The Messy Middle
by Trista Schoonmaker
"The middle is messy, but it's also where the magic happens." (Brené Brown, Rising Strong)
I recently worked with James (not his real name), a senior manager who was hoping to improve his ability to give feedback to his employees. His pattern was to delay—again and again—even as certain behaviors kept showing up. Eventually, he would decide it was just too late to say anything at all. He was stuck in a pattern of complete avoidance—and with some employees, this avoidance had been going on for years!
James knew something had to change. He brought three specific examples to a coaching session so we could practice together. We talked about how conversations like this have a distinct beginning, middle, and end.
I asked him to choose one example and practice just the beginning of that conversation.
James: “I’ve noticed [x], and I’ve seen that it’s had [this] impact on others on the team.” (So far, so good.) “So next time, if you’d just try to do it [this way], I think it will be better for everyone.” (Wait, what?)
Do you see the problem? (Without having taken my training on difficult conversations, it might not be obvious, so keep reading. . .)
The beginning of the conversation is where you describe your observations and the impact, from your perspective. The end of the conversation is where you reach a shared agreement about what will happen moving forward. But what James skipped was the middle of the conversation—which is where all the magic happens!
The middle of the conversation is messy because it’s full of different perspectives and frustrations—it’s where all the emotions live. It’s the part where you listen and try to see through the other person’s eyes. It’s where you get everything out on the table so you can unpack what’s really happening.
It’s unpredictable and often uncomfortable—but that’s exactly why it matters. If you already knew how it was going to end, you wouldn’t need to have the conversation.
The middle of the conversation also where all the human connection lives. It’s where we stretch beyond own view and build understanding together. It’s where empathy grows, and where we find the courage to create a new shared approach.
When James thought about difficult conversations, he only saw the beginning and the end, and it felt forced and controlling. At some level, he couldn’t see the point, so he avoided them until his employees’ negative behaviors were overwhelming.
James could immediately see that by skipping the middle, he wasn’t just avoiding discomfort—he was missing opportunities for connection and insight. The behaviors kept repeating because he didn’t yet understand what was driving them. And underneath his avoidance was a fear of the awkwardness—the embarrassment, guilt, or tension that might arise when employees felt exposed.
But as we talked, he began to see the power of staying with that discomfort. Allowing time for connection, even when it feels awkward, makes the conversation more meaningful. By the time you get to the end, agreements feel more collaborative and less directive, more like creative solutions than commands from an authoritarian boss.
The middle of the conversation is messy. But without it, there’s no space for growth, no real opportunity for change. It’s in the vulnerability of that messiness that we find the courage to reconnect and move forward together.
So next time you’re heading into a tough conversation, don’t rush to the end. Linger in the middle long enough for something new to emerge. Because when we allow ourselves to stay in the messy middle, we don’t just solve problems—we strengthen relationships.