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.
Conflict EQ Q&A
In this week's Conflict EQ Lens, we explore what happens in the "messy middle" of difficult conversations. Many people are comfortable starting a conversation and eager to reach a solution, but they often rush past the most important part—the space where understanding, empathy, and meaningful change are created.
What is the "messy middle" of a difficult conversation?
The messy middle is the part of the conversation between raising an issue and reaching an agreement. It is the space where people explore different perspectives, express concerns, share emotions, ask questions, and develop a deeper understanding of what is happening beneath the surface.
Why do people try to skip the middle?
Many people find the middle uncomfortable because it contains uncertainty, disagreement, emotion, vulnerability, and unpredictability. The temptation is often to move quickly toward solutions, advice, or decisions rather than remain in a conversation that feels messy or unresolved.
What happens when we rush to solutions?
When people move too quickly to problem-solving, they often miss important information. They may fail to understand the other person's perspective, overlook root causes, or create agreements that feel imposed rather than collaborative. The issue may appear resolved while the underlying concerns remain unaddressed.
Why is listening important in difficult conversations?
Listening creates opportunities for understanding. When people feel heard, they are more likely to engage honestly, share relevant information, and participate in finding solutions. Listening also helps uncover assumptions, emotions, motivations, and concerns that may not be immediately visible.
How does empathy develop during conflict?
Empathy often develops in the middle of the conversation. As people hear each other's experiences, challenges, concerns, and perspectives, they gain a more complete understanding of what is happening. Empathy does not require agreement; it requires understanding.
What role does curiosity play in conflict?
Curiosity helps people move beyond assumptions and certainty. Instead of focusing solely on defending a position, curious individuals ask questions, seek understanding, and remain open to information they may not have considered. Curiosity creates space for learning and connection.
How can leaders stay in the messy middle longer?
Leaders can slow down the conversation, ask open-ended questions, listen without immediately solving, acknowledge emotions, explore different perspectives, and tolerate temporary uncertainty. Staying in the middle requires patience and a willingness to remain present when answers are not yet clear.
Why do better agreements emerge from the middle?
When people fully explore the situation before deciding what to do next, solutions tend to be more collaborative, sustainable, and effective. Agreements developed through shared understanding often create greater commitment than solutions imposed too quickly.
What is Conflict EQ?
Conflict EQ is the ability to remain grounded, curious, and constructive when tension, disagreement, or difficult conversations arise. A core element of Conflict EQ is the ability to stay present in the messy middle of a conversation long enough for understanding, connection, and meaningful solutions to emerge.