How WIN Time is Transforming Schools: 4 Must-Do Steps for Leaders

The Book. The System. The Software That’s Reshaping Intervention in Schools.

You and I have been in education for quite a while now, right?

(Can you believe it’s been over 27 years in my case?)

That doesn’t make it any easier when big shifts in our field shake the foundation of how we support students. And that’s exactly what’s happening right now: schools are expected to deliver personalized learning, measurable student growth, and targeted intervention—without any additional time, staffing, or resources.

If you’ve been feeling the pressure, I get it.
But more importantly, I want to help you take action.

Today’s post breaks down what’s changed in our schools, how it affects your campus or district, and outlines four specific steps you can take right now to strengthen your intervention efforts and position your school for success.

Let’s dive in.

What’s the Update All About?

If you haven’t heard, intervention and enrichment are no longer supplemental—they are essential. State and local accountability measures have made it clear: schools must not only support students beyond core instruction, but they must also document progress, show growth, and respond to data in real time.

Here’s how this is impacting school leaders:

• Campuses are struggling to find time for intervention without cutting into core instruction.
• Teachers are overwhelmed by student data and unsure how to turn it into instructional action.
• Leaders are seeking systems that are manageable, scalable, and centered around student needs.
• Districts are under pressure to show that every student is making progress.
• Time and staffing shortages are making it difficult to build anything sustainable.

This all sounds challenging—because it is.
But you don’t need to start from scratch. That’s where WIN Time comes in.

Four Things You Should Do Right Now

1. Define the Vision Behind Your WIN Time

Early in my journey, I made the same mistake I now help others avoid. I jumped straight to the schedule without first establishing the why and what behind WIN Time. The result was misalignment, confusion, and lackluster results.

Before implementing anything, get clear on this:
What should WIN Time look, feel, and sound like on your campus?

Communicate that vision consistently, and you’ll see your team begin to align their efforts with purpose.

Need help getting started?
The book WIN Time: Fearlessly Transforming Your School outlines every step of the process—and it’s a game changer.

2. Build a System That Works, Not a One-Time Fix

WIN Time is not a block on the schedule. It’s a schoolwide system for delivering intervention and enrichment based on real-time student data.

The most effective schools I’ve worked with use a system that includes:

• Data-driven student grouping
• Targeted instruction aligned to gaps
• Clearly defined roles and responsibilities
• Regular data check-ins and instructional adjustments

This is the system I walk through in the book and support with ready-to-use templates and forms. If you’re not building a structure, you’re setting yourself up to repeat the same cycle year after year.

3. Keep the Process Simple and Sustainable

It’s easy to overcomplicate things—especially when the stakes are high. I’ve seen districts build massive spreadsheets, create new roles, or implement layers of tracking systems that ultimately fall apart after a few weeks.

Start with what matters: student needs, instructional strategies, and accountability. Then grow from there.

One school I coached recently went from scattered efforts to a laser-focused model by doing one thing: simplifying the process and clarifying who was responsible for what.

The result? Higher engagement from staff, and real gains for students.

4. Use the Software That Saves You Time and Tracks What Matters

The WIN Time Software was built to take everything in the book—and make it digital, fast, and easy to manage.

This all-in-one platform allows you to:

• Group students automatically based on data
• Adjust assignments as needs change
• Track interventions and enrichment in real time

The software is priced at just $5 per student, making it accessible for even the smallest districts. And it’s not just efficient—it’s built by educators, for educators.

Want to see it in action?
Click here to schedule a demo

WIN Time is now under the ownership of Enriching Students, a trusted leader in EdTech known for empowering schools with smart, student-centered scheduling solutions. This partnership brings even greater support, innovation, and reliability to the WIN Time Software.

Conclusion

If you’ve been feeling the weight of rising expectations and dwindling time, you’re not alone. But you don’t have to stay stuck in reaction mode.

With a clear vision, a proven system, and the right tools, you can build an intervention model that actually works—and one that works for every student.

At Principal Principles, we believe in making school improvement practical and powerful. That’s why we’ve developed resources at every level to help schools like yours WIN.

Your next steps:

• Get the book and start building your WIN Time foundation
• Schedule a software demo and see what’s possible with a few clicks

Have questions or need help getting started?
Contact my team at [email protected] or find us on social @principalprinciples.

Let’s build something better—together.