Learning to Lead


Learning to lead is a challenging and empowering experience at Castilleja. Grounded in research and informed by decades of work, Castilleja’s unique leadership development program is woven seamlessly throughout the daily lives of its students in and out of the classroom and beyond the Circle.


Our schedule (including interdisciplinary time blocks), pedagogical principles, opt-in enrichment experiences, and commitment to skill-building across grades 6 - 12 all ensure that every girl graduates from Castilleja understanding and proud of her own personal leadership style.

Exercising Choice

Leadership competencies are best taught and practiced through experiences that girls find personally compelling. At Castilleja we intentionally design opportunities for each girl to exercise choice and learn within a context that is meaningful to her.

In Middle School students are introduced to the concepts of initiative, agility, and purpose through:


  • Grade-level partnerships with community organizations inspire a variety of opportunities for collaboration. Partnership programming is designed to expose students to our extended community and a wide variety of experiences and life stories.
  • Global Week extends learning beyond the classroom and offers students a range of ways to express their understanding of and point-of-view about the year’s theme.
  • Electives allow students to explore a new topic, delve more deeply into an area of interest, and exercise choice. Whether students are gardening with our Upper School biology teacher, electrifying greeting cards in our makerspace, playing flag football with our Middle School Athletics Director, or crafting Pysanky eggs with a Science teacher, all students are expressing curiosity, developing a flexible approach to problem-solving, and reflecting on how they collaborate best with others.

Upper School students exercise choice through:


  • Grade-level programming including Vision and Voice, Community Connections, Global Investigators and Leadership Lab.
  • ACE Org participation that often leads to leadership roles in Junior and Senior year.
  • Annual events and workshops such as Global Week, C-STEAM, C-HUMANITIES, and RM-4 designed to expose students to new ideas, innovations, and professions.

Building Capacity

At Castilleja students are encouraged to step up and into opportunities at school and in our local and global community. As they exercise choice, they are filled with a sense of agency and supported appropriately to develop the skills and competencies necessary to deliver on their hopes and meet their goals.

Students build capacity through practice. You may find them:


  • Proposing and then “pitching” for the next Arrillaga Annual Speaker
  • Responding to the national call for a student walk-out against gun violence
  • Raising awareness and funds in support of victims of a natural disaster
  • Running a debate and mock election in November
  • Applying for the Katherine Hass Fellowship for Exploration, Empathy, and Inclusion and working with a mentor to develop their ideas and complete a project of their choice senior year
  • Leading programming in junior and senior year advisory and wellness that highlights the importance of initiative, agility, and purpose
  • Selecting a favorite option from a series of senior mini-courses on topics ranging from financial planning to mindfulness to philosophy

The Learning and Leading Portfolio

Using the Learning and Leading Portfolio, students reflect on their learned leadership skills starting in 6th grade and continue through their high school graduation. The Learning and Leading Portfolio is a unique tool that frames and articulates each student's unique leadership development both inside and beyond the classroom and captures their growth in six core leadership competency areas: curiosity, purposeful reflection, embracing ambiguity, problem-solving, empathy and collaboration.
Over their seven years at Castilleja, students are mentored to self-assess and are externally assessed by peers, faculty, and advisors on these core competencies as they move from novice to mastery.