Start at the Bottom: Leadership Lessons from a Crooked Shirt

Late-Lee, I’ve been getting “schooled” by my husband—again. This time it wasn’t about how I load the dishwasher or whether towels should be folded in thirds or halves. No, this time it was about buttoning a shirt.

He starts at the bottom and works his way up. I, naturally, start at the top and work my way down. I mean there are more than two ways to skin a cat, right? But more times than I’d like to admit, I get to the bottom and realize I’ve got one button left with no hole to put it in. Every. Single. Time. Then I have to unbutton the whole thing and start over.

Standing there, staring at my crooked shirt, I had a thought: This is exactly what happens when leaders try to lead from the top down without making sure things are aligned.

In schools, we do this more than we realize. We roll out big initiatives, focus on frameworks, timelines, and catchy acronyms. We start at the top. And it sounds solid—until we get to the people closest to the work and realize something doesn’t fit.

It looks good on paper, but it’s misaligned in practice. Just like my shirt, the whole thing ends up a little off. And that’s when we’re faced with a choice: fix it, or pretend not to notice and keep going crooked.

Start from the Bottom

Strong leadership doesn’t start at the top. It starts with the folks closest to the work.

It’s the teacher managing 27 different needs and a pacing guide. Or, the para keeping small group instruction on track. It’s even the cafeteria manager who knows who skipped breakfast. And let’s not forget the coach noticing both instructional gaps and emotional ones.

When we begin by listening—really listening—we build plans that make sense and hold up under pressure.

Check for Alignment

Before you launch something new, take a minute to ask yourself…

Have I talked to the people doing the work? What are they seeing and experiencing? Does this plan make sense at every level—student, teacher, leader, and family? Are we addressing the root cause, or just reacting to a symptom? Have I made space for feedback—and am I actually listening? If I were in the classroom or hallway, would this feel doable?

Sometimes the smartest thing a leader can do is pause and look down—not out of defeat, but to make sure everything lines up. Starting from the bottom might take a little longer, but it saves you from having to redo it all later.

And let’s be honest—nobody has time for that.