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Curiosity Over Judgment: A Leadership Mindset – Stephanie Weese

By Stephanie Weese, CFO, MSBO Board President, Assistant Superintendent of Administrative Services, Livingston ESA 

I recently heard the phrase, “Be Curious, Not Judgmental.” It made me pause and reflect. How does anyone actually do that? How do you stop your brain from “being judgy?” I don’t know about your brain, but my brain is always forming judgments! 

Curious to learn more, I asked my colleague who introduced me to the phrase where he had heard it and what it meant to him. He explained that he first encountered it in an episode of Ted Lasso (a show I have yet to watch) and that, to him, it meant being open-minded and actively listening. 

This concept struck me in a way I hadn’t expected. I had never really considered how being judgmental could limit my ability to listen and be curious. I also wondered—how could I control my judgment when it’s such an ingrained part of who I am? It even shows up in my Myers-Briggs results: ESTJ—it’s right there! 

Determined to explore this idea, I began an experiment. Throughout my workday, I made a conscious effort to ask more questions in conversations and meetings. I tried simple prompts like: Can you say more about that? What motivated you? Or I just asked Why? 

At first, this was difficult. My brain wasn’t particularly cooperative—it had already formed conclusions and was ready to move forward. The intentional pause I was inserting felt like a roadblock, and the questioning felt unfamiliar, even intrusive. But something unexpected happened. When I asked questions out of genuine curiosity, the conversations became richer. More information was shared, perspectives broadened, and decisions felt more collaborative. Who knew?!  As I am writing this article, I am definitely feeling like I should have known this, just fyi. 

Simon Sinek speaks frequently about the power of curiosity in leadership. He emphasizes that great leaders don’t assume they have all the answers—they ask questions, seek to understand, and create environments where people feel heard. By shifting from judgment to curiosity, we create space for learning, innovation, and deeper connections. 

I recognize that curiosity isn’t always practical—some situations require quick decisions without time for deep inquiry. But when time allows, leading with curiosity fosters trust, collaboration, and better outcomes. It’s a practice I’ll continue to refine, and I encourage you to try it, too. You might be surprised by what you discover. 

 

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