Difficult Conversations - What Makes Them So Hard

Jordan Brown

You know which conversations I hate?

I bet you can guess.

Difficult conversations.

They're the worst.

Difficult conversations run the gamut from telling your boss that you don't enjoy the work you're doing and you're thinking of leaving--to telling your neighbor that you don't appreciate how loud they're being at 1 AM in the morning.

But what makes them so difficult?

Turns out, it's not the nature of the conversation itself. It's something that can learn to get better at over time.

I Used to Dread Difficult Conversations


Difficult conversations can be terrifying.



Even thought I still strongly dislike them, I used to absolutely dread difficult conversations.

I used to lose sleep over them.

I'd worry and worry before they even happened.

It seems like a waste a time to do this, but I know I'm not alone. Many people dread difficult conversations.

But why?

Aren't we all humans? Don't we converse as part of our daily lives? Aren't we born for this typical kind of interaction?

Yes to all of the above. But there's a catch. Conversations aren't that cut and dry.


Let's talk about family. We all have them, in whatever shape and form they come in.


My grandmother, my last remaining grandparent, is very old at this point. She's always been a bit ornery, to say the least, but things have gotten much, much worse over the last 10-15 years. And now, now she's dealing with what's looks like dementia, which is only exacerbating the behavioral and personality issues that were already present for her entire life.

She has an interesting habit of making things all about herself. You can try to talk about whatever you like, but the conversation will ultimately come back to her and how she's been wronged.

First, let's give her credit. The daughter of immigrants to the United States, she grew up in a time and a place where much was thrust upon her when she didn't ask for it. She claims she often needed to translate for her parents. She claims that her mother was very cruel to her.

And she'll still remind you of it to this day, every time the situation seems to call for it, even if, to others, the situation certainly does not seem to call for it.

There are things about my grandmother that make conversations, shall we say, difficult.

But if we know all this about my grandmother, and we know that she's been acting like this for many, many years, why are the conversations so difficult in the first place? Shouldn't it be simple to prepare for and disregard the jabs and negative comments that are sure to come?

The answer lies not in what she does, but in the other piece of the difficult-conversation puzzle.


Your Role (Any My Role) In Difficult Conversations


I'm going to be the guinea pig here.

Deep down, I think I know why difficult conversations are so difficult.

It's not about what needs to be said. I always know what needs to be said. I know when I need to stand up for myself or share a difficult truth. That's not the hard part.

The hard part is the unknown--the variables I can't control.

Tell someone you like them, and you have no idea if they'll return the favor.

Tell your neighbor you don't appreciate how they're acting, and there is no guarantee they'll hear you out.

Difficult conversations are difficult because we have no control over what happens next.

This is terrifying for a number of reasons.

If we have no control, then we have no idea what we might need to do to respond. The brain can only work through so many scenarios before the action of life takes place. It can't predict everything. And so while the brain is an amazing asset when it comes to analyzing and preparing for what might come, it's a full-body experience when you're tethered to the present reality of a demanding and quite difficult conversation.

My father is the primary decision-maker for my grandmother at this point. He helps her make decisions with her money. He helps guide her treatment at an assisted-living facility. And he helps her make sense of world that has never seemed to go her way right from the beginning of when her story began.

Years ago, he hated it. He wished he didn't have to deal with this sort of thing. It made him so angry.

But something changed over the last three to five years. And I'll let you in on a little secret--it was not the nature of the conversations. They were as difficult as ever.

But the great secret and simple truth here is the relative nature of difficult conversations. What once seemed impossible can later become tolerable. And that's how it's become for my dad.

These days, he doesn't get as angry when he recounts what my grandma said to him. He doesn't fret about her illogical reasoning or her rude interactions with others. Because he's learned something incredibly important.

The conversations were never difficult because of what my grandma said or did. The conversations were difficult because of what those words and actions drummed up within my dad--and all the other people who interacted with her.

My dad, over time, learned that he didn't need to say or do the perfect thing to get through a difficult conversation. He got through it by getting through it.

Now, I get it. That sounds like a vague and ridiculous way to explain a very real problem for many people, the fact you and I have to navigate difficult conversations all of the time.

But think about it. If someone calls you a name, does it automatically ruin your day? Does it have to? Or do you have some degree of control in how you respond?


What Makes Difficult Conversations So Hard


What once was a nightmare becomes a silly affair. Difficult conversations are typical not because of what happens to you, but because of what you think and feel related to what happens to you.

You can't have a difficult conversation with yourself because you know the battle is one-sided--and so it's no longer a battle. The battle has to have two people to exist. And the really surprising part is that you determine the nature of the battle.

Our minds create the storylines, and our hearts add fuel to the fire. If we didn't have this ability, life would likely lose all meaning. It would be flashes of colors and lights and strange interactions with roaming creatures.

There's something much more meaningful about this all.

Conversations are difficult because we care about one another.

If we didn't, we wouldn't have these conversations at all.