Ensuring That Your Strategic Development Plans Are Effective

Over my 30-year career, I’ve helped create and/or hone several strategic plans. Some were mandated, such as No Child Left Behind, while others were more organic, visionary, and school-driven.

Regardless of the plan, I always questioned how effective it was at balancing the big-picture vision with the day-to-day work. Too often, strategic plans aren’t implemented because they lack the specificity needed to turn vision into action. As superintendent of the New Castle County Vocational Technical School District, I initiated a shift that required us to rethink how we were going to achieve and live out our vision.

In the aftermath of Covid-19, we confronted learning loss and were dedicated to supporting student well-being. As a result, we shifted from strategic planning to strategic development. We needed a system to keep us focused on where we were headed but flexible in how we arrived there.

Our central guiding question was: How can we align our goals with our initiatives, track progress in real time, and maintain unwavering focus, while remaining nimble as circumstances change?

Develop a Small Set of Core Priorities

As I gathered feedback and evidence from our administrative council—four directors, four principals, and multiple supervisors—I realized that we needed to sharpen our priorities, streamline our initiatives, and unify them into a few clear disciplines. Input from each person was critical to ensure that we were on target. Our “Core Four” priorities emerged:

1. Systems and Safety Excellence
2. Learning That Transforms
3. Belonging and Well-Being
4. Vision-Driven Innovation

The process occurred over several months and was woven intentionally into our administrative council agenda, so it never became an added burden. While these are slightly different from our original four from the pandemic, the intent and focus remain. Every initiative, strategy, and conversation connects back to one of these core areas. They help us identify the essential work and enable us to prioritize efforts to ensure coherence among our initiatives.

Practical leadership takeaway: Define three to four priorities that encapsulate your core work and what you must accomplish as a school or district. The fewer the better.

Keeping Goals Alive

Our core disciplines are the lens through which every decision, resource allocation, and critical move is made. Each pillar is anchored by clear goals, aligned strategies, and specific key performance indicators (KPIs) to measure success. While the Core Four remain constant, the goals, strategies, and KPIs are reviewed four times a year to evaluate progress and adapt in real time.

A pivotal moment in shaping this mindset came through an executive coach who helped me get clarity and be intentional about where we were headed. She said, “Joe, every time you speak, you create a mountaintop. But between those peaks is a valley that fills with assumption, rumor, or someone else’s narrative.”

That insight is why I established our planning process and meeting cadence—to organize the work and reduce those “misinformation valley" moments.

In my district, I’ve established a four-meeting cadence with the administrators from each school and division (a total of 10 individuals) to keep our priorities at the forefront and prevent initiative drift. It proceeds as follows:

Summer institute: In July, all district and school administrators meet during a two-day administrative workshop to align goals to the Core Four, review key data, identify high-leverage strategies, and set targeted KPIs.

Fall check-in: Schools and divisions solidify their goals. I meet individually with the 10 administrators to ensure alignment, sustainability, and accountability.

Midyear review: I meet with administrators to review their progress, make midcourse corrections, and ensure overall alignment between the district and school initiatives.

End-of-year review: Each school and district division formally documents outcomes, reflects on successes and challenges, identifies how the initiatives supported one another, and begins to determine how the goals should be refined for the upcoming year.

Although this is time-intensive, I’m able to ensure that everyone is on the same page, and I can coach the people I directly supervise so that they lead more effectively. I also aligned our process to the state evaluation system in order to avoid duplicating efforts, draining resources, and wasting time.

Practical leadership takeaway: Schedule predictable checkpoints—don’t leave progress monitoring to chance.

This quarterly rhythm keeps our goals at the forefront and reinforces accountability across the team, without becoming rigid or bureaucratic. It’s the heartbeat of our strategic development process, where I work alongside teams to establish goals, ensure alignment with our vision, and continuously calibrate our efforts.

Here’s what one of our Core Four goals might look like:

Core Four: Belonging and Well-Being

Goal 1: Supporting the Needs of the Whole Student (academically, socially, and emotionally)

Strategy: Strengthen MTSS tiered supports so that every student receives the appropriate level of intervention, ranging from universal social and emotional learning (SEL) practices to targeted small group supports and intensive individualized plans.

Activity: Provide professional learning on trauma-informed practices.

Train staff on the “window of tolerance” framework so that teachers can recognize signs of dysregulation in students and respond with de-escalation techniques.

KPI: Ninety percent of staff will complete professional learning on trauma-informed practices and demonstrate proficiency (via observation or coaching feedback) in using at least one de-escalation strategy in classroom or student support settings.

This approach reduces frustration because we aren’t jumping from initiative to initiative. It strengthens cross-department collaboration and fosters coherence, shared understanding, and ownership.

Breaking Down Silos

As superintendent, it’s my job to set the vision and ensure that we stay the course. Each school and district division moves toward the same destination. My responsibility is to ensure coordination, alignment, and communication, and that we advance together.

Cross-division and school collaboration creates alignment and harmony. The SEL goal mentioned above begins in Student Services, but it directly connects to Instructional Services and provides the foundation that schools need for effective execution.

Misaligned goals and disjointed efforts are one of the great chasms between district offices and schools. By intentionally requiring divisions and schools to plan together, we eliminate silos and create coherence. Strategic development allows me to ask the following questions:

1. Where are we advancing that is directly aligned to our Core Four?
2. Do we need to refine or reset our expectations or approach?
3. Are we measuring what matters with our KPIs?

Rather than viewing misalignment as failure, treat it as valuable feedback. I also strive to make humility a structural part of the process, so that my team can help me recognize necessary changes and needs that arise. It’s an opportunity to break down the hierarchy, identify blind spots, and recalibrate.

Practical leadership takeaway: Use misalignment as data, not as a dead end.

Strategic Development as an Ongoing Practice

In my experience, shifting from strategic planning to strategic development has created a system that’s flexible enough to adapt and focused enough to stay aligned with our core priorities. Annual updates keep us current, structured checkpoints ensure accountability, and cross-divisional conversations build coherence. Strategic development is a discipline that creates opportunities for leaders to operate on purpose, with intention.