The biggest mistake we make during difficult conversations
My team and I have been through a lot together.
We’ve worked hard to learn how to navigate difficult conversations and say tough-but-important things to each other, and we’ve gotten pretty great at it. So great, in fact, that I’ve often said, “There’s nothing we can’t talk about.”
But that doesn’t mean talking about it is easy.
I recently had a series of conversations with a member of my team that were among the most difficult I’ve had in my career—and maybe even my life. It was an extremely hard situation, but it showed me what’s possible when two people commit to avoiding one of the biggest mistakes people make during difficult moments in a relationship.
In today’s post and the one coming next week, I’m going to take you on a journey. I’m going to walk you through this experience I had and the conversations that were a part of it because I think they demonstrate what can happen when we make a really powerful decision that can positively affect the outcome of a difficult moment.
Let’s dive in . . .
The first thing you need to know is that I had these conversations with Monique, who has generously given me permission to share our experience with you.
Monique is our team’s Chief of Growth and my right hand and thought partner in the business. We’ve been working together for 13 years, and she’s the member of my team I work with the closest. She leads all things strategy and partners with me on big decisions about our future and how we will get there.
She is also one of my closest friends.
Because of the dynamic of our thought partnership, I’ve had more difficult conversations with Monique than anyone else in the world. Just to give you an idea of what I mean by “difficult”: She is the one I first talked to about no longer wanting to run a cleaning business. In fact, she confronted me about it. She called me out for avoiding the decision for so long instead of being courageous about it. Our conversations helped me decide to evolve our business into one that feels so much more authentic to me.
And that doesn’t even scratch the surface of the types of conversations Monique and I have had over the years.
Up until a few weeks ago, I didn’t think it was possible to increase the level of trust we’ve built. But . . . I was wrong.
I’ll tell you more about the specifics of our conversations in my post next week, but here’s what started it all:
I’d been feeling some resentment toward Monique building up inside of me. But because of how much I care about her, I didn’t want to bring up these feelings. In the grand scheme of things, they weren’t that big of a deal to me; I thought they were feelings I needed to work through on my own. I didn’t want to bring them up and risk damaging our relationship over something that didn’t feel like an overwhelming issue.
I also didn’t feel like there was a solution to these feelings. So, in my mind, I thought, why would I bring it up? Why would I stir the pot without a solution?
As I was noticing these feelings in myself, I happened to have a call with my therapist, and it became the topic of our conversation. My therapist did what any good therapist would do: She encouraged me to share my feelings with Monique, even if there wasn’t a solution for them. My resentment wasn’t all-consuming, but I was still carrying it around, and she helped me see that if I really cared about Monique, I owed it to her to tell her how I was feeling. I knew she would do the same for me.
And so . . . right after I hung up with my therapist, I reached out to Monique. (I actually wrote a post about that conversation and published it a couple of months ago—I just didn’t share that it was about Monique.)
After I shared these thoughts with her, she had a choice: She could either shut down and disengage, or she could get curious about my feelings, sit with the hurt and discomfort, and think about what my feelings brought up in her.
She chose to do the latter and go there with me.
After sitting with what I’d shared for a bit, Monique told me that my words had hurt her. But still, she listened to and acknowledged them. In my response, I did the same for her. We didn’t find (or even look for) a solution because our only goal was for each person to feel heard, and we achieved that.
We both ended that conversation feeling better . . . or so I thought.
A month or so later, I noticed some of the same feelings of resentment creeping back in for me, and I started to pick up on the same in Monique. It wasn’t anything huge, but Monique and I know each other well enough to know when the other is even slightly frustrated.
It seems like my therapy calls happen on the most serendipitous of days: After I first noticed our renewed frustration, I had a therapy call and brought this up. This time, for sure, I saw no point in talking about it with Monique. We had already had a great conversation; I love her; I love our relationship; I know it’s normal and okay for us to be frustrated with each other sometimes; it’s all good . . . right?
Again, my therapist helped me see that even though these feelings were small and we’d already had a conversation about them, I owed it to Monique—and to myself—to acknowledge that my feelings had returned and that I knew hers had, too.
So again, I reached out to Monique right after that call. We love to send each other voice messages on WhatsApp; it’s primarily how we communicate. We love being able to hear each other's voices, and the format also gives us time and space to process what the other person has shared before we share our own thoughts in response.
I sent Monique a voice message and told her what I had told my therapist. I shared what was coming up for me, and I asked her to share what was coming up for her.
I told Monique that I wanted her to share all of it—and I mean all. I wanted her to tell me every single frustration she had, no matter how hard it was for her to say.
Again, Monique had a choice: She could shut down or keep her answers surface-level, or she could really go there with me.
She went there.
Some of what Monique said was really hard for me to hear. It was hard to sit in my own discomfort and know the things I had done to hurt and frustrate her.
Then, the choice was mine: Do I shut down, or do I keep going there with her?
I wanted so badly to go there with Monique, but it was so hard. Tears are rare in our conversations, and we both had shed a few so far.
This is not common for me, but there was a point when I was trying to record a response, and I just couldn’t get the words out. I kept trying and stopping, trying and stopping.
I felt at a loss. I knew I had hurt Monique. I knew I didn’t mean to. I knew that I was hurting, too. I knew that she didn’t mean to hurt me. I knew that we both cared about one another so much; I just didn’t know how to fix it. I didn’t know what words could possibly do that. I felt defeated about how to express what was in my heart.
I didn’t want to give up, but I was really struggling. And the thing about WhatsApp is that the other person can see when you are recording and re-recording a message. Monique could tell that I was struggling, and so she offered to get on the phone with me to help me get the words out.
I called her right then and there. And it was so hard.
There were starts and stops. Messy words. Things that didn’t come out exactly right.
But the whole time, we were in it together. It didn’t feel like it was me vs. Monique for a single second; it was the two of us against this misunderstanding between us. We shoved our egos out of the way, and with every question, we built more and more clarity and understanding. Every word we said came with so much compassion and love.
After that conversation, we went back and forth a few more times. I think we had 10 or 15 conversations in all, each one peeling back another layer.
Then, something truly unexpected and beautiful happened: We had the biggest light bulb moment.
After all of these conversations, we had finally, finally uncovered the real issue. Turns out that it wasn’t anything that either of us had originally thought. And once we figured it out, the solution was so obviously clear. We were instantly on the same page and aligned on where we wanted to go, and we knew exactly how to get there.
While that’s great, it’s actually not the best outcome of this journey. By far, the greatest result is the trust that Monique and I have and the new depth of our relationship. I mean, wow. It’s beyond anything that I ever thought possible.
In our last conversation, we both shared how it felt to go through this journey together. How it feels to be truly understood. How it feels to have a conversation with someone who is willing to go there with you. How it feels to sit in discomfort and pain and to make it to the other side, still together.
Of course, I had a therapy call later that day. I decided to use that call to unpack the experience and how moving it was for me to go on this journey with Monique.
That’s when my therapist said something I hadn’t considered before: She shared that often in difficult moments in relationships, we reach a fork in the road, and we have to make a critical decision: Am I going to keep leaning in, or am I going to shut down?
She helped me see that what Monique and I did is avoid the biggest mistake that many people make in their relationships: Instead of shutting down, we both chose over and over again to keep leaning in. Even in our weakest moments—even if it meant helping the other person—we both chose to be curious, hold space for one another, and continue being vulnerable. Even when we disagreed. Even when we felt misunderstood. Even when it hurt.
My relationship with Monique inspires me to want to cultivate more relationships in my life where there can be such radical honesty and a commitment to keep going there together, no matter how hard it feels.
Think about your own relationships: What do you do when the going gets tough? (And if it’s a real relationship, it will get tough.) Maybe the next time you encounter this fork in the road, you’ll think of my experience with Monique. What might be possible if you choose to lean in?
Of course, there might be some relationships where it doesn’t make sense to keep leaning in. Someone who is knowingly causing you harm, abusing you, gaslighting you—I’m not talking about these relationships. You have to do what is best for your own well-being.
But when it’s someone you care about? Remember that leaning in can take your relationship to an even deeper, more trusting place. (And even when the conversation or feedback seems small, it can still be mighty for your relationship.)
If this post spoke to you, I’d love to know: Can you think of conversations where you or the other person chose not to lean in? Or a time when you did? How did that affect your relationship? Hit “reply” and tell me all about it. I’d love to learn about your experiences with this very hard and very human topic.
And if you haven’t already, you can download our guide to giving and receiving feedback to learn how to level-up your feedback conversations. This is a starting point for having honest and compassionate conversations that can take your relationships to the next level.
I’ll be back next week with part two, which will be about the light bulb moment Monique and I arrived at in our conversation . . . and what we did about it!
Big hugs,
