What I Witnessed in New York City Changed How I Think About Board Leadership

By Sterrin Bird, Wingspan Philanthropy

There is nothing quite like New York City in early spring — that particular kind of day when the cold finally loosens its grip just enough, and the city exhales. Everyone spills onto the sidewalks as if released from hibernation. The energy is almost electric with gratitude.

I arrived in that city this week for two days with the leadership and board of Girls Inc. And what I witnessed — I have been praying for it, honestly, since the advent of AI and the whiplash and chaos surrounding its application in individual giving.

I Have Sat in More Board Meetings Than I Can Count

The pattern has been remarkably consistent across decades and organizations. Someone drives to the meeting compiling data on impact. Reports go out in advance. Everyone arrives having skimmed — or not read — what was sent. And then the group spends its precious time together reviewing what they already received.

It is a ritual dressed up as governance. And it has always left me quietly heartbroken — not because the people in the room don’t care, but because the format keeps them from remembering why they said yes in the first place.

This week was totally different.

Then She Opened the Hard Conversation

The board meeting itself was full of important business — resolutions, budgets, plans. But what struck me was how Stephanie held space for her board. She didn’t present at them. She convened them. She created something rare: a safe and thoughtful container for honest discussion about the industry, the moment, and how Girls Inc. would move forward — together, with them.

Everything was on the table. AI and its implications. Impact reporting. The state of philanthropy. The critical importance of investing in people and in learning. These are precisely the conversations most boards avoid — too uncertain, too messy, too far from the comfort of a clean resolution.

And nobody ran from them.

That is not a small thing. In a sector experiencing genuine disruption — funding landscapes shifting, political headwinds, the pressure to prove impact in increasingly transactional ways — a leader who can hold that kind of psychological safety with her board isn’t just doing good governance. She is modeling exactly what Girls Inc. stands for. She is being the mission.

The Container Comes First

The hard conversation was possible because of what came before it. The luncheon. The girls in the room. The decision to lead with belonging before moving to business. Stephanie built the container before she opened it. People could go to difficult places together because they had already been reminded of what they were there for.

This is what I call leading with intention: many voices, varied perspectives, and shared values. It is not a retreat or a trust fall exercise. It is a leader choosing to treat her board as partners in discernment rather than validators of decisions already made.

And it is what I have been praying for. Proof that in the middle of all the noise — the AI hype, the data dashboards, the algorithmic approaches to human generosity — some leaders are choosing a different way. A human way.