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October 12, 2022

How should you rethink your approach to strategic planning?

Craig Shelley

Farra Trompeter, co-director, and Craig Shelley, partner and chief growth officer at Orr Group discuss different approaches to develop and apply your organization’s strategic plan.


Farra Trompeter: Welcome to the Smart Communications Podcast. This is Farra Trompeter, co-director and member-owner at Big Duck. So, for many years, being entrenched in the nonprofit world of communications and fundraising, I had been thinking a lot about strategic planning, as I’m sure you all have. And a few years ago, our friends and client at Youth Collaboratory introduced me to a process called the Real-Time Strategic Planning Framework, which I was very intrigued by, and eventually got to co-facilitate a strategic planning session using this model at NTEN when I was the board chair. And the model comes from the folks at La Piana. David La Piana and Melissa Mendes Campos wrote a book a few years ago called The Nonprofit Strategy Revolution, Real-Time Strategic Planning in a Rapid-Response World. So I’m going to start off and mention, it’s a great book to read if you’re trying to rethink your approach to strategic planning, but if you’re not ready to read the book or you have and you want some new approaches, you’ve come to the right podcast.

Farra Trompeter: Today, we’re going to talk about, “How should you rethink your approach to strategic planning?” I’m delighted to be joined by Craig Shelley, who uses he/him pronouns. Craig is Partner and Chief Growth Officer at Orr Group, which provides full-service support to nonprofits in six key areas: strategy, fundraising campaigns, talent, planned giving, and leadership. Craig brings a change management and entrepreneurial approach to strategy, organizational development, fundraising, and board optimization. Craig is a certified fundraising executive, CFRE, and frequently speaks at conferences and publishes articles on leadership and philanthropy. He’s also the president-elect of the board of the Association of Fundraising Professionals (AFP) New York City Chapter, which is actually how we met. And you may recognize his name because Craig was on the podcast a few years ago, way back in Episode 24, exploring how you can communicate better with the board. Craig, welcome back to the show.

Craig Shelley: Great to be here, Farra. Thank you.

Farra Trompeter: All right, so, Craig, back in December 2020, you wrote a blog post for the Orr Group titled “The Urgency of Now: We Need a New Approach to Planning.” Let’s start there. What are the problems that you see with the current approaches to most nonprofits’ take on strategic planning?

Craig Shelley: The basic premise, if you think about it, right, like the whole world is changing and it’s changing faster than ever. Yet by and large, you know, nonprofits, they’re doing strategic planning, if they do it at all, through the same slow, laborious process they’ve always used, right? I mean, that just doesn’t seem sufficient to me anymore. That first year, the pandemic really drove that home for me. I realized every assumption I made in February of 2020, I’d thrown out the window and dramatically changed strategies by May of 2020. So, how is any organization operating with a set of strategies that came up with 10 years ago, five years ago?

Farra Trompeter: Yeah, if you’ve done your strategic plan at all. The other thing I find, a lot of organizations or staff that I talk to, especially when I do workshops out and about around the country, folks don’t even know where their organization’s strategic plan is. “Where is it? Who has it? How do I even access it?” Sometimes if an organization has a strategic plan, it’s only really been crafted and seen by the board and the staff or the senior staff and not everyone on staff. And to your point, if they’ve done the strategic plan, it may be outdated the second they’ve hit finish. So, let’s talk about it. What are some new or different approaches that you’ve seen actually work when it comes to really rethinking the approach to strategic planning?

Craig Shelley: I think there’s a few things just sort of fundamentally that you can do. The first is really to go long on vision and short on specifics, right? So, like, the change you want to make in the world, I mean, that is what it is and that’s your north star, to use cliche, right? Like, that doesn’t change. But you have to understand that the circumstances you’re operating it in, they can change quickly, they can change unexpectedly. So don’t plan yourself down to what am I doing in the third week of April three years from now, right? Like, think about, “All right, this is our vision and it’s big, but the specifics that’s going to stay a little cloudy,” and you’ll kind of figure that out as you go.

Craig Shelley: I think the next thing I would say is, “Your vision needs to be bigger.” I promise you, the world needs you to be audacious. Your stakeholders, your donors, they want you to be audacious. You know, incremental change, no one’s here for that anymore. You know, we’re not living in a time where that’s good enough. It’s kind of “Go big or go home” or maybe “Go big or don’t bother me,” right? So, I mean, I think go big with your vision, and don’t apologize for that.

Craig Shelley: You’ve also got to be flexible. These last couple years we’ve been living in basically simultaneous crisis and the organizations and leaders that have succeeded are the ones that have been flexible. You know, I know myself personally, I’ve been willing to make decisions and then remake them again the next day and remake them again the day after that. I’ve never hesitated to make a decision, and I don’t think good leaders do hesitate, but right now they’re willing to kind of remake and change. You know, the facts are going to change. You have to be willing to change with them. And that’s, I think, also why my last point would be, like, strategic planning is an ongoing function, right? This is no longer, like, we’re going to bring together a group of people for three weeks or a Saturday afternoon and, “Voila, we have a strategic plan.” You need to have a group and a mechanism and a process that’s in place constantly evolving your strategies and the tactics that are going to help you achieve those strategies.

Farra Trompeter: Great, so I’m hearing go long, be bold, be flexible, and make it ongoing. Keep it alive. And that’s, again, some of the things that I love about that Real-Time Strategic Planning Framework, and I know there’s other frameworks that you and your colleagues have actually experimented with. In fact, I know another blog on your site that I appreciated by your colleagues, Regina Cialone and Ryan Grosso wrote all about situational strategic planning. So maybe you can talk about what is situational strategic planning, and how can organizations really incorporate that.

Craig Shelley: In many ways, that’s the process by which you’re flexible and by which you live in sort of a constant state of strategic planning that we were just talking about. It can be reassessing your framework regularly. You know, on some schedule you say, “Once a year we’re going to get together and look at our strategic framework,” or as facts change, you can kind of do that. It can be doing sort of a specific assessment or a kind of fast-break strategic plan to react to circumstances – you’re in a PR crisis, economic climate changes – where you can bring people together and sort of reassess that. It can just be facilitating conversations with your leadership about, you know, what is their vision for the future. You know, periodically I think that evolves. Again, the world is changing, let’s have these conversations. I think what Regina and Ryan were really suggesting, and which I very much buy into, is that doing things like this can provide clarity to all of your stakeholders about, “Where are we going, why are we going there, and how are we going to get there?”

Farra Trompeter: Great. Now, let’s say a nonprofit actually is planning in all the ways that you’re talking about, embracing a big vision while also providing more room to adapt and be flexible and keep it ongoing. Are there any examples you can share where you’ve actually seen organizations do this in practice? What does it really look like?

Craig Shelley: Yeah, I think one of the most exciting ones I’ve seen that really does it at scale and a real big way is an organization called Co-Impact. They’re a donor collaborative. They’re focused on systems change and gender equity in the Global South. They’re a pretty young organization, they were incubated at Rockefeller Foundation. Maybe they’ve been operating, plus or minus, on their own five years. Their founder, Olivia Leland, was the executive director of The Giving Pledge. Basically, their original premise was, “There’s a better way to do philanthropy,” and in doing better, it was going to require a longer view because it takes longer to actually change things, as I think we all know, or even if we don’t always want to admit it. And that to move the, like, kind of needle on really big issues in the world, it wasn’t going to do to just kind of do the one spot sort of solutions that we’ve always funded. So that’s a huge vision.

Craig Shelley: They started singularly saying, you know, systems change was where they wanted to focus. They raised about $500 million for that purpose. And then as they, fundamentally, they wanted to invest in organizations that were on the ground, right? Like, that they didn’t have the answers sitting in London or sitting in New York. You needed to go to the communities to find the answers. So, as they did that and they put that first $500 million to work, they started to recognize that, really, gender was sort of the thing, right? Like, if they could unlock gender equity, that was a requirement to sort of do the other work they were already trying to do. So they didn’t, like, shy away from that. They then just launched a billion-dollar fund to raise money for that and said, “Okay, we’ll keep doing the work we’re doing, we’ll also now try and do this other solution,” and they’re about halfway through that goal now.

Craig Shelley: And as they listen to grant recipients, they’re locally led and they’re sort of letting that drive them, but then they’re also doing the same thing with their donors, right? They had a sort of theory of, “This is how billionaires across the world wanted to work together on philanthropy,” and shockingly they’re finding that maybe some of those assumptions weren’t right, right? So they’re constantly evolving, they question their assumptions, they do what we’ve described as situational strategic planning constantly, they’re always pulling things back and pulling things apart and putting them back together, and it’s been amazing to kind of be up close to that. And yeah, I think they’re, on a global scale, doing exactly what we’re talking about.

Craig Shelley: A little smaller closer to home, I’d also say, Orr Group. We’ve doubled in size over the last few years, and that’s essentially by taking these approaches. It really crystallized for us, when the pandemic hit, that there was a unique value that we were able to bring into the sector and we could facilitate the business of philanthropy in a different way. But we had a question that involved what we were doing, right? Like, I think, honestly, we had a bit of a ceiling on what we thought we could do. Like, “Hey, this was our lane, this is where we should be,” really allowed us to sort of, like, open up our vision, sort of recognized it needed to be bigger, right? So, we went sort of “long on vision, short on specifics, big on what we wanted to accomplish,” and then just sort of thought of, “What are the things we really needed to commit to?” So we committed to talent, we committed to the things that we knew were the strategies that were going to unlock us and allow us to do this, and if we’d stuck with the strategy that, you know, we made through a traditional means that said, “All right, what’s a five-year plan?” we’d be 25% smaller than we are today based on what the plan we set out in 2019 is, right? So, we saw the circumstances on the ground and we changed and evolved as we went, and that’s what we really think organizations need to do.

Farra Trompeter: You’re reminding me also of the whole Jim Collins, “Big Hairy Audacious Goal.” That may or may not be something you’re a fan of, but it sounds like you’re really pushing people to go further. Like, as soon as you think you’ve imagined what you might be able to accomplish with your organization, just keep pushing yourself and say, “What would it look like if you did more? Were able to accomplish more?” And just keep it going and going and going?

Craig Shelley: Yeah, I love all of his books, but I also will tell you that I had a boss who was obsessed with him so now I cannot say BHAG with a straight face because I spent, like, years listening all about it. But yeah, basically that’s what we’re talking about.

Farra Trompeter: Right. There’s always, you know, choice and pains with all of this. One other thing you mentioned that I just want to maybe, maybe it comes back to adding to your suggestions earlier, is also I would add, perhaps, be responsive. One of the things I appreciated in your comment about Co-Impact and that example was the piece where you noted how they were really listening to their grant recipients and locally-led organizations and going to the community to say, “Hey, what do you need from us? Not just what do we think the world needs from us or the state or the community, wherever we’re operating in, but what does the community need for us?,” and making sure that’s part of your strategic planning process, which I don’t always see. We often come in and get strategic planning processes. Sometimes we’re part of them, particularly, when mission, vision, values are involved, but I think that piece of taking a step and really examining what’s needed and talking to the people who are ultimately the recipients of your services is also critical. And I appreciate that it was part of the Co-Impact example.

Craig Shelley: Yeah, I think if at this point you’re getting up in the morning and, like, putting on a cape and thinking you’re going to go save the world, that’s not the way the world works anymore. Again, whether that’s listening to the communities you serve, whether that’s listening to your employees, there is not a world in which, at least in the world that I operate and I live in, right, there’s not a world in which you get to just dictate “this is what we’re doing” anymore. It’s very much, if you’re not doing all of this through collaboration and through listening, you’re 100% going to fall right on your face. Because if you’re, like, at the front of the herd and “follow me boys,” that doesn’t work anymore. No one’s going to follow you, you’ll be by yourself pretty quick.

Farra Trompeter: Yeah, a hundred percent. I’m wondering if you can share some practical tips for nonprofits who might be in the midst of a traditional strategic planning process. What can they do differently? How can they challenge those tried and true approaches? Or if someone is listening and they want to bring some new ideas to their organization or really get other folks to rethink it, what might they do?

Craig Shelley: The first thing I would do is I’d throw out this sort of standard five-year plan. Like, that’s ridiculous. You know, go out no more than three years. Even that’s too long, but I feel that’s kind of a compromise for me. It’s silly to think you know what you’re going to be doing longer than that. Challenge yourself to think bigger. Again, this whole idea, “this is not a time to be timid in this world.” And then really lean into the fact that this is going to be an ongoing forever process, right? Like, don’t start with the, “We’re starting today and we want to be finished by the end of the first quarter.” You know, you could say, “By the end of the first quarter we want to have a plan for the next three years. And then at the beginning of the second quarter, we immediately want to already be re-evaluating that plan because everything is changing,” right? So, like, you’ve got to accept that it’s ongoing, and then you’ve got to get comfortable with the idea of, like, planning and action need to be happening in parallel, right? Cause you do see organizations that are like, “Well we have to stop to do the strategic plan so how would we plan forever?” Well, news alert, the world isn’t stopping so you can’t stop your work. You have to plan simultaneously to doing.

Farra Trompeter: You’re making me also think about approaches to project management, which for many years have been what’s called “waterfall.” Once one step happens, then the next step happens, and the next step. And I think in the world of website development and other projects, we’ve seen them embrace a project management style called “agile,” which I can’t say I’m an expert on at all, but I’ve definitely heard about and read about, which is much more ongoing and building and constantly pivoting. So, you’re setting off light bulbs for me. Craig, I have a bonus question for you, which is that sometimes I see organizations say “strategic framework,” other times I see them say “strategic plan.” How do you define those two differently or as the same?

Craig Shelley: Yeah, I think the framework is where you start, right? So, the framework is, like, kind of the big, “What are the main goals? What are the main strategies? How are we going to do it?” And then your strategic plan is where you start to get more specific, you start to define how you’re going to measure things, you start to put timelines in place, you get a little bit into tactics, again, recognizing we’re going to be super flexible on tactics. But the framework is like the “pick up the one page that sort of has a bunch of boxes and grids and says, okay, this is how it all sort of fits together,” and I like that only in that, like, if you can’t explain it in that way, like, if you can’t simplify it to that point, you’re probably never going to explain it in a way that anyone is going to be able to follow. If you can get that, then you can get into all the stuff that maybe most people are never going to worry about but you need, but you need to start with that framework.

Farra Trompeter: Appreciate that. Well, for those of you who’d like to learn more about Orr Group go to, that’s You can also find them in all the major social media platforms, Facebook, Instagram, LinkedIn, and Twitter. And if you want to connect with Craig, you can find Craig on LinkedIn or on Twitter @craigshelley, C-R-A-I-G-S-H-E-L-L-E-Y. Craig, thanks again for joining us.

Craig Shelley: Great to be here. I appreciate it, Farra. Thank you.