Last year, I conducted a site visit in D.C. with a nonprofit that had submitted a relatively large funding request to a foundation. It was fairly well known that the organization had been struggling. The Post had written a few articles and there had been lengthy community discussions.

I asked a lot of questions – some of them were hard. The site visit included several senior members of the team, as well as Board members. They appeared to be transparent in their answers. They seemed to be making progress towards strengthening their operations and getting back on track. Before the funding recommendation was made, I requested updated documents. There were still some red flags, but the organization was doing much-needed work. Rather than suggest that they get their full 2-year funding request, I recommended that the organization get a limited amount of money in Year 1. If they were able to achieve their goals and if their organization was continuing to strengthen its finances and operations, I suggested that they get additional funding in Year 2. I shared this with the applicant prior to submitting the recommendation, as I wanted them to be able to make the appropriate preparations should they be approved for funding.

Three months later, the organization shut its doors completely.

My first reaction was disappointment. The organization was providing critical services needed by the community. There were so many people who were relying on them, and I wasn’t sure if others in the community had the capacity to provide assistance.

My second reaction was one of second-guessing. Had I not asked the right questions? Had I not dug deep enough? Did I make a bad recommendation? What could I have done differently?

My third reaction was one of skepticism. Had the organization been honest in its answers to me? I know, all too well, the power of “spin.” Had they made it sound like they were getting back on track, when they were, in actuality, still struggling? And again – should I have asked tougher questions or dug deeper?

The discernment process can be tricky. When an organization is requesting funding, it always wants to put its best face on. It’s human nature. And we have yet to figure out how to create the space to have really honest conversations. I wonder if things would have turned out differently had the organization been able to say, “We’re struggling, and we could use your brainpower and those of your colleagues to help us figure this out.”

I’m not sure that I’ll ever know the answer as to what really happened. And I’m still not certain what I could have done differently. But I know that I’ll continue to ask myself anyway.