Having difficult conversations

A man and woman talking to each other at a picnic table

A person’s success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have.

Tim Ferriss

I had one yesterday morning.

After months of patiently figuring out what I wanted to say and when I wanted to say it, I called one of my best friends.

The goal was to lovingly and respectfully tell him that I didn’t want to be the only one putting in effort in our friendship anymore. In so many words, I said, “I know you love me and care about this relationship, I just wish you would show it.”

As expected, he took it incredibly well. He apologized immediately and declared he could easily make a change.

I felt so grateful. One, because I have a friend I can have open, honest, and productive conversations with. But two, because one of my strengths is initiating possibly difficult conversations.

Not all of my uncomfortable phone calls have been successful, though.

There’s no guarantee that the other person won’t get insulted or defensive. The only things within our control are our energy, our intentions, and how well we listen.

All easier said than done.

Here’s a simple checklist I use before preparing for a difficult conversation:

1) Do I care about this person?

2) Will having this conversation benefit both of us in the long run?

Example: Ending a relationship you don’t feel invested in—hurting someone in the short term, but saving them even worse heartache in the long term.

3) If they were to handle this horribly (this meaning my open and honest thoughts and feelings), is this someone I want in my life anyway?


I’ve had a number of difficult conversations over the past few years—most received well, some received poorly.

Here’s what I’ve learned…

Firstly, people are surprisingly willing to have deep and uncomfortable conversations…but most people are hesitant to initiate them. In other words, they want to resolve the tension, they’re just waiting on us to make the first move.

My advice: Get good at making the first move.

It takes practice, but it’s a crazy rewarding and useful skill to improve.

And finally, as we improve this skill of starting necessary conversations, we improve as people.

We begin to get clearer on what we value and what we don’t. We also get better at fighting for those values.

What do you value? When’s the last time you had a difficult conversation about it?