Leadership Fellows Program

Oct 24, 2025 6:00PM—Oct 26, 2025 12:00PM

Location

Upham Hotel in Santa Barbara

Cost $5,600 members; $8,400 non-members

Categories Hybrid, Leadership, Ongoing Program

Leadership Fellows Program

RETREAT: October 24 - 26, 2025 at The Upham Hotel

SESSION 1: December 12, 2025 | 10:00am - 12:00pm | Virtual

SESSION 2: January 9, 2026 | 10:00am - 12:00pm | Virtual

COACHING SESSION: Virtual

SESSION 3: March 13, 2026 | 10:30am - 3:30pm | Northern CA Location TBD

SESSION 4: May 1, 2026 | 10:30am - 3:30pm | Southern CA Location TBD

APPLY NOW

PROGRAM DESCRIPTION

Priority Applications are Due by June 1!

The job of an independent school leader can be complicated and rewarding—and on some days, it’s pretty darn tough. Often working directly with many constituent groups, school leaders require a myriad of interpersonal and professional skills in order to lead, to collaborate effectively, and to have impact. With an ever-more complicated world landscape, it’s essential to not only be an effective leader but also make the work joyful and sustainable by better knowing oneself and the needs of the position.

This Fellowship for experienced educators from throughout California supports the unique demands of independent school leaders—the only program of its kind in the state! Facilitated by two Heads of School (one former and one current), the Leadership Fellows Program offers time for personal reflection on one’s leadership journey, practical knowledge and skill development specifically targeted to independent school leadership, as well as supportive professional connections.

The program opens with a two-day retreat in Santa Barbara designed to allow the cohort to connect and reflect as well as engage in sessions designed to hone leadership capacities. Other sessions might include case studies, problem-based discussions, career planning and strategy, and activities that will challenge participants to reflect on their roles and encourage the development of their leadership skills.

Goals:

To provide experienced preK-12 leaders with the knowledge, skills, and resources important for senior level leadership;
To provide time and space to “see oneself” clearly and reflect on where each person is–uniquely–in their leadership journey;
To address topics such as leadership EQ, communication, team building, systems thinking, strategic planning, and organizational health;
To develop and strengthen relationships and networks of support among school leaders.

CATDC is delighted to structure Leadership Fellows in primarily an in-person model with three in person meetings and two on-line meetings to stay connected between sessions. In addition to a two night retreat in Santa Barbara, we will include two virtual cohort check-ins, and two in person day-long sessions, one in Northern and one in Southern California. In addition, participants will visit a colleague’s school in their area and have a virtual individual mentoring session with one of the facilitators.

AUDIENCE

Individuals who are or aspire to be senior leaders and/or heads of school. Preferably participants will have five years experience in a leadership capacity in academic roles (academic deans, division directors or deans of curriculum/teaching and learning, DEI) or non-academic ones (admissions, development, communications, or finance).

EARN GRADUATE LEVEL CREDITS

CATDC is partnering with Courses4Teachers to offer University of the Pacific graduate-level professional development semester units/credits for your participation in Leadership Fellows!

Testimonials

Leadership fellows is honestly the best kept secret in terms of professional development for headship. I was privileged to be a part of the second cohort of this group and the relationships formed there and the coaching I received are why I am able to confidently serve as a head of school now. I continue to lean on those connections and feel fully supported even now – I can’t speak highly enough of this opportunity and encourage everyone interested in serving as a head to make the commitment!

I had no idea how much I would learn from my cohort group, and how bonded we would become during this process. The role playing was incredibly helpful, and all the guest speakers brought excellent (and differing) perspectives to the conversation.

I loved that the group was coming from different types of schools (sizes, grades, etc.). Building those bonds is what is the most important to me! The program leaders are both invested and extremely knowledgeable.

I appreciated knowing that not everyone in the program wants to be a director, that there are other ways to lead. Also, It was reaffirming to hear that other schools are having the same issues as mine, and seeing perspectives from other departments was extremely helpful and opened my eyes to some other job opportunities.

APPLICATION PROCESS

Enrollment in this program is limited and by application only. Requirements for consideration of admission to this program include:

Application submission: Priority applications are due June 1 with our first round of participants announced June 15. If there is still space left in the program, a second round of applications will be due on September 19 with our full cohort announced on October 1. Please find our application form here.
A $500 program deposit to be submitted via Eventbrite, refunded if you are not accepted.

SCHOLARSHIPS

Thanks to the Janet McGarvey Fund, CATDC is offering a limited number of scholarships to participants in our Leadership Fellows Program.

Eligibility: CATDC’s Leadership Fellows Scholarships are intended for individuals who otherwise would not be able to participate in the program due to limitations in professional development funds at their school sites. In addition to demonstrated financial need on the part of their school, we will prioritize scholarships for individuals who bring diversity to the program in terms of experience and regional representation. We are also asking schools to make some contribution to the registration costs. See more details below.

Please apply for a scholarship if your school does not have the resources to pay a full registration fee, and ensure you can attend if accepted and granted funding.

Scholarships will be given to offset registration costs.

In order for your application to be considered, this statement of finance form must be completed by your Head of School or Business Office.

Scholarship applications and statements of finance will be due June 1, and recipients will be notified by June 15.

FACILITATORS

Phil Gutierrez is the Head of School at Marin Primary & Middle School in Larkspur, CA. Before MP&MS, he was the Head of School at Mid-Peninsula High School in Menlo Park, CA. Prior to headship, Phil worked at The Branson School in Ross, CA for 22 years, first as an English teacher and then in a variety of administrative roles, including class dean, Director of Admission, and Assistant Head of School for Advancement and External Affairs. Phil currently serves on the boards of CATDC and Live Oak School, and he previously served on the CAIS and Mark Day School boards. He is also on the faculty of the NAIS School Leadership Institute in Washington DC. Phil holds his B.A. in English, with a minor in Spanish, from U.C. Berkeley and his M.A. from Stanford. He and his wife, Robbie, are parents of two adult children. Phil loves to play the guitar, read, and entertain the family's black Labrador retriever.

Crystal Land currently works as a strategic plan and leadership consultant for Leadership+Design following a long career working and leading in independent schools. Crystal retired in 2022 as the Head of School at Head-Royce School where she served in a variety of roles from Assistant Head of School and Admissions Director to English teacher. Crystal studies and applies the best practices in authentic and effective leadership and thrives on mentoring and building capacity in aspiring leaders. She has designed and facilitated workshops in the Bay Area and nationwide on topics including strategic planning, developing capacity and collaboration in leadership teams, writing and reflection, school governance and conflict resolution. She holds a M.A. in English from Middlebury College, a M.A. in Education from Stanford University and a B.A. from U.C. Berkeley in English and Political Science. Crystal and her husband, Will Miller, live in Marin County where they enjoy the outdoors, spending time with their adult children, and pampering one adored Goldendoodle.

Cancellation Policy

Life happens. We understand that there will be times when you cannot attend a workshop that you have registered and paid for. We strive to be as helpful and flexible as possible when things out of your control happen. Please visit our FAQ page for detailed information about our cancellation policy and answers to frequently asked questions about enrollment and membership.