166: This Could Have Been An Email | What Is Nonprofit Strategic Planning? with R. Perry Monastero

166: This Could Have Been An Email | What Is Nonprofit Strategic Planning? with R. Perry Monastero

Author: Jess Birken, MNM, JD June 11, 2026 Duration: 22:31

Your nonprofit hosted its first ever strategic planning retreat… and it was a complete disaster. So, what do you do now??

I'm joined by R. Perry Monastero, owner of RPM Consulting Group, to dig into a listener question that had us both saying "oof" out loud. A brand new board member sat through a nightmare retreat full of college-style exercises and definition debates. They want to help the board get back on track, but they don't want to step on toes as the newest person in the room.

Real Listener Question:

"We had our first ever strategic planning retreat, and it was a NIGHTMARE. We came up with words like 'diversity' and 'integrity' and sat around debating definitions for the entire retreat. Afterwards, the ED and president drafted a new mission statement and emailed it to the board with a litany of questions. I want to help us get back on track. What do I do?"

Perry and I break down what strategic planning actually is, why this retreat probably wasn't really strategic planning at all, and how a new board member can navigate the situation gracefully.

What You'll Learn:

  • What real nonprofit strategic planning looks like versus what a lot of orgs end up doing
  • Why a retreat without a facilitator is often a setup for disengagement
  • Why "this could have been an email" is the millennial response to bad governance
  • How to ask great questions as a new board member without ruffling feathers
  • Why you don't have to do a deep-dive strategic plan every single time
  • When to bring in outside expertise and where to find reliable nonprofit resources

Bottom line: You wouldn't have your best friend clean your teeth instead of a dentist. So why would you skip professional support for one of the most important conversations your nonprofit will have?

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Ever find yourself wishing for a direct line to seasoned nonprofit leaders, a chance to unpack the real challenges that don’t make it into the glossy annual reports? Charity Therapy is that conversation. With host Jess Birken, who brings her background as a lawyer and a Master of Nonprofit Management to the table, each session feels like pulling up a chair with a trusted advisor. The discussions move beyond theory, tackling the granular details of operations that leaders actually face-whether it’s navigating a tricky IRS compliance question, rebuilding a fundraising strategy from the ground up, or managing the complex interpersonal dynamics that define any mission-driven team. This podcast digs into the operational heart of the sector, offering pragmatic insights you can apply directly to your own work. It’s a resource built on the understanding that running a nonprofit is a continuous practice of problem-solving, and Jess guides these explorations with clarity and a deep respect for the work. Tune in for honest dialogue that treats the daily grind of management as the serious and nuanced craft that it is.
Author: Language: English Episodes: 50

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