When, how, why to ask – our theory of questions

dara 330 2014



This post was inspired by reflections on Mamie Kanfer Stewart’s ELI Talk.

As children we were taught “there’s no such thing as a stupid question.” Today, thanks to the story of Nobel Laureate Isidor I. Rabi, many parents are now inspired by his mother’s example and, in an effort to foster children who are creative and critical thinkers ask “Did you ask a good question today?” instead of “What did you do today?”

did you ask a good question

But we can also go too far, making a fetish out of asking questions, even and especially the good ones.

In her ELI Talk “Teaching an Organization to Fish,” our board member Mamie Kanfer Stewart offers many strong suggestions for how philanthropists can better support their grantees; the one that struck me and changed the way I work is the assertion that we should ask a question only if the answer will effect whether we will make the donation.

Philanthropists want to make good decisions, and those of us who are professionals working with philanthropists feel responsible to be careful stewards of funds that are not ours. Add to that the knowledge that there are so many worthy causes and asking questions becomes very important. Due diligence on our grantees and the nuances of each grant are how we justify our funding decisions in a competitive marketplace. But how much understanding is enough? Mamie’s benchmark of “will it change whether I make a donation” is a practical one. It takes us out of the realm of being what Barry Schwarz in Paradox of Choice calls Maximizers – trying to find the absolute best donation – to Satisficers – understanding whether this choice is strong enough to meet our needs and then stopping our search.

There are no stupid questions. But there are questions that have more or less utility. And sometimes questions can cover our own insecurities. As philanthropists and professionals we often understand the subject matter of the nonprofit’s work very well, but we need the people on the ground to make change happen, and this creates a challenging dynamic. Being reliant on someone can make us vulnerable, especially when we are self aware enough to realize we can easily fall victim to the old Yiddish proverb “with money in your pocket, you are wise and you are handsome and you sing well too.” We can be unsure whether we are being flattered and feel the need to prove ourselves. So we ask questions, to reassure both ourselves and the prospective grantees that we do know what we’re doing . . . but as Mamie points out, sometimes we take it too far and those questions are extraneous to building a necessary understanding.

with money in your pocket

At the Foundation, we ask a lot of questions. And I’d like to think that most of them are useful. That, in a nutshell, seems a good litmus test to apply before asking a question. A question should have a purpose. We hope to be a partner to our grantees, not just a funder – a subtle distinction, and we acknowledge the different dollars and skills that we and our grantees bring to such a partnership, and how those influence the dynamics of the relationship. Early on in our due diligence process, asking hard questions allows us to understand how a partner thinks; later in the process we hope our questions will help them think about their work in different ways. There is value in asking these questions, and in partnership.

But Mamie’s prompt helped me to reflect on our due diligence practices – that even useful questions might be used more strategically and sparingly. To that end, there are two practices we increasingly utilize that can also help us get more expeditiously to a decision making point.

First, is to utilize our peers as a resource. Increasingly we’ve had opportunities to participate in funding collaborations. These are great opportunities for us to no have to do all the due diligence because a trusted peer has done it. Yes, we’ll often have a few specific questions related to our strategies and organizational goals, but largely we can rely on the answers provided to our funding partner, which hopefully cuts down on work for everyone.

The second way is to understand what questions we have that don’t have answers – yet. We’ve created a list of Learning Objectives which are questions we have that we believe will help both us and practitioners who are applying Jewish wisdom to do our work better. Instead of asking questions where funding decisions depend on the answers, we make funding decisions based on the questions we will be able to explore during the grant.

Calling out what we don’t know and what we’d like to learn is not only a way to make good choices about where to fund, but also helps us set our own expectations. Hopefully the project will yield useful information; but sometimes things won’t go as expected and that learning mindset helps take the pressure off “having all the answers.” These questions become an area for shared learning that helps the organization do its work better, helps us understand where future funding might do the most good, and, critically, helps both of us to share the knowledge of what works with the wider field.

And on a daily basis, I must thank Mamie: doing a “gut check” of whether a question is worth asking is terribly useful. It’s incredibly freeing not to feel like you have to ask another question. It saves the grantees effort and it saves me work too. And that gives us time to get to know one another and to do other work — either apart or together – because, as the Yiddish Proverb says, “even the most expensive clock has no more than sixty minutes.”

Only 60 minutes

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