The Habit of Difficult Conversations

What they are, How to have them, and When to let them go.


Did you know there is an optimum ratio between positive and negative interactions? The ratio is 5 to 1.* Meaning that in good relationships, for every 5 positive interactions you have 1 negative.

Ask yourself, do you have more negative interactions than positive ones? If the answer is yes, then you’ve got more positive work to do. If the answer is no, and you have more than five positives to one negative, you are not sharing enough.

We all know how to have a good time, so the question is: How do we share more often even though is difficult to navigate through those challenging conversations?

To aid us, Douglas Stone, Bruce Patton, and Sheila Heen wrote a fantastic book on the subject, called Difficult Conversations. Unless referenced otherwise, most of what we talk about here is from their book.


What They Are

Difficult conversations are challenging because they are actually three conversations in one:

  • The “What Happened?” Conversation. “Most difficult conversations involve disagreement about what has happened or what should happen. Who said what and who did what? Who’s right, who meant what, and who’s to blame?”

  • The Feelings Conversation. Difficult conversation also asks and answers questions about feelings. Are my feelings valid? Appropriate? Should I acknowledge or deny them, put them on the table or check them at the door? What do I do about the other person’s feelings? Are they angry or hurt?

  • The Identity Conversation. “This is the conversation we each have with ourselves about what this situation means to us. We conduct an internal debate whether this means we are competent or incompetent, a good person or bad, worthy of love or unlovable. What impact might it have on our self-image and self-esteem, our future, and our well-being?”

The answers we give to each question “determine in large part whether we feel “balanced” during the conversation, or whether we feel off-center and anxious.”


How To Have Them

I used to have two modes of handling difficult conversations. One would be a careful and passionate speech about why I was right (and they were wrong), and the other was just avoidance until I exploded in a burst of anger. Unfortunately, neither strategy would be satisfying.

Little did I know that “There is no such thing as a diplomatic hand grenade.” Coated with sugar, thrown hard or soft, a hand grenade is still going to do damage. […] And keeping it to yourself is no better. Choosing not to deliver a difficult message is like hanging to a hand grenade once you’ve pulled the pin.”


So how do we do a better job? We shift our focus.


Shift of Focus

We tend to think that facts present themselves to everyone equally. We consider them, think about them, and come to conclusions so we can act. And that would be a perfectly reasonable solution if there weren’t so many facts and so many different interpretations we can have.****

Each of us perceives the world differently because we have complex and diverse personality traits that influence how we interpret reality.** Instead of thinking of both of you as enemies in a battle, think of you as opponent processors who need to fine-calibrate each other to better answer complex situations.*** This way you can shift your focus from a Battle of Messages to a Learning Conversation, learning more about what you know, (your own experiences, stories, feelings, and identity issues) and what you don’t know (their intentions, perspectives, and feelings).

So let’s see how shifting our focus changes each type of conversation.


The “What Happened?” Conversation



The Feelings Conversation

A conversation that doesn’t acknowledge feelings is similar to watching a movie without sound. Sure, you’ll understand the plot, but it will lack depth, character, and nuance. Acknowledging and being curious about feelings grounds and transforms the conversation into reality.




However, don’t confuse “being emotional with expressing emotions clearly, they are different. You can express emotions well without being emotional, and you can be extremely emotional without expressing much of anything at all. Sharing feelings well and clearly requires thoughtfulness.”

So, to express emotions well without being emotional, you can adopt two rules:

  • Rule 1: Before you say what you are feeling, negotiate with your feelings;

  • Rule 2: Try to get everything you are feeling into the conversation.

To negotiate with your feelings, understand that fundamentally, your “feelings are formed in response to thoughts.” They are just data about what you think is going on. If you get a clearer picture about what you are feeling, (such as what stories you are telling yourself; whether your assumptions about both of you are reasonable; and the contribution of each part has in the discussion,) you will be able to negotiate with your feelings and share them into the conversation.

It’s your responsibility to understand (yours and theirs) feelings and share them clearly before you move on to problem-solving.


The Identity Conversation


On the surface, we avoid difficult conversations because we dread having to face the other person, but when we dig a little deeper it’s because doing so means we have to face our own identities.

Are you aware of your identity issues?

Difficult conversations usually bring to the surface our vulnerabilities. It’s as if all of the sudden someone pushed a button and our identity is under attack, “Am I competent or incompetent, good or evil, worthy of love or unlovable?”

This is known as ‘All-or-Nothing’ Syndrome. It’s a mental shortcut meant to drive you into quick action which sometimes can have disastrous consequences. Fortunately for us, it’s pretty easy to fix this kind of thinking. How?


Be Self Aware and Don’t Neglect the “And”

When do you feel triggered? Why? Does it tell the whole truth? What does it say about you?

If you’ve learned anything from this text until now, is that you have to shift your focus from a battle to a curious mindset. So be curious and willing to integrate new information into your pure identity by not neglecting the “and.”

I learned this from former NBA player Larry Sanders, who said, “Don’t neglect the ‘and.’

“You sound selfish!

 — AND I’m loving, AND I’m caring, AND I’m fearful sometimes, AND I’m also brave. We all are more than just one thing.”

This is how you ground your identity and guide difficult conversations into a more constructive and healthy path.


Quick Bonus: When To Let Them Go

Even though it would be satisfying to cross every t and dot every i, life is too short to have all the difficult conversations that come your way.

So when do you let them go?

After you walked your way through the Three Conversations, “think clearly about what you know (your own feelings, your own experiences, and story, your identity issues), and what you don’t know (their intentions, their perspectives, or feelings).”

Just consider these key three questions.

  • Is the Real Conflict Inside you?

Sometimes it’s more about what’s inside you than what is actually happening. If you gain some perspective, you might discover it's alright and you can let it go.

  • Is there a better way to address the issue than talking about it?

Other times what actually needs to happen is to change your actions. How you contribute to what’s going on is a good way to change the outcome.

  • Do you have a Purpose that makes sense?

Finally, what’s the purpose of discussing the issue? Does it make sense? If you want to have a difficult discussion just for the sake of it, you will get lost and just end nowhere. There needs to be purpose in what you are doing.


That’s it. A lot of moving parts and points of view. If I mastered it, I’m sure you can do it too.

Talk to you soon,


Lucas Napier Better Habits, Better Health

*John Gottman and Robert Levenson

** Five-Factor Theory ***Iain McGilchrist — The Master and His Emissary: The Divided Brain and the Making of the Western World

**** Jordan Peterson - Discovering Personality

***** BJ Fogg — Tiny Habits

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