Professional Retreat for
Experienced Women Enrollment Leaders
June 21-24, 2026
Harmon Guest House in Healdsburg, CA
The Lookout is more than a conference. It’s a curated space for the kind of insight and connection that only emerges when we step outside of our daily work. Together, we’ll explore our leadership journeys, sharpen our signature presence, and unpack real dilemmas and opportunities shaping our roles.
Together, we will engage in a blend of inner reflection, shared learning, and practical tools to support continued growth. And yes, there will be time to rest, laugh, and enjoy the beauty of wine country!
Registration will close March 13 and we anticipate selling out prior to that date.
Schedule Overview
Sunday | Arrival & Orientation
We’ll begin with an opening gathering to build shared language and set the tone for a thoughtful, connected few days.
Monday | Personal Foundation & Reflection
Monday focuses on the internal work that supports long-term leadership:
Clarifying values and alignment
Reflecting on leadership journeys and formative experiences
Exploring signature presence, power, and authority
We’ll wrap up mid-afternoon, leaving time to rest, explore Healdsburg, or simply enjoy unscheduled space.
Tuesday | Professional Application
Tuesday turns outward to the realities of senior leadership:
Working through real “thorny dilemmas”
Applying leadership frameworks to complex decisions
Exploring your professional trajectory
Paired walking conversations for clarity and integration
Identifying a small set of concrete commitments for how participants want to lead differently
We’ll close the day with a group dinner to celebrate connection and shared learning.
Wednesday | Integration & Closing
A final morning session helps pull things together and look ahead with intention.
Beyond the retreat
Participants are also invited to four virtual follow-up gatherings during the 2026–27 school year, offering continued conversation, support, and accountability once everyone is back in the flow of school life.
About Crystal Land
Crystal Land (she/her) is a Partner at Leadership+Design. Crystal has spent her career as a leader in independent schools and as a facilitator with schools and teams. Prior to joining L+D, Crystal served as Head of School at The Head-Royce School in Oakland, where she also served in a variety of roles from Assistant Head of School and Admissions Director to English teacher over her 30+ year career. Over the past two decades, Crystal has designed and facilitated workshops for school leaders in the Bay Area and nationwide on topics including strategic planning, developing capacity in leadership teams, school governance, writing and meditation and women in leadership. She writes articles and thought pieces for various publications and has presented locally and nationally on effective school leadership.
Crystal has served on the Boards of the Global OnLine Academy, the Seven Hills School, the CAIS Secondary School Accreditation panel, Vincent Academy, and the California Teacher Development Collaborative (CATDC); she is currently a trustee at Marin Primary and Middle School. 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. She appreciates big messy problems and truly enjoys helping leaders and schools find ways to successfully navigate them. She and her husband lives in Marin, CA and are the parents of two adult children and one beloved dog.
About Dana Nelson-Isaacs
Dana Nelson-Isaacs has spent more than 25 years helping schools thrive. Known for her thoughtful insight and candid, collaborative style, she partners with admission teams, heads of school, and boards to strengthen enrollment strategy, communications, and community engagement. Dana's professional journey spans a wide range of institutions, including K-12, boarding and day, and single- and all-gender schools. Before launching her consulting practice in 2013, she held key roles in enrollment and marketing. A dynamic speaker and facilitator, she leads workshops and speaks regularly at conferences. Dana also facilitates The Assembly, a mastermind group for school leaders, and provides one-on-one and team-based executive coaching. She lives in Northern California with her husband and their high-school-aged daughter.
About Harmon Guest House
The Harmon Guest House is an elegant, modern sanctuary situated just steps from the historic Healdsburg Plaza in the heart of Sonoma Wine Country. This is more than a venue, it's a creative retreat, where locally-sourced art and thoughtful design elevate every conversation.
Please book via this link to ensure you receive the group rate.
