Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs

If you've ever lost sleep over your board, there might be a structural reason for it — one that goes all the way back to the colonial era. Hillary shares her latest learning from helping organizations make board governance shifts. Hillary is joined by Rea Carey, a nonprofit consultant with over thirty years of experience leading organizations through some of the most significant LGBTQ+ advoca...

Nonprofits are asked constantly to plan for scale, and most of us answer with ambitions to get bigger. But what if the right answer has nothing to do with size? Hillary reframes the scale question entirely: scale isn't about growth, it's about influence. And sometimes the most influential thing an organization can do is change how it operates, not how large it becomes. Hillary is joined...

The for-profit world has product engineers, design sprints, and rapid iteration cycles. The nonprofit sector has… a debrief meeting. In this episode, Hillary asks what would happen if we closed that gap. Hillary breaks down what a "product" actually looks like in the social sector and introduces a way of testing it borrowed straight from tech startups. Then she sits down with Matteo Moor...

Description: The nonprofit sector is drawn to the idea of flat org charts — but most organizations don't have great examples of what that actually looks like in practice. Why do we cling to hierarchy even when it conflicts with the values we're trying to model? And what does it actually take — not just philosophically, but day-to-day — to share power inside an organization? Hillary explo...

The nonprofit sector is entering a King Tide Era — a convergence of political, economic, and environmental pressures that won’t just strain the social sector, but fundamentally reconfigure it.  Hillary explores uncomfortable questions: What if the nonprofit model isn’t the best vehicle for solving the problems we care about? What happens when philanthropy becomes volatile, identity-conflicted, and...

Frontline supervisors might be the key to our workplace culture. And they may need our attention. Supervisors are asked to do everything — schedule, train, manage quality, order supplies, write reports. And yet the one skill that might actually make their jobs easier is the one we almost never teach them: how to coach. Hillary thinks that the answer to your productivity challenges might not be mor...

Most of us in the nonprofit world were taught that real evaluation requires a research team, a grant, and a methodology section. So we measure what's easy to count — and quietly avoid the things that actually matter. This episode is about doing it differently. Hillary challenges the way program evaluation typically works: heavy on outputs, allergic to nuance, and overly deferential to "c...

Big bet philanthropists don’t fund “best practices.” They fund breakthroughs. In this episode, Hillary challenges the idea that multimillion-dollar philanthropy is unpredictable or out of reach. She argues that big bet funders behave less like traditional donors and more like venture investors—seeking leaders who are building for exponential impact, not linear growth. You’ll hear Hillary’s latest...

Hillary breaks down why the next 5–8 years will require nonprofits to make sharper, more disciplined decisions about their revenue streams. We walk through the five major philanthropic strategies—major gifts, annual giving, grants, events, and corporate sponsorships—and learn how to assess whether your current approaches are scaling and operationalized enough to take on something new. She’s joined...

Annual reports have become one of the most expensive—and least read—projects nonprofits produce. They’re often treated like a compliance task: dense, polite, exhaustive, and forgettable. In this episode we ask a different question: What if your annual report actually added value to your audience’s life? Drawing on principles of journalism, Hillary explores how nonprofit leaders can shift from acti...

Nonprofits tackle big problems — but often without naming the root cause that actually drives their work. In this episode, Hillary Frances breaks down how clarifying your problem statement can transform your strategy, sharpen your identity, and make your interventions more potent. Featuring Josh Jones, CEO of Neighborhood in Virginia, who has spent years reshaping his beliefs about poverty from a...

Description: Data collection inside nonprofits has become a dreaded chore. In this episode, Hillary explores how nonprofit leaders can shift data collection from a burdensome, compliance-driven exercise into a lean, human-centered practice rooted in curiosity. Drawing on her background as both a research-trained academic and a practitioner, Hillary breaks down how to design data systems that answe...

What Hillary loves most about this episode: I ask horsewomen to talk about whether or not impact statements are helpful. Turns out, they love theirs and they’re using it to design their equestrian workforce program. Description: In this episode, Hillary Frances makes the case for impact statements that declare what it will take to solve a problem once and for all. Drawing lessons from tech’s 10x t...

What Hillary loves about this episode: It captures my clearest thinking on how to make donor meetings worth showing up for — and tests it alongside a young Indigenous woman fundraiser who’s done code-switching to fit white norms and is building donor relationships rooted in curiosity, respect, and shared work. Description: Many fundraisers dread donor meetings — and, truth be told, many donors do...

Tailwinds: Ideas Fueling Nonprofit Innovators and Social Entrepreneurs. Tailwinds is a project that brings momentum to the leaders tackling the world’s most impossible problems. Created by Flying Whale Strategies, the show delivers ideas, insight, and energy to the people doing work that often feels impossible. Each episode features brass tacks strategy that can be implemented tomorrow. Hillary Fr...