The Digital Paradox: Leading K–12 Transformation with Vision and Pragmatism

 

Success in digital transformation comes from visionary leadership focused on process improvement and empowering people, rather than relying solely on new technology.

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Amy Durgin, PhD

 Published November 2025

School business leaders are no strangers to change. From balancing budgets to managing evolving instructional tools, every day brings new challenges and opportunities. When it comes to digital transformation (DX), the goal isn’t just to modernize systems — it’s to make school operations smarter, more efficient, and better aligned with student success.

Start Small: The “Day-Forward” Strategy 


A full-scale conversion of every paper file into digital form can sound daunting, but it’s also not the most pragmatic solution. The more sustainable, cost-effective approach is to implement a “day-forward” strategy. That means redesigning your administrative processes so that every new student registration, permission slip, IEP update, and staff record is born digital. 


Tools that were once more expensive are no longer so. More affordable cloud tools today can help ensure the proper creation, filing, and accessibility of digital-born files, while existing scanners can handle the conversion of any lingering incoming paper. Over time, paper files naturally phase out as digital systems become the norm.

Reframing the Investment 

As Gregory Long, director of purchasing and distribution for Florida’s Seminole County Public Schools, puts it: “Change often happens piecemeal because we don’t have the dollars to do it all at once.” 

That reality makes prioritization key. A phased approach allows districts to focus first on high-impact areas — those that save the most time or reduce the most manual work. 

Digital transformation isn’t just about technology — it’s about reclaiming time. Every minute staff spend searching for paper files is time not spent supporting students, training staff, or planning strategically. Viewing DX as a strategic investment in operational excellence helps districts free up their most valuable resource: people.

Viewing DX as a strategic investment in operational excellence helps districts free up their most valuable resource: people.

Building a Culture of Change 

Successful DX starts with leadership — and not just at the top. When district leaders model empathy, clear communication, and openness to small-scale experimentation, they create an environment where innovation can thrive. 

Try starting small: 

  • Pilot a digital process with a few trusted users. 
  • Gather feedback, refine, and prove its value. 
  • Use those early wins to build momentum across departments. 

As Dave Miyashiro, a K-12 leader with decades of DX experience, has observed, "What I learned from prior implementations is that having everybody learn on their own is a recipe for disaster. You have to make the commitment to learn together as a collaborative group." 

Technology is easier than ever to scale. The real challenge — and opportunity — is guiding people through change. 


Vision and Courage 

The most successful digital transformations aren’t driven by the newest software — they’re powered by leaders who have the vision to see what’s possible and the courage to challenge old assumptions. 

By focusing on process redesign over product hype and collaboration over compliance, school district leaders turn uncertainty into a strategic advantage. The result? Stronger systems, more engaged teams, and a culture ready for whatever comes next.

  

   

The Leader You Are. The Change You Drive.

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