71: An Interim Executive Director case study with Dress for Success Tampa Bay
Laurell Jones served with distinction in the United States Air Force and retired in the rank of Lieutenant Colonel. During her 23 year career she held multiple roles in financial management and financial analysis with increasing levels of leadership responsibility in international and US based locations. In Laurell’s post military career she was a Senior Managing Consultant with IBM for 14 years. Laurell has been a volunteer with Dress for Success Tampa Bay since 2018 and currently serves as the President of the Board of Directors. Laurell is passionate about empowering women to achieve economic independence. Laurell is a graduate of Syracuse University and also holds an MBA and MPA. She resides in Tampa with her husband. In her free time, Laurell enjoys mentoring youth, gardening, traveling and exploring Tampa.
Judy Bensinger has a passion for women’s empowerment. Judy is on the Hillsborough County Commission on the Status of Women, the board of directors of Dress for Success Tampa Bay, and the Advisory Board of Gems. She is also a team leader for a new, international women’s organization: Age of Possibility. Judy sees 2025 as a great year full of opportunity and promise.
Tanya Cielo is Sky Marketing’s founder and Lead Strategist, and her passion is marketing! She is a certified marketing facilitator with more than 20 years of marketing experience for media companies such as Clear Channel, Cox Radio, Beasley Broadcasting, and AOL. Her work brings new life to her client’s marketing efforts and results in revenue growth. Tanya loves networking and is a member of several organizations. She is the Board Chair for the South Tampa Chamber of Commerce and a Board member for Dress for Success Tampa Bay and FBI Tampa Citizen's Academy.
Main quote:
"Our organization fell prey to what many organizations do when you're going about the business of the organization: looking at what's urgent and what's important. Succession planning, I can't underline enough as important. Make sure you carve out time for that very important activity of succession planning, because if you don’t, there may become a time when it becomes not only urgent, but a crisis."
Additional Quotes:
"One of the best gifts you gave us was the organizational assessment. Something we had not done as a board, something we had not done as an organization. It is a foundation, we'll continue to build on for years to come. That is invaluable."
"I always believe change and transition will lead to positive growth. No matter where you're starting, I believe when you bring in new individuals, new mindsets, new exposure to things, you're going to get better because you're not starting from ground zero."
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Transcript:
I am so excited to have this conversation with the three of you, and I've already read your bios and shared all of the wonderful things about the three of you. So I'm excited to just jump right into the first question and I'm excited for this conversation. So I would love for one of you to give a brief intro to the reason that dress for success in Tampa Bay was in need of interim leadership support.
Let me go answer that question. So there was a time in September of 2023 when we suddenly and unexpectedly lost our very beloved executive director, Katie McGill. She went away on vacation one day and passed away the next day. So that obviously immediately threw us into not just grieving, but also a crisis situation.
So she had been the executive director for 17 of the then 25 years that the organization had been in existence. So as you can imagine, a huge gap was created. And so we knew that we needed, obviously, to have a new executive director come on board. But we made the decision, and I really appreciate that the board trusted the vision that I had for us to not just hire the next executive director, but to actually have an interim executive director, and we were so fabulously excited when that person was you, Naomi.
It was, it was such a wonderful experience and it was so great to meet you all through that process. I would love to know a little bit more about your overall experience as board members, especially as you were discussing and making those decisions to bring on someone as an interim. And maybe the most, the biggest question is what things do you know now that you might have wished that you knew then?
Well, I think we all agreed that we didn't want to rush the process of bringing in an executive director. We wanted a very thoughtful process. We wanted a well organized process. We wanted to leverage our relationships with people that we knew that might be good prospects, and also be open to people that we didn't know who looked really good on paper.
So we wanted to take our time with it. You know, our late executive director was such a force in the community, so well known, and so beloved. We knew that we couldn't replace her. So the key for us was to not just quickly settle on someone, but to really, really be intentional about finding the right one.
So we were so fortunate that our interim executive director, uh, search led to someone of such a high caliber, Naomi. And, uh, through that, we learned a lot more about what we would be looking for down the line. In hiring an actual executive director. So it was a wonderful process. It was it was long. It was difficult at times.
And I think what would have helped us because ultimately with you, certainly with our interim executive search, we ended up doing a great job and it worked out well, but we really hadn't. Started our succession planning as an organization, as a board of directors, and so we didn't have all the tools that we needed to to really, really conduct that kind of a search.
So I think that's the 1 thing that will stick out in our minds. While that was a major factor on our list of strategic planning. Somehow we got to almost everything but that. So we were very fortunate that, in spite of that, things still worked out. You know, I just want to comment one of the things when you talk about, you know, succession planning, and it was on our strategic plan, both in 2023 as it was in 2024.
But I think our organization fell to prey to what many organizations do. When you're going about the business of the organization, you're looking at what's urgent. And what's important. And so a lot of our energy was focused on what was, what was then urgent, but succession planning, I can't footstomp it, underline it enough is important.
And so I would definitely encourage anyone else who's listening to this podcast for your organization, make sure that you carve out time for that very important activity of succession planning, because. Otherwise, if you don't, there may become a time when it becomes not only urgent, but a crisis. And, you know, we talk about succession planning.
We're here, of course, talking about the executive director, but really succession planning covers the waterfront for an organization. You also have to think about, and we're still on that journey, about succession planning for the staff, because that's also a critical element. So I would just definitely want to highlight those things.
We talk about succession planning. It was basically on the to do list, but we never got to it until it became a crisis. So I wouldn't anyone else make the important carve out some time and make it a place where you don't have to have it as an urgent activity. Yeah, I love that up Laurel and I, we, I had an, uh, episode a couple of weeks ago and I'll link it in the show notes about the Eisenhower matrix, which is the urgent, important, not important, not urgent and how we.
Things on, and you're so right that succession planning always ends up in the bottom of the list. And I would add to what you said, Rell too, that, uh, succession planning for board of directors is also really important, you know, because that's another huge disruption potentially to an organization when there's not that plan in place.
So thank you for bringing that up. Mm-hmm . What I thought was neat was because it did turn into a crisis situation, us as executive committee, you know, we have to protect not only the organization, but the board. And so the opportunity to have an interim executive director allowed us to have a tad bit of.
You know, calmness as we also dealt with the 99 million other things that were happening because you were able to just step in immediately with all your background and all your, you know, experience and say, like, okay, these are all the things that we need to take care of, you are taking best practices that have worked well for you and other organizations and putting them in.
And I mean, The modest, you know, changes because of who we are is just for success. You know, you were able to adapt there quickly, but it gave such a sense of calmness to the board because we were, you know, like, Oh, my gosh, there's so much to do. What about this? What about this? What about that? And you just came in and we're like, Let me show you.
I've got a plan. And so it really allowed us to focus on the things that we only that we could do. And that way you could really guide us on all the other areas and what to do next. So it really created a sense of calmness. I thought amongst the board. Yeah, I love that you said that, Tanya. And I think the other piece of it too, for those of you that are listening, you can create a succession plan and know that you'll have to revisit it.
It's not a one and done. So I think that's the other. Thing that I recommend to folks is not to try and make it perfect. Just start the conversation because at least with the conversation, then the board executive leadership and staff know that it's something that we don't have to shy away from. I think it's just like will and estate planning.
It's the last thing any of us want to think about, but it becomes very important for those that are left behind if there's not a plan in place. What was at risk or what could have jeopardized the organization's mission if Dress for Success Tampa Bay, uh, the board didn't prioritize interim leadership?
You've touched on it a little bit, but I'd love to know if you have more thoughts on that. I think everything was at risk dress for success. Tampa Bay has such a fine reputation for outstanding leadership in the community that was at risk. Certainly our fundraising potential was at risk. We had a number of obligations grant based requirements.
We had. Services to provide for women. Yet we were still dealing with such a shocking loss. And so while we were going through that and trying to recalibrate, we needed someone at the helm. So that executive, that interim executive. director presence was very, very important. It was imperative. I'm so glad that there was no hesitation about doing it, that there was no talk about, let's just get somebody in here as soon as we can and name an executive director, that we didn't go that route.
That was really, really important. You know, one of the things that I think was so valuable that because we took the time and we were able to bring in someone. You nail me his time. You mentioned bringing in your best practices. One of I think the best gifts that you gave to us and left with us was the organizational assessment.
You know, that was an opportunity. That was something that we had not done as a board, something we had not done as an organization. And that then that talk about and it's definitely not a one and done. That is something that that is a foundation, but we'll continue to build on that for years to come. And that is invaluable.
And we didn't we didn't have those best practices at our fingertips. And so bringing you in with that experience is an interim that was priceless. And so that I think will definitely help to shape our future for years to come. The other thing that I think is so powerful about organizational assessments is it just gives a starting place, especially as you bring in new board members or as the new ED comes in, it's just something to kind of rest on of saying, Okay, here's a map, at least to get us going.
And like you said, it's not a one and done, it will need to be adjusted, especially as different environmental changes happen to the nonprofit or the sector overall. So board members will be listening to this. And I would love someone to talk or many of you to talk about proactively preparing for succession planning and interim leadership.
How did the interim period reshape your understanding as a board member about the board's responsibility in succession planning and maybe even the board's role overall in the difference between working board and governing? That's a lot of questions all in one, but welcome your thoughts. To talk about the difference between a working board and a governing board, you know, for years, we had always called ourselves a working board, and we weren't.
But what I've learned in the process is that we needed to focus on working on the things that we, only we, the board can do, and that is governance. And so I think that space really kind of changed our focus. You know, we had a lot of Operational touch points that we were involved in, and we still have some of that, but we're trying to shift our direction because the importance of governance, which is what only we can do, whether it's in our assessment of our board as a whole, the assessment of the organization, the planning that's necessary.
to make it a better organization, the training that's necessary even for board members. One of the things that, um, you know, that I talked about during my tenure as president is that I would like to have board members when they leave here, leave the board address for success and they go somewhere else.
That they're even better than when they started with us, because what we're really doing is feeding the community, right? So I think all of that when we talk about governance and training and direction, I think that was that was a new touch point for us. And I think it's kind of shifting and, you know, sort of steering a ship.
It's not a quick process, but if you don't start, it'll never happen. And that's sort of where we are now. This allowed us to almost reshape and redefine kind of what we were all really going to focus on as an organization and then individually in our roles. And sometimes, you know, there's that saying, if you're too close to it, you just kind of continue doing the same thing over and over again.
And you think, wow, we're doing great. And it takes sometimes a jolt to step back and say like, wow, well, what would it look like if, and then now we've. Totally redefined it. And so we sort of had an internal catchphrase of, you know, just for success 2. 0. And that's really steered us into a really successful big view moving forward.
That was one of the things that I was so impressed with you all as a board and and there's other board members, just for those listening on these three represent the officers of the board at the time I was as interim, but the full board was so raring to go on. Let's use this opportunity to Build what 2.
0 could look like. And that's not something that everyone's willing to do. So I just want to make sure to give you all a kudos as well, because I think that's really, really imperative, especially when you have a moment like you all did, where you had to take a different step because of Katie's passing and being able to take that fully with innovation.
And what does Dress for Success Tampa Bay? What does the community need was really, really invaluable, I think, for the organization. So you all went through an executive search at the end of the interim period. What advice would you give a board member about how to interview and select first the interim executive director and CEO, and then maybe do you have any advice for how to conduct an ED search when you need to not replace but bring on the next leader?
And we did that was so important was and you, you see two of the member or three of the members, there were four of us on a committee that was formed because you can't have the entire board immersed in the process that that's just to that would be just messy. And so We had that that committee that ad hoc committee that was formed.
And so we got together. And so we developed the parameters for the search. We did the, you know, the reach out and we actually did the interviewing and all of that. But we kept the board informed. And that's a critical piece of it as well. And so of course, they trusted us. I mean, we were, we're, you know, a third of the board, right, or fourth of the board.
And so that helped. But we did ask all of the other members to, to, to attend every interview or to provide questions and all of that to be a part of the process. But I think having that, um, that ad hoc committee is crucial to have that kind of organization. We were very fortunate. One of our board members, uh, Rebecca Sanford, who I asked to lead the committee, is an HR guru.
So that was a plus. And so that really helped to steer us because again, it was a new process for all of us. So I think having that committee was, was, uh, something that was definitely needed and made a difference. I agree. I think you really do need a collaborative effort, a good team of people who are fair people who have sound judgment.
And certainly, if you're fortunate enough, as we were someone with HR experience, and I think you want to structure that interview process around. a key question of how does this prospect, this person match our organization's needs, not only professionally, but personally. And I think that was a huge factor, Naomi, in our success of having you.
You want to look obviously at leadership skills. You want to look obviously at intellect and communication skills, but then there's this one intangible quality. energy. How do you feel when that person speaks to you? How do you feel when they respond to a question from you during the interview process?
How do you believe they would make other people feel within the organization? So we're looking not just for a set of skills. We're really looking for a person, a personality, uh, an energy. And I think that was especially important for our organization. Dress for success because we're all about empowering women and dealing with vulnerable women, dealing with women often in crisis.
And so we needed a special person to be at the helm for that situation. So I like the idea of thinking about not just, you know, what you see on paper and this person has a PhD and that kind of thing, but who is she, who is he as a, as a person. beyond just being a professional. And the other E that I would add to that was empathy.
And that's never in a resume, but that's what came through clearly to all of us and made us just so excited because it was a very, um, delicate situation. You know, as Judy said, we would never, we will never replace Katie, but we did need someone to step into that function, but they had to do it with empathy, with concern.
with the understanding that not just the board members, but all of the clients that we serve, the staff had this relationship that had now taken a different direction. And so that was invaluable, but it wasn't on, I don't think that was on your resume, but it came through certainly in the interview. And it certainly came through in the nine months or so that we were together.
That's crucial for success as well. Yeah. And I think I would also add to that Katie's and this is similar at so many nonprofits across the country, Katie was deeply embedded in the community. And so it wasn't just the board, the staff and the clientele and the folks that were being served by dress for success, but it was the mayor of Tampa.
It was other nonprofits. It was the folks. You know, near the buildings that Dress for Success inhabits. Everyone knew Katie. And so I think that's something that as, as you're listening to this episode, uh, with these three board members, um, that I want to just underline, you need to really be aware of what your organization needs for that interim period and, you know, how much external facing, how much internal facing.
Is this an opportunity where you You're ready for 2. 0, or does it need to be just steady in the ship and continuing business as usual? So being aware of those questions is going to be really important as you search for an interim. The last thing I would add is I think to start early, because start earlier than you think.
Even when you're like, well, we're not ready. Doesn't matter. Get the ball rolling, because I mean, it took us months and. You know, we were really fortunate both ways for for interim and our, you know, current executive director, but just like dating. Sometimes you have to kiss a lot of frogs, right to find your prince or princess.
And so we were very fortunate, you know, in our case that we fell in love with Naomi right away. And, um, you know, we're very fortunate to with our current executive director, Lisette, but it takes longer than you think. There's just, and also there's circumstances outside of people's controls. People move, things happen.
And so you may have someone that you're really, you know, hot on, and then there's, there's a change or you just never know. And so we would say now knowing, you know, the, this, what we went through, like we probably would have started earlier if, if that was possible, because you just never know. And what was the worst case?
That could happen. We'd find someone, you know, earlier. Great. But I mean, I think that we all sort of, not, I don't want to say underestimated, but we just didn't know that it was going to take so long. And certainly, uh, you, at the end of the day, we want to create as the consistency as quickly as possible.
Yeah. Well, and I think there's also the reality, too, that board members are volunteers. And so you all have other things, other boards that you're serving on, other careers, family, what have you. And so I think that's the thing, too. It's easy for me in my seat to say you should do these things in these orders on this timeline.
Um, but as a board, um, you know, you have to balance other things. So it does, it's another reason to move succession planning and the conversation around what does it look like when we need to fill a gap. Higher. Yeah, I have a couple of final questions just more around your personal relationship with change and transition, but I wanted to just leave space if there's anything else about interim leadership or your process and experience through all of this that you wanted to share.
You know, one of the things that I the advice that I would give to others and we came to this a little later, you know, we were very fortunate for the executive director search. We had a HR firm that did a pro bono search for us. That was truly priceless. It was, I mean, that was a five month process. And so, you know, we use their use the resources that they normally would, you know, like linked in and all of that indeed.
But one of the things that I think we should have honed in on more was making sure that our network clearly understood what we were looking for and what our timeline was, even after the process have been going on for several months. individuals in the community like, Oh, I didn't realize that was going on right now.
Hey, have you looked at this person? How about this person? And so I think you want to take advantage of that, particularly in our place, you know, being so embedded in the community for, you know, quarter of a century, we have a big network. And so to capitalize on that, I think we started with that really a little later than we should have.
And I would definitely recommend others make sure that, you know, you put that out on your social media page. Hey, looking for an ed and then you can sift through because you're still going to go through the interview process, but to, to broaden the aperture, to make sure that you get the broadest number of candidates.
I think that is helpful. And so the community. Is invested in that as well, because they want us to succeed. And that's one of the ways that they wanted to, they contributed like, Hey, did you know this person might be interested. And so I would definitely say, open it up to your network. The other thing I remember us talking a lot about was shifting even the mindset between you're not looking for your next permanent.
Uh, executive director, you're, you're just looking for the next one. Um, and I think we had a lot of great conversations around kind of just our normalcy of thinking that someone's going to be there forever, uh, and, uh, looking at it more in the reality that people do leave for a number of reasons and in a number of different ways.
And that's very helpful to keep that in mind because it's very rare, I think, particularly in a nonprofit organization to have someone with a tenure of 15, 16 years. I mean, it essentially rarely happens. So, yes, that's that's really important in a strange way. Again, going kind of back to the whole word reset.
This allowed us and you really showed us the difference between how we were doing it over and over and over again. And what's possible. So, I think that. Thanks. You know, you, you asked the question, what is, how do we adapt to change or what does change mean to us? I mean, in your personal and your professional life, it kind of means different things, but what I really appreciated was how you were able to immediately meet with all of us, meet with all the staff members and then help us.
Number one, because we were still so heartbroken over the circumstance, but also we focus us on like, you know, help us continue forward with the mission because it's more than us. It's the whole community and we have to get it together and we have to stay strong and we have to move forward and be even stronger so that we can continue helping and empowering women in our community.
And I think I would say to respond to that, Tanya, for folks that are listening who might be in a position of, of being the next person, the next ED after a loss or after a tragedy or a sudden departure, um, I think that the one recommendation I would give that I experienced with you all is just keep the lines of communication open about the reality that it's hard and that it's messy and that it's not going to be easy.
Perfect. Um, but in communication, if those communication lines are strong, and especially between board chair and board officers, the work can continue. Um, it just has to be done with a little bit more thoughtfulness and intention, I think. So it's a good segue into that question. Um, what few words or phrase would each of you use to describe your own relationship to change and transition?
I think mine is a positive relationship. So Some of the words that come to mind when I think of change are, um, energized, energy, optimism. And the reason for that, because I always believe change and transition will eventually lead to positive growth. So, no matter where you're starting, I believe when you bring in new individuals, new mindsets, new exposure to things, you're going to get better.
Because you're not starting from ground zero, they're starting on the shoulders of those that they come on and you just continue to build and grow up. So for me, I mean, I recognize certainly that there's a learning curve associated when you bring someone new into the organization. And I think that's part of the expectation you have to have.
But the ultimate goal and the ultimate result is going to be a positive improvement. An impact. So for me, definitely energy and optimism for sure. It's almost like the oxygen, right? That creates what's next, the evolution of either your personal life or your business or whatever it is, because otherwise everything just remains complacent and then there's no growth or anything like that.
So I would almost categorize it as, you know, the oxygen. Mm hmm. I think for so many of us, and especially businesses, organizations, groups, our relationship to change has to do with whether or not we were expecting it, and we're perhaps preparing for it, as opposed to whether or not we were surprised, even shocked by it, and simply had no idea how we were going to wrap our arms around whatever it was that happened.
But I'll say, as I was just telling one of my children today, Progress rarely happens without change. And so that's an important, you know, sometimes we come to these situations under the most unfortunate set of, you know, experiences, but it ends up being something positive and something that we can grow from and move forward as a result of, I think that's important to remember.
And I just want to share a little something that I happened to be reading from a book. There is a way to live. With our hands a little less gripped on the steering wheel. Finding our faith, not in whether everything goes according to plan, but in our ability to adapt regardless. And I think, um, that's what we have to do sometimes as non profit groups, as boards, uh, as families, as people.
That's powerful. That's a really great, perfect, unexpected way to end. This conversation, uh, Judy, I'm glad that you shared that. What is that from? Is it from a devotional or a book? So it's from a great book, a great bestseller called The Pivot Year. Okay. It is exceptional. I would highly recommend it. Okay.
I will check it out. Yeah, I think what's interesting too that I want to just give you all kudos for is you were able to grasp the really awkward tension between holding space for Katie's legacy and welcoming something new and that can be something really awkward as people are talking about interim leadership or executive leadership departure because you don't want to look.
or you don't want to disrupt or disrespect the legacy of the outgoing leader. And so I just want to give you all, um, your flowers for helping guide that process, helping guide the board, helping guide the staff and the organization and the broader community through messaging, the way that you communicated everything out, um, to say, we miss Katie desperately.
And because of the great work that she was able to do, we're excited and we owe it to the community to keep it going forward. And so just another reminder, uh, of. Being able to, you can do both. You can protect the legacy of someone who's outgoing and also welcome in 2. 0. I actually have my, one of my, um, dress for success.
I remember that. Yes. Yes. Um, as we close, is there anything else that you got, you all would like to share, uh, about either the process, uh, recommendations or advice to folks or any just final words? Well, definitely appreciation for all that you did for us laying that foundation so that we can continue to grow.
The journey is not over. We still have a long way to go, but I think we're so much further along than we would have been if we had not gone through the interim executive process. So just really love and appreciation. That's what I have. So thank you. Paper, it looks like, oh, we could save this money. And especially as a nonprofit, right, you're looking at every dollar and you think, well, if we just save this salary money, you know, and we could hire somebody, blah, blah, blah, blah.
But really at the end of the day, it's almost an opportunity cost because what, what you've provided for the organization in our most dire time of need was exactly what we needed. And we would have.
So I think that that's the other kind of hurdle you have to get over in your brain is that on paper, you think like, well, we can say the salary and it's going to cost this amount, blah, blah, blah, but it actually would probably cost you more. Had you not, if, had we not moved forward with an interim director, well, another interesting nugget to keep in mind for organizations going through these kind of transitions is, Once the interim director leaves, you may find yourself going through another adjustment, especially if you have someone like Naomi Hannaway.
I think for me, and for many of us, that was another adjustment, uh, Naomi, when you left. Because Nine months is a long time to work with someone in a situation like ours. And so we had so much faith in you. We loved you so much personally. We had the utmost respect for you and the job you were doing. So we found ourselves as we got closer and closer and closer to the date that you were leaving in another adjustment.
So be prepared for that as well. Yeah, and that's that is the very awkward part of this is that there's always going to be a goodbye. And so it's how do you as an interim, my struggle is, when do I start pulling back so that that makes it a little bit easier versus staying 100 percent embedded and integrated.
It's a really Yeah. Okay. It's a really delicate balance, but I'm so thankful that we had the opportunity to have our lives intersect for a while. Thank you for your trust in the interim process and their trust in me. And I have to give a little shout out also to third sector, um, for matching us and bringing us together.
Thank you to all three of you for your work and your service to not only dress for success, but the whole entire community of Tampa. And thanks for joining me for this conversation. Thank you. Certainly a pleasure, an absolute pleasure, and a wonderful reunion. And yes, it's been good to see you all. Thank you.
Thank you. If you are an organizational leader, board member, or a curious staff member, take the Leaving Well Assessment to discover your organization's transition readiness archetype. It's quick and easy, and you can find it at naomihataway. com forward slash assessment. That's Naomi, N A O M I H Hattaway, H A T T A W A Y dot com forward slash assessment to learn more about leaving well and how you can implement and embed the framework and culture in your own life and workplace.
You can also see that information on my website. It's time for each of us to look ourselves in the mirror and finally admit we are playing a powerful role in the system. We can either exist outside of our power or choose to decide to shift culture and to create transformation. Until next time, I'm your host, Naomi Hadaway, and you've been listening to Leaving Well, a navigation guide for workplace transitions.