THE MESSY MIDDLE AND THE MYTH OF COMFORT
We are in the messy middle.
I’m leading a newer team made up of highly capable individuals with strong opinions and strong ownership. As the work has progressed, we’ve started to experience tension. We’ve revisited decisions that were already made, raised dissenting perspectives, and pushed for forward progress even when alignment wasn’t immediate. These are the kinds of moments where you quietly question your own effectiveness and wonder whether something has gone off track.
During a recent meeting checkout, I caught myself before defaulting to self-criticism. It’s easy to go there, especially when you’re trying to understand your role in what’s unfolding and where you might be “at cause” in the situation. Instead, I named my appreciation for how the group was challenging both the work and the process.
What the team reflected back stayed with me. They noted that the reason we were in the messy middle to begin with was because the space allowed for it. The expectation wasn’t perfect execution or forced positivity. It was honesty, ownership, and a willingness to engage even when things felt uncomfortable.
This is where psychological safety is often misunderstood.
Psychological safety doesn’t mean meetings feel good or comfortable, or that alignment and decisions come easily. In many cases, it looks almost like the opposite: disagreements surface, the elephant in the room gets named, and people leave meetings thinking, “that was hard.”
That uneasy feeling is easy to misread. We tend to interpret it as failure, assuming that tension means something isn’t working. More often, it’s a signal that something is working. It’s evidence that people trust the space enough to speak honestly, challenge one another, and stay engaged rather than withdrawing or disengaging quietly.
Psychological safety isn’t created by saying you want it or by setting it as an expectation. It’s built and rebuilt (because sometimes it will be lost) through how people show up with one another. It’s shaped by tone, by how disagreement is handled, by whether accountability and respect can coexist, and by whether discomfort is met with curiosity instead of defensiveness.
If you’re leading or facilitating a team where things feel tense, uncomfortable, or unfinished, that doesn’t automatically mean something is wrong. It may mean the space is safe enough for the work to get real.
The messy middle isn’t a sign of failure, it’s where meaningful progress happens.
If you’re curious about how you create (or recreate) that kind of space on your team, I’m always open to conversations about what leadership looks like win the messy middle.