Thought Leadership

Real-World Insight. Field-Shaping Practice.

Thought-leadership isn’t a side note—it’s how we shape the future of our field.
Grounded in what’s possible, it helps us reimagine what’s needed.

At its best, philanthropy is a bold act of imagination. Through blogs, articles, workshops, trainings, retreats, and dynamic conference sessions, Sylia Obagi brings real-world experience to elevate board and staff leadership and create the conditions for meaningful change to truly take root. Her thought-leadership evokes what’s possible, not accepting the status quo, and sparking the clarity, courage, and connection needed to move the sector forward.

Workshops

We understand the vital importance of nonprofit effectiveness and philanthropic impact, and that strengthening the organizations that support our communities is essential to advancing our shared interests. We offer workshops and training, grounded in real-world experience and generative leadership. Our audiences include board directors, executive leaders, trustees, high-net-worth family members, and grantmaking staff.

Topics:

The World Has Changed, Have You? Designing Private Foundations for Adaptability & Impact

A culture of generative leadership and adaptability, which begins at the board and executive staff level, is essential for grantmakers to support the resilience and relevance of their grantees and of their own grantmaking institutions. This highly interactive workshop will engage grantmakers in a robust conversation about how grantmakers can leverage their grant investments and other capital to support innovation in their field and prepare grantees for the realities of the 21st century.

Elevate Your Board’s Performance through Sense-making and the Generative Mode of Governance

Drawing on the seminal work, Governance as Leadership: Reframing the Work for the Nonprofit Board, this workshop explores how high-performing boards know when and how to use the fiduciary, strategic, and generative modes of governance. Participants learn how the generative mode—emphasizing sense-making, inquiry, and dialogue—unlocks a board’s collective wisdom. Through hands-on exploration, leaders will deepen their capacity to govern for adaptability, innovation, and shared meaning within their institutions

Think Governance First! Assessing Nonprofit Boards for High-Performance to Support Your Grantmaking’s Impact

Governance is an art form, and one size does not fit all organizations. Boards must adapt as organizations evolve and the sector changes. A grantee’s board is the most critical leadership asset in helping an organization deliver its mission and goals. When grantees deliver desired outcomes, the grantmakers who fund them feel more aligned with their missions. Grantmakers who build trusting relationships with grantees and effective board-focused due diligence can better support their grantees through capacity-building investments to strengthen nonprofit board performance. Assessing grantee board quality and identifying potential red flags requires a well-designed due diligence process tailored to the risk and size of a grant investment and a set of customizable due diligence tools that align with a grantmaker’s practices and values.

Navigating Disruptions Successfully through Enlightened Leadership

Major organizational transitions are inevitable and triggered by a variety of circumstances, including the retirement of a founder, a change in strategy, disruptive external trends such as artificial intelligence, or a significant change in financial circumstances. This workshop is designed for executive and board leaders to become adaptable architects of their foundation’s future, rather than being reactive to transitions. The Wheel of Change by Robert Gass, and the Three-A Framework of Aspirations, Agreement, and Adaptability will be shared as a tool to help leaders create a generative organizational culture that designs forward-looking governance, program, and management systems that are in line with the organization’s values and adapt to the realities of the 21st century.

  • We create learning experiences through dynamic workshops that reflect each client’s unique goals and help clients turn bold ideas into meaningful action that advances the field. Other workshop topics include:

    • A Holistic Approach to Design, Launch, Scale, Private, And Family Foundations. 

    • The Wheel of Change – A Framework to Build a High-performing Culture

    • Three Pillars of High-Performing Boards & Nonprofits

    • Building Adaptable & Agile Boards

    • Next-Gen Leadership Development & Coaching.

    • Designing & Leading Regional, Public-Private Collaborations.

    • Creating & Convening Peer Funders as a Community of Practice.

Speaking Engagements

Through national conferences and convenings, we design and lead sessions that spark learning, challenge assumptions, and elevate what’s possible in philanthropy, building a more adaptive, effective, and values-driven field.

Philanthropy SE CEO Forum 2026
Governance as Leadership Case Studies: Applying the Three Modes of Governance to a Changing Sector.

Philanthropy SE Annual Conference 2025
Trustee Only Session: The World Has Changed, Have You? Navigating Through Enlightened Disruptions.
&
Center Thriving Youth in Grantmaker Practices. Creating Conditions for Youth to Thrive

Blue Sky Funders Network 2025
Funder Briefing: Nature as a Health Equity Tool.

Philanthropy SE CEO Forum 2025
Governance as Leadership:  Elevating Board Performance!

Exponent Philanthropy Annual Conferences 2024
Building High-performing Boards

National Center on Family Philanthropy Bi-Annual Conferences 2024
Embracing the Shift: Change Management for Senior Staff Leaders

Publications & Videos

Through writing and public dialogue, I explore the questions, tensions, and possibilities at the heart of effective philanthropy.

Featured Article

Rebranding the Nonprofit Sector in 8 Steps

Interview

Understanding the Philanthropy Power Dynamic

Curriculum Development.

Under her leadership at the Annenberg Foundation, Sylia created Annenberg Alchemy which has become the nation’s most extensive capacity-building program for nonprofit executives and board leaders, and continued through 2026. Under her tenure, over 2,000 CEOs and Board Chairs participated in the program. Eventually, she co-created Think Money First!, a deep-dive, executive and board coaching, and change management training to strengthen the capabilities of nonprofit grantees of various philanthropic institutions to deliver on their missions sustainably. To date, over 200 organizations have participated in the Think Money First! workshop and coaching. Finally, Sylia created Think Governance First! to support grantmaking staff with conducting due diligence on grantee board effectiveness and investing in board capacity building.