Challenge Success and Pinewood School

How Pinewood School Approached Well-Being and Engagement for Upper School Students

Pinewood School’s Upper Campus has partnered with Challenge Success for three years. Building on survey data and ongoing leadership consultation, the school has engaged in meaningful work around student well-being, engagement, belonging, grading reform, leadership development, and parent education. A hallmark of the partnership has been Pinewood’s commitment to centering student voice, using student feedback and survey findings to inform school improvement efforts and ensure that decisions are grounded in the lived experiences of students.

School Partner 2023-24, 2024-25, 2025-26

About Pinewood School

Pinewood School is a K-12 independent school in Los Altos, CA, with three campuses serving a total of 600 students. Their mission is to empower students to seek knowledge, demonstrate character, build confidence, and experience joy in an uplifting community.

Independent School

K-12

600 Students

phase 1

Ignite

An important first step for every school in the partnership is to intentionally form their 10-person change team that meets with the Challenge Success Coach five times throughout the school year. Because the Challenge Success Change Process prioritizes the voice and perspective of students and actively includes multiple perspectives, cultures, and identities, all teams must include at least two students in addition to school staff and parents/caregivers. Pinewood’s team included:

3 Students
2 Administrators
2 Parents
3 Teachers

Pinewood School partnered with Challenge Success to gain a deeper understanding of the student experience and address growing concerns related to student stress, engagement, and assessment practices. Through survey data, student voice initiatives, and collaboration with students, families, faculty, and school leaders, the partnership has helped Pinewood identify opportunities to strengthen well-being, promote meaningful engagement, and foster a climate of care where students feel known, valued, and supported.

Center the Student Experience

Pinewood School’s Upper Campus student survey, alongside the school’s own observations and anecdotal data, revealed many strengths, including a strong sense of school culture and positive student-teacher relationships. At the same time, the data highlighted opportunities to deepen student engagement and reduce stress related to assessments and workload.

To better understand the student experience beyond the survey data, the school engaged the community in several Listening In Protocols, including Dialogue Night and an “I Wish” Campaign, to better understand the school experience. The team examined their data and compared it to Challenge Success national averages, uncovering many bright spots as well as key areas for growth, helping to inform future priorities and action planning.

Caring School Climate: Small, family/community, and caring/welcoming are the top words students use to describe the school

Respectful Learning Environment: The vast majority of students think a lot or all of their teachers treat students with respect and value and listen to students’ ideas

Opportunity to Improve Engagement: Students are doing their work, but more students could be finding their schoolwork meaningful.

Physical Symptoms of Stress: Many students report a physical health symptom due to stress in the past month

Academic Worry: Many students students often or always worry about taking assessments

Define an Improvement Aim

With support from their Challenge Success Coach, the team unpacked the student experience to better understand the underlying root causes of the survey findings. By the end of Phase 1, the team had developed new skills, perspectives, and knowledge, and was ready to create a clear aim for improvement.

Their aim was to develop a more balanced testing schedule and proactively plan for the future, drawing on Challenge Success research and expertise to inform more equitable and aligned assessment approaches. Leadership also recognized the ongoing need for faculty professional development to apply new strategies to promote engagement in learning.

phase 2

Engage

In Phase 2, the team is charged with co-designing change ideas with specific goals aligned with their vision. This process involves brainstorming, creative ideation, consulting with their coach, using practices from the SPACE Framework for School Change, and collaborating to create an action plan. Teams then put the plan into action by implementing change ideas, monitoring and assessing the progress as they move through Cycles of Inquiry.

Design + Test Change Ideas

After team discussions around which strategies would have the most impact and the ease of implementation as well as incorporating input from teachers and school leaders, they landed on the following change areas:

Pinewood Conflict Calendar paper version

change idea #1

Test and Project Calendar

A quick win to decrease student stress was to create an assessment and project conflict calendar so that students could avoid having too many deadlines or major assessments in a given week. After the success of the pilot they created a shareable, digital version and guidelines for providing notice to students.

change idea #2

Assessment Policy Alignment

Pinewood School engaged in a multi-year process to examine grading and assessment practices through the lens of rigor, equity, and student well-being. Using Challenge Success survey data, student voice initiatives, and faculty collaboration, the school identified assessment-related stress and inconsistencies in grading as opportunities for growth. Faculty participated in professional development and department-level calibration work to explore grading philosophies, assessment weighting, retakes, and late work practices. This thoughtful and iterative process ultimately led Pinewood to adopt a 50–100 grading scale to promote more equitable and accurate representations of student learning while maintaining high expectations.

Student voice played a central role throughout the work. Student representatives met directly with department heads and faculty to share their experiences with assessments, highlighting the challenges of overlapping tests, heavy homework loads, and high-stakes grading. Students emphasized that clearer expectations, assessment spacing, flexibility, and opportunities for retakes support deeper learning and engagement. They also expressed strong support for the 50–100 grading scale, noting that it maintains accountability while allowing students to recover from mistakes and continue learning.

Administration adopted a revised assessment policy, codified in both the faculty and student handbooks, to create greater clarity and consistency around assessment practices. The policy defines major and minor assessments, establishes advanced communication through Schoology and the conflict calendar, and limits students to no more than two major assessments per day. These changes aim to maintain academic rigor while reducing unnecessary student stress and supporting a more balanced learning experience.

change idea #3

Conduct parent and faculty workshops

Pinewood invested extensively in parent education and faculty professional development to build a shared understanding of student well-being and learning. Workshops included The Well-Balanced Student, A Healthier Approach to College Admissions, Designing with Purpose, Pedagogy that Engages, Faculty and Staff Well-Being, Rethinking Assessment, and Dialogue Night, and Engaged Learning in an AI World, equipping families and educators with research-based strategies to support healthy, engaging learning environments.

Reflect on Progress

The following reflections were gathered from the team at the end of the 2024-25 year:

I think that the most valuable part of the experience was being able to make an impact on my school in a positive way. It also helped me see the issues other students are facing, and allowed me to think about how to help there as well.
Pinewood Upper School Student

I have loved working with an outside organization to get perspective on issues that similar schools face, and I also learn a lot by listening to the opinions and lived experiences of other constituents at my school besides teachers (parents, students).
Pinewood School Faculty Member

I have appreciated being able to work together as a team to move forward some initiatives that the school has been struggling with for years. We have made real progress. I really appreciate the cooperative nature of the work, and the research-based approach to strategies for working with students and creating a healthy environment.
Pinewood School Administrator

phase 3

Sustain

For the 2026–27 school year, Pinewood will continue its partnership with Challenge Success through ongoing leadership consultation, faculty professional learning, and parent education. Building on the progress made over the past three years, the school will focus on strengthening engagement, deepening alignment around grading and assessment practices, and continuing to use student voice to inform decision-making. This work will continue to be intentionally integrated across the Lower, Middle, and Upper School campuses, fostering a cohesive approach to supporting students throughout their educational journey.

Through regular collaboration with school leaders, workshops for faculty and families, and continued examination of survey data and emerging research, Pinewood aims to further cultivate a learning environment that promotes academic excellence, student well-being, meaningful engagement, and a strong sense of belonging.

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