Learning to Lead


Learning to lead is a challenging and empowering experience at Castilleja. Grounded in research and informed by experience, our leadership development program is woven into daily life around and beyond the Circle.


As our students grow as leaders, we help them think about two important concepts: exercising choice and building capacity. Exercising choice fills students with a sense of agency, allowing them to take active roles in reaching their goals and exploring new ideas. Building capacity involves developing and reflecting on specific leadership skills and competencies. In addition to these themes, our pedagogical principles and enrichment experiences ensure that every student graduates from Castilleja with an appreciation of her own personal leadership style.

Initiative, Agility, and Purpose

In Middle School, learning to lead begins with understanding the importance of initiative, agility, and purpose. Students define these terms in relation to leadership and explore how they use these qualities both to lead and to collaborate effectively. 

Middle School students grow as leaders through:


  • Theme-based Global Week exploration that extends learning beyond the classroom and provides students with a range of ways to express their points-of-view.
  • Electives that allow students to delve more deeply into an area of interest and develop a flexible approach to problem-solving and teamwork.

The Learning and Leading Portfolio

Upper School students use our Learning and Leading Portfolio to identify their strengths and choices as leaders. This unique tool helps each student frame and articulate her leadership development by reflecting on growth in six core leadership competencies: curiosity, purposeful reflection, embracing ambiguity, problem-solving, empathy, and collaboration. Students learn to assess themselves in these areas and and are also reviewed by peers, faculty, and advisors to gain deeper insight.

Upper School students grow as leaders through:


  • Grade-level, student-driven programming and outreach, including Global Investigators and Leadership Lab.
  • ACE Organization participation in clubs that tackle local and global issues and offer leadership roles in junior and senior year.
  • Annual events and workshops such as Global Week and Beyond the Circle, programs that are designed to expose students to new ideas, innovations, and professions.

Meaningful Action

Our core leadership competencies are best practiced through experiences that the students find personally compelling, so we design opportunities for each student to learn within a context that is meaningful for her. 

Students explore by:


  • Proposing and then “pitching” for the next Arrillaga Annual Speaker.
  • Raising awareness and funds in support of victims of a natural disaster.
  • Developing a theme or connection for a new ACE Org.
  • Establishing a new Affinity Group for members of our community who share a common identifier.
  • Applying for the Katherine Hass Fellowship for Exploration, Empathy, and Inclusion and working with a mentor to 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.