"The difference between skeptical and stuck"
In my last email, I shared a moment where I wasn’t sure if I was dealing with healthy skepticism or something else. A concern had been raised, fairly. I listened, adapted the plan, kept the team involved. But when the same concern came up again the next day, unchanged, I was left wondering. Was this person trying to improve the outcome, or trying to avoid the change? It got me thinking about how easy it is to confuse skepticism with negativity, especially when you're leading change. They can sound similar: both come with doubts, questions, discomfort. But they come from very different places, and they lead to very different outcomes. Skepticism is forward-facing. It says, “I’m not convinced, help me understand.” It invites discussion, asks for clarity, and—crucially—stays open to changing its mind. Skepticism can be uncomfortable, but it’s generative. It sharpens thinking. Negativity is stuck. It says, “This won’t work,” but doesn’t want to explore why. It resists alternatives. It raises the same point not to engage, but to anchor. It can wear the clothes of skepticism, but underneath, it’s fear, frustration, or fatigue. And here’s the hard part: What helped me in this situation wasn’t trying to label the other person. It was noticing how I was reacting. If I felt the urge to explain again, to justify again, to solve the same concern again, I paused. Because that usually means I’ve left the space of healthy dialogue and entered a loop. And in the messy middle, loops can look like progress. But they just burn time, erode trust, and confuse the team. So next time a concern comes up, especially one I’ve heard before, I’ll ask myself:
Until next time, ✉️ Enjoying The Messy Middle? If someone sent this email your way and you’d like to get it direct, you can sign up here. |