Are You Really Learning and Improving?



6 Questions to Regularly Ask Yourself and Your Partners

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 within your team, and it must lead to decision making. It can’t simply exist inside a program officer’s head. One of our clients asks themselves, “What will make or break this grant?” when deciding whether to recommend a significant grant to their board. 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.

Chances are, you already have many 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 minimal cost: conduct an online survey, convene all your stakeholders, or solicit outside perspectives.

Of course, learning often requires that you ask the right questions. Below are six that will get you started, but based on your own focus and curiosity, I’m sure you can develop even more that you can regularly ask yourselves and your partners.

  1. What are the top three things we have learned about our strategy thus far?
  2. If we could do it all over again, what would we do differently?
  3. What progress are we making on our strategy overall?
  4. What are some of the early accomplishments/wins?
  5. What has been the most challenging?
  6. If we were board members, what would we want to know about what has been learned/accomplished?

I realize that introspection and learning take an investment in time — but it’s time well spent. Intentional learning also can feel as if you’re intentionally hunting for failures, so it’s important to keep an eye out for things done well and areas where you can improve. In either case, you’ll find opportunities that you can embrace in real time as your work progresses, rather than waiting for a post-mortem evaluation after everything is ended and it’s too late to increase your impact.

For additional insight into intentional learning and the best practice of grantmaking, download the free white paper 5 Best Practices of Extraordinary Grantmakers.

Additional Reading:

© 2018 Kris Putnam-Walkerly. All rights reserved. Permission granted to excerpt or reprint with attribution.

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Kris Putnam-Walkerly, MSW, has helped to transform the impact of top global philanthropies for almost 20 years. A member of the Million Dollar Consultant Hall of Fame and named one of America’s Top 25 Philanthropy Speakers. Author of the award-winning book Confident Giving: Sage Advice for Funders, which was named one of “The 10 Best Corporate Social Responsibility Books.” For more ways to improve your giving, visit Putnam Consulting Group.


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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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