Its a rather typical activity nonprofits and foundations do from time to time: hold a one-day strategic planning retreat to get to know one another better, exchange ideas, and set some goals. I’ve facilitated many of them over the years, and have found that they often try to do too much and so have difficulty leading to tangible next steps.

A few years back, I was hired by a foundation to lead one of these retreats. To prepare, I read about the foundation’s mission to advance social justice and was particularly interested in learning more about how they distributed its nearly $20 million of yearly funding.

As I traveled by plane for the meeting, I was excited about the prospects for the meeting. I had developed an agenda for the day ahead of time that would allow each program officer time to share her or his perspective at the meeting about why they fund the way they do. Others would be allowed to ask questions. The ultimate objective was for people to get to know each other better, come to a better understanding of each other’s point of view on social justice and consider how they might fund together in the future, across their specific program lines.

The day went as planned, with a series of presentations from one program officer after another. Some questions were asked, and some ideas were exchanged for how they might work together. But I found myself struck by what comprised most of the presentations: a combination of vagueness, grandiose and rather abstract expressions about the pursuit of social justice in the world, and long explanations of how and why they make funding decisions that made it feel in parts like a seminar or academic class.

Still, I must admit that over the course of the day I found myself enamored by the passion of these program officers and by some very interesting material they brought up. For example, one presentation went into how media and television shape our perceptions, which was fascinating. At times, I felt as if I was attending an Aspen Ideas Festival.

Toward the end of the meeting, I shifted the agenda in a different direction. It was a risky move, because I had been asked to plan the day carefully, and everyone participating that day had signed off on the agenda. But I went off script and posed two questions to the group:

How do you know if your grant making is advancing social justice? What measures are you using?

I didn’t realize it at the time, but I was putting the meeting in the context of the question I’ve been asking in my blog posts: To what end?

Yeah, said one of the program officers. That’s something we hope to get to. The entire group agreed, and that was the end of that.

Id heard the same response before. But no one ever seems to get to the to-what-end question.

Heading home that evening on the plane, I sat there alternating between some excitement about having been part of such an intellectually thought-provoking day and a lot more bewilderment about what had transpired.

There’s an overused expression in the business world, the 30,000-foot view, to describe getting the big picture. It comes from the cruising altitude of a lot of airplane flights, because from that far up you can see out the window far and wide. But you don’t see things with any precision. That’s how I was feeling. The foundation’s discussion had spent a lot of time at 30,000 feet, but it wasn’t clear to me how that foundation would ever know whether any of its 30,000-feet thinking had actually led to changing people’s lives for the better.

Two men were sitting near me on the plane, one across the aisle and the other in the seat in front of me. Both looked to be in their late twenties. They began to strike up a conversation given where they were seated it was impossible for me not to overhear about how they had both just flown from small towns in Alabama. They had both had a layover for the night in New Orleans on their way to Boston. They expressed their excitement over leaving Alabama for the first time, and how cool they found NOLA. They were delighted just by the chance to see different places and have different experiences than they were used to.

It took only a short while into their conversation before they realized they were heading to Boston for the same reason. Remarkably, the two young men had applied for the same job, and the company was willing to fly them into town and pay their room and board for six months while they underwent training, at the end of which they would be tested for whether they were suitable for the full-time position.

I grew curious and wanted to learn more. So I joined the conversation. I asked them why they were looking for jobs so far from their homes, and they both said that Alabama just didn’t have the same kind of opportunity. Like so many people who come from parts of the country where there is less opportunity for meaningful work, both had strung together various jobs, been in community college, but we’re not seeing that leading them to much of a future. They wanted to find employment that would not only support them but, one day, the families they hoped to start.

When I shared with them that snow was coming soon to Boston, their eyes lit up. Neither man had ever seen snow. Those two young men were so enthusiastic about everything that was ahead.

On the way home from the airport, I found myself thinking about the discussion with the program officers at the foundation retreat. Was anything we had talked about going to help those two young men or others like them? They were seeking secure, good-paying jobs along their lifelong pathways to success, and yet something that straightforward seems so out of reach for so many people in the United States today.

I asked myself whether I should have pushed harder at the end of the meeting when the group was unwilling to begin discussing how they might measure their success. I admit that I held back because I was hoping to get hired again.

That experience has stuck with me ever since. Each day, I try to remember to ask myself whether the work I’m doing is leading to tangible improvements in people’s lives. It’s difficult to do, as I, like others at Root Cause and all nonprofits, get caught up by so many distractions not to mention the power dynamics inherent in the fact that we are so reliant on funding from foundations, which can make it difficult at times to speak up.

But the lesson for me that I hope others in our sector can take from my experience is that while its easy to stay at 30,000 feet, its a lot harder to be precisebecause being precise makes us accountable. I believe, in all honesty, that our lack of precision and the lack of accountability that results is why nonprofits, foundations, and government have not seen the change they seek.

I wish I could follow up with those two young men to see how things went with them. I’m sure there’s a lot more to learn from their story. But I never got their contact information. I do think about them frequently, and hope my actions somehow support their efforts and those of others navigating their lifelong pathways from healthy birth to quality education, to a well-paying job, and healthy and secure aging.

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