February 27, 2026

Leading with Creativity: LEAD Local Arts & Culture Day

Leaders gathered at Filoli for LEAD Local: Arts & Culture Day, engaging in creative practice and conversation about how the arts strengthen leadership and community.

Leadership is often associated with strategy, analysis, and decision-making. But at Leadership Council SMC’s recent LEAD Local: Arts & Culture workshop, leaders explored another essential leadership skill: Creativity.

At the sold-out gathering at Filoli, participants stepped away from their daily routines to experience creativity, not as a luxury, but as a vital practice. They explored how the arts can strengthen leadership, deepen community connections, and help build a thriving civic ecosystem in San Mateo County. 

“Art Is Not Self-Indulgent. It Is Life-Giving”

With pastels scattered across the tables and collage materials spread out in colorful piles, leaders leaned over their work with their sleeves rolled up, laughing, experimenting, then quietly concentrating as their creations began to take shape.

Guided by local San Mateo County artists Deborah Shea and Ellen Brook, participants stepped into hands-on artistic exploration. Deborah led a pastel drawing exercise, while Ellen invited participants to create a “message in a bottle” collage. 

What began with tentative strokes quickly turned into full creative immersion. This was not about perfection or productivity, but about process: experimenting, playing, and trusting creative instincts.

The energy in the room was unmistakable: curiosity, concentration, and genuine joy.

Through these guided activities, participants experienced how stepping outside their usual frameworks can open new ways of thinking.

“Wow… hands-on art is such a reminder that we have multiple parts of our brain and senses to bring to everything we do. Opening up to looking at things we face in our lives by bringing a new perspective is so rewarding and refreshing.”

Advancing the Arts in San Mateo County

In addition to hands-on creative exploration, Arts & Culture Day highlighted the vibrant network of artists, organizations, and partnerships that shape San Mateo County’s cultural life. Through conversations with artists, cultural leaders, and community advocates, participants explored how the arts contribute to civic life as part of the social infrastructure that brings people together, sparks dialogue, and strengthens shared identity.

Helping frame these conversations, Aimee Shapiro, Executive Director of the San Mateo County Office of Arts & Culture, highlighted the broad network of programs, partnerships, and initiatives that support artists and cultural organizations across the County. She illustrated how public investment and collaboration help ensure that creative expression remains visible and accessible. 

The conversation expanded as Aimee moderated a dynamic panel featuring Kara Newport, President & CEO of Filoli; Marianna Stark, Principal of M Stark Gallery; Erika Adkins, Board Member at Art Bias; and James Siegel, Executive Director of Dragonfly Community Arts. Together, they discussed the elements of today’s arts ecosystem, what feels most promising and most fragile, and why the arts matter in a county often defined by innovation and growth.

One theme emerged clearly: The arts are not peripheral to civic life. They help create spaces where people gather, share stories, and see one another in new ways. One panelist noted:

“The arts create space to listen, to reflect, and to see one another differently.”

The conversation also challenged leaders to think about access and inclusion within the creative sector, and how communities can ensure that arts experiences remain available to everyone. A participant reflected on how the discussion shifted her perspective:

“I learned there are so many programs available that are fighting to break the stigma that art is a luxury for the affluent. This idea that art is for everyone — and also necessary, like a doctor visit — really changed how I will treat art moving forward.”

Participants were encouraged to think about their own role in sustaining this ecosystem. What does meaningful support for artists and arts organizations look like? Who is still missing from our creative spaces? And how can leaders across sectors help expand access to creative experiences?

Examples of innovative collaborations are already underway. Pamela Estes, Executive Director of the Redwood City Parks & Arts Foundation, shared how community partnerships make large-scale arts programming possible. From cultural festivals to public performances that invite residents to experience creativity together, Redwood City offers a powerful example of how thriving arts ecosystems are built through intentional partnerships among nonprofits, local government, cultural organizations, and community supporters.

Strengthened Through Creativity and Connection

Leaders left the workshop with both ideas and intentions: bringing arts practices into everyday meetings, drafting agendas in color, embracing non-linear thinking, visiting local arts spaces, and applying creative thinking more intentionally in their work and lives.

At the close, leaders lingered in conversation, artwork in hand, and joined tours of Filoli’s beautiful gardens and historic home. It was a joyful reminder that creativity can spark not only new ideas, but new relationships. Ninety-three percent of participants reported connecting with someone at this LEAD Local workshop that they would not otherwise have met, a powerful reflection of Leadership Council SMC’s mission to strengthen leaders by connecting, inspiring, and educating across sectors and communities.

With Gratitude

Our heartfelt thanks to Filoli and its extraordinary team for graciously hosting LEAD Local: Arts & Culture Day in their inspiring setting. 

We are grateful to Aimee Shapiro, Executive Director of the San Mateo County Office of Arts & Culture, for her thoughtful presentation and for moderating an energizing panel discussion. Thank you to our outstanding panelists for their insights and perspectives on the County’s creative ecosystem: Kara Newport, President & CEO of Filoli; Marianna Stark, Principal of M Stark Gallery; Erika Adkins, Board Member at Art Bias; and James Siegel, Executive Director of Dragonfly Community Arts.

We are also grateful to Pamela Estes, Executive Director of the Redwood City Parks & Arts Foundation, for highlighting the power of intentional community arts partnerships, and local artists Deborah Shea and Ellen Brook for leading such engaging hands-on experiences.

Thank you to our participants for bringing curiosity, openness, and enthusiasm to the day.