
Succession planning gets treated like a worst-case scenario when it should be a regular part of nonprofit leadership. In this episode, Glennda and I get candid about our own transitions—and what we wish we’d known sooner.
Loading summary
Joan Gary
There's never a bad time to talk about succession planning, so why the hell do we never talk about it? And why does it always have to involve someone being hit by a bus? One of our areas of coaching expertise is succession planning and leadership transitions. Business is brisk. The average tenure of a nonprofit executive director is five years. So that means that your organization has just navigated one or there's one just around the bend. In that context alone, this should be a real and ongoing conversation in your organization.
Glenda
It also happens that both Joan and I have had our own experience in this arena in the past year, and we learned a lot lessons that we feel could be quite valuable to each of you. So here's what we did. We each made a list based on the title what Do Nonprofits not get about Succession Planning? And we didn't share those lists with each other, but we are going to share them with all of you now so you can benefit from our mistakes and learnings. Let's go. Welcome to Nonprofits Are Messy with Joan, Gary and experts. This podcast is your go to space for insights, advice, and inspiration, designed to help nonprofit leaders overcome challenges and drive impact. Whether you're navigating small beginnings or leading a larger organization, we're here to support you every step of the way. Together with Joan and a diverse group of expert guests, we tackle the big questions nonprofit leaders face and offer actionable advice to fuel your leadership journey. A special thank you to donorperfect for sponsoring this episode and supporting nonprofits that we love. Now, let's jump in.
Joan Gary
So I think you should go first. Glenda, you were the successful executive director for the New York LGBT center for 14 years. You announced to your board that you were leaving nine months before December 31, when your contract expired. You had, as I understand it, made it mighty clear to board leadership, sort of more on the down low, that you did not plan to renew your contract. So what are some of the things you learned right away that your organization just really wasn't getting about all this?
Glenda
So, to be honest and fair, I think there were things I didn't get. I thought I knew and I didn't, and I learned along the way. And then there were things that they didn't get, and then things we all didn't get. So I would say, for me, I wasn't really able to grasp how emotional it would be to leave after 14 years. And for you.
Joan Gary
For you.
Glenda
For me. For me.
Joan Gary
Yeah.
Glenda
Joan, you've known me a long time, and I can cry on occasion. Not often, but on occasion. And So I really needed to be emotionally prepared. And the way that I did that was two things. One, I got a coach myself highly recommend that. It really kept me very rational and very focused on what was at hand and what was coming up. And then second, I would prep for every single speech because sometimes the emotion catches you and you're going to get up in front of people in different ways for the last time. You don't not want to have written down what you really want to make sure you say whether it's through tears or not. So that's the first thing that I learned. Do you want to volley back and forth or you want me to.
Joan Gary
I was going to ask. I feel like I deal with a lot of clients who think it's going to be easier that think that getting ready, that my organization's in good shape, that everything's going to be just fine. Not when I'm pitching them on. You need a coach to help you through this necessarily. But I do feel like there's a certain cluelessness on the part of some executive directors about what all this looks like. And we'll talk a little bit more about the pre announcement stuff, but I don't know if you have a thought about that.
Glenda
I think that's true when executive directors. I'll say and because that's the seat I was sitting in when I went through this transition. I did feel like every. Like things were fine. Like the board. I had been working for years to get the staff, the board, the donors, the community in a place that would be ready for its first fill in the blank executive director, its first trans executive director, its first leader of color executive director. And so I had been thinking about all of that and thought I was in a really good place. The thing I didn't fully grasp was it was in a really good place in part because I was still there as the linchpin. That's the piece of bing, bing, bing.
Joan Gary
Bing, bing, bing, bing, bing. Yes.
Glenda
Like take, take me out of the equation because that's what this is and it doesn't work quite so well. So you've really, you've really got to.
Joan Gary
Think about that because what has. Because what's really happened. What's really happened is that the moment you have announced that you are leaving, the person that everyone relies on to lead, to do all the things to drive is leaving.
Glenda
Yeah.
Joan Gary
Which creates an emotional kind of component and it also creates a leadership void in some ways. Right. Because you can't drive that process in the way that you drive other processes. Or had for the last 14 years.
Glenda
Yeah. Yeah, that's absolutely true. And I think that's why it was so helpful. I ended up working with Ray Carey from Carry Forward, Consultant, consulting at C. She was amazing and really helped me. The time goes so quickly. You know what they say about your wedding. They're like, you spend months and months and months and months planning it, and then it's over. And in some ways, it felt like transitioning. Even though I was there for months and months and months and months, months. It just went so quickly. And being really prepared for all of those things, I needed to be emotionally aware, professionally aware, and I needed to understand. And the board did, too. The boundaries were shift. You know, I was the person that I was completely the communication between myself and the board, as I should be between the staff and the board as the executive director. And I could not do that towards the end, as they were really executing the search and getting further and further along, I was completely out of that.
Joan Gary
Yeah. I was coaching someone who said, I am really struggling with not knowing things.
Glenda
I felt that I wanted. I was tempted.
Joan Gary
Yeah. I am accustomed to knowing all the things.
Glenda
Yeah. Yeah.
Joan Gary
And so I think that that's interesting. Tell me about. I have a theory, and you can back with me.
Glenda
Yeah.
Joan Gary
I have a theory that the moment you say, I am leaving, your power diminishes. And you've actually handed the baton of leadership to your board chair. And that the board has a new, powerful responsibility that they are often ill equipped for because they relied so heavily on a terrific edge. But that there's this power dynamic, and that boards really are not prepared. They're not ready. They don't get it. But I remember actually, at my synagogue, and we had a rabbi for a long, long time. I remember there being a service at the synagogue where my rabbis announced that he was leaving. We all knew he was leaving, and that we had a rock star board chair. And when he got up to speak and there was this comfort in the room that this is gonna be okay, because Kenny understands that he has the power and the responsibility to replace our rabbi with a rock star. And so my philosophy is that the power shifts from the staff, from the ed to the board in that moment.
Glenda
I agree that the power does shift. I think to have a smooth transition. It doesn't shift like a light switch. It's not like in that moment, you tell. You know, I told my board chair, I'm leaving, and I handed him the baton and I walked out of the room. It's like the Way, thank God it didn't work that way. I mean, the way it really worked was like. And you're. You're sort of alluding to this with the synagogue example also. Like, we knew he was leaving. Like, I told my board chair, I told the executive committee, I told the full board, I told my executive staff, like, and then we together came up with a plan for how is this going to work. The board leadership definitely had more power from that moment going forward because they had to run this process without me, the process of finding a new me, a new CEO. I have seen organizations where the board says, oh, you're leaving? Okay, we got it from here. And essentially shuts the executive director out, does not ask them things, starts running the organization directly, and it's a freaking mess. Please don't do it. Don't do it. There's no need to do it that way. Like, you have trusted this person to run the organization. You can still trust them to help figure out what this transition should be. And I. I've seen situations where EDs have acted poorly in that. So that happens, too, you know, where an ED might say, I'm leaving, and then they're out, in which case the board has to come in and do that. But I think in most cases, the ED is willing to, like, they want. I desperately wanted this to go well. I really did not. Even though I didn't have all the power, I. I really, with all my heart, like, wanted this to go as well as it possibly could for the organization.
Joan Gary
Yep. I think that's an interesting segue, because I think that one of the things that nonprofit leaders really don't get about succession planning is that it starts so far in advance of the moment you say, I'm leaving. And your comment actually about wanting desperately for it to go well, one of the things that I often say to my clients when they're kind of like two years out from saying, I'm going to retire or this isn't the gig I want to retire from, I'll say, okay, I want you to visualize your best friend on Earth, and I want you to imagine that that person is going to succeed you. Okay, good one. So your job over the next two years is to ensure that your best friend doesn't call six months later and say, are you kidding me right now? You left me to clean. What did you do? You didn't tell me that the person who's in charge of X is a problem. Right. And so I consider it. It's almost like after my wife's Television career. She bought and fixed houses for a while and did a lot of staging. Right. Is getting your house ready to sell that there's some nice, interesting analogy there, but that you want the person who succeeds you to be successful. And if you leave an organization, let's say, oh, you know, it wasn't problematic for me to have 11 direct reports. I don't know why that would be a problem. I don't know why that would be a problem for a new person. Like, no, a new person will not. The best candidates will take one look at your org chart and say, are you kidding me right now? Right. And so that was a long winded way of saying succession planning is a multi year process.
Glenda
Yes.
Joan Gary
And what gets in the way? What gets in the way of boards and staffs having that conversation two or three years ahead? What do you think, Glenda?
Glenda
I wish I could make a smart ass remark, but I can't think quickly enough. So I will just say the answer, which is, I think it's two things, actually. I think this is a topic that people are scared of. Everyone works in non profit. Yeah.
Joan Gary
Fear.
Glenda
Everyone who works in nonprofit, either board or staff has seen a leadership transition go badly. And so we are all kind of scarred and gun shy and use whatever analogies you want around this very thing. Because when it goes poorly, we usually see it and it's terrible and we feel bad for the organization and all the people. And we don't unfortunately see a ton of examples where it goes really well because those don't make headlines, you know, so that's right.
Joan Gary
And isn't that the irony? And then I'll let you go to number two, four, five, whatever numbers order you want.
Glenda
Just two. Just two.
Joan Gary
Just two. They don't go well because people don't talk about them. Yes. Because they don't prepare for them.
Glenda
Right. I believe they call that a vicious cycle. Yeah.
Joan Gary
Yeah, right.
Glenda
You're totally right.
Joan Gary
Number two.
Glenda
Now, number two, I think whenever we say. I think sometimes in nonprofits we use complicated words to talk about very simple things. And I think when we say succession planning, people think you gotta have a retreat, you gotta hire someone to facilitate it. You have to come up with a, you know, dozen or so page opus to plan how this is gonna happen. It does not have to be like that. It can be very simple. Succession means who comes next, period. So you have your board chair, who comes next. You have your treasurer, who comes next. You have your executive director, who comes next. Having the conversation doesn't mean it's Happening, it just means you're having a conversation to figure out a potential plan if it does happen one year, two years, three, four, five down the road. So I think the fear and also the way it's built up in people's minds that it needs to be this arduous, painful, long process. And it really doesn't. These are conversations we should be having all the time.
Joan Gary
So I worked with a client and the executive director has not identified when they will leave the organization. But the board chair, recognizing that the executive director is a dominant force in their organization, wanted to build an organization wide succession plan. And we sort of actually reframed it as organizational hygiene. Yeah, right. It's like, okay, so if you're going to talk about who's going to replace me as the executive director, I suppose we should say, what's the development plan for the people in the program department to make sure that there might be a viable internal candidate to replace your program director if your program director leaves or gets poached or. Right. So that it becomes something that isn't just about one person, it becomes about the organization. One thing I think we do, I think we totally suck at is you have a really good board chair. But do we have a really good succession plan for who's next? Or do we just keep our fingers crossed that the person we kind of want is in the bathroom when there's a vote?
Glenda
Are we still doing it that way? Whoever's not there get voluntold?
Joan Gary
No, I think possibly. Well, and it actually, it's actually worth spending a minute to say, and you tell me. Cause you've seen a lot, you've seen a lot over these 14 years. I believe that prospective executive director candidates are much more savvy about what they're looking for in an organization. So once upon a time it was whoever was in the bathroom during the vote. But now I think prospects know that a great board chair can make or break their own ability to succeed. I don't know if you, if you have seen or heard people talk about that.
Glenda
I agree. And I would. Let me, let me offer a strong caution for organizations out there who have not handled transitions. Well, I'm not going to name names, but I think we could all, I imagine we could all think of at least one organization who has been through at least one poor transition. The executive director was summarily fired and everyone was traumatized. The board decided one day, like, we're just going to take this over other candidates, executive director candidates, board candidates, staff candidates, see that and it doesn't help with recruiting. It sends a really. In fact, it's a big barrier. I have talked to a number of executive directors who have said, God, I. That I love the job over there of this, but I can't imagine working with that board. Do you see what they did to so and so or. Yeah, you know, I can't imagine joining the board of that. Do you see what the. The executive director runs that show the board has no power. You know, it really. These things do get out into the community and they do have an impact. So I think it's in all of our best interest board, staff, the entire nonprofit sector to get better at this. It really would be better for continuity, talent, retention, all of those things. It has an impact when it's handled poorly.
Joan Gary
Right. And so I would say that in the context of what we just talked about, that one thing that nonprofit leaders, board and staff really don't understand about succession planning is that doing this well, this having great organizations, organizational hygiene, having a transition playbook, that what they don't get is that the organization actually has to market itself to recruit a rock star.
Glenda
Yes.
Joan Gary
They don't just magically appear, they aren't. It isn't just the job of the search firm that they have to. That the organization has to show up as an organization that that person says, I want. I love that mission. I think that board chair is someone I could partner with. Right. I met the leadership team and I think the structure feels about right to me. Right. That makes me as a rock star, say, yeah, I'm interested in this job in a three dimensional way. Yeah. Agree. So we're gonna take a short break and when we come back, we're gonna talk about what this kind of the idea of what a transition playbook might look like and how we might be able to reframe away from this. Once a year, let's go into an executive session and we'll talk about what happens when Joan or Glenda get hit by buses and they think they have done succession planning. And we'll talk a little bit about what does it look like a couple of years ahead? I mean, because you started to think about it a couple of years ahead. What are some of the things and the choices that people can make to be ready?
Glenda
Yeah.
Joan Gary
Are you a staff or board member of a small to mid sized nonprofit? Now you might feel alone, but trust me, you are not. I built the nonprofit leadership lab for the millions who are just like you. You'll find time saving resources when your pants are on fire. Opportunities to uplevel your skills and a warm, nurturing, private community of what we call superheroes. Thousands of board and staff leaders call the Lab home. And we'd love for you to join us. Learn more@nonprofitleadershiplab.com podcast.
Glenda
So we're back and there's so much to talk about with this topic. It's so rich. I really just want to highlight from the first part Joan's suggestion of instead of calling this succession planning, calling it organizational hygiene. My suggestion is instead of saying what if so and so got hit by a bus, could we say what if so and so won the lottery and they just want to go sit on an island somewhere? Like we make it positive. You know, it's always such a negative thing and I think that contributes to the fear. So maybe there's something we could do there. But we're talking about this. Joan, you actually went through a leadership transition this year. You had founded, you have founded the nonprofit Leadership Lab and Joan Gary Consulting, and you were doing that with your business partner, Scott Paley. And this last year you brought me in as the lab's first CEO, but I did that. That started earlier. So what, what are some of the things that you did? And then I'm happy to share some of the things I did ahead of time to prepare for that kind of succession transition.
Joan Gary
Yeah. So we also worked with someone outside and we worked with someone who has been working with us on creating a more culturally intelligent organization and enabling us to lead a community of board and staff leaders from English speaking countries around the world who are diverse and who feel a real sense of belonging. And that was also something I was like, oh, so we have to do work first. Right? Okay, so I got that, I got past that. And I think we did some really, we really did some good work in doing that. And we used, we hired originally the Rabin group out of D.C. and our lead was a gentleman named Dr. Pablo Ataola. And he ultimately struck out on his own and has continued as a coach for us. And he gets us and objectively and he coached us and said, what's the profile of the person you're looking for? Right. What's the ideal candidate look like? Not like a job description, but what are the hard skills, the soft skills. Right. To work with in this kind of a startup company where there are a couple of owners like some pretty good landmines ahead. And I really feel like he knew and helped us to clarify the profile of the person that we were looking for. Now it just so happened I Didn't have to look further than my own backyard for a particularly good candidate that fit those qualifications. But that conversation started with way back and it was before there was a job description even written. Right. And so that was. It was also a new position. And there needed to be a lot of trust because it's a very mission driven for profit enterprise. And as a founder, having trust in that person felt really like non negotiable.
Glenda
Totally. Totally. That makes so much sense. And that I can. I can relate to that. I can remember going into the pandemic in 2020 and I didn't actually leave until the end of 2023. In 2019, looking at our board and seeing that we did not have any nonprofit experience on our board, i00 and it just so happened we were so lucky. There was a donor to the organization who I was building a relationship with. He was the chief operating officer and financial officer at a private school in the city. So he didn't have fundraising responsibilities. He knew nonprofits in and out and he loved the center. And so he was someone we brought onto our board. And it was immediately like, oh, there's another. There's a person on the board that now understands the sector that the center works in. And it was so great. And he wound up being the board chair and being the person to lead the search for the new executive director. And those wheels were put in motion years before I left. So that's maybe a good example of like, doesn't have to be a big complicated thing. It's just looking around and saying what's missing. You know, there were more complicated things like, okay, this works because, you know, at one time in the organization's history, the board was majority white and I'm white. And I realized this is not going to fly if a leader of color wants to come in and run this organization. And so we went through a very large multi pronged racial equity transformation that started with staff leadership and then spread to entire staff community. And then the board. And the board started on that journey and went through that as well. That was not an easy transition, but one that was well worth it. And now the center has its first black woman executive director.
Joan Gary
Moral in the story you just told me is that we had to go back several years for you to look at the composition of your board. You had to look several years out to say we're going to need to go on a racial equity journey in order to be marketable to a diverse pool of prospects and to set anyone up for success in the job. And that's what I, I spoke at Stanford two years ago. I like to say it's probably the only way I would have gotten into Stanford. And they asked me to talk about this very topic. And I, I said maybe we reframe it as a transition playbook. That is something that gets updated regularly. And you hit on one of them, which is the board composition matrix and education. Right. Is what are the gap skills on your board? What are the leadership pipeline if you're going to leave in three years. Right. And maybe you don't know, but pretend it's three, pretend it's two. Right? Right. So you hit on one of them. I clowned around about organizational structure. Right.
Glenda
Yeah.
Joan Gary
Is the structure set up to recruit somebody? Terrific. If you have, if you've gotten accustomed to having 11 direct reports, I don't know why you have and I wouldn't recommend it. But I can tell you that it is not a big selling point to me if I am your leading candidate. So org structure.
Glenda
Yep.
Joan Gary
Tell me about. So you're three years out and I, you know, you were pretty clear that when you signed your last contract, it was going to be your last contract and it was going to be a couple of years. How did you approach program priorities? Right. So sort of like what did you want to. Because that's another piece of the transition playbook. Things that you were uniquely suited to move downfield or things that maybe the organization wanted to get off the ground that you were uniquely suited to jumpstart. How did you think about the work of the center and its impact in that final three years of your contract? Because I think that's an important piece of the puzzle as well.
Glenda
It is because the reality is an existing leader has already built the relationships with donors and foundations and corporations to have that, that foundation of trust to be able to ask for funding for extraordinary things or new things or whatever, and a new executive director coming in. It takes time to build that. They will have relationships that you don't have, but they also don't have the history that you do have. So it was about thinking, what are the relationships I have and how do I want to make sure to leverage them to benefit the organization as much as possible before I leave. And so for us, we had a state certified substance abuse outpatient treatment program that was really successful and really well respected. Usually the component to that, the other partner is a mental health outpatient treatment facility. And we did not have that. And so we looked around and said, is this needed? I mean, you remember the pandemic yes. Hell, yes. Absolutely. More than needed. Can we do it? How will we raise the money? How will we actually do this? And so we started on that journey, applying for the application to become an Official Article 31 in New York State, a mental health clinic, and started raising the money and raised the majority of the money for that. That before I left and then got the official. You know, it took over a year to get the approval for the actual license. Things don't move quickly sometimes in government, but putting those wheels in motion while I was still there, firmly there and running the organization, I think was critical to getting something really exciting and really needed off the ground before the new person even stepped in the door.
Joan Gary
Right, because you were uniquely qualified to do that.
Glenda
Exactly, exactly. And it feels really good that I was able to, you know, they reached out. Hey, we got the approval today. It was after I left. Everything had been set up for months, but I still celebrated, you know, in my house, that victory. I think that it brings up another point that you and I often talk about, Joan, when we talk about succession and transition, which is. And I touched on it briefly, those. Those key relationships, like, those key relationships like there I have seen organizations, and I think we were probably like this at one point, where they suddenly realize, oh, shit, the CEO has all the key relationships. The board doesn't have any. That it all sits with one person. Sometimes that's board chair, sometimes that's CEO. So how do you. How have you helped clients or how have you seen organizations go through another key component of that transition playbook, I think, which is institutionalizing those relationships?
Joan Gary
I bet you heard this more than a few times in 14 years. Because I. I know. I heard it when I was at Glad, which is, well, I'm giving this money to GLAAD because you're @ the helm.
Glenda
Yes, many times.
Joan Gary
Right. And first of all, it is not flattering. I never found that flattering. I always found that scary.
Glenda
Yes.
Joan Gary
And I. And I always found that it was very, very, very important to reframe that. Right. And to be able to say, this is a team sport, what we got going on at the center, or glaad. And so I think that's a really important thing to think about. I also think three years out, you've got to start putting other people in front of your donors. Right. You've got to start impressing the hell out of them of the people you hired. Of the people. Right. And it could be program people, it could be the development people, it could be some rock star board member Right. But what you're trying to do is not necessarily reattach the relationship to someone else. You're trying to actually attach the relationship more fully to the organization. So a person, the funder, the donor can say, wow, this whole ship is really set up for sustainability and impact, and that's great. And that's what that is what will, at the end of the day, keep a donor from saying, oh, there's going.
Glenda
To be a transition.
Joan Gary
You know, I'd like to wait and see. You can actually cut off the wait and see. If three years ahead of time, you're starting to market the great work of your other staff members, not just development. It's not like you're just switching, you know, to your major gifts officer, to your program. People invite them, make sure that they're part of an eco. They see the whole ecosystem.
Glenda
Yeah.
Joan Gary
So that when you're. When. When you're announcing and you're talking to them and they're saying, oh, my gosh. Well, I. I really did originally give to Glenda, but over the last couple of years, I've really gotten the opportunity to see the whole place in action in a different way. And I'm just impressed with what has been built and I want to be part of its sustainability 100%.
Glenda
I mean, I said when I talked to my board about leaving, I know this is worrisome and that this will have an impact, but I assure you, the team, the executive team that I have built is really strong. You all think it's all me. It's not. It's not like this team does so much, and that is so important. That was the. I think that was a big key to the success of the transition I went through. Through was having really strong staff and board leads.
Joan Gary
The other thing, and curious about your thoughts about this, about talk about your executive team and the people who work for them. Because the transitions do often. That's another thing that worries boards. Oh, my gosh. Glenda's going. Will so and so go, too. Right. They're so tight. They're so close. Right. Is that relationship more a lot about Glenda? Right. And part of organizational hygiene and the transition playbook is looking at that department.
Glenda
Yeah.
Joan Gary
Right underneath that executive team member to sort of. To kind of assess what's happening there. And I wondered if you had experience in thinking that through as you got closer to announcing. Yeah.
Glenda
I think I really like the point you made about this is not just about one person. So often we talk about this like the executive director, the CEO is leaving what do you do? There's a whole cascade. There's a whole org chart and hierarchy underneath the executive director and above the executive director and the board. And thinking about all of the key positions, you know, who's a rising star, who's about to burn out, who in the organization? I mean, usually the question that always comes up is, is there anyone here who could be the executive director, anyone going to apply for this position, Anyone qualified? And we, we just happen. We did not happen to have that people that wanted to apply for that position or were a great fit for that position. So I know organizations, and one of the methods you can use is to hire someone and cultivate them to be that person. I have seen organizations successfully do that. That was not the position we were in, but we were in a position where we had strong executives, strong senior directors. Like there was a pipeline of leadership that we had been cultivating for years. And part of it, maybe five or six years before I left, we decided the leadership is too concentrated. We just had an executive team that was four or five of us and it was not spread out enough. So we created a senior directors level and team, and we started developing leadership there so folks could go up into that executive level. So there was another level of leadership for the staff and the community to rely on. And I think that really helped the organization in a lot of ways.
Joan Gary
I think that's really super smart. And I think that leadership development within each department is something that often falls by the wayside and is essential to the sustainability. In a time when the executive director is moving on, another client who is thinking about moving on and says, as you did, that given the work that we do where so many of our clients are people of color, I really feel like the person who succeeds me, we should have a very diverse candidate pool. And I said, okay. I said, you have in this case, over a thousand people who work for you. This is just one person in the organization. I said, who are your rock star people of color in that group? We made a list, and one by one we went through and we said, could this person replace you? No. Could this person replace you? No. And we went through. And the answer was no everywhere. And the answer. You'll laugh at me when I say this. I said, what would have to be true for one of those people for you to say yes? How could you invest in one or more of these people so that you could say yes, so that they would be viable candidates to replace you? And so that began a conversation between my client and a couple of those people about what are the development plans for that person, should that person go out on more asks, whatever that, you know, that, whatever, you know, whatever that that might be. So I think that's, that's really, that's another part of this whole. You call it succession planning, call it organizational hygiene, call it just, you know, just making sure the organization is solid, steady, the right people are on the bus, that you're building leadership pipelines, board and staff. And those things are really important. One of the exercises that I do with clients who are pretty clear they're going to leave in the next two to three years is I actually, I have them write their exit press release.
Glenda
Yeah, Ray did that.
Joan Gary
Yeah. Have them write their exit press release and what they wanted to be able to say they accomplished. Right. And, and then we took that exit press release and we looked where there were gaps. Right. That were the unfinished business or something. I really want to be able to say, blah. Okay. So then we set those as priorities for the executive director over that three year period. Totally. And ask, and ask the ED to talk to the board chair and say these, these are the things I believe should be my priorities over the next couple of years. And it gave and provided an accountability mechanism for the executive director, which can all often be a challenge, especially if someone is retiring because it is very hard to move out someone who's retired and is really kind of done. But a press release can actually ignite somebody who really wants to retire to say, I want to get these things done so that it's really part of sort of my legacy, my exit, that sort of thing.
Glenda
Yeah, yeah, yeah.
Joan Gary
It sounds like the mental health program was one of those things for you.
Glenda
That was, it was, it was something people had been asking for and asking us about for years and we just, we're not able to do it. I think looking at like I'm not going to be doing this forever, what are the things that I am uniquely suited to do and that I want to do before I leave that will really help the organization? So I, I think, Joan, as, as we're getting sort of to the end of our, our time together, I wonder if there's kind of one or two. I don't know, I won't restrict you three. A couple of things you want people to remember about succession planning. What do you want to leave our dear listeners with on this topic? And I, I shall do the same.
Joan Gary
Well, one very quick thing that is very tactical is I, I want everybody to know that job descriptions don't actually Take four months to write.
Glenda
They don't.
Joan Gary
No. Boards seem to think that they take four months, and those are four very valuable months. And you all could sit down and write one right now and you could update it every year so that it is 95% done at the time your person says they're leaving. I have seen so many stalled. The search committee is stalling for me. Yeah, I have seen so many stalled searches because the boards are copy editing a job description when they could just simply say, messiah wanted. Right. Someone who could do all the things. It could be very simple. Anyway, that wasn't really what I was going to get at. I think the way I guess I would leave it this way is we are actually doing this, converse, having this conversation, because we want to reframe what this is. We want to eliminate the fear. We want to actually tell you that the fear is actually driving inaction, which is actually the vicious cycle that Glenda referenced earlier, which is actually then everybody putting their heads in the sand and continuing to have these ridiculous conversations about buses. But I would say when I think about what this process is about, I ask you to think about this. Who would not want to build a smart, sustainable organizational structure? Who does not want to do everything they can to recruit the best possible candidate? Who doesn't want to avoid a failed search? Who doesn't want to hold the executive director accountable to key priorities and to be fair, who doesn't want to be ready if there really is a bus or a lottery? And if these are things you want, this is the way to get at them. And if you think about it that way, you'd absolutely make it a priority to dig into it and to dig into it, maybe using your executive committee and holding the staff accountable to continue to work on this on an ongoing basis. Because these are the things that every nonprofit needs and these are strategies to get there. And I fear that we look at it too much as oh rather than opportunities.
Glenda
100%. I completely agree with that. And the one thing I would want to say that we haven't said is I think a lot of times in nonprofits, it's good to remember to not let the perfect be the enemy of the good. And this is one of those times. There are so many examples. And I think your example with the four months to write job description is a good one. Like that does not need to be perfect. That is not going to be the make or break thing to get you the best candidate. I think people, and maybe even myself, like, come into this thinking there is One right way to do a succession, to do an executive or a leadership transition. It's more art than that. There are some things that we've talked about that you should do. Years ahead, months ahead, you should think about. But it really does also require you to just know yourself and your organization and figure out what is the best way for us to do this. It's not. If it were as simple as ABC and everybody just do this, we wouldn't have bad transitions. You know, everything would be great. So I think I say that, and I think that's applicable for board. I think Borg can sometimes get caught up. What's the best for. Oh, my God, we only have three months. We should have four months. What are we going to do? And then there's paralyzation or the executive director. I could say this, you know, I wanted everything to be tied up perfectly with a bow, and I could just hand it to Carla and be like, here it is. It's.
Joan Gary
I.
Glenda
It's great. Everything is great. And you can never do that. There's always. It's a point in time. So I. I just want to. I want to caution us, because I know how passionate we are as nonprofit leaders to. To take it easy on ourselves and each other and do this as good as we can, but to not hold up that it needs to be perfect, or there's some way that it even can be, because it really can.
Joan Gary
And as we close out here, I think that the key word here is intentionality. Right? To be intentional, not perfect, be intentional. And the last thing I'm going to say is the next time you're going to go to a board meeting and you know they're going to go into executive session to talk about the whole bus thing, and, you know, that's on the agenda. Can I suggest that you send this podcast to your board to listen to ahead of time and have a conversation about it in executive session and try to think, get them to begin to think, Think about this. And for you to begin to think about this in a. In a very different kind of way, because that's part of board education, too. So with that said, fun conversation, enjoyed it, and hope you all, as listeners, gleaned something from it.
Glenda
And nobody needs to get hit by a bus. We're banning that right now from here to. For everybody's going to win the lottery instead.
Joan Gary
So steer clear of buses, stay safe, do your best to stay sane, and we'll see you next time.
Glenda
Thanks so much, everyone. Thank you for spending time with us today. We hope this conversation provides valuable insights as you navigate the messy but meaningful world of nonprofits. Attend a Special thanks to DonorPerfect for sponsoring this episode and for their dedication to empowering nonprofits like yours to do more good. For more resources to support your work, visit joengarry.com podcast. We think you'll find a lot of helpful things there. Most importantly, thank you for all you do to make the world a better place, one small or large step at a time. Talk to you all next time.
Title: Nonprofits Are Messy: Lessons in Leadership | Fundraising | Board Development | Communications
Host/Author: Joan Garry
Episode Release Date: August 7, 2025
In Episode 234 of "Nonprofits Are Messy," Joan Garry and guest Glenda delve deep into the often-overlooked topic of succession planning within nonprofit organizations. The discussion emphasizes the critical importance of proactive leadership transitions, moving beyond the clichéd "someone gets hit by a bus" scenario.
Key Points:
Glenda shares her recent experience as the Executive Director of the New York LGBT Center, where she announced her departure nine months before her contract expired.
Notable Quote:
“I wasn't really able to grasp how emotional it would be to leave after 14 years.”
— Glenda [00:46]
Glenda discusses the emotional challenges she faced and the strategies she employed to navigate her transition effectively, including hiring a coach and meticulously preparing for her final speeches to maintain professionalism despite emotional turbulence.
Both Joan and Glenda highlight common misconceptions and fears surrounding succession planning in nonprofits.
Key Points:
Fear and Scarcity of Positive Examples:
Many nonprofit leaders fear succession planning because they have only witnessed poorly handled transitions, which often result in organizational turmoil.
Notable Quote:
“Everyone works in nonprofit. Everyone who works in nonprofit, either board or staff, has seen a leadership transition go badly.”
— Glenda [14:08]
Perception of Complexity:
Succession planning is often perceived as an arduous and complex process, deterring organizations from initiating it early.
Notable Quote:
“Succession means who comes next, period. So you have your board chair, who comes next. You have your treasurer, who comes next.”
— Glenda [15:03]
Joan and Glenda provide actionable strategies to streamline succession planning and integrate it seamlessly into organizational practices.
Key Strategies:
Early and Ongoing Planning:
Succession planning should commence years before the actual transition to ensure a smooth handover.
Notable Quote:
“Succession planning is a multi-year process.”
— Joan Gary [13:39]
Reframing Succession Planning:
Transitioning the narrative from potential crises to positive growth opportunities can reduce fear and encourage proactive planning.
Notable Quote:
“Maybe there's something we could do to say what if so and so won the lottery and they just want to go sit on an island somewhere.”
— Glenda [20:30]
Simplifying the Process:
Organizations often overcomplicate succession planning. Simplifying job descriptions and focusing on core competencies can expedite the process.
Notable Quote:
“Job descriptions don't actually take four months to write.”
— Joan Gary [43:21]
Organizational Hygiene:
Viewing succession planning as part of maintaining organizational health rather than an isolated task promotes a culture of readiness.
Notable Quote:
“Reframing it as organizational hygiene.”
— Glenda [16:19]
Joan emphasizes that effective succession planning contributes to the overall sustainability and resilience of the organization.
Key Points:
Marketing the Organization:
Building a strong organizational reputation helps attract top-tier candidates during leadership searches.
Diverse and Inclusive Practices:
Ensuring diversity within the board and leadership teams enhances the organization's appeal to a broader pool of candidates.
Notable Quote:
“Is the structure set up to recruit somebody? It should not be based on the previous leader's preferences alone.”
— Joan Gary [29:11]
Glenda discusses the importance of developing leadership pipelines within the organization to ensure multiple candidates are prepared for executive roles.
Key Points:
Creating Leadership Layers:
Establishing senior director levels helps distribute leadership responsibilities and prepares internal candidates for higher roles.
Cultivating Internal Talent:
Investing in staff development ensures that potential leaders are ready to step up when needed.
Notable Quote:
“We created a senior directors level and team, and we started developing leadership there so folks could go up into that executive level.”
— Glenda [37:14]
Both speakers highlight the necessity of institutionalizing key relationships within the organization to prevent dependence on a single individual.
Key Points:
Distributing Relationships:
Encouraging multiple team members to build and maintain relationships with donors and stakeholders ensures continuity.
Team-Oriented Approach:
Shifting the focus from individual leaders to the collective strength of the team fosters a more resilient organizational structure.
Notable Quote:
“You start to market the great work of your other staff members, not just development.”
— Joan Gary [34:55]
As the conversation concludes, Joan and Glenda offer essential advice for nonprofit leaders grappling with succession planning.
Key Takeaways:
Intentionality Over Perfection:
Being deliberate and thoughtful in succession planning is more important than striving for an unattainable perfect process.
Notable Quote:
“Be intentional, not perfect.”
— Joan Gary [48:12]
Simplify and Act:
Avoid overcomplicating the process and take actionable steps to initiate and maintain succession planning.
Notable Quote:
“Don't let the perfect be the enemy of the good.”
— Glenda [46:59]
Cultivate a Positive Narrative:
Shift the focus from potential disruptions to opportunities for growth and sustainability.
Notable Quote:
“Think about what these processes are about—building a smart, sustainable organizational structure.”
— Joan Gary [43:34]
Leverage Organizational Strengths:
Utilize existing relationships and organizational achievements to attract and retain high-caliber leadership candidates.
Notable Quote:
“Ensure that your organization is set up for sustainability and impact.”
— Joan Gary [35:23]
Conclusion
Episode 234 serves as a comprehensive guide for nonprofit leaders, emphasizing that effective succession planning is integral to organizational longevity and success. By addressing fears, simplifying processes, and fostering a culture of intentionality, nonprofits can navigate leadership transitions smoothly and sustainably.