She Said “It’s Okay to Make Mistakes” a Hundred Times. Her Team Didn’t Believe Her.
Use this one activity to build an organization that learns from failure (for real).
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She’s a first-year principal who is anything but new to her building. Five years watching. Five years taking notes. When she finally got the seat, she moved fast. Bold decisions. High expectations. “Guns blazing,” in her own words. The kind of leader who would rather lose positions than people, and who refuses to spend another year waiting and praying for things to change.
The boldness worked. The building is moving. The vision is landing.
But it came with a cost she didn’t see coming.
Her two assistant principals have had a hard year. Tough conversations. Real accountability. Some disciplinary decisions.
All of it necessary.
And some of it counterproductive.
Because now both of them hesitate to make decisions. They’re worried about the repercussions of choosing wrong.
One of them spirals for days after a single mistake. Sky’s falling. Can’t rebound. Replays it over and over.
She doesn’t want her team living in that space. She wants to spend the summer rebuilding the dynamic. Supportive. Safe to take risks. A place where mistakes are okay — as long as they’re not sloppy ones.
And she wants to do it without taking her foot off the gas.
What She’d Already Tried
She’d told them mistakes are okay. “A hundred times,” she said.
And she’d modeled it. Or thought she had.
Every Monday in their admin meeting, she names her own misses. Dropped balls. Things she’d handle differently.
Her APs respond by comforting her. You have a million things going on. You had the best interest in mind. You’ll bounce back.
They give her good advice. They just don’t take it themselves. One of them spirals for days after a single mistake.
The Coaching Conversation
The question that opened the door for her:



