Empower Your Philanthropy With These Four Questions

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Transform your giving and accelerate your speed to impact.

Questions are surprisingly powerful. The right questions spark learning, fuel innovation, create clarity, build trust, mitigate risk, and save money. That sounds pretty good, right? I believe that achieving a transformational impact as a philanthropist starts with asking the right questions.

In my book Delusional Altruism, I define the 12 most important questions high-performing philanthropists should ask regularly. Asking (and answering) these questions will transform your giving and accelerate your speed to impact. Here are the four to ask first:

The first question is “Why?”

There are two reasons philanthropists need to ask, “Why?”

First, ask why to understand your purpose. Philanthropists need to understand why they do what they do, not just what they do or how. They need to understand their raison d’être, the reason they exist.

Knowing why is the basis for everything you do. In his book Start with Why, Simon Sinek explains that people conduct business with others whose purpose aligns with theirs. People don’t buy what you do, they buy why you do it. In philanthropy, that means others will join your purpose — your why — because it aligns with theirs.

Here is an example. The Lippman Kanfer Family Foundation in Akron, Ohio, knows the why of its family philanthropy: to “build and sustain a multigenerational family culture of tzedakah.” Tzedakah means “philanthropy” in Hebrew. The Kanfers determined that the purpose of their foundation is to encourage their multigenerational family to be philanthropic while facilitating thoughtful giving.

As a result, they organize their grantmaking into themed three-year cycles. Every three years, the family chooses a societal issue, learns about it together, and makes grants based on what they learn. They organize how they give based on their why.

The second reason to ask, “Why?” is to question your assumptions.

In philanthropy, there is no shortage of causes to support. This is especially true now, during the global COVID-19 pandemic. Likewise, there is no shortage of good-sounding ideas and potential solutions: trauma-informed care, gender equality, crowd-funding, design thinking, big bets, collective impact and increasing a foundation’s annual payout beyond 5%. If you don’t ask, “Why?” you might jump into supporting one of these causes without knowing whether it’s right for you.

So if someone suggests you need to shift your entire grantmaking strategy over the next year to meet basic needs during this health crisis, increase your annual grant payout to 7% instead of 5% or apply a gender-equity lens to all your philanthropy, the first thing you should ask is, “Why?”

Nothing is wrong with these ideas. But they might not be right for you. Before jumping in, you need to explore them. You must know why — why is this the most important thing for us to do right now? What will be the impact on our current grantees or on our assets if we switch our approach?

The second question you should ask is, “What do I already know?”

I have great news for you! You already know 80% of the answer to any question you have about your philanthropy.

Now for the bad news: You probably aren’t taking the time to think about what you already know. This is a problem because you are probably wasting time and money by having other people answer your questions.

If you ask yourself, “What do I already know?” you will answer your question faster and for less money.

Whenever you have a question in philanthropy, you should first spend some time — even an hour — to brainstorm everything you already know about the topic. Write it all down. I mean literally pull out your notepad, laptop or easel paper. Do this by yourself or in a group. Ask, “What do I/we already know?”

I recently spoke with the CEO of an association of foundations. He wanted to conduct strategic planning, but first, he wanted to conduct a six-month learning tour to understand the members’ needs and trends. He asked if I could help. The plan was to organize multiple town hall meetings across many cities, inviting foundation leaders to have facilitated conversations. I told him he would be wasting a tremendous amount of money and time. He and his team already knew 80% of what they needed to know.

This is an organization with talented, knowledgeable staff who are regularly talking with members. The board is comprised of amazing and diverse philanthropy leaders who represent the organization’s entire geographic footprint. They had already been commissioning research about issues and trends in the region. They organized annual meetings and convenings where they regularly learned with their members and outside experts. They knew a tremendous amount. But it literally didn’t occur to the CEO to start by trying to capture what they already knew — the 80% — and use that as a basis for informing their strategy.

This leads me to the third question philanthropists should ask: “What don’t I know?”

You know a lot. And, yes, there’s still a lot you don’t know.

Let’s go back to the example of the foundation association. After spending days (or even weeks) reviewing and reflecting on that 80% of the staff and board already know about member needs and trends, they should then ask, “What don’t we know?”

Then they can collect the missing 20% of information and insight in the easiest, quickest way. It will take them less time and money to get answers to fewer, more specific questions. And especially now, as we recognize how quickly the world can change around us, increasing the speed at which we gather information and use it to inform decision-making is critical.

The final question I want you to think about is, “Does this bring me joy?”

Philanthropists should gain more than they give. Yes, you read that correctly.

I don’t mean they should financially gain more than they give. And I’m certainly not suggesting that gains in publicity or celebrity status should surpass charitable contributions.

I’m talking about joy. Giving should bring joy. The joy of knowing you improved someone’s life. The joy of realizing that your philanthropic contribution helped a village have clean drinking water, gave an emerging leader resources to put her dream for gender empowerment into action, or enabled an important nonprofit to survive and even strengthen operations during the COVID-19 crisis.

The work you personally do as a philanthropist should also bring you joy, whether it’s speaking, planning, meeting with grantees, leading your community’s crisis response, or reviewing proposals.

That doesn’t mean philanthropy is easy. Being philanthropic in the face of widespread social and economic challenges can test our endurance and try our spirits. And sometimes the joy gets squeezed right out of us by overflowing inboxes, time spent with people we dislike and frantic year-end deadlines. But, on balance, regardless of what’s happening in the world around us, the act of giving should bring you joy.

Asking the right questions can bring you joy as well when you see how they help you and your organization learn, grow, and increase your philanthropic impact. Start now with these first four powerful questions, and transform your giving.

Learn more in my new book, Delusional Altruism.

This article was adapted by and published by Thrive Global.

© 2020 Kris Putnam-Walkerly. All rights reserved. Permission granted to excerpt or reprint with attribution.

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About Kris Putnam-Walkerly

I’m a global philanthropy expert, advisor, and award-winning author. I’ve helped hundreds of ultra-high net worth donors, celebrities, foundations, Fortune 500 companies, and wealth advisors strategically influence and allocate over half a billion dollars in grants and gifts. I was named one of “America’s Top 20 Philanthropy Speakers” three years in a row, I write about philanthropy for Forbes.com, CEO World, Alliance Magazine, De Dikke Blauwe and am frequently quoted in leading publications such as Bloomberg, NPR, and WSJ.

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