The 3 Questions That Make or Break Your Strategic Plan

For all my Doer and Dreamer friends. “Feet on the ground, head in the sky” – Talking Heads.

I just finished a conversation with a school that completed its strategic plan. I could sense both relief and anxiety in equal measure. The relief? It’s done. The anxiety? Now what?

Whether you’ve just completed a plan or see one in your near future, there are 3 questions that every school should answer to move forward with excitement and confidence.

1. Who are you—really?

Right now. Not who you hope to be in the future or how your alumni remember you, but who are you authentically right now?

The 80/20 rule applies here: 80% authentically true today, 20% aspirational—meaning you’ve already made investments to get there. But 20% is the exception, not the rule. Get the rule right first.

To think about where you want and intend to go is dream work! It’s the what if, full of possibility—if you get there, then you’ll be better, stronger, faster, different. But clarifying your current identity turns dreamers into doers. If your community can’t articulate who you are today, how will they tell your story tomorrow? Prospective families live in the here and now. You need to, too.

Start by measuring the gap between how you see yourself and how the market sees you. That gap tells you what you can—and should—say about who you are today.

2. Who are you for? And equally important: who are you NOT for?

Strategic planning often focuses on growth—more students, more programs, more buildings, more reach. But growth without clarity about your mission-aligned community leads to mission drift and enrollment challenges. The schools that thrive know exactly who they serve best and the benefits they receive from being part of your community.

Are you trying to be everything to everyone—spreading your team thin and diluting what makes you special?

3. What story are people already telling about you?

This is your brand. As my friend Torsie Judkins, Head of School at Wingra School, says: “If you’re not telling your story, someone else is. And it’s not accurate.”

Word-of-mouth is the #1 way families discover and learn more about schools. While you’re busy planning your future, your community is already talking about you—at soccer games, school pickups, dinner parties. Their current narrative matters. Strategic planning built on a shaky brand foundation is just wishful thinking.

Have you equipped your community to tell your story compellingly and consistently to clear up misperceptions?

All three questions need answers before you can meaningfully plan where you’re going. Strategic planning without brand clarity is just wishful thinking.

But the best schools I know? They’re doers and dreamers. They know who they are today and have a plan for the future.

Need help making sure your strategic plan is built on a foundation that’s authentic, clear, and compelling? We should talk.