Leading Through the Messy Middle of Change
I attended a webinar yesterday on leading transformation or change. The presenters walked through five stages of the process — and if you’ve been in leadership for a while, it was likely familiar territory in one framework or another.
One thing struck me that I wanted to share with you, which is the importance of attending to people’s emotions during the “messy” middle phase.
This is the phase after the excitement of the launch has faded, before the finish line is visible, and when the work feels heaviest.
I’ve learned to anticipate this phase with clients. And whether I’m working with an individual leader or a team, I know it’s coming. While I’m confident in my ability to sense when that phase has started, I like to check my gut with evidence.
Here are a few telltale signs that a team has entered the messy middle:
People become unclear about the outcomes. “Why are we doing this?” “Was the old way really broken?” “Is this actually necessary for growth?”
Frustration starts to build around progress. The visible results may feel too slow — or too small — to justify the level of effort people are putting in.
People begin retreating to old patterns. They’re tired. Doubt starts creeping in. The outcomes they once felt excited about suddenly feel uncertain, and old habits begin to look comforting because they’re familiar and easier.
The messy middle is one of the hardest parts of transformation. It’s also one of my favorite phases — because it’s often a sign that real change is happening.
Transformation is difficult work, whether you’re talking about an individual or an organization. If no one is questioning the process, chances are no one is stretching enough for meaningful change to occur.
That's why it’s critical to attend to people’s emotions during the messy phase. Do you need to act like the team therapist? Absolutely not. But acknowledging frustration, validating uncertainty, and consistently reinforcing the purpose behind the work can go a very long way.
The confusion, questioning, and frustration are often symptoms of fear and anxiety. And that makes this a critical leadership moment: reassuring people that things are working, even when progress feels slow and the climb feels steep. Because that’s what meaningful change often feels like in the middle of the process.
If you, or your team, are navigating change — or preparing for it — and you want to think through strategies for leading through the messy middle, I’d love to connect.
