Administration & Leadership

Using Design Thinking to Solve Wicked Schoolwide Problems

This five-step process helps school leaders guide their community through conversations about how to address tough issues.

April 2, 2025

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Stuart Kinlough / Ikon Images

As author Robin Sharma notes in his book The Monk Who Sold His Ferrari, “Change is hard at first, messy in the middle, and gorgeous at the end.” This conclusion certainly rings true for school leaders who confront daily issues that are both complicated, in that they involve many steps, and complex, in that they involve numerous stakeholders who occupy different roles in the school community and therefore have different perspectives on what should be done.

Consider, for example, the difficulty of addressing a multisided, emotionally laden question like grading practices. Topics such as whether teachers are grading too frequently result in round after round of committee discussions, public presentations, and policy debates—but few significant changes. In fact, the perceived difficulty of change may convince school leaders to avoid the challenges altogether, preferring the status quo to potentially difficult discussions. So, when a school decides it needs to tackle a wicked problem like grading, it helps to have a process to follow that accounts for all of the varying views.

Design thinking is one such strategy. It provides a structured yet flexible process for school leaders to examine and then reshape policies and practices in a way that is responsive to concerns of all stakeholders. Design thinking promotes collaboration among parties holding differing points of view. It helps them develop innovative—and practical—ideas that address the essence of an issue and lead the way toward sustainable change. In the sections that follow, we will provide a brief guide to administrative applications of design thinking, using a real-world example to illustrate its power to deliver meaningful change.

What is Design Thinking?

The design thinking process includes five phases to explore a problem and come up with a solution. As we explore in our book From Conflict to Collaboration: A School Leader’s Guide to Unleashing Conflict’s Problem-Solving Power, design thinking is particularly well suited to tackling “wicked problems”—that is, situations where solutions appear hard to define, elements seem to contradict each other, and people are initially at loggerheads. It has been widely used in fields such as business, engineering, and health care but has seen only limited use in schools. Its sensitivity to stakeholders’ underlying needs and their desires for input into solutions can help educators craft solutions that ultimately gain widespread support.

It’s important to note that design thinking is an iterative process, which means that each phase can loop back to any other phase to gather data, promote creativity, and refine thinking.

Let’s now consider how design thinking can be applied to one of the challenging issues confronting schools today.

Rethinking wicked problems through design thinking

Grading policies are among the most debated aspects of schooling. What should grades reflect? Mastery of standards? Degree of improvement? Effort? Design thinking presents an opportunity to navigate these points of turbulence and reach an agreement that addresses divergent perspectives and interests. Before starting the process, assemble a small working group (the “design team”) comprising school leadership, teachers, parents, and, if appropriate, students.

Empathize: In this stage, the goal is to understand the needs and perspectives of those affected by the problem. Ask the design team to begin by gathering input. For example, the team can conduct interviews with students to understand how the current grading system affects their motivation and achievement. Engage teachers about their views of the purpose of grades, as well as challenges they encounter. Survey parents to discover their perspectives. Use an organizing tool like an empathy map (available through Figma) to record findings. 

Define: Here, you should clearly identify the problem you’re trying to solve. Once a wide sampling of data has been collected and reviewed, work with the team to identify the core issues that emerge. Then, define the problem by forming an essential question premised on the themes reported in the Empathize phase. Based on what the group uncovered from the round of interviews, the essential question might be phrased in this way: How might we create a grading system that facilitates student growth while maintaining standards of accountability?

Ideate: This phase is often the most energized part of the process. Here the team employs a “think without the box” strategy to generate as many potential solutions as possible.

In Ideate, the design team embarks on a wide-ranging effort to develop innovative solutions for the guiding question developed in Define. There are many strategies for encouraging creative thinking, ranging from traditional brainstorming to a technique called “worst idea.” At this point, quantity is preferred over quality—there will be time for refinement and evaluation later. Make sure the team withholds judgment on any of the suggestions, as premature assessment can stifle the pursuit of innovative solutions. No idea is too ambitious or unconventional.

Ideas at this stage might include implementing standards-based grading, incorporating self-assessments, or allowing students to revise work for improved scores.

Prototype: Here, you select the most promising ideas, then develop tangible models that can be evaluated and refined. The team considers the ideas generated. Each one is assessed based on its potential to address the guiding question identified in Define. The team then selects the most promising ideas and refines them to make abstract ideas more concrete.

In the grading initiative, for instance, the team would identify one or two innovative models that combine opportunities for students to revise work for improved grades while evaluating progress toward learning standards. They might agree, for example, to pilot rubrics for students to self-reflect and then self-revise their own work.  

Next, the prototypes are tested on a limited scope, perhaps in one grade (e.g., fourth grade) or one content area (e.g., social studies), to determine strengths and weaknesses. Data and feedback would be assessed according to agreed-upon criteria, with further refinements being made to eliminate unproductive features. Extending our example, teachers in the pilot study would collect data assessing changes in outcomes following the opportunity to revise work and results of a survey to ascertain student attitudes toward learning given the opportunity to self-revise. Additional feedback would be collected from teachers implementing the prototype.

Test: Operationalize the best prototypes and put them into practice to observe their impact, gather and review feedback, and make needed improvements. Select the best option, based on criteria aligned with the problem definition. 

In this phase, the team selects the model that best satisfies the essential question raised in Define and produces a plan to bring the innovation to scale. We suggest that the team use three filters to accomplish this sorting process:

  1. Desirability. Does this solution directly address the issue? Did the evidence from prototyping indicate that the solution effectively addresses the problem? In the example, aforementioned data collection would be used to evaluate desirability. 
  2. Feasibility. Does the solution require resources (time, professional development, materials, staffing) that are within reach of the school or school district? (Such as analyzing curriculum materials and planning time, professional development, etc., needed to scale the grading exemplar to more grades and curriculum areas.)
  3. Sustainability. Is the solution one that can become part of “the way we do things around here”? Will its results continue to demonstrate value over time, promote widespread ownership of the solution, and thereby become an accepted part of practice?  

Even at this late stage, previous phases may be revisited, if data and feedback indicate that the Define question has not been addressed completely. If results prove positive, a full implementation process can proceed.

School leaders can use design thinking to tackle many other wicked problems: updating math curricula or increasing teacher retention, for example. The process provides a pathway forward when solutions initially appear unattainable. Design thinking empowers stakeholders to actively participate in the decision-making process and fosters collective ownership of results. As school communities become increasingly facile with design thinking practices, they create an environment in which collaboration blossoms and school improvement thrives, the “gorgeous” ending envisioned in Sharma’s quote.

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