Asking Questions as a Powerful Way to Learn

Whether in the realm of business, journalism, relationships, or of course in our nonprofit and social sector, the act of “questioning” can be powerful. A piece in the Harvard Business Review last year noted, “Questioning is a uniquely powerful tool for unlocking value in organizations: It spurs learning and the exchange of ideas, it fuels innovation and performance improvement, it builds rapport and trust among team members. And it can mitigate business risk by uncovering unforeseen pitfalls and hazards.”

In other words, to “question” makes sense. This is why for over a decade, the Jim Joseph Foundation has invested in the process of defining and pursuing questions. We have seen this process lead to important learning opportunities. But, who exactly are these learning opportunities for (that is a good question!)? In the past, we emphasized the critical nature of supporting the capacity of grantees to answer questions they create – “What will we achieve and how will we do that?” “Did we see the changes we wanted to see?” “How could we be more successful in the future?”

Now we are beginning to ask what questions the foundation should be creating for ourselves. Many are questions similar to those found in evaluations of grantee-partner programs but adapted to a larger, cross-portfolio level.

Recently, in a facilitated team exercise, members of the foundation’s program team were asked to examine the assumptions we make in our work and then to consider how we might test those assumptions.  The exercise was valuable in that we learned that there are many assumptions we all make, and some assumptions only a few of us make. These include, but aren’t limited to, assumptions about elements of immersive and ongoing learning experiences, issues of depth and breadth in programming, and the value of risk-taking. We then had to ask which of these questions would we want to actually test to see if our assumptions were true and what would lead to more meaningful grantmaking endeavors.

In moving forward, the foundation will continue to ask many of the same questions our grantee-partners know well:

  • Did a grantee-partner do what they said they would do?
  • Were the desired outcomes achieved?  Why or why not?
  • What could be changed or improved in grantee-partners programming or organization to reach better results in the future?

Beyond this, in the near future we will begin to shift and prioritize other kinds of questions as well:

  • To what extent do cohorts or sets of grants help the foundation achieve our goals?
  • Overall, do our investments across grantee-partners lead us to our outcomes?  Why or why not?
  • What could be changed or improved in our grantmaking to get better results in the future?
  • What are the best measures of our desired outcomes?

To help us develop a framework of foundation-wide outcomes measurement, we decided to seek the help of Arabella Advisors. Over the upcoming nine months, they will design a structure for us to systematically learn from our grantmaking in order to 1) understand progress toward outcomes and 2) inform future grantmaking decisions. From this, we’ll be able to:

  • Develop learning questions, indicators, and measures within and across our strategic priorities,
  • Create and pilot a process for collecting and analyzing data from grantees,
  • Build a system that communicates the results of our grantmaking, and
  • Map out a 3- to 5-year research agenda focused on our investments in Jewish learning that will benefit the larger field.

With newly finalized strategic priorities, defining the correct learning questions to ask and answer is an important next step. Measurement, evaluation, and research remain consistent threads through our work. As funders, it’s important to plan, question, and test assumptions in order to ensure we are accomplishing what we set out to. For the Jim Joseph Foundation, this work will lead to a better understanding of our aspiration to “best support more young Jews – with their families and friends – to find connection, meaning, and purpose through Jewish learning.” We look forward to formulating our questions, documenting our learning, and keeping the field informed along the way.


About the author(s)

Director of Learning and Evaluation
Jim Joseph Foundation