Because philanthropy can create a world that works for everyone

We provide philanthropic advisory services to high-wealth families, private foundations, and donors, as well as to the experts who support them.

  • The Generative Group

    The Generative Group supports the philanthropic strategies of high-wealth families, private foundations, and donors to transform charitable giving into meaningful social change.

  • We help you create a more vibrant world where all people thrive.

    Improving lives and changing the world are both journey and destination. This is true for even the most effective philanthropists. The path is illuminated by answers to questions rooted in your values and aspirations, such as:

    What issues are we passionate about addressing and why?

    What’s the best way to create lasting, positive change?

    How do we navigate through complex issues and entrenched systems?

    Who can we learn from?

    AND

    Where do we start?

  • The answers are within. We help you surface and discover them.

    The Generative Group embraces listening, collaboration, and adaptability to generate possibilities and solutions for philanthropy. We work with you to design and build the right framework, anchored in your values, to ensure your giving has the impact you envision.

  • Philanthropic expertise. Business acumen. Heart.

    We offer you real-world experience and deep expertise in both philanthropy and business. We’re guided by an unwavering belief in the positive power of change. The result is innovation, agility and high performance – the hallmarks of modern philanthropy.

  • Helping generative leaders create effective social change.

    Our approach is grounded in the principles and values of “Generative Leadership.” We believe in the ability to evoke creativity in people, challenge orthodoxies and the status quo, and provide conditions in which good things come into being.

Collaborator-in-Chief.
Hands-on Leader of Philanthropic-Inspired Change.

Architect and builder with grantmaking, governance, finance, and operational expertise to move seamlessly between designing and executing on client philanthropic strategies.

Sylia Obagi, Chief Strategist and founder of The Generative Group, is an innovator, coalition builder and hands-on manager of philanthropic-inspired change. After more than two decades of direct experience in philanthropy, including the launch of four important grantmaking foundations, she formed The Generative Group to help donors, private and family foundations, and social-purpose organizations maintain a deep commitment to their core values as they invest in social change, and generate impact with their giving.

Sylia has first-hand knowledge, real world experiences, and tools to guide clients through various stages of evolution. She is a reputable, non-traditional thinker ready to help clients challenge themselves for positive social change.

Sylia’s programmatic, governance, finance, and operational expertise can help clients identify philanthropic strategies, as well as design the road maps for successful implementation. As founder of The Generative Group she brings together the right team and the right mix of services to support client priorities.

With more than 20 years of experience, accomplishments include:

  • Philanthropy

    As an executive leader, designed, scaled, and managed multiple sophisticated private foundations  with assets ranging from $100M to $2B, and launched their cutting-edge philanthropic strategies.

  • Governance & Leadership

    Created Annenberg Alchemy, the nation’s largest leadership and governance program. Trained over 2K board and executive leaders to build adaptive and sustainable organizations.

  • Regional Collaborations

    Led several city-wide public-private partnerships, such as LAnSync securing over $300M million in new funding for LA, and Project One Health delivering outsized impact addressing youth wellbeing.

  • Conferences and Coaching

    Active voice in the sector providing workshops at national conferences on building high-performing cultures, organizations and boards. Provide leadership coaching and trainings to executive staff and board.

Our approach is grounded in the principles and values of “Generative Leadership”

Generative leadership is about evoking creativity in people and providing conditions in which good things come into being. We believe client answers are within, and we help surface and discover them.

We create a disciplined yet adaptable change-management approach to achieve success.”

We believe:

  • Generative thinking is about learning, sense-making, and challenging norms.

  • Courageous leaders create conditions favorable to transformative solutions.

  • Aspirations, values, purpose, and shared vision guide forward movement.

  • Solutions follow from asking the right questions and not the expedient ones.

  • Curiosity and collaboration unlock the wisdom of the collective and fuels innovation.

  • Systems thinking leads to holistic solutions and advances teams and organization.

  • Resilience comes from embracing change and creating opportunities for evolution.

Our Approach

Generative leadership & thinking is at the heart of everything we do

Our Services

Transforming Charitable Giving into Social Impact

The Generative Group helps clients design, build, scale, and strengthen their philanthropic impact, grant programs, and community initiatives.

We work with clients to define their values, conceptualize goals, and define roadmaps for fulfill their vision. We help clients identify the partnerships, peer groups, governance and operating models needed to execute successfully.

We create a unique mix of services for grantmakers, funders, donors and their grantees based upon the unique goals and needs of each organization.

  • Philanthropic Advisory Services

    Strategic Planning

    Governance & Board Development

    Next Gen Engagement & Leadership

    Internal Operations

    Interim Executive Services

    Leadership Development & Coaching

    Retreats & Facilitation

    Trainings and Workshops

  • We provide customized consulting services, workshops, cohort training programs, or board retreats for grantees and charitable organizations to support their efforts to break the culture of scarcity, build adaptive capacity, and develop financial sustainability frameworks.

Contact us.

Connect with Sylia on LinkedIn