles to keep in mind as you navigate dreaded conversations? 

• Principle 1: Signal Safety
• Principle 2: Orient Toward the Future
• Principle 3: Build Confidence
• Principle 4: Encourage Ownership
• Principle 5: Model Curiosity
• Principle 6: Think in Systems
• Principle 7: Evaluate Experimentally

You can remember these, of course, with the acronym SSOTTFBCEOMCTISEE.

Your Turn

We'll explore each of these principles in an upcoming issue of this newsletter. For now, practice noticing when you can get by with techniques (because techniques can save time by being wonderfully efficient short-cuts), and when you must rely on principles.

If you'd like to become a conversational grandmaster who looks forward to every interaction — even the challenging ones — you can start with my (and Peter Bregman's) book, You Can Change Other People. (Great book, embarrassing title.) If you'd like to accelerate your progress toward becoming a truly "Trigger-Free Leader," let's talk. Click here to schedule a discovery call.

Bonus Time-Waster

Here are some of my favorite (clean) Russian chess insults:

Твой конь — корова. (Your knight is a cow.)

У тебя мозги как у пешки. (You have the brain of a pawn.)

Ты играешь как рыба. (You play like a fish.)