I tend to think philanthropy has a valuable role to play in American education. As I suggest in A Search for Common Ground, unlike those who insist that education giving is “anti-democratic,” I believe philanthropy can make “for a more pluralistic, responsive education system by supporting voices, programs, and organizations that challenge the routines of district and state machinery.” It can offer a lifeline to those otherwise boxed out by teachers’ unions, education bureaucracies, textbook companies, and ed. schools.

Yet, just because philanthropy can play this role doesn’t mean that it will. Indeed, too often, as in the cases of Race to the Top and the Common Core State Standards, philanthropy has lined up alongside powerful interests. In those instances, philanthropy fails to promote a healthy Tocquevillian dynamism and instead morphs into an agent of groupthink and self-deception.

An eternal question in the philanthropic community is how to learn from past missteps. One currently popular tack is to shift toward “place-based philanthropy,” in which funders eschew sweeping policy agendas in favor of working more closely with a given community (ideally allowing them to better understand and address local needs and challenges).

Conceptually, the appeal is obvious. In practice, it can be tough (see Challenge, Annenberg). To help make sense of the challenges, I’ve commissioned a series of scholars and analysts to think through these issues. In the latest, University of Arkansas’s inimitable Jay Greene has penned a bracing piece in which he explains that big donors can be lulled by their financial resources, political capital, and well-educated staff into underestimating the financial, political, and information constraints they face when they turn to place-based philanthropy.

As Greene writes, “Place-based philanthropy may make it easier for foundations to achieve their preferred solutions in particular locations at the cost of identifying whether those solutions were correct to begin with and determining how well their implementation is going.” In other words, place-based giving may help with financial and political constraints (making it easier to get things done) even as it exacerbates information challenges (making it tougher to know if those things are actually helpful).

What does Greene have in mind? Well, when big funders work in particular communities, they immediately become the 800-pound gorilla. It’s easy for donors to inadvertently dominate the space—even when trying to step gingerly. After all, there’s immense pressure on local nonprofits and public agencies not to get left out. They want to be dealt in, which means they don’t want to be seen as critical or difficult. The pressure on everyone to play nice makes it hard for funders to get reliable feedback or independent advice from local actors. As Greene puts it, it may be that “no organized groups are left to force foundations to consider they are mistaken, and no financial reality test reveals lack of support.”

This all poses a number of intriguing challenges for communities, donors, and educators. Greene offered a few thoughts on what donors, in particular, might do about it.

Put simply, he says, “The easier it is for a foundation to win politically, the harder it is for the foundation to learn that what it won was poorly conceived.” An important response, he suggests, is for funders to “subject their efforts to market or reality tests” by seeing whether proposed reforms attract political support from their beneficiaries. Greene argues that “if the reforms can garner enough financial and political backing to survive independently of foundation support, it is a much safer bet that they are serving people’s needs cost-effectively.” In short, rather than be frustrated by budgetary or political realities, Greene urges funders to “embrace those constraints as ways of learning about whether their efforts are faring well and producing success.”

The insights build off of Greene’s invaluable previous scholarship on education giving, especially his iconic “Buckets into the Sea” chapter (from my 2005 Best of Intentions volume). Greene is a savvy, farsighted thinker, and I do hope funders—and community leaders—will ponder what he has to say.