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 Frances interviews social sector leaders who are in the messy middle of building their organizations. And since we are talking about bold solutions to intractable problems, she also brings in insight from the for-profit world.
Designing annual reports that people read
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 acting like summarizers to thinking like magazine editors. She breaks down why so many reports feel like catalogs of activity instead of narratives of learning, and offers a practical playbook for building a cohesive...
The problem you name is the solution you build
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 personal failure to systemic inequity. Josh and Hillary discuss what workforce development programming would look like if we believed it was caused by systemic forces.
This episode gives you a formula to write a problem st...
Building a data collection plan we don't dread
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 answer the questions you actually care about—rather than metrics that simply communicate how busy you’ve been.
The episode offers a practical framework for building a data collection plan you don’t dread, including how to distin...
Impact statements the world has been waiting for us to write
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 thinking, she explores why incremental gains rarely lead to systems change — and why definitive language can unlock sharper strategy, stronger alignment, and unexpected funding opportunities.
H...
Inviting donors to meetings you look forward to
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 too. In this episode, Hillary Frances reframes the purpose of donor conversations and explains how to design meetings that both you and your donors genuinely look forward to. She breaks down w...
Tailwinds Trailer
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 Frances interviews social sector leaders who are in the messy middle of building their organizations. And since we are talking about bold solutions to intractable problems, she also brings in insight from the for-profit world.
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