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

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?

Resources from this Episode

• R. Perry Monastero / RPM Consulting Group: https://rpmcg.com
• BoardSource: https://boardsource.org
• National Council of Nonprofits: https://www.councilofnonprofits.org
• Standards for Excellence Institute: https://standardsforexcellence.org
• Episode Transcript: https://birkenlaw.com/wp-content/uploads/2026/06/CT166_Transcript.pdf

Connect with Us

• Jess Birken: https://www.linkedin.com/in/jessbirken/
• R. Perry Monastero: https://www.linkedin.com/in/perrymonastero/

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Transcript

Jess Birken 00:00:02  Welcome to Charity therapy, the podcast where we explore the ups and downs of the nonprofit sector and answer your burning questions. I'm your host, Jess Birken, owner of Birken Law Office, and I'm excited you're here. Imagine hanging out with me and my super smart, funny, nonprofit expert pals. You get to ask them anything about your nitty gritty nonprofit life and get their wisdom for free. Whether you're a seasoned pro or just strapping on your nonprofit boots, we're here to share stories and remind you you're not alone on this journey. So get ready to join the conversation and bring me the tough questions I ain't scared. Ready to rock? Let's dive in. Hello and welcome to this episode of Charity therapy. Today I am joined by my friend Perry Monastero. Perry owns RPM consulting Group, where he helps nonprofits grow and level up. Perry, thank you so much for being here today, buddy.

 

Perry Monastero 00:00:59  Thanks, Jess. It's, a pleasure to be here. I'm going to consider you my therapist today.

 

Jess Birken 00:01:06  Okay, I accept, I accept.

 

Jess Birken 00:01:08  I feel like, yeah, that that could be a thing. We can work through some issues, you know? Absolutely. There's. There's a never ending pool of stuff to be worked through in life lately, you know?

 

Perry Monastero 00:01:20  Oh, indeed. Indeed. But, I we'll stay on topic. Okay. Okay. Fair enough. With the non. Fair enough.

 

Jess Birken 00:01:29  Well, okay. So I have a listener question for us obviously. But before we get into that I wanted to just like ask you because I talk to nonprofits all the time who are kind of going through some sort of phase of growth or change, right? And that's often like when people reach out to a lawyers, something's changing. Sometimes it's good, sometimes it's bad. And there's there's often there's talk about strategic planning. Either they're coming to me as a result of something they decided, or we might need some strategic planning going forward because maybe things haven't been going well, but I feel like people don't always mean the same thing when they say strategic planning.

 

Jess Birken 00:02:16  So to you in Perry's brain, what what really is strategic planning for you for nonprofits?

 

Perry Monastero 00:02:25  So much to go through because you make some really great points. The last one that I took away from your leadership is around what do people consider strategic planning? And if you're asking me, well, since you did ask me, I think that there's a part of strategic planning that looks at the environment in which you're in the communities that you're serving, trying to get a sense of what are the best strategies to bring a solution to the universe. And also then it's how do you put that into play? How do you build an action plan? Some organizations look at one versus the other. I like to do planning with organizations where we do both. We're looking at the opportunities and the aspirations combined with what results do we want to get, 2 or 3, etc..

 

Jess Birken 00:03:16  Yes, I love that because I feel like so much of the time, well, so much of the time, especially for smaller organizations, there is no strategic plan.

 

Jess Birken 00:03:25  It's just hopping from one thing to the next. Maybe it's like chasing grant opportunities or putting out fires, but just even taking the time to put together a plan and say, what is it we're trying to accomplish here? Like, what would we like to have seen happen by the end of three years or five years from now? I love that, I love that. Okay. With that in mind. Okay, let's dig into this juicy question. Are you prepared? Ready?

 

Perry Monastero 00:03:56  I'm ready. I'm ready for a juicy question.

 

Jess Birken 00:03:58  Revealed some expertise. Here we go. All right. We had our first ever strategic planning retreat a couple of months ago, led by our executive director and the president, and it was a nightmare and they put it in all caps. Nightmare at the retreat. We basically came up with a bunch of words like diversity and integrity and just sat around debating definitions of words and what our values should be. The literal entire retreat was spent on this. Afterwards, the Ed and the president drafted a new mission statement and emailed it to the board, along with a ton of questions that honestly sounded like a college exercise.

 

Jess Birken 00:04:43  Okay, things like read these five other org mission statements which is most effective? Or describe the tone in three words. I cannot imagine that this is what strategic planning actually is. I would like to help us get back on track and engage the board in a better way. But I don't want to step on toes either. I'm the newest member of the board, and I'm just not sure how other directors are feeling about it all. What do I do? Lily.

 

Perry Monastero 00:05:16  What do you do? It sounds like there's not an external facilitator for this plan. Is that correct?

 

Jess Birken 00:05:22  I clocked that, too. Yes. They say it was led by the Ed and the president. President of the board, I assume.

 

Perry Monastero 00:05:29  Right. Jess, I'm sure you appreciate the principle of board engagement and processes related to high level policy and strategy and goal setting, not the day to day work of the how that staff make things happen. And yet I'm sitting here thinking, this is a pace example of how to disengage your board.

 

Perry Monastero 00:05:51  Yeah. With this effort, I mean, kudos to the president and the executive director working together, because that relationship is indeed so important and yet at the expense of the engagement of the board. I think this is not how I would go about strategic plan, and it's that where's the buy in there? Well, I'm like.

 

Jess Birken 00:06:14  I don't think this even is strategic planning is the thing.

 

Perry Monastero 00:06:18  Oh, that is the question, right? It is not.

 

Jess Birken 00:06:21  Well, I mean, it's based on what you said at the top and my limited experience being on boards. It feels okay. The phrase that came up for me, Perry, was, this could have been an email.

 

Perry Monastero 00:06:36  Do you know what? I had the same millennial, and I'm I'm not even a millennial. And it's the same response.

 

Jess Birken 00:06:42  And it's like, not that this literally could have been an email, but like, right, this didn't need to be the entire board spending a whole retreat working on our core values. I feel like this was something that could have been done in a small group, in a committee and then, like floated up for the board to approve it.

 

Jess Birken 00:07:03  And it's just maybe the sense that I got from this, the person writing in is like they felt like their time was being wasted. Like this was a waste of my time you know. Yeah. And that, that's where I think it's disengaging. Yeah. Big time.

 

Perry Monastero 00:07:20  I think you nailed it. It does feel I sense that they are feeling disenfranchised, disengaged and questioning their relevance on the board because they're they're new. Do they want to. Do they want to raise a stink? How. You know, if I was a new board member and this was my first foray into planning for this organization, I might reconsider my participation on this particular board. On the one hand, on the other hand, it could be an opportunity to put forth a suggestion to bring in an outside person, somebody that knows and understands the mission of the organization so that perhaps the board president and the executive director don't feel the urgency to manage it themselves. That's maybe one way to approach it. I noted that the listener question included a question, or maybe it was embedded.

 

Perry Monastero 00:08:16  Is is discussing the vision something that is done during a strategic plan? And for some organizations, it is because they use their mission values and vision statements. And if they only have two of those three, that's fine, but they use them to guide the prioritization of their goals.

 

Jess Birken 00:08:37  Yes. And sometimes you have to reboot those things like fair. You know that's.

 

Perry Monastero 00:08:41  True. Yes. Yeah. But I don't like how I don't think doing it the way it's described in the, in the question is the best way to get the most rich, Engaging, thoughtful strategic response from board members. Let's try something else. Let's try something else.

 

Jess Birken 00:09:03  Right? Yeah. I mean, I have sat on a board where we did strategic planning and things were not going well for the organization financially, and it was necessary to really like, okay, we need to go back to basics here, and we need to hit the reset button and define who are we here for, what are we here for? Because that's going to guide where we go over the next 3 to 5 years.

 

Jess Birken 00:09:29  And so it could be they don't say that that's what's going on. But it could be that something like that was happening. But I think what's to me what's missing is the part where you go, okay, now that we've decided that. Where are we going? What are we doing? Right. I think this is for a different episode, but I'm also a little curious if this board member felt like some of this core values discussion was performative, and.

 

Perry Monastero 00:10:01  I picked up on that a little bit. Yeah. Yeah.

 

Jess Birken 00:10:04  Because sometimes people like to just pick words that sound good and it may not really be leading anywhere. Right? So I mean, you know, objection calls for speculation, but it feels a little bit like that's in there with the kind of this was a waste of time because I don't even know what this organization's mission is. Right. Right. They didn't share it. And it's not evident in the question. So it's just like a vibes thing. Okay, so for this person right.

 

Jess Birken 00:10:33  How do you how do you knowing their new knowing this situation. And let's assume that they don't want to quit and we don't want them to quit. How do you move this forward.

 

Perry Monastero 00:10:45  Well I started to think an answer to that question a minute ago when I was sharing that it might be useful to talk to the board president about the possibility of bringing in the third party, or maybe just share their own experience participating in the process so far. And sometimes the inquiry can lead to retrospection on the part of a leader. Is this being driven by the executive director who's trying to meet a requirement of a funder, that they have a strategic plan in a short period of time to meet a funding requirement? I've seen that on many occasions.

 

Jess Birken 00:11:23  Yes.

 

Perry Monastero 00:11:24  It forces an organization. Right? Right. And there's, you know, what they could do if that's the situation, is they write up an action plan and it's a roadmap for a year, and it gives them some time to build a real strategy. Like let's, let's, let's try to uncover what is motivating the rush to the the document.

 

Perry Monastero 00:11:45  Maybe that's the motivation. It could also be the the CEO might be feeling, oh my gosh, our strategic plan expired or is about to expire, and they feel the need to rush. you know, there's another way to handle that reaffirming conversations and strategic conversations for their own planning. And it may not necessarily need to involve the board of directors at that time, just building some building some space where they can prepare for a more meaningful strategic planning process. On the other hand. I just want to say one other thing. Sometimes organizations undertake a strategic plan, and they want to do a deep dive when it's not necessarily needed, because the depth of the last dive is still relevant for their moment today. Now, that may not be the case for for so many organizations living in the moment right now, but for others, it may not be necessary to do a super reexamination of the organization's envisioned values. They may be right on track.

 

Jess Birken 00:12:57  Okay, I love that. And what kind of like high level? What I'm hearing is the takeaway of all of that is maybe the way forward for this director is to get curious, right? Rather than going in and saying this process was horrible and I hated it, which is I can tell that they don't want to do that, right? Like they're like, well, I'm new here.

 

Jess Birken 00:13:20  I don't feel comfortable telling people that sucked, but you just raised a whole bunch of things that it may be that we're not doing a great job of like kind of communicating some of the underlying factors. It's just like, hey, board, we're doing this retreat, show up, be here please. Thank you. Maybe getting curious and trying to learn what was behind that. Why why were we doing this retreat and learning? Because if there was a funder who was dangling $1 million grant. But you got to have a strategic three year plan. That's a real good to know, right? Because now that explains why we didn't have a consultant, why the process seemed unhinged, why, you know, all of that. And so before kind of like rushing to judgment, getting curious I think is probably step one is just based on everything you just said. I'm like, oh, we should be asking questions. We should be asking questions and trying to learn more. You know, I'm new here. Can you.

 

Jess Birken 00:14:22  Can you share with me some of the insights around the strategic planning process and the retreat and what led to that? You know, are there past copies of strategic plans that I can look at? You know, I just kind of like to get my bearings, kind of play the dumb card. I think that is probably step one. And I love I really want to call out that idea that you said about sometimes we don't have to go super deep. And so again curiosity is there a previous strategic plan that really was just like so comprehensive that now we're, we're sort of maybe the E.D. and the president are like we need to do something. So I guess we could work on our core values because we're in year seven of implementing all this other stuff that we planned out, and we don't need to kind of do this, but we feel obligated to like, give the board an experience. I mean, who knows? Right. So, I mean, you know, the experience doesn't sound like it was great.

 

Jess Birken 00:15:29  Let's let's be real. But you just you don't know what's motivating it. So I, I and I just love that as a nugget of wisdom, regardless of the circumstance, that you don't have to reinvent the wheel every single time. Yes. Is that feels like for a lot of groups, that's going to be earth shattering wisdom. So I really love that you brought that up. And then just like what? Okay, so the person gets curious, they get some information. How do you think that this what would be the best way for a new director to sort of frame up a conversation around bringing in somebody? Let's assume that they really should have brought in somebody. If you're a new director, how do you how do you pose that?

 

Perry Monastero 00:16:17  It can be a quandary if you're new to board leadership to begin with, because what qualifications and experience matters to one organization might be different than a different organization. And so people who are on boards may not have the the lay of the land of services are great providers to them.

 

Perry Monastero 00:16:40  And sometimes I make references to some sage websites and organizations that provide general counsel, and I'm not referring to legal advice. I'm referring to general assistance to nonprofits. Board members. Some come to mind. Include a board source is one place for word leaders to learn about some standards. And then there's another place. I'm a licensed consultant with the National Standards for Excellence Institute. They have a number of resources for board leaders who are looking to learn more about planning and policymaking. National Council for non-profits is another great source of seasoned advice that you can seek on most any topic, and I think it's useful to hear our own internal search engines to places where there are folks that do this type of work on a regular basis that understand governance, and that could help give confidence to a newer board member. I mean, maybe this person has other experience with other boards. And so these references, they already are familiar with these resources they may be familiar with. I like to say your point about being curious. What I'd like to say is I think that's really important.

 

Perry Monastero 00:18:05  Sometimes best board members I have ever seen are those that ask the great question or a poignant question at the right moment. It needs to be asked, and they're doing so much good service to the organization just by asking the question that helps them understand something, and then it leads other board members to similarly come to the same conclusion that what that person is asking is worthy of further inquiry.

 

Jess Birken 00:18:37  Yes, I love that. Okay, so I feel like we have some really good takeaways here. So going all the way back to the top strategic planning, let's be thinking about what outcomes do we want to see in the world? Right. That seems inherent to any strategic planning conversation and. Absolutely. And then two, when things aren't going well, in your sense as a director, get curious and start asking questions. Maybe not like, you know, the Spanish Inquisition, but like, genuinely be curious.

 

Perry Monastero 00:19:12  Yeah.

 

Jess Birken 00:19:13  Especially if actions seem out of alignment or weird because we, you know, there may be things that you don't know.

 

Jess Birken 00:19:20  And so getting curious is number two. Three is kind of a dogleg. And it's that remember that you don't have to reinvent the wheel every single time you go through strategic planning. I think that's a really big nugget of wisdom there, that it is okay to have a shallower dive every other time or whatever makes sense in your organization's plan. And then I think a big one is just consider bringing in outside expertise who can guide you through a process, right? You wouldn't have your best friend clean your teeth instead of a dentist. That just doesn't make any sense because your best friend is not. They may be great, but they're not an expert in that.

 

Jess Birken 00:20:06  No no no.

 

Perry Monastero 00:20:08  So I'm quite I'm quite horrified by that.

 

Jess Birken 00:20:12  Right. The image I just had in my head.

 

Jess Birken 00:20:14  I'm pretty sure I got a cavity. Can you just like, you know, I got a dremel back here. You can. No, of course not. So consider, if you can afford it, bring in outside expertise because it really makes a huge difference.

 

Jess Birken 00:20:27  And then that last bit, if you need help communicating around these concepts because you're feeling unsure, you're feeling like, what do I know. I'm new here. Check out National Council of Non-profits, check out board source. There are a billion resources out there to help you communicate these best practices to your fellow directors. Did I miss anything in that sum up?

 

Perry Monastero 00:20:50  I think that was outstanding. I think I'm getting a, You get an A, you get 95. I'll stop. Oh!

 

Jess Birken 00:20:59  95. Ooh. He's a stingy grader. Stingy grader. No one hundred's from Perry.

 

Perry Monastero 00:21:04  I've been told I'm stingy, I know.

 

Jess Birken 00:21:07  You leave those four star reviews, aren't you? You're one of those people who leaves, like, a four star review because you just don't do five star reviews.

 

Perry Monastero 00:21:15  Oh, no, I think I think a 95 is a five star.

 

Jess Birken 00:21:19  Okay. All right. This is good. This is very important. We're establishing Perry's rating criteria right now. That's right. Well, folks, if you want to leave a rating, don't make it four stars, because, you know, this podcast is awesome and it deserves five.

 

Jess Birken 00:21:33  So do me a huge favor and go push the five star button right now. Leave a review, subscribe in your podcast app or on YouTube. It really does help other people find the show. Perry. If people want to get in touch with you. Where would they find you?

 

Perry Monastero 00:21:50  They would find me on our website, which is RPMC. There is a form online that folks want to send us a message there.

 

Jess Birken 00:22:02  Amazing. We will put that in the show notes. Perry, thank you so much for being here. I so appreciate you.

 

Perry Monastero 00:22:10  My pleasure. Five stars to you and your entire team. Jess. I feel adequately therapeutic today.

 

Jess Birken 00:22:19  If you have a question or a story to share, or you're in a weird situation where you're a new director and you don't know what to do, get at me. I want to hear from you. Send me a note online at Charity Therapy Show. And as always, thank you for listening.