Less Updates, More Conversation
Chapter Leadership Brief 10.17.25
by Carolyn Vine
Chief Development Officer, Robin Hood
At Robin Hood, we’re fortunate to have a distinguished board that brings both generosity and insight to our fight against poverty in New York City. These are people who could spend their Tuesday afternoons doing just about anything, yet they choose to sit around our conference table wrestling with questions about resource allocation and fundraising strategy. Recently we decided to ask them a simple question. How can we make these meetings more valuable for you?
Their answer caught us off guard in the best possible way. They told us they want less information and more conversation.
It turns out our high-achieving, data-loving board members weren’t hungry for more PowerPoints or longer updates from staff. Instead, they wanted to dig into the messy, important stuff — the strategic debates that don’t have easy answers. They asked for discussions about how we allocate resources across our portfolios, real talk about our fundraising challenges, and honest conversations about what is working and what is not.
They also said they would like more time set aside for dialogue with one another rather than presentations from us. Suggestions included devoting a larger share of the agenda to discussion, experimenting with round robins or breakouts, and creating more informal moments for social connection. The common thread was clear. They see real value in space for candor and relationship-building.
They spoke about what they called our “meeting hygiene.” They asked for cleaner pre-reads with a simple “Top 5/Bottom 5” from our CEO, dashboards that do not just celebrate wins but acknowledge struggles, and agendas built around conversations we actually need to have rather than information we need to deliver.
Here is what we learned. Our board members are not just donors or advisors. They are ambassadors who take our story into their networks every day. They do not need another slide deck — they need talking points that stick, stories that resonate, and the kind of insights that only come from genuine dialogue with peers who care as much as they do.
Our hope is that board members will leave meetings not just informed but energized, having the kinds of conversations that lead to introductions, advocacy, and the kind of sustained commitment that transforms an organization.
Your board doesn’t need more slides. They need conversation — and you might be surprised where it leads.
Carolyn oversees all fundraising activities at Robin Hood and leads the Development, Marketing, and Events team in their work raising funds to support the organization in its critical poverty-fighting work. In that capacity, she is responsible for reaching annual fundraising goals of more than $150 million and driving Robin Hood’s development strategy by identifying new partners and initiatives to expand its fundraising platform, including planned giving, an endowment campaign, and a next-generation leadership group. Prior to joining Robin Hood in 2010, Carolyn worked at the global investment firm, D. E. Shaw & Co., in the Resource Development and Fundamental Research groups, focusing on business development, recruiting, and research. She has an M.Sc. in African Studies from the University of Oxford. She earned a B.A. in English Literature from Columbia University. A native New Yorker, Carolyn is passionate about making this city a more equitable engine of opportunity for all, and she has fought to do so in her fundraising roles at Robin Hood for over ten years. She lives in Manhattan with her husband and two small children.