Nonprofits Are Messy Podcast

Ep 248: Strategic Planning for Nonprofits: Simple, Agile, and Real (with Sophia Shaw and Adam Wolford)

by Glennda Testone

Strategic planning doesn’t have to be expensive, exhausting, or end up on a shelf. In this episode, Glennda Testone talks with Sophia Shaw and Adam Wolford of PlanPerfect about a smarter, more accessible approach to nonprofit strategic planning – especially for small to mid-sized organizations.

SUBSCRIBE ON

Subscribe on Apple Podcasts
Subscribe on Android
Subscribe on IHeart
Subscribe on Spotify

When someone mentions strategic planning, what do you think?

If your first reaction is something like, “we don’t have time for that…” or “we tried that and it went nowhere…” you’re not alone.

In this episode, Glennda sits down with Sophia Shaw and Adam Wolford, co-founders of PlanPerfect, to challenge the biggest myths about nonprofit strategic planning – that it’s expensive, time-consuming, overly complex, or only for large organizations with deep pockets.

Those myths may be compelling, but in this conversation, they uncover that the opposite is true. Sophia and Adam argue that the problem isn’t strategic planning itself, but how we’ve been doing it.

Too often, planning becomes a one-time event. A lengthy consultant engagement, an 80-page PDF, a retreat full of sticky notes, and then a document that quietly gathers dust. Instead, this episode proposes thinking of strategy as an operating system – something living, flexible, and revisited regularly. 

Mission and heart matter deeply, but impact requires structure. This conversation reframes strategic planning from a burdensome obligation into a practical, empowering tool.

TUNE IN TO LEARN:

  • Strategic planning myths – busted: Why it doesn’t have to be expensive, exhausting, or reserved for big organizations.
  • Why small nonprofits need strategy most: How clarity prevents wasted time and resources when margins are tight.
  • From document to operating system: What it looks like to treat strategy as something living and revisited – not a one-time event.

KEY QUOTES:

  • “[I]f you don’t have a plan now, it’s not your fault. More of a fault of our, you know, a system, leading up to this moment….it’s now this remarkably beautiful moment where all voices can be heard if we’re listening, and that really, that is a very powerful way of making a difference.” – Sophia Shaw

  • “[N]ow you’re not just stuck with a PDF document of your strategic plan. It lives in the system where she can start to farm this out to her team and her board to go execute it.” – Adam Wolford

  • “[Y]ou have to have the heart and the passion and the drive, but you also have to have the plan and the outcomes and the impact that you’re trying to measure. So just, while, we’re myth busting, I guess I’ll throw another one in there which is nonprofit folks can plan really successfully.” – Glennda Testone

ABOUT GUEST:

Sophia Shaw, Social Impact Software Founder

Sophia is the co-founder of PlanPerfect, a ground-breaking social-impact software company that helps nonprofits build and execute strategic plans with ease, affordability, and confidence. She is the former President and CEO of the Chicago Botanic Garden and has taught social impact and nonprofit governance at the Kellogg School of Management. Over nearly four decades in the nonprofit sector, she has served as a trustee, board president, donor, volunteer, and strategic planning consultant.

She is also a certified USAT paratriathlon and open water swimming coach, a mental health volunteer, and a Trustee of Wellesley College. Sophia holds a B.A. from Wellesley College, an M.A. from the University of Chicago, and an MBA from the Kellogg School of Management at Northwestern University.

Adam Wolford, Plan Perfect Co-Founder

Adam has over a decade of experience in technology development, strategy, and operations. He began his career as a management consultant at Accenture and Deloitte before moving into the startup world, where he became head of product for the endurance industry’s top technology platform. He has also been actively involved in nonprofit board service and volunteer work, currently serving on the board of the Intuit Art Museum. Adam holds a B.S. in chemical engineering from Cornell University and an MBA from the Kellogg School of Management at Northwestern University.

RESOURCES:

Disclosure of Material Connection: Some of the links in the post above are “affiliate links.” This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. I am disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.”

Donor Perfect

Sponsored By DonorPerfect

DonorPerfect provides nonprofits with powerful fundraising tools to drive success. Built on a foundation of integrity and innovation, the company prioritizes its clients over investors, cultivating a culture of collaboration, continuous improvement, and a commitment to making a difference. Check out their resource(s) below.

Sponsored By DRG Talent Consulting Experts

DRG is a talent advisory group helping nonprofit organizations to identify, attract, and nurture innovative, diverse leadership. Our team of 40+ experts serves over 200 nonprofits a year of all sizes and in various sectors across the country. Learn more at drgtalent.com.

Check out their resource(s) below.

  • Interviewing with Reduced Bias
    This guide from DRG Talent gives practical tips and strategies to help interviewers recognize and reduce bias, so your hiring conversations are fairer and your team selection more effective.