How do you plan and communicate about leaving an organization?

​​​​Farra Trompeter: Welcome to the Smart Communications podcast. This is Farra Trompeter, co-director and worker-owner at Big Duck. Today we’re gonna ask the question: how do you plan and communicate about leaving an organization? Something that may be on your mind or perhaps on the mind of folks who you work with. And I am delighted to be joined by none other than Sarah Durham, who is no stranger to any of our loyal listeners out there. Sarah was the original host of the Smart Communications podcast and was the primary host for many of our first few episodes in our first few years. So you likely have heard and listened to Sarah over the years. Maybe you’ve even had a chance to meet her in your work with Big Duck. Sarah, she/her, is also the founder of Big Duck, which she sold to our staff in 2021. More about that shortly. Sarah now runs Compton Durham LLC, where she advises executive directors and owner-level executives as an International Coaching Federation (ICF) credentialed coach. In addition to being on Big Duck’s board, she’s also a board member for the National Brain Tumor Society and Workshop 13, a small arts organization in central Massachusetts. Sarah, welcome back to the show.

​​Sarah Durham: Hey Farra, so nice to be here again. Thanks for having me.

​​Farra Trompeter: Of course. So we are recording this conversation in November 2024, three years almost to the day after you sold Big Duck to our team and we became a worker-owned cooperative. You blogged about that moment in a post on our website called When it’s time to say goodbye, which we’ll link to in this transcript at bigduck.com/insights. But I want to start with that: Big Duck was your company for 27 years, congrats on our 30th coming up, and you made this decision mid-career, in your own professional development. How did you know it was time to go?

​​Sarah Durham: So as I was thinking about this conversation with you, I was thinking about the idea of founder syndrome, which is something that a lot of people at a lot of nonprofits talk about, think about, and struggle with. And was something that when I was at Big Duck, we used to talk about with some of our clients. And so very early in my career, I spent some time thinking about a couple of things. The first and foremost was, what kind of career did I want to have? I loved founding Big Duck, running Big Duck, working with people like you every day. It was all good. But I didn’t want to have a career where I never left or where I turned into one of those founders who couldn’t evolve, couldn’t let go, couldn’t let other people lead. So it’s not necessarily that I knew it was time to let go, it’s more that from the start I thought it would be wise to sort of set a milestone, look ahead and think about chapters in my own career, and to be very deliberate about knowing when, you know, maybe my Big Duck chapter had come to a close. Of course, it’s great for new voices to lead and to make space at the table for other people. So that’s an added incentive that I felt and I think a huge benefit for any nonprofit or for-profit business, too.

​​Farra Trompeter: Well I loved working with you too and so did everyone else. So I know that deciding though to leave Big Duck was a big deal and even opting to sell the company to us, the staff versus another company was an even bigger deal. Some might argue an even riskier move. We’ve podcasted about the benefits of worker ownership. We’ll also link to that conversation in the transcript. And I’m just curious for you, what felt like the biggest risks and rewards back then, if you can rewind in your brain three, four years ago and we started having these conversations to now. Here you are three years later, the coop turned three, you’ve seen the evolution of Big Duck beyond the time that you were officially on staff and now you’re one of our board members. Talk a little bit about that moment and what again, the risks and rewards.

​​Sarah Durham: Yeah, I think about this a lot, not only because of my own personal journey, but also because now in my work as a coach, I coach a lot of people who are thinking about their own transitions and a lot of small business owners thinking about the pros and cons of employee ownership. So for me, I think there were, and still are, many more rewards than risks, but the risks are significant from the perspective of an owner who’s selling their company. The rewards is that, you know, worker-owned cooperatives are for somebody with, you know, progressive values and maybe interested in business models that are not purely traditionally capitalist, really such a great way to go. It’s such a gift to be able to see the business that you’ve created move into the hands of the many, rather than the few. And in particular, it gives people the opportunity to really have, kind of, skin in the game or an ownership perspective or leaderly perspective in something without having to buy in and spend a lot of money to get there. ​​I mean, you do buy-in in a worker-owned cooperative, and worker-owners at Big Duck have bought in, but it’s not the same as spending hundreds of thousands or millions of dollars to become an owner.

Sarah Durham: So there are tons and tons of rewards. I think the last one, which is a little bit less personal and more general is that it’s kind of an exciting thing to be contributing to and working through a business model that is, I don’t know, bucking a little bit of the traditional capitalist perspective. There are a number of risks too. I think there are risks for the worker-owners because you’re taking on a kind of leadership and responsibility that may be new for many people, but for an entrepreneur looking to sell their business, definitely a coop conversion is much more financially risky. If I had sold my business to an individual or to another business, there would be an individual or a business personally on the hook. So if that person defaulted on the loan, I’d have somebody I could go after. In a coop conversion, that’s not the case.

​​Sarah Durham: So you have to be comfortable and confident that the business you’re leaving is going to survive and thrive. That’s certainly a risk that I think puts a lot of people off and makes it harder to go through this process. And for many people selling to your employees is less financially beneficial. If you were selling your business to private equity or to, you know, a company with very deep pockets, you’d probably make more money. That of course depends on the specific deal.

​​Farra Trompeter: And you started with rewards, and I’m actually just gonna come back to that for a minute. Here we are now three years later. You talked about the rewards, especially around connecting to your values, feeling good about, you know, challenging the traditional capitalist model. Here we are three years later. Are there any other maybe unexpected rewards that have come that you didn’t quite anticipate when you were making this decision back in 2021?

​​Sarah Durham: Well, as you mentioned earlier, I sit on the board of Big Duck, so I get to observe what’s going on in the business from the vantage point of a board member. But that’s a lot more removed than my vantage point when I was in the business on a day-to-day basis. And I would say that one of the biggest rewards for me now, three years later, and this isn’t unexpected, I had hoped this would happen, but it’s being able to be much more in a backseat position and see other people leading, innovating, and doing cool things.

Sarah Durham: And you know, you and I have talked about this, but for the benefit of your listeners, like this summer for instance, I had some things come up and I missed two board meetings. And in those two board meetings, there were a number of really important issues being discussed and issues that I felt really strongly about. And I was really bummed I couldn’t be in those conversations. I was eager to lend my voice to them, eager to influence the votes on a couple of these issues. But other than a conversation or two with you, I just wasn’t able to participate. And in the end, when I read the minutes of those board meetings, those conversations unfolded in such a terrific way and the votes went really well. The votes went the way I was hoping they would go. And that made me feel so great. It made me feel so great that I didn’t have to be in the room pushing an agenda that the board members who are all worker-owners really saw the complexity of these issues and really made some decisions that were in the best interest of the business and themselves in the long term. So that’s a real reward that feels really not that different to my experience as a parent. You know, I have two daughters who are about to turn 21 and when I see them out in the world being functional human beings, I feel like, “Wow, this is really awesome.”

​​Farra Trompeter: Gonna have a moment processing the fact that your kids are 21 and that I’ve known them since they were four, but that’s another conversation for another day.

​​Sarah Durham: That’s another conversation.

​​Farra Trompeter: Ah, where does the time go? So, you know, it’s interesting as you’re talking, the idea of trust, I feel like is coming through, right? Being able to trust the people who you are transitioning your organization or your business to. Being able to trust the people who are around the table who are also making decisions. And I know that there are lots of people out there that might be founders of nonprofits, leaders, board members listening. And on the off-chance there’s someone out there who’s listening and wondering, “Hmm, is it time for me to go?” What insights would you share with them? Maybe it’s about trust, maybe it’s something else. What are some factors that typically influence a decision to leave? And I know again, like you said, not just for you, this comes up in a lot of your coaching conversations. So give us a little of that Coach Sarah Magic.

​​Sarah Durham: Yeah, well I can tell you that one of the things that was important for me to think about and I always encourage other people to think about, is first of all, to know what you’re good at. One of the things I saw in my own leadership when I ran Big Duck and when I ran Advomatic, which was a digital agency I owned for a few years too, is that I like to build things and I like to fix things. So I like to create new things. In fact, this podcast was one of those things that I created at a time in Big Duck where there were so many great people in the company, like you, who were doing so many great things that I was aware that I was sometimes like getting in the way. You know, I was like messing things up for other leaders in the company. And so I decided to go off and start a podcast to give myself something to do.

​​Sarah Durham: And so I think it’s important to know, like, what are you best at? Are you a builder? Are you an optimizer? Are you a problem solver? And how can you be useful in a way that’s personally meaningful for you, but also productive for the company and not disruptive to the other people you work with? I think when you have built something and you’ve run something for so long, it’s very easy to get stuck in a little bit of a, I dunno, a loop about “This is how we do it, this is how we do it.” And to really make space for other people at the table, you do have to trust them and you also have to acknowledge that they need the space to fail. And that’s one of the really hard things too, is just sort of being okay with it may not go the way you want. It might even go really badly, but you’re never gonna be able to really let go unless other people get the opportunity to step in.

​​Sarah Durham: The last thing I would say about this is in my coaching practice, one of the things that I think is interesting to explore with people is: What is your definition of success? I think it’s important personally to have a definition of success and for many of us, it doesn’t fall into the traditional sort of capitalist archetype of financial wellbeing. Of course, you’d like financial stability and well-being, but that’s not the only metric. So there’s a Maya Angelou quote that I love and I often find useful, which is “Success is liking what you do, liking how you do it, and liking who you are when you’re doing it.” So I think that’s a good question to ask yourself, if you’ve been doing whatever you’ve been doing for a long time, do you still like it? Do you like how you do it? And do you like who you are when you’re doing it? And for me, probably, like you know, 23, 24 years into running Big Duck, I started to not say yes all the time and that was also a good indicator that maybe it was time for me to do something else.

​​Farra Trompeter: I appreciate that. It’s a very useful question that I’ll be writing down, putting on a Post-it note, and reflecting on. So thank you for that. I can’t help but talk about the communications part of the decision of leaving an organization. And as you know, well, it’s essential to intentionally plan how you’re going to announce and roll out significant changes, whether that’s related to your organization, your brand, or your position. And I’m curious when you think about, maybe back again, rewinding the clock a few years, what are some of the ways you approach communicating about your exit plans at Big Duck? Because you had to first tell us, you had to tell clients, you had to tell partners. How did you think about that kind of rollout plan, as we would say?

​​Sarah Durham: Yeah, and it’s funny to be asked this question by you on a podcast because you were essential to figuring all of this out, as you were to so many of these conversations. But I think the best way to paraphrase it is that first the communications about anybody’s exit start internally, obviously. For me, in my journey to exit the company, there were really three key phases. The first phase was with you and with Elizabeth Ricca, who were both really essential to the health and wellbeing and day-to-day operations of the company. So I needed you two to know, to help me figure out the path forward, to be allies and advocates on the journey. If you weren’t on the bus, the bus was gonna, you know, go off in the ditch. So that was phase one. Phase two was once we sort of had this idea of like, “Oh, maybe the coop is the way to go and we think it might be feasible,” then we brought sort of the team leads or leadership group into the conversation. So that was really getting the buy-in and the support and the understanding and making sure there was interest from a lot of people who’d been at the company for a while, who held some senior roles and roles of management.

Sarah Durham: And then finally there was the broader staff population, getting people excited about the transition and comfortable with my going. I guess internally, there is one other piece that I do think is important, which is that I did, kind of, make it publicly known a long time before I left that at some point I did wanna leave. And I think that that was good because if you say, “Well, like at some point in the future I want to leave,” then people don’t flip out, but they just know that that’s there and it’s less startling than when, you know, they think you’re never gonna leave and all of a sudden you’re talking about leaving this year.

​​Sarah Durham: Externally we, of course, did it together. We developed a communications plan and we did it in phases and actually found the external piece of it was really fast and smooth. I don’t think we had any big roadblocks. And I think one of the reasons that was successful was, again, to your credit and the credit of many people, there were a lot of people who had trusting important relationships with our clients and our partners and the wonderful team who produces this podcast and other people. So my departure, maybe people had personal feelings about me, but they had no doubts that they were gonna continue to be in great hands with the team at Big Duck. And that was really the most important thing. That came way before anything we said. It was really in what we did for years and years before my departure.

​​Farra Trompeter: Well, and I would say that, I mean I think that’s one of the things that I remember at a retreat in 2011.

​​Sarah Durham: Back when we were three years old in 2011.

​​Farra Trompeter: Exactly. I remember we were mapping out the one-year, the three-year, the five-year, the 10-year vision, and like 2021, you’re like, “Yeah, I might leave or transition my role, maybe work part-time at Big Duck.” I remember going “What?” And I was like, “Okay, well I have 10 years to plan for that,” but you know, it was in the recess of my mind. So when you brought it back up, I was like, “Okay, Sarah did give us a heads up about this.” I hadn’t thought about it in a minute, but you are someone who is so, who’s so intentional and plans these things. And I think even if, you don’t necessarily have to have a 10-year plan for making an exit, but I do think maybe asking yourself some of the questions that Sarah highlighted. If you start realizing it might be time to go thinking about how are you building trust within your team with other folks and externally so that when that comes, I mean I remember we hosted some open town halls for people to ask us questions. And the most questions we actually got were from other agencies who were like, “Hey, tell us about this model. This is great.” It wasn’t really so much from clients or from our partners. So again, that was some very well-intentioned planning, but even thinking about this in phases, as you said.

Farra Trompeter: Now, before we go, I do have one more question and I’m curious, what advice would you give to leaders today who might be in the midst of succession planning? Maybe they are thinking about leaving and as a bonus, I’m curious if you also have any tips for staff who might want to gently suggest that their leaders consider succession or what Amy Sample Ward of NTEN previously described on this podcast as “continuity planning”, which I also like that phrase a lot and we’ll link to the podcast conversation with Amy in the show notes. But yeah, so advice for leaders today who are, who are in the midst of it themselves, and maybe any advice for staff who are thinking, “Hey, you know what, it might be time for my leader or my founder to consider this, but I’m not sure how to talk about it.”

​​Sarah Durham: Yeah, so first of all, I believe so much in succession planning and contingency planning. Continuity planning is a great way to put it. Really, in order to do those things well, there has to be acknowledgment that the nonprofit or the business or whatever the structure is you work in, kind of is a thing on its own that needs to be looked after and might be bigger than any one person in it. So there is, I think this kind of weird illusion that a lot of people operate on. It’s the illusion that when we come to work someplace or when we start something that we’re never ever gonna leave. And that’s just not true. It’s good business to really think of like what would happen if you left? What would happen if you got sick when took a leave of absence? And actually, one of the people I met when I was training to become a coach had worked in a number of corporations, big corporations, where part of your job description was to write your own contingency plan, which you’d update regularly, and also to find your successor so that if you unexpectedly took a leave of absence, the person had already been identified who was gonna step into your role. So I’m a big fan of doing that. I think it’s a very healthy thing to do.

​​Sarah Durham: But to the other part of your question about what about the staff person who feels like they need to bring this up, which is such a sensitive topic, particularly with a founder because you’re challenging perhaps their fantasies about their own importance or their own, you know, whatever. Who knows what that’s really about? And it’s speaking truth to power in a way that is challenging. One thing that happened in my career that I think of as a great example of this, and I often encourage people to do, is a thousand years ago when Big Duck was just a few years old, I had a staff person, a graphic designer named Sabrina Funk, who saw the need for me to do some professional development around management. She saw that I could be a better manager and I had room to grow and that maybe that was something I was gonna be sensitive about.

​​Sarah Durham: So one day she brought in an article, and the article was in a trade magazine and she said, “You know I read this article and I just thought there was a lot of stuff in here that you would find interesting and might wanna think about.” And I read the article and it stung a little bit because it was sort of obvious that she was giving me this article as, like, a very gentle way to say “You could be a better manager.” But she was 100% right, you know? And the fact that I was able to read this article and process it and, you know, use it as a jumping-off point for my own professional development was a safe way for me to do it. So I often encourage people to find something that feels safe and not confrontational for the person you’re talking to. Maybe send them a video or an article, maybe share the podcast interview with Amy Sample Ward,

Farra Trompeter: Or maybe this podcast.

​​Sarah Durham: Yeah, yeah, exactly. And just gently suggest it as food for thought. There’s so many great resources out there. I also think it’s a really, really healthy thing if you are in an operations-related position to bake succession and contingency planning into the fabric of your organization as a norm. That everybody has to do it. It is something that’s talked about. It is something in your staff handbook. The more it’s just in there and out there, the more it’s not weird when we start talking about it with a person. And that is, of course, different than saying, “And I think you should go,” right? That’s a different thing. And I think probably for that, you really need very close, trusted advisors to have that conversation, or board members, you know, that’s gonna be a tricky case-by-case thing.

​​Farra Trompeter: Yeah, well that’s great. And that podcast with Amy, Amy does talk about how at NTEN, I think everyone does have a continuity plan, and so definitely worth a listen. So if you’re out there, you wanna get even more helpful guidance from Sarah, be sure to check out her website comptondurham.com. We will link to that as well. Sarah’s got some great blogs, workshops, and more. You can also connect with Sarah on LinkedIn. Sarah, thank you so much for joining us. Thank you for starting Big Duck, starting this podcast, and being here today.

​​Sarah Durham: Oh well, Farra, thank you. It is always fun to hang out with you and always fun to be on this podcast. So shout out to you for your leadership.

​​Farra Trompeter: All right. Thanks everyone for listening. We hope this gave you some good food for thought.