Ask One Question To Save Time, Save Money And Achieve Greater Impact


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Change the outcomes in your philanthropic journey.

Learning isn’t hard to do, but it must be intentional and continuous. Whatever role you play in philanthropy—be it donor, foundation leader or trustee—in order to make a real impact, you have to ask the right questions.

And there is one question that is guaranteed to save time and money and help achieve dramatic results. It’s a simple question, but the answers you receive can help you start out with a sound strategy, change your outcomes and change the way you think about your giving.

That question is this: “If you could do it all over again, what would you do differently?”

Yes, it’s really that simple.

If you ask others that question while or after they attempt the same thing you’re trying to do, I promise you will reap benefits. Listen to what they have to say, implement their suggestions and you will save time, financial resources and headaches. You will also have a much more successful grantmaking program. And it will happen much faster than if you hadn’t asked the question. Why make the same mistakes someone else already made?

Asking this vital question can help you take several crucial steps in your philanthropic journey: [below are examples, not steps to take] Let me tell you what happened when three different philanthropists asked this question:

1. Make a communications plan. I was working with a community foundation implementing a human services initiative, so we visited other communities across the country that were doing the same thing. We asked each of them, “If you could develop your initiative all over again, what would you do differently?”

Each one of them said, “If I could do it all over again, I would develop a communications plan from the very beginning.” Bingo!

The organizations all agreed that without such a plan, they were hindered throughout their entire initiative by poor communication and coordination and lack of awareness among key stakeholders.

2. Collect data to track impact. Another important discovery we made by asking this crucial question? We learned most foundations wished they had invested more in grantee data collection. Years into a new initiative, their grantees are unable to collect the data they need to make an impact, because they don’t have the in-house capacity. That means they have to stop their efforts and set up that capacity at a time when they should be making progress. Learn from those foundations, implement that suggestion from the start and save yourself time and money.

3. Get input from the community. When asked the critical question, one organization responded that they should have gotten out of the office and into the community they served before determining their strategy. Unfortunately, this is a common oversight. In this case, they were addressing issues facing the elderly. They had reams of data about illness, clinical services, nutrition and mobility. But they didn’t go talk to those who serve the elderly one-on-one, or to the elderly themselves. They missed the important moments of deep understanding that can come when one sees how local, state or national policies play out on the ground. Their impact was not what it could have been.

The conclusion is simple, right? Ask the question, listen to the answer, implement the suggestion, save yourself time and resources, get faster results and have greater impact. You have the resources and tools you need to make it happen. Don’t be afraid to reach out for advice to a fellow donor, consultant or foundation that has worked on similar issues. I guarantee it works!

Guess what? This isn’t the only important question to ask. In my forthcoming book, Delusional Altruism, I share 12 questions philanthropists should ask to have a transformational impact. The book is being published by Wiley in February. I can’t wait to share it with you!

Want to bounce some ideas or questions off an experienced philanthropy advisor? I’ve been working with high-net-worth donors, foundations, and corporations for more than 20 years. If you’d like help navigating your charitable giving, an advisor is a great place to start. Simply set up a call with me, or shoot me an email. I look forward to hearing from you!

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This article was originally written for and published by Forbes.

© 2019 Kris Putnam-Walkerly. All rights reserved. Permission granted to excerpt or reprint with attribution.

About Kris Putnam-Walkerly


I’m a global philanthropy expert, advisor and award-winning author. I help ultra-high net worth donors, celebrities, foundations and Fortune 500 companies dramatically increase the clarity, speed, impact and joy of their giving. I’m the author of Confident Giving: Sage Advice for Funders, was named one of “America’s Top 25 Philanthropy Speakers”(along with U2’s Bono!), I write about philanthropy for Forbes.comAlliance MagazineDe Dikke Blauwe and am frequently quoted in leading publications such as BloombergNPRand WSJ.

Whether you are just getting started in philanthropy, want to refresh your giving strategy, or need to catapult yourself to your desired future, I can help. Let’s talk! Call me at +1-800-598-2102 x1, email me at or schedule a call.


Kris is knowledgeable about all the different, nuanced aspects of philanthropic strategy and understands why not all grantmakers are the same. I appreciate the way she repeatedly brings a fresh perspective to our work.

Kathy Smith, Senior Program Officer, Walton Family Foundation 


Want to learn more? Visit my website to learn how I help funders, access free resources, and read client testimonials.

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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