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Bear With Me, Issue 23 “The Window Watcher.

Cameron
Cameron
August 18, 2026
1 min read
Bear With Me, Issue 23 “The Window Watcher.
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There is a difference between being observed and feeling watched.

At one point in my career, I looked up and realized my principal was standing outside the room, silently watching me through the small window in the door. There was no knock, no conversation, and no indication that this was part of a normal walkthrough. Just someone watching.

It sounds almost funny now, which is part of why I turned the experience into Bear With Me. At the time, though, it did not feel funny.

School leaders absolutely have a responsibility to know what is happening in classrooms and workspaces. Walkthroughs, observations, and informal check-ins can all be valuable tools. But the way they are handled matters. When observation feels secretive, punitive, or intentionally unsettling, it can quickly erode trust.

Good leadership does not require employees to feel comfortable every second. Accountability is necessary. Expectations matter. But people should still understand that the person evaluating them is also there to help them succeed.

A knock on the door would not have changed the principal’s authority to observe me. It would have changed the tone of the interaction.

That distinction has stayed with me. Leadership is not only about what you are allowed to do. It is also about how your actions are experienced by the people you lead.

Sometimes the smallest behaviors send the clearest message.

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Cameron

Written by

Cameron

Founder of New To Education, building a global platform connecting education, business, and opportunity.

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