How to build a less hierarchical org chart

How to answer the scale question

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 by Sarah Cryder, Executive Director of City Kids Wilderness Project, who brings her own definition of scale to the table — one that has nothing to do with serving more people and everything to do with doing the work better. You'll hear them talk about: * How to answer the scale question without promising to expand * The difference between getting bigger and getting smarter — and why Sarah calls growth "getting fatter" * How a shared staffing model with Outward Bound could change who gets to work in the outdoor industry Not every organization should grow, but every organization should know what role it intends to play in the long arc of change. Guest: Sarah Cryder is the Executive Director of City Kids Wilderness Project [https://citykidsdc.org/]. She has an extensive strategic business planning and project management background. Prior to joining City Kids, she worked with local and national charter and district schools, foundations, entrepreneurs, and nonprofit service providers with a mission focused on improving education and life outcomes for underserved children. Sarah has also consulted with the D.C. Public Schools to implement evidence-based mental health intervention pilot programs, research successful national pilot interventions, and evaluate program outcomes through data-driven metrics. Sarah holds a Master of Public Policy from Georgetown University and a Bachelor’s degree from Boston College. Mentioned: Big Bet Bummer [https://ssir.org/articles/entry/big-bet-philanthropy-bummer?utm_source=Enews&utm_medium=Email&utm_campaign=SSIR_Now#], Kevin Starr Scale Really Matters, [https://ssir.org/articles/entry/scale-really-matters] Kevin Starr What’s your Endgame [https://globaldevincubator.org/wp-content/uploads/2016/02/Winter_2015_Whats_Your_Endgame.pdf], Alice Gugelev & Andrew Stern Stages of Startups [https://www.ycombinator.com/library/Ek-stages-of-startups], Y Combinator Against Rushing to Scale [https://ssir.org/articles/entry/against-rushing-to-scale?utm_source=Master+List&utm_campaign=0304702654-EMAIL_CAMPAIGN_2026_05_07_COPY_01&utm_medium=email&utm_term=0_0afc163dad-090db8cbe0-42770940], Randy Moore Get in touch [https://www.buzzsprout.com/2561655/fan_mail/new]

What If nonprofits had product designers?

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 Moore, a product designer at one of the world's largest tech companies, for a conversation that is equal parts art studio, tinkerer's lab, and science research center — Matteo's words. You'll hear them talk about: * The awkward robot that delivers toothbrushes to hotel rooms — and what it taught a startup about observation * How experimentation can actually speed things up rather than slow you down * The Effort Impact Scale — a dead simple quadrant for deciding what to fix next * What the scientific method you learned in middle school has to do with your next program cycle Guest: Matteo Moore is a Product Designer with nearly two decades of experience designing products that people actually want to use. His career spans startups, media, education, and enterprise. He has scaled design sprint methodologies across large organizations and spent years mentoring designers at every level. Matteo's origin story is not a typical one for tech. He holds a Bachelor of Arts in Fine Arts and English Literature from the University of Colorado Boulder, a Master of Architecture from the University of Colorado Denver, and studied architecture abroad at Sapienza Università di Roma. That cross-disciplinary foundation — art, language, space, and systems — shapes the way he thinks about every product he touches. He describes his workspace as one part artist studio, one part tinkerer's lab, and one part science research center. That combination is exactly what makes him such a compelling voice on design: he brings the curiosity of an artist, the rigor of a researcher, and the humility of someone who has learned not to hold his work too precious. Mentioned:  Michael Seibel, How to build product as a small startup [https://www.ycombinator.com/people/michael-seibel]. Knapp, Jake, et al. Sprint. Bantam Press, 2016. Get in touch [https://www.buzzsprout.com/2561655/fan_mail/new]

How to build a less hierarchical org chart

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 explores the conditions that make less hierarchical structures work, and the internal work that has to happen before you ever touch the org chart. You'll also hear from three co-executive directors at All Souls Church [https://www.allsoulsboulder.org/] in Boulder, Colorado, who stopped theorizing about shared leadership and started living it. You'll hear about: * Teal organizations, holacracy, and mutual aid — and what each model actually looks like in practice * The three things less hierarchical org charts require before they can work * Why collective liberation work has to come before you flatten the org chart Mentioned: Laloux, F. (2014). Reinventing organizations: A guide to creating organizations inspired by the next stage of human consciousness. Nelson Parker. Mont, S. (2017, January 9). Autopsy of a failed holacracy: Lessons in justice, equity, and self-management. [https://nonprofitquarterly.org/autopsy-failed-holacracy-lessons-justice-equity-self-management/] Nonprofit Quarterly. Valve Handbook [https://www.valvesoftware.com/en/publications] Guests:  Leah Cousin. Leah joined the staff in 2016 after being part of the community at All Souls for nearly a decade. She enjoys reigning in the vision filled minds of those around her in the office and producing action plans to achieve those visions. She is passionate about all things vegetables: farming, cooking, and sitting around a table with friends and family to enjoy a meal.  Rachel Zylstra. Rachel is a lifelong learner, adventurer, friend, partner, mother, teacher, and 7 on the Enneagram. She’s been on staff at All Souls Church of Boulder since 2014. She is passionate about discovering and exploring faith through the lens of wonder, healing, and finding the childlikeness in all of us.  Will Forsythe. Will was born and raised in Colorado, and is now serving as the Pastor of All Souls Church of Boulder.  Will graduated from Western Theological Seminary in Holland, MI.  He has worked in youth ministry, missions, and church planting, but is excited to now call Boulder home. In his free time, Will can be found fishing, reading Russian literature, biking, or drinking a good IPA. Get in touch [https://www.buzzsprout.com/2561655/fan_mail/new]

How to prepare for the King Tide Era

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 driven by instinct more than strategy? And what can we learn from mutual aid networks that are already operating without hierarchy, predictability, or formal structure? Hillary is joined by Dan Reed of Praxis, a longtime collaborator and mentor, for a conversation that moves from personal apprenticeship to the future of capital itself. You’ll hear them talk about: * The Impact Returns Reversal for philanthropists * How we ask what’s possible versus what’s feasible and the Overton Window * Philanthropy’s identity crisis * How to identify leaders worth investing in within 5 minutes * How our obsession with impact might be making us dangerous About Dan: Dan Reed is a partner at Praxis Capital [https://www.praxis.co/], an accelerator based in NYC supporting founders, funders, and innovators motivated by their faith to address the major issues of our time. Dan is animated by the power of generous, risk-forward capital to transform culture. At Praxis, he helps cultivate a community of funders committed to activating capital toward redemptive purposes. Previously, Dan served in leadership roles at National Right Work Committee, Denver Public Schools Foundation, and Morris Animal Foundation. In 2015, he founded Seed, a training and coaching company designed to help social entrepreneurs fundraise for scale. He loves the work of building new things and people that put their hands to the task.  Dan holds a BA in History and Philosophy from Geneva College. After many years in the mountain west, Dan lives in the small town of Beaver, PA. Research for this Episode:  A new mindset changes donors' relationship with philanthropy. [https://www.fidelitycharitable.org/insights/2021-future-of-philanthropy/new-mindset.html]  What's your endgame? [https://ssir.org/articles/entry/whats_your_endgame] The Innovator’s Tale of the Phoenix and Dragon. [https://doi.org/10.48558/FNWV-3443] The T-Rex and the Snowshoe Hare: What’s Next for Philanthropy in the 2020s. [https://doi.org/10.48558/CTCQ-3C83]  The Black Panther Party: Challenging Police and Promoting Social Change. [https://nmaahc.si.edu/explore/stories/black-panther-party-challenging-police-and-promoting-social-change]  What can mutual aid do in a disaster? [https://sojo.net/articles/what-can-mutual-aid-do-disaster]  Megatrends: Five global shifts reshaping the world we live in. [https://www.pwc.com/gx/en/issues/megatrends.html]  Six paradoxes of leadership. [https://www.pwc.com/gx/en/issues/succeeding-in-uncertainty/six-paradoxes-of-leadership.html]  Big Bet Philanthropy and the Big Shift to Working With Government [https://ssir.org/articles/entry/big-bet-philanthropy-government-scaling].  Philanthropic leaders reflect on major trends – and tensions. [https://thephilanthropist.ca/2024/08/philanthropic-leaders-reflect-on-major-trends-and-tensions/] Grappling With Systems Collapse: How Social Sector Leaders Can Respond. [https://ssir.org/articles/entry/grappling-with-systems-collapse]  Coronavirus volunteering: how you can help through a mutual aid group. [https://www.vox.com/future-perfect/2020/3/24/21188779/mutual-aid-coronavirus-covid-19-volunteering]  Get in touch [https://www.buzzsprout.com/2561655/fan_mail/new]

Supervisors as teachers not bosses

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 more accountability, but more adult learning. She walks through the mechanics of in-the-moment reflection, a 30-second coaching practice that can dramatically shift a worker's motivation, and makes the case for internal certifications as a tool any organization can build, regardless of sector or budget. Then she hands the mic to her ex-wife, Steph Frances — founder of Prodigy Ventures and Little Square Studio— who has spent her career proving that the young adults most workplaces give up on are often the ones most hungry to grow. Some things you'll hear: * How Prodigy reviewed footage of baristas working a rush, NFL-style, and why apprentices loved it * What happened when a shift leader jumped over the espresso counter at a customer — and how that became a breakthrough coaching moment * Why one apprentice literally sprinted to work, and what that tells us about intrinsic motivation * The difference between a "blue ribbon for showing up" culture and one where people actually want to get better * How to build an internal certification from scratch using questions you can ask your own supervisors this week Guest: Steph Frances [https://www.littlesquare.org/your-partner] is the founder of Prodigy Ventures, a social enterprise and apprenticeship for young adults in northeast Denver. Over eight years as Executive Director, Steph led Prodigy’s enterprise to double-digit year-over-year sales growth, raised over $5M and built an apprenticeship model for disconnected youth with an 85% completion rate.  Most recently, Steph served as the National Vice President of Programs and Training for Momentum Advisory Collective, the capacity-building organization for Cafe Momentum.  In her role as a consultant over the past ten years, Steph has worked with social enterprises around the country, most closely with REDF ESEs in start-up, program development, certification, strategic planning and fundraising. Steph is also a proud 2020 Livingston Fellow, and a Denver Business Journal Outstanding Women in Business finalist. She was trained at Eagle Rock’s School of Professional Studies, has a Master’s in Nonprofit Management from Regis University and is an altMBA graduate. Steph also serves on the Board of Directors for BuCu West, a community-based economic development organization in Denver’s Westwood neighborhood; she is also a member of the Globeville, Elyria, Swansea Community Investment Fund at National Western Authority. Get in touch [https://www.buzzsprout.com/2561655/fan_mail/new]