What do you want people to remember about how you led?

The Courage to Say Yes: Your Leadership Story Matters

February brings a question that stops educational leaders in their tracks. Leadership blogger Dan Rockwell posed it to two young American men returning from service in Beirut: "How would you like others to be different after hearing your story?"

One of them, Tyler, answered without hesitation: "I want them to be ready to say yes. Take chances. Don't put things off."

This is what makes that response so powerful for educational leaders: Tyler wasn't thinking about his résumé or his accomplishments. He was thinking about his influence on others, his legacy—the ripple effect of his choices on others. That's the shift from management to leadership. Leaders think of themselves with others in mind.

So pause for a moment and ask yourself Rockwell's question: How would you like others to be different because of your leadership story? What do you want people to be ready to do because they witnessed your courage? Your answer to that question reveals everything about the leader you're becoming.

Here’s where I think it’s even more interesting. Peter Block, in his book The Answer to How is Yes: Acting on What Matters, cuts through all our strategic planning and careful calculations with a radical idea--real change is moral, not technical. He challenges us to stop worrying immediately about techniques, next steps, or anticipated resistance. Instead, he asks us to decide what we won't tolerate anymore and what we can't not address—and then do something about it.

Think about the gap between those two ideas. We know what we won't tolerate anymore. We see what we can't not address. But we get stuck in the "how"—waiting for the perfect strategy, the right buy-in, the ideal conditions. Meanwhile, students wait. Staff members lose hope. Opportunities slip away. The things that matter most get postponed indefinitely while we figure out the technical details.

Block is asking educational leaders to make a moral commitment first, then figure out the strategy as we go. When do we just need to say yes, move forward, and in the process, figure out our next best step? That's not reckless leadership—that's courageous leadership. It's the willingness to act on what matters before you have all the answers.

And the beautiful connection is here: the way you answer Rockwell's question about your leadership story should inform what Block is challenging you to say yes to. If you want others to "take chances and not put things off, then you have to model that yourself. You can't inspire courage in others while you're waiting for perfect conditions. You can't teach people to say yes while you're stuck in strategy mode.

What do you need to say yes to right now? What have you been putting off because you don't have the perfect plan? What matters so much that you can't not address it, even if you're still figuring out the how?

The most powerful leadership stories aren't about people who had all the answers. They're about people who had the courage to act on what mattered, even when the path wasn't clear. They're about leaders who decided some things were too important to wait for the perfect strategy. They're about educators who said yes when it would have been easier to say, "Let me think about it."

February is the month when New Year's resolutions typically die. It's when the initial enthusiasm fades and reality sets in. It's the perfect time to ask yourself Block's question: What won't you tolerate anymore? What can't you not address? And then, following Tyler's example, just say yes. Take the chance. Don't put it off.

The technical details will work themselves out. But the moral courage to say yes and move forward, that has to come from you. And that decision—that moment of courage—becomes part of your leadership story.

What do you want people to remember about how you led? Let that answer give you the courage to say yes to what matters most.

Real change is moral, not technical. And your story is being written right now.

Sources:

• Dan Rockwell, "The Question I've Never Asked," Leadership Freak blog, December 23, 2025

• Peter Block, The Answer to How is Yes: Acting on What Matters (as referenced in Jennifer Abrahamson's newsletter)