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168: Oh, You Dreamers | Can a Flat Organizational Structure Work for a Nonprofit? with Dr. Pablo Otaola

Charity Therapy

Release Date: 07/09/2026

170: Shots Fired! | Can a Nonprofit Fire Its Own Board? show art 170: Shots Fired! | Can a Nonprofit Fire Its Own Board?

Charity Therapy

What if you could just... skip the whole “having a board of directors” part of running a nonprofit? Turns out, you’re not the only one who've thought about it! We all know every nonprofit pro has quietly wondered at some point whether they really need a board at all. This week's listener question puts that quiet part out loud, and we dig into what's really going on when a board goes off the rails. Real Listener Question: “I work for a small business league and our whole board is useless. They do nothing to help us but keep finding random projects for us to do. The directors all say...

info_outline 169: Different Flavors, Same Ice Cream | How Can a Nonprofit Organization Offer Retirement Benefits? with Christopher Tipper show art 169: Different Flavors, Same Ice Cream | How Can a Nonprofit Organization Offer Retirement Benefits? with Christopher Tipper

Charity Therapy

Your nonprofit is doing well, but you're worried you'll lose good employees if you don't offer retirement benefits. You’ve heard of a 401(k), but is that the right move? I'm joined by of to break down retirement benefit options for small nonprofits. Christopher helps us wade through the alphabet soup of 403(b)s, 401(k)s, and simple IRAs. Real Listener Question: “I’m an Executive Director of a small org, and I've been advocating to my board that it's time to offer more benefits, including a 401(k). I realize it's a selfish ask since I'd benefit too, but I think it would help us recruit...

info_outline 168: Oh, You Dreamers | Can a Flat Organizational Structure Work for a Nonprofit? with Dr. Pablo Otaola show art 168: Oh, You Dreamers | Can a Flat Organizational Structure Work for a Nonprofit? with Dr. Pablo Otaola

Charity Therapy

A nonprofit was built to run like a co-op. Everyone's equal. There's no HR. Is that your dream, or a nightmare that feel suspiciously like high school? I'm joined by , CEO of , to tackle a listener question about this exact scenario. An executive director walked into an organization built on flat structure ideals, but instead of a utopia they found bullying, cliques, and power plays.. Real Listener Question: “I'm an ED for a nonprofit with a flat structure. We supposed to run like a co-op, where everyone but the board and ED shares the same title. The goal was to create a fair and equitable...

info_outline 167: A Lawsuit Magnet | Do Nonprofits Really Need Directors and Officers Insurance? With Cody Wiswasser show art 167: A Lawsuit Magnet | Do Nonprofits Really Need Directors and Officers Insurance? With Cody Wiswasser

Charity Therapy

You're sitting on a nonprofit board. You haven't done anything wrong. Could someone really sue you personally over it? The unfortunate answer is YES, and the costs can pile up fast. I'm joined by Cody Wiswasser, an insurance professional at , to tackle a question from a small animal rescue trying to decide whether directors and officers insurance is actually worth the cost. The short answer is yes, but Cody walks me through why that is, and what most nonprofit boards don't realize about their exposure. Real Listener Question: “We recently learned about directors and officers insurance but...

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

Charity Therapy

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 , owner of , 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...

info_outline 165: The Past Tense of Sync | How to Get a New IRS Determination Letter show art 165: The Past Tense of Sync | How to Get a New IRS Determination Letter

Charity Therapy

So you’ve submitted your IRS application and you’re anxiously awaiting the letter in the mail with their response. But what if it just… never comes?? Meghan and I tackle a listener question from a new nonprofit that did everything right – they got their tax-exempt status (yay!) but still can't find the actual letter. What do you do? Real Listener Question: “My org got approved as a 501(c)(3) according to the IRS bulk list for my state. But I never actually received the determination letter and it's not on the website. Is this common? I know that many grants ask for the actual letter,...

info_outline 164: Ermahgerd! | How to Evaluate Executive Director Performance with Debbie Rabishaw show art 164: Ermahgerd! | How to Evaluate Executive Director Performance with Debbie Rabishaw

Charity Therapy

So a nonprofit hires an Executive Director, skips all the onboarding, sets no goals, and now… wants to fire them. Yikes! I'm joined by , founder of HR consulting firm , to tackle a listener question that has more layers than an onion. A small nonprofit is in the middle of transitioning from a working board to a governing board, their new ED is getting mixed reviews, and some board members have already gone rogue. Things are messy, and Debbie and I have thoughts. Real Listener Question: “We hired a new executive director a year ago but didn't set any goals for her. A new evaluation...

info_outline 163: A Runway of Snacks | Can a Religious Nonprofit Apply for Status with the IRS 1023-EZ Short Form? show art 163: A Runway of Snacks | Can a Religious Nonprofit Apply for Status with the IRS 1023-EZ Short Form?

Charity Therapy

So you’re a charity grounded in religious values. Does that make you a church in the eyes of the IRS? Meghan and I dig into a listener question that had me doing a genuine double take. A religious nonprofit submitted the 1023-EZ short form and got rejected because the IRS decided they were a church. What gives?! Real Listener Question: “The IRS rejected our 1023-EZ because they think we are a church, which would require the full 1023 form. But we are not a church. We are a religious organization. How do I fix the application to get them to accept our 1023-EZ?” Meghan and I break down the...

info_outline 162: No, Not the Tomatoes! | Are Nonprofit Startup Costs Tax-Deductible Donations for the Founder? show art 162: No, Not the Tomatoes! | Are Nonprofit Startup Costs Tax-Deductible Donations for the Founder?

Charity Therapy

You scraped together your own money to start a brand-new nonprofit. You’re out the money, but can you at least take a tax deduction? Meghan and I are back with a question from a new nonprofit founder who wants to know if the startup cash they put in before getting their 501c3 status counts as a tax-deductible donation. It's one of the most common questions we hear from new founders, and the answer involves a pretty handy IRS rule most people don't know about. Real Listener Question: “In June 2025, two friends and I created a housing placement nonprofit and each put our own money in to get...

info_outline 161: A Rinky-Dink Outfit | Why Recording In-Kind Donations Matters For Your Nonprofit show art 161: A Rinky-Dink Outfit | Why Recording In-Kind Donations Matters For Your Nonprofit

Charity Therapy

Your nonprofit is doing real work, but do your financials show it? In this episode, Meghan and I tackle a listener question from a small nonprofit that's running into a big problem: their numbers don't match their story. The for-profit company supporting them pays for nearly everything, but none of that shows up on the books, and funders are raising eyebrows. Real Listener Question: “Our employees, office space, and equipment are all paid for by a for-profit company and donated to our nonprofit. Our financials make it look like we're barely doing anything. I've been tasked with finding major...

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More Episodes

A nonprofit was built to run like a co-op. Everyone's equal. There's no HR. Is that your dream, or a nightmare that feel suspiciously like high school?

I'm joined by Dr. Pablo Otaola, CEO of Thriving Culture LLC, to tackle a listener question about this exact scenario. An executive director walked into an organization built on flat structure ideals, but instead of a utopia they found bullying, cliques, and power plays..

Real Listener Question:

“I'm an ED for a nonprofit with a flat structure. We supposed to run like a co-op, where everyone but the board and ED shares the same title. The goal was to create a fair and equitable environment, but in practice it's like high school. Bullying, power plays, cliques trying to control the group with zero accountability. How do I change the organization?”

Pablo and I break down the problems we’ve seen with flat organizational structures, what actually creates a thriving culture, and how a nonprofit leader can start changing the DNA of an org that's been stuck for years.

What You'll Learn:

  • The building blocks of a healthy organizational culture
  • Why flat structures look SO good on paper but may fall flat (pun intended!) in real life
  • Why "no HR" is a legal red flag no matter how good your intentions are
  • How a leader's personality can get embedded into org culture
  • What it really takes to change a culture that’s been encoded for years
  • When to stop reading blogs and get outside help from someone who's done this before

Bottom line: You don't hire the surgeon not to cut you. If your culture is broken, it's okay to ask for help. Change is uncomfortable, but it’s the only way forward!

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