13 Questions To Learn From Your Grantmaking


Most philanthropies seek to be strategic and have an impact. Yet few build their own internal capacity to be strategic grantmakers. In particular, most funders forget to intentionally learn from their initial piloting and testing of strategies so that they can make early modifications and course corrections.

Learning isn’t hard to do, but it must be intentional, documented, discussed among your team, and lead to decision-making. It can’t simply exist inside a program officer’s head. One of our clients, the Kate B. Reynolds Charitable Trust, asks themselves “What will make or break this grant?” when deciding whether to recommend a significant grant to their board, so that they are clear on the risks involved and what needs to happen to make the grant successful. The answer is documented in the staff summary of the grant. Six to nine months later, like clockwork, they revisit the grant during program team meetings to assess progress on that risk, and identify ways they can help ensure success. That is intentional learning.
You already have all kinds of information that can inform your learning: grantee reports, grantee convenings, evaluations conducted by grantees, dashboards, your understanding of changing conditions (staff turnover, local or federal policy changes, the economy, etc.), and the observations, knowledge and instinct of your staff and consultants. You could also seek new insights at little cost: conduct an online survey, convene all your stakeholders, or solicit outside perspectives.
Below are 13 questions you can ask yourselves and your partners:
  1. What are the top 3 things you have learned about your strategy thus far?
  2. If you could do it all over again, what would you do differently?
  3. What has surprised you? What are you seeing that is different than what you originally expected?
  4. What progress are you making on your strategy overall?
  5. What progress have you made on each of your short term and long term outcomes?
  6. What are some of the early accomplishments/wins?
  7. What has been the most challenging?
  8. Are there areas where you have not yet made much progress? Why?
  9. What are the current conditions now compared to when the foundation launched this strategy, and how has/will that impact the work? (e.g., policies, systems, other funding streams, staff changes, etc.)
  10. Have you made modifications or improvements to any aspect of your strategy, approach or funding since this strategy was created (or since you started working at the foundation)? Has that helped?
  11. At this time, do you anticipate making any modifications or improvements? If so, what are they? By when will you make that decision?
  12. What opportunities do you see with this strategy going forward?
  13. If you were a board member, what would you want know about what has been learned/accomplished?
After answering these questions, summarize your key insights and discuss them with your team. Based on what you have learned thus far, what refinements or modifications could be made to ensure success? Make them. And six months from now, check back in on them and see what you’ve learned.
Kris Putnam-Walkerly is a philanthropy expert and advisor. Read more about how you can learn from your grantmaking by listening to her Smart Philanthropy podcast series on iTunes, including “Who Is On Your Red Team?” and “How To Conduct Retrospective Evaluations”, or read her article “One Question Guaranteed To Save Funders Time, Save Money, and Achieve Results“.


Upcoming speaking events: Kris will be speaking on “Tips, Tools and Lessons on Multi-Media Storytelling” at the Southeastern Council on Foundations annual meeting on November 12th in Asheville, NC.
Kris is a sought after philanthropy advisor, expert and award-winning author. She has helped over 90 foundations and philanthropists strategically allocate and assess over half a billion dollars in grants and gifts.

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