Episode 270: If Your Plan Starts in August, You May Already Be Behind

This week kicks off a three-part solo series focused on one critical question:

How do we actually plan for success in the coming school year?

April is a time when leaders are deep in planning—budgets, staffing, schedules, and resources are all coming together. But too often, we focus on what we’re going to do without fully thinking through how we set our teams up for success.

In this episode, Darrin challenges a common leadership assumption—that the work starts in August—and introduces a different way of thinking.

Because August isn’t the starting line.

It’s the reveal.

In This Episode

• Why so many leadership teams delay their real work until August
• The danger of treating the start of the school year as the starting point
• How lack of clarity shows up immediately when the year begins
• A powerful shift in thinking: “What must be true by August?”
• An introduction to backward mapping as a leadership strategy
• A simple exercise you can use right now to begin planning differently

Key Takeaway

Great leaders don’t wait for August to get started.

They use the time leading up to the school year to build clarity, align their teams, and create momentum—so when the year begins, they’re ready.

Try This

Pick one initiative or priority for next year and ask yourself:

What are three things that must be true by August for this to succeed?

Your answers will reveal exactly where your focus should be right now.

What’s Coming Next

Next week, we tackle a real challenge many leaders face:

What do you do when your team is in transition and August really is when everyone comes together?

Even in times of change, there are steps you can take now to set yourself up for success.

Sponsor Spotlight: HeyTutor

Strong leadership requires focus—and that’s hard to maintain when leaders are pulled into operational work that can be handled by the right partners.

That’s why Darrin highlights the work of HeyTutor, a sponsor of the Leaning Into Leadership podcast.

HeyTutor provides:

• High-quality, evidence-based math and ELA tutoring
• Full program management (recruiting, training, scheduling)
• Clear data tracking through an easy-to-use dashboard

Their support helps leadership teams stay focused on what matters most—leading people and improving outcomes.

Learn more: heytutor.com