As I talk to people at the innovative edge of philanthropy and resident-centered investing, here's a question I often ask:

What pulls you off course?

I ask because I've seen too much good work veer off track over the years—or go completely in the ditch, never to be seen again.

In earlier blog posts, I've written about two big things that pull well-intentioned funders off course: forgetting about core identity and not thinking enough about who's doing the work. Here's another, stickier one: board members.

Board challenges came up repeatedly in my conversations, but one story stands out. A foundation leader told me, without hesitation, that her board members were among her biggest challenges. Her board loved the foundation's small grants program—they loved hearing about the ideas that came in and seeing what happened. They said it was some of the best and most important work the foundation was doing. So what could pull their favorite work off course?

Their over-eagerness to help, combined with naiveté about their own understanding of the problems community residents were trying to solve.

The example I remember most was about snow shovels. A group had requested a modest grant for snow shovels that could be used by neighbors to clear snow. One enthusiastic board member moved to increase the grant so the group could buy a snow blower instead, assuming the request was simply about snow removal. After all, he had a snow blower and found it far more efficient than the back-breaking work of shoveling.

The grant was made for snow shovels, but only because the program officer was in the room with full permission to participate in grant conversations, and was able to explain that the group had been intentional about their choice. They understood that many shovels would allow many people to participate. They chose shovels because shovels don't break down, need gasoline, require special instructions or liability insurance, or demand locked storage. Shovels were the more community-friendly option. Their request was indeed about snow removal, but it was just as much about what they could manage, what could be accessible to the most people, and what made sense to them. It was about community.

During my years with Grassroots Grantmakers, I heard a lot about boards. There were board members who challenged the validity of small grants programs because they couldn't imagine much happening with small amounts of money. They focused on what the grant dollars were buying rather than the intent of the activity being supported. "We're buying t-shirts?" Staff members who weren't allowed to attend board meetings told me they missed opportunities to challenge the misguided snow-blower decision or the "we're buying t-shirts" criticism. I experienced these same challenges in my own work.

I also heard about pressure from board members to "prove it." This pressure comes in the most well-meaning and responsible package—making sure the board does its job as good stewards of financial resources. But prove-it pressure is complicated.

Sometimes the demand is based on mismatched assumptions about investing in community residents and the informal groups they form to get things done. If the expectation is about how many widgets are produced, how many services are provided, how much progress is being made in turning informal groups into staffed nonprofits, or how beginning efforts are impacting policy, you have a real problem. These assumptions or expectations might be appropriate for other types of grantmaking, but not for this work.

Even when the prove-it question is grounded in good understanding of why it is important to invest in residents - to grow social capital and community connectedness, change perceptions about what's possible, discover and cultivate new leaders, expand circles of involvement, AND do something concrete about problems residents identify as important—the question remains difficult to answer. Well-constructed evaluations can provide evidence that investing in resident voice and power is smart and even essential for community well-being and vibrancy. But as more than one foundation executive mentioned, the costs in both time and money associated with such evaluations can overshadow the amount actually being invested in the work itself.

So how do you handle this challenge beyond confronting off-course pulls in the moment? People I spoke with emphasized two things: thinking hard about board composition, with the goal of having a board that includes different types of people who bring different perspectives and life experiences, and devoting considerable time and attention on a regular basis to board member engagement and education.

Board diversity in itself is important. But I believe that board diversity plus an organizational culture that expects board members to be engaged outside of meetings, and welcomes board outsiders (including staff) into deliberation and decision-making, goes a long way toward ensuring ongoing attention to board member engagement and education. It's this combination—diversity of perspective and inclusive culture—that helps keep good work on course.