Malcolm Gladwell is known for his claim that one must practice a skill for 10,000 hours to achieve true expertise. In my role as head of Overdeck Family Foundation for over a decade, and after approximately 19,000 hours on the job, I can confidently say I am not an expert on philanthropy. However, I have gained a great deal of knowledge, which I’ve distilled into 10 lessons to share with you today.

1. Defining your stakeholders, and ensuring your work resonates with all of them, is critical for leading family philanthropy in today’s era.

Leading a family philanthropy today requires that the needs and motivations of three primary stakeholders are met: trustees, staff, and grantees. This is increasingly challenging given increased political polarization nationwide, but finding the areas where there is overlap in people’s values and ideas is essential for achieving alignment and shared direction.

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Clarity and alignment amongst the primary stakeholders felt nearly impossible during the first few years in my role because we were still learning what the needs and interests of each stakeholder were. But in 2019, after years of over-dialing towards one group or the other, I led a redesign of our funding model, pivoting to a venture-inspired model that was able to exist at the intersection of needs and motivations for all three parties. This revised funding model allowed us to pursue both direct impact and ecosystem investments in ways that were both measurable and catalytic, addressing the needs of each group without alienating another. For example, our grantees see the model as more responsive; our team sees the model as giving them more purpose and professional growth; and our trustees see the model as helping them more accurately understand the impact of our work.

2. The pursuit of philanthropic excellence is possible, but only if you define and measure it.

In philanthropy, there is no sector-wide definition of excellence. Historically, the success of a foundation’s grantmaking has been defined by its donors or trustees—but each donor defines success differently. At Overdeck Family Foundation, our trustees define our Foundation’s success based on how our grantmaking leads to measurable improvement in academic and socioemotional outcomes for all children. To complement the progress towards our mission, we measure success in how our team supports and responds to the needs of grantees, as well as how learning-oriented, collaborative, and inclusive we are as an employer.

Measuring progress toward each of these metrics is critical. To understand whether we are measurably improving outcomes for children, our team supports grantees to build logic models and add internal data capacity so they can track how they’re driving short-term outputs and long-term outcomes. We care about how much it costs for a grantee to deliver outcomes for children (cost-effectiveness) because we know the education system is constrained by time and financial resources.

Internally, we assess how we show up for our grantees through the Center for Effective Philanthropy’s (CEP) Grantee Perception Survey. We publish our results publicly and carefully listen to the feedback, taking a great deal of responsibility in how we respond to it year after year.

Like most learning organizations, we’ve also established core values that guide our culture. Through employee surveys, we evaluate our progress twice a year, share the data with our team, and make necessary adjustments. We care that our organization provides a place for individuals to pursue mission-oriented work, feel valued, and grow professionally—our results show we’re doing just that.

3. “Both/And” thinking is critical for driving lasting impact in education.

In education, there are dichotomies everywhere you look: academic versus socioemotional outcomes, ecosystem change versus direct impact, and the strength of evidence in one setting versus implementation fidelity.

I’ve found that, more often than not, “both/and” can best serve shared goals. In service of this, we designed our work to support programs that advance BOTH academic AND socioemotional outcomes, which are inextricably linked. And, in our revised venture-inspired funding model, we fund BOTH direct impact AND ecosystem work; the former allows us to fund innovation and growth while the latter clears the path to scale for our grantees through research and field building.

Additionally, we do our best to support both evidence AND implementation, an area where the education sector struggles. Over the past several years, we’ve seen many organizations emerge from research institutions with a strong evidence base, but with no growth plan or revenue models, preventing them from replicating their program elsewhere. We’ve also seen many organizations that are eager to scale their program or model without sufficient evidence to show that it can drive outcomes for students.

This inflection point is a real opportunity for philanthropy. While the federal government plays a crucial role in helping effective programs scale, philanthropy can provide risk capital to support innovation, evidence building, and R&D. For example, if an organization has a strong evidence base but is limited in its growth capabilities, philanthropy can provide funding to help them experiment with different program models and revenue streams, as we did for LENA’s group coaching programs. Alternatively, as we did for Springboard Collaborative, if an organization is on the cusp of growth but limited in evidence, philanthropy can fund research to help ensure the program is effective.

By acknowledging and prioritizing both/and, philanthropy can help make the most impact toward the desired outcome.

4. Clear and transparent communication is key for driving the advancement of shared goals.

Philanthropy is not known for its transparency. For the first several years of the Foundation’s existence, we hardly released any information about our work. But over time, it felt valuable to share lessons learned about our approach, funding criteria, and grantees. Doing so not only helped build trust and transparency with thought leaders, potential grantees, and the public, but it also strengthened our ability to attract organizations that aligned with our goals and values. All this led to better outcomes and impact, which led to more collaboration and knowledge-sharing opportunities within the sector.

Over the past few years, Overdeck Family Foundation has intentionally chosen to embrace transparency throughout our work. Every grant we make is published on our website, and earlier this year, we launched a repository to amplify the research we’ve funded across portfolios. On our blog, we communicate key funding decisions through quarterly funding announcements and dive deeper into strategy positions by lifting up insights into how our grantees are shaping the education landscape. From our CEP survey results, we’ve seen that these changes have been appreciated by grantees and have taken away some of the inconsistency and confusion they previously experienced through our (lack of) communication.

5. Strategic capacity building and trust-based philanthropy can work in concert to support grantee success.

Early in the launch of our venture-inspired funding model, it became clear that many of our grantees faced shared challenges when it came to achieving their short- and long-term goals. In 2019, we started offering light capacity-building support to our grantees to address these common roadblocks. Through the CEP survey, we learned that 95 percent of grantees who received capacity-building support felt it provided a moderate or major benefit to their work or organization.

Today, we’ve built on our early success by offering a three-tiered approach to capacity-building. In the Stanford Social Innovation Review, Lucy Brainard and I share examples of how strategic capacity building can work in concert with trust-based philanthropy to achieve greater impact for grantees than funding can alone. In the article, we articulate that as nonprofits seek support beyond grantmaking dollars, funders have an opportunity to play a strategic, hands-on role in helping grantees become more cost-effective, sustainable, and scalable.

“With so much change on the horizon for nonprofits, now is not the time for foundations to walk away from capacity-building support. Instead, funders should play a more strategic and hands-on role that involves engaging in transparent conversations with grantees, acknowledging valuable perspectives on both sides, and co-creating plans to address agreed-on challenges.”

6. Philanthropy can and should play a complementary role to the government.

The U.S. spends over $700 billion on K-12 public education; private philanthropy adds $5 billion. Philanthropy does not have the budget of the government, nor should it replace what the government does.

It’s become ever more clear to me that philanthropy’s role is to do what the government cannot, which is supporting organizations that are developing and validating solutions that are too new and unproven for the government to support.

That is why our sweet spot as a funder is to help organizations either develop new programmatic models or build the evidence base for existing models. Once an organization is able to show impact and has the capacity to scale that impact, we believe our role is to help that organization reach more people, ideally by accessing local, state, and federal funding. Over the past 10 years, we’ve supported several organizations that have received government funding, including Nurse-Family Partnership, Reach Out and Read, ParentCorps, Saga Education, Zearn, Waterford Upstart, Springboard Collaborative, LENA, and the New Jersey Tutoring Corps.

7. Making collaboration a mandate can catalyze the philanthropic sector.

Historically, foundations have had the tendency to “own” initiatives, but I believe that collaborative efforts can often lead to more significant impact and scale, since different organizations bring unique strengths and expertise to the table.

Over the years, Overdeck Family Foundation has played an instrumental role in launching collaborative efforts such as the Data Funder Collaborative, now comprising over 25 data-oriented foundations that, together, aim to strengthen the state of data in education. Other joint efforts like the Instructional Materials Funder Group, launched in 2017 with approximately 10 funders, lifted up key insights from leaders on the ground who saw the potential of edtech products to provide higher quality content to kids nationwide.

Both of these groups take great responsibility in ensuring that foundations consider the voices of practitioners and education leaders when working to understand a problem and an opportunity, as well as potential solutions. This helps improve the chances that what gets funded actually leads to the intended outcomes.

Collaboration is embedded in our Foundation’s core values, which guide how we do our work and these successes are a demonstration of it in action. This particular value, known as “Learn Better, Together,” assumes that forging partnerships will lead to the possibility that the sum can be greater than its parts.

Core to this value is the recognition that philanthropy is just one piece of the puzzle, and working with others can help bridge gaps and create a more holistic approach to addressing social challenges.

8. Philanthropy can move fast—but it often relies on a crisis to do so.

Philanthropy sometimes gets a reputation for moving too slowly, especially when the opportunities for improvement feel endless. And that’s not entirely untrue—foundations too often do spend time engaging in a lot of internal work that does not necessarily translate to achieving their mission.

The COVID-19 pandemic showed us what can happen when philanthropy is mobilized to act by crisis. Funders played a unique role during the pandemic, especially at the outset, because of their ability to 1) build and maintain relationships with communities and provide immediate need-based support and 2) quickly respond to emerging needs and adapt to changing circumstances.

On Saturday, March 14, 2020, a few days after learning about COVID’s arrival in the U.S., I wrote an email to our trustees, suggesting several non-financial actions we could take to support grantees, including moving restricted dollars to general operating support, providing financial planning support, re-defining grant goals to accommodate what felt realistic, and reducing the reporting/monitoring burden for grants. In the weeks following, we provided approximately $2.6 million in rapid response grants with limited application burden to grantees to help position them to continue their work despite fast-changing and unpredictable external conditions. We weren’t alone in our response, as philanthropies across the country demonstrated their resilience during the crisis, while continuing to serve as a trusting, timely, and relevant partner.

9. To be truly impactful, philanthropy needs to embrace two time horizons: the present and the future.

Investing in both the current and future state is essential for long-term impact for foundations. For example, it’s imperative to support organizations that are making an impact right now, like helping Zearn conduct a program evaluation to better understand its impact on elementary and middle students’ math learning, or helping TalkingPoints grow their internal infrastructure to connect more families and educators through a multilingual, two-way messaging platform. At the same time, it’s also important to invest in programs and initiatives that will create sustainable and lasting change in the future by helping shape and develop ecosystems. For example, funding EdReports, which is working to expand the evidence base of high-quality instructional materials in the future, helping districts select standard-aligned instructional materials for their students down the line.

By investing in the current state, we can support organizations that are providing immediate impact and making a measurable difference in the lives of children. By investing in the future state, we can support organizations that are working towards systemic change, addressing root causes of social issues, and creating long-term solutions. It’s important to strike a balance between the two and to have a clear strategy for how investments in both the current and future state will be made. This approach can help create a more sustainable and resilient philanthropic portfolio that can make a lasting impact.

10. Philanthropy holds a responsibility to amplify hope, possibility, and inspiration.

As one of the sectors with resources and influence, philanthropy holds a responsibility to amplify hope, possibility, and inspiration in both the good times and in the face of unexpected challenges. While philanthropic efforts may be focused on addressing social challenges and driving change, it’s crucial not to lose sight of the bigger picture and the positive impact that can come from inspiring and uplifting individuals and communities.

By supporting programs that promote hope and possibility, like The 74’s “16 Under 16 in STEM” initiative which spotlights exceptional young people in STEM, foundations can help create a more optimistic and resilient society. Additionally, by intentionally showcasing the inspiring work of grantees and sharing the on-the-ground stories of beneficiaries, philanthropic organizations can inspire others to get involved and contribute to positive social change.

I believe that philanthropy will continue to exist in America’s societal fabric for the foreseeable future. It is our responsibility to ensure it lives up to its potential.


Header image courtesy of Andrew Neel on Unsplash