Navigating the foster care and juvenile justice systems, enduring abuse, struggling to make ends meet and battling despair were the stories shared by four youth panelists a few months ago at the Santa Clara County Children’s Summit. These four panelists are youth members on the Leadership Council of the Santa Clara County Opportunity Youth Partnership, a collaborative with more than 35 community partners that are committed to recalibrating the trajectories of young people. In July 2012, the Aspen Forum for Community Solutions and Opportunity Youth Incentive Fund was launched in response to the more than 6.7 million “opportunity youth,” defined as young people between the ages of 16 to 24 who are neither enrolled in school nor participating in the labor market. These youth represent enormous economic and social potential, and successfully reconnecting them to our nation’s economy requires community collaborations that effectively remove barriers and build and deepen education and employment pathways. Local sites in both Santa Clara and Oakland have been chosen to participate as part of this national partnership and, as a member of the national leadership council, I was asked to moderate the youth panel at the recent Children’s Summit.

As one of the panelists recounted his own odyssey to the nearly 200 nonprofit executives, government employees, advocates, and grantmakers in attendance, he began to cry, and it was clear to everyone that he was no longer merely re-telling the ordeal, but reliving it. The conferees shifted uncomfortably in their seats. As the panel’s moderator, no one was more uncomfortable than me.

Let’s back up a little bit. Eighteen months ago, I began working at the William and Flora Hewlett Foundation as a two-year Fellow, the first fellow hired in a new initiative that introduces early-career professionals to philanthropy. The idea is to provide the fellows with the experience they need to improve the practice of charitable giving, while helping donors refresh their strategies with new perspectives. In other words, we are tasked, virtually from our first day of work, with both learning about philanthropy and with helping experienced program staff tackle thorny dilemmas. I work in – the Effective Philanthropy Group where Director Fay Twersky constantly challenges her team to ask the tough questions about situations exactly like the one that confronted me at the Children’s Summit.

One of the things we’ve learned is that there are few things more useful to donors and advocates than storytelling: personal narratives keep us in touch with the people we are trying to support, and trigger the discourse that, in turn sparks the imagination. That’s when great and transformative things happen in the world.

But in the process of trying to unlock grantmaking’s black box by encouraging panelists to share their stories, I had also helped to unlock Pandora’s Box, unleashing from it this young man’s great pain. Was I helping to exploit someone who I claimed I wanted to help?

Perhaps the most profound lesson that I have learned as a Fellow is that, for all our talk of outcomes and data-driven grantmaking, we’re still dealing, on the most molecular level, with human beings. Fay is a proponent of evidence and numbers, but does not shy away from words like “empathy” or “compassion;” she often exhorts us to examine our own privilege and to integrate the voices of the communities we serve into our work. Finally, I cleared my throat and, with all the gravitas that I could muster, said:

“I want to take a minute to pause here and acknowledge how vulnerable this young man has been with us,” I said. “We often ask young people to share their stories with crowds like this, but we don’t do the same ourselves. Maybe now is a good time to pause and just acknowledge how much courage this takes.”

I wasn’t quite sure if I had done the right thing, but the young man seemed to appreciate what I had said. Later, during lunch, an administrator at a local nonprofit who was attending the summit, approached me and said, “You know, “those panels are always hard. How do we avoid tokenizing youth, but at the same time gain some real understanding to help organizations do their work better?”  I think she said it best. As we talked for a few additional moments we both acknowledged the difficult paradox often faced in this work.

During my time at the Hewlett Foundation, I have learned a great deal. I have worked closely with Foundation partners and local grantees such as the Aspen Forum for Community Solutions, and Kids in Common (part of Planned Parenthood Mar Monte) and all of them have contributed tremendously to my education as I begin to ponder my next steps in philanthropy.

Of everything I’ve learned however, I think the most profound is this: we can always do a better job of trying to authentically engage and listen to the stories of the communities we serve. It can make all of us stronger at the work we do.