5 Principles for Reflective Practice in Philanthropy

Several friends and colleagues are presently stepping into leadership positions of different philanthropic programs focused on U.S. democracy. I have appreciated the chance to talk with them about my recent experience in a similar role at the Hewlett Foundation. They have often wanted to know: How did I approach the work? What are the pitfalls to avoid?

These questions and conversations have prompted me to distill a set of principles I came to see as especially helpful during my time in philanthropy. The principles are not so much about substantive focus areas or specific grant practices–i.e., the “what” and the “how” of the work – which naturally vary based on the institution and circumstances. 

Rather, the five principles below are meant for philanthropy program leaders who aspire to be reflective practitioners in their roles. I am sharing them here in case it helps leaders so inclined hold space for the complexity and learning inherent in ambitious philanthropic endeavors.

1) Turn anxiety into curiosity. “What should we do?” It is easy to be overwhelmed by this fraught question when developing a strategy for a new philanthropic program or reassessing that of an existing one. The implicit, angst-producing assumption underlying it is there is one right answer, and your job is to gather and analyze data and strategize your way to it. But in complex systems marked by dynamic competition between advocates and non-linear change, philanthropic programs can reasonably pursue progress in different ways. It makes more sense to ask, “What could we do?” This opens the door to curiosity and exploration, considering and comparing various alternatives, and selecting those that represent the best fit for your program based on a holistic judgment. It helps you realize all the ways you could proceed. It clarifies the theory of change and trade-offs embodied in your initial choices. And it leaves you less apt to be unduly wedded to your initial choices when it is time to revisit them.

2) Don’t try to figure everything out up front. I spent many years as a nonprofit strategy consultant before moving to the philanthropy world. One pattern I observed as a consultant is that the normal constraints limiting nonprofit grant seekers’ consumption of strategic planning services–limited money and management bandwidth–did not apply to grant makers. Foundations had all the time and money they needed. They were thus more prone to analysis paralysis, of trying to get to “the answer” on paper or in spreadsheets from their offices in Seattle, Silicon Valley, or Manhattan. On more than one occasion, I felt obliged to encourage foundation clients to wrap up the planning and get going out in the wild. With philanthropy meant to change complex systems, much of the work necessary to confirm a program is generally headed in the right direction must be done through trial and error. Ultimately only by making and learning from grants can philanthropic programs grasp the dynamics and key players in the field–current and potential grantees, coalitions, co-funders, policy-makers etc.

3) Expect blind alleys – and serendipity. Even if a program is observing the first two principles, it will invariably be surprised by grants and lines of grant making that once held great promise but nonetheless fizzle out. There will also be efforts that seemed shaky at the outset, or were not even on the radar screen, that yield outlandish and unexpected success. Many different variables can produce these unexpected outcomes. Leaders and organizations turn out to be much more or less effective than indicated by their initial impressions. Sudden shifts in political or coalition contexts advantage some approaches and hamstring others. The key for program leaders is to lean in to the surprises, understand the factors that produced them, and act decisively. Scale up the unexpected successes, and scale back or shut down the disappointments, in short order. It is a mistake to stay the course when, for better or worse, things do not play out as expected.

4) Evaluate, reflect, learn, and adapt as you go. Instead of waiting until a strategy has played out before evaluating it, programs working to change complex systems need to begin assessing and adjusting their strategy from the outset. And rather than keeping their evaluators at arm’s length, this approach creates both the opportunity and need to bring them onto the extended team, as counselors and strategic advisors. The ongoing work of learning and course correction benefits from a regular cadence of meetings or summits in which the program and its evaluation partners can take stock together. Sharing what the program is learning and how it is refining its work as a result with partners and the public is another constructive discipline. Ultimately, given the uncertainty and contingency involved, this is how philanthropic programs funding systems change and policy advocacy can hold themselves accountable. Only rarely can they pledge to deliver particular results in a given time frame. But they can and should commit to a continual and transparent process of assessing, learning from, and adapting their work. 

5) Ask: How will I need to change? Thus far we have been talking about changing systems and policies via strategies and implementation plans “out there” in the world. But reflective practice in philanthropy programs also requires change and development within individual leaders. People step into these roles from many different backgrounds. Some have been grant makers already, while others have been nonprofit leaders, advocates, consultants, civil servants, lawyers, researchers, organizers, etc. Each of these backgrounds can be beneficial. But inevitably there are other dispositions program leaders need to bring to bear. Likewise with one’s personal style, e.g., being a hands-off- or a micro-manager, preferring to operate in inquiry or advocacy mode, wanting to lead out front or be a guide by the side. The right mix will vary depending on the particulars of the institution, role, and team. The point is that it behooves new program leaders to intentionally decide what they want to keep, stop, or start doing as they step into their roles. They should also revisit this assessment on a regular basis, as the work unfolds and new demands might arise.

Pulling the camera back

Looking back over these principles, several themes run across them: empirical humility and curiosity vis-a-vis the complex system(s) you seek to change; a commitment to learning; an openness to being surprised; and a belief things can always be improved, not only out in the world and your strategy for changing it, but also in your own worldviews, capacities, and mindsets.

I should acknowledge two false impressions that sets of principles distilled in retrospect like those above can readily give. First, I could not have begun to articulate them when I started out in philanthropy. This was wisdom I picked up in the course of my journey. 

Second, while I have shared my own synthesis, it rests on ideas and approaches developed by others. They have been passed on to me by a range of colleagues, advisors, evaluators, and mentors who have long been dedicated to reflective practice in philanthropy. 

For those of you who might like to go deeper, I conclude with an annotated bibliography of resources on this general topic I have found especially illuminating.

Resources for Reflective Practitioners in Philanthropy

Julia Coffman and Tanya Beer, “Evaluation to Support Strategic Learning: Principles and Practices.” We had the very good fortune of working with Julia and Tanya on a developmental evaluation during the initial five years of Hewlett’s work on U.S. democracy. This concept note outlines the fruitful ways in which they joined forces with us and helped us improve our work.

Jan Jaffe, “Philanthropy’s Reflective Practices: Build What You Bring to the Work.” Jan is a wise philanthropy hand who founded Grantcraft at the Ford Foundation and is now a senior partner at The Giving Practice of Philanthropy Northwest. Her “DIY Guide” deftly encapsulates the concept of reflective practice and its applications in philanthropy.

Patricia Patrizzi, et al. “Eyes Wide Open: Learning as Strategy Under Conditions of Complexity and Uncertainty.” This article, by evaluators associated with the Evaluation Roundtable, flags common traps that keep foundations from learning and adapting and how to avoid them. The traps include “1) linearity and certainty bias; 2) the autopilot effect; and 3) indicator blindness.”

Michael Quinn Patton, Developmental Evaluation: Applying Complexity Concepts to Enhance Innovation and Use. Patton is perhaps the leading thinker, practitioner, and explainer of developmental evaluation. This text provides a comprehensive overview of the approach.

Dave Snowden’s The Cynefin Framework, and various things he and his colleagues have written about and around it, helped me finally get complexity theory and the salient differences between ordered, chaotic, and complex systems. His three-minute video on how to organize a party for eleven-year-old boys puts the framework’s key insights in a hilarious nutshell.  

Steve Teles and Mark Schmitt, “The Elusive Craft of Evaluating Advocacy.” Steve is a  political scientist at Johns Hopkins and a fellow at the Niskanen Center. Mark was a grantmaker at Open Society who now leads New America’s Political Reform Program. Their paper puts the challenges of doing and evaluating advocacy in a realistic and sharply drawn political context.

By way of a deeper dive in my own experience, in “The Hewlett Foundation as a Formative Institution,” I consider the many ways in which the Foundation made me a more reflective practitioner during my time working there. I trace the evolution of our program strategy as we applied the principles above in “Reflections on the First EIght Years of Our U.S. Democracy Grantmaking.” With co-author Jillian Galbete, I do the same for “the how” of our work in: “Streamlining a Foundation Initiative’s Grant Practices.” We didn’t always practice what I have been preaching here, but we tried to!


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