37: Leading Through the Messy Middle (with CEO Annie Bacci)

Most leadership stories begin with a crisis and end with a comeback.

But what about everything in between?

In this episode, we're talking about the messy middle, that season where funding is uncertain, difficult decisions have to be made, your team is looking to you for answers, and you have no idea how the story will end.

My guest, Annie Bacci, CEO of TGTHR on a mission to end youth homelessness, shares an honest, behind-the-scenes look at what it really feels like to lead through organizational uncertainty. From navigating layoffs and rebuilding culture to balancing transparency with responsibility, Annie reminds us that leadership isn't about having all the answers...it's about continuing to move forward with courage.

If you're carrying the weight of leadership right now, this conversation will remind you that you're not alone.

Top 3 Takeaways

1. Leadership is often lonely, but it doesn't have to be isolating.

Annie shares why every CEO needs trusted peers, mentors, and advisors, while recognizing that some decisions ultimately rest on the leader's shoulders alone.

2. Progress through uncertainty is rarely linear.

Some weeks you'll feel like you're making real progress. Other weeks it may feel like you're back where you started. That's not failure. It's the reality of leading through change.

3. Focus on the next right step.

When the future feels uncertain, don't try to solve everything at once. Celebrate small wins, stay anchored in your priorities, and keep moving your mission forward one small step at a time.

In This Episode, We Discuss:

• Why most leadership stories skip the messy middle
• Making high-stakes decisions without knowing the outcome
• The difference between feeling lonely and feeling isolated as a CEO
• How to balance transparency with responsible leadership
• Practical ways to reduce rumors and build trust through communication
• Why celebrating small wins keeps teams moving forward
• Creating leadership anchors that help you decide what deserves your time and attention
• Building resilience when progress feels slow or uncertain

Remember: You don't have to know how the story ends to lead well today. Sometimes the most important work of leadership happens long before the breakthrough.

CONNECT WITH MARCIA

Join 10-Week CEO+ED CARES Mastermind → culturecares.com/mastermind

Free Weekly Leadership Insights → culturecares.com → Click Subscribe 

Meet Marcia on LinkedIn → linkedin.com/in/marciabeckner 

Visit the Culture CARES Website → culturecares.com 

Explore the Podcast → culturecares.com/podcast

ENJOY THE SHOW? If this episode resonated, here's how you can support:

1. Subscribe on Apple Podcasts or Spotify or your favorite platform
2. Leave a review (it helps more nonprofit leaders find the show)

Don't forget to share this episode with a CEO or Executive Director who needs to hear it.

Transcript

SPEAKER_01 0:05

Welcome to Nonprofit CEO Spark, the podcast for bold leaders ready to navigate growth and change with energy and confidence. I'm Marcia Beckner, nonprofit founder, former executive director, and culture strategist with nearly 20 years in the social impact world. Each week, I help nonprofit leaders stop spinning out, set boundaries, and design inclusive cultures where all staff can thrive. If you're ready to reignite your leadership without sacrificing your well-being, hit subscribe and let's spark your next chapter together. Welcome back to the Nonprofit CEO Spark Podcast. I'm Marcia Beckner, your host. Today we're talking about something that everyone listening right now will be able to relate to. I can promise you that. Most leadership stories get told in two versions, the before and the after. Everyone loves a good makeover show, right? Well, people talk about the breakthrough after the culture is stabilized, after the hard decision workout, after the team rebuilt trust, and after the organization finds its footing again. But very few people talk honestly about the middle or what we're calling the messy middle, the part where you're still leading while things feel uncertain, where you're carrying pressure privately while trying to create steadiness for everyone else, where the staff dynamics feel fragile, communication is harder, and you're making important decisions without fully knowing how they'll turn out. And the truth is, most nonprofit CEOs and executive directors are not living in the polished after version of leadership, right? Most are leading in the messy middle every single day. And in this episode, we're having a real conversation about what leadership actually feels like during seasons of change, instability, and uncertainty while you're still trying to move the mission forward. Because the messy middle is not a sign that you're failing. It's where your leadership is actually formed. So I really am excited to introduce you to my guest today, Annie Bacci. She is the CEO of Together. And Annie, welcome to the show. Great. Thank you so much, Marsha. I'm really happy to be here with you today. Happy you're here too. Thank you so much. This is a really important conversation so that people don't feel so alone as they're going through the messy middle. And I can tell you, as someone who's been an executive director before for 10 years, 10 years felt like the messy middle. Like, what's the clear beginning? What's the clear ending? Do those even actually exist? So let's talk about reality today. Annie, first, tell everyone a little bit about yourself and your organization and where you are today.

SPEAKER_00 3:06

So our organization is together. Our mission is to end youth homelessness. And I have been the CEO here for about two and a half years. Before coming to Together, I've spent my career working in homelessness and housing, really working mostly with communities, states, cities, counties, around how do you strategically address people experiencing homelessness in your community and find sustainable solutions. I actually started my career as a case manager working with youth who were experiencing homelessness in 2004 in Denver. And so when I had seen this role come available at Together as the CEO, I was ready to really start working locally again. I had been working nationally with different communities, and I'd always had a passion for the youth work. And so it seemed like a great full circle moment to come to together and lead this team and this mission forward.

SPEAKER_01 4:11

That's amazing. So you're working with, you know, one of the most vulnerable communities here in the States. And thank you for doing this work. You're brave, you're bold, you're you're doing something that most people wouldn't even know how to step into. And you're doing it every day. And that's so admirable. So thank you, Annie. I just wanted to pause for a second.

SPEAKER_00 4:34

Thank you.

SPEAKER_01 4:35

You started two and a half years ago, which was probably 2024-ish.

SPEAKER_00 4:41

Yeah, late 2023.

SPEAKER_01 4:43

Yeah, late 2023. Okay. And then we had 2024 and 2025, which I don't have to tell most people listening that there were massive changes last year and threats to our local communities, um, including, I'm sure, your organization. So tell us, like when there's funding uncertainty, like was that what happened to you last year like something dramatic that that caused some significant turmoil?

SPEAKER_00 5:17

Yeah, I think that um together is really facing multiple uh headwinds. And I think what I've learned is that's often the case. It's usually not as simple as, you know, funding uncertainty or one funding cut. It's usually layered upon multiple vulnerabilities within an organization. And so, you know, when I arrived at Together in late 2023, and part of what really excited me about the role is that Together was ostensibly in a period of growth. We had been an organization based in Boulder, Colorado. We had just expanded to open new housing in Denver in 2024. I was really excited about the expansion. Um, we had grown our staff to really be able to serve young people in these growing programs. Um, and what I learned shortly after arriving at Together and really digging into some of the financials and the operations is that, you know, and this is again not uncommon in nonprofits, there was expansion based on vision and hope without real infrastructure built behind it. So, you know, we had the organization had opened a lot of programs that we didn't have long-term committed funding to run in perpetuity. And, you know, there were, this was sort of a foundational vulnerability that was helped along by the PPP that came during 2024. Um, we also received quite a bit of ARPA funding from local and state governments, which really helped bolster the organization and in a way kind of cover up or extend the period of operational stability that then it felt like very abruptly shifted in 2025, with ARPA and stimulus funds sunsetting, the economy changing, the federal administration changing. And so we did have then several inflection points, including a sudden and um significant funding cut that threw us into a real reactive period of having to make some hard decisions very quickly, um, including closing programs and um downsizing and having to lay off a significant number of team members, which was extremely painful. And, you know, we're still living with um what happens on the other side of contraction after a period of growth.

SPEAKER_01 7:56

Wow. Okay, that is a lot, Annie. That is significant. How are you? I always go to kind of the health and well-being of you leading through this time. How are you managing the stress that comes with those massive changes?

SPEAKER_00 8:15

That's a great question. And, you know, I love your work, Marsha, because you talk a lot about, you know, how leadership can feel isolating at times. And, you know, I would say, you know, I haven't felt isolated in this period, but I have felt lonely at different periods because, you know, there's a really limited number of people that you can lean on and really share kind of um the details of and the nuances of what you're holding with decisions, and you're also carrying the awareness that your decisions have real impact on people's lives. Um, I feel lucky that I have I had developed some great tools and practices before coming into this role around self-care and how I have like a kitchen cabinet of folks that I know I can call and process things with, even if they're not ready for public consumption. Um so I've been utilizing that. I think that it really isn't linear. So that's you know something I want to say for other leaders out there, especially when you are in a turnaround or restabilization moment. It feels like, oh, once the tanker starts turning, we're gonna hit our stride and find our footing, and every day will get easier. Um, and that hasn't been my experience. I think, you know, I have weeks where I think, wow, things are clicking and the culture is feeling like it's growing and getting stronger. Um, and then the next week, you know, two or three things will happen where it just feels like, oh, we're back to square one, or you know, we're still not out of the woods yet, even though we all really want to be. Um, and so I think it's coming back again and again to the tools and that, you know, that it's normal to have a path that isn't linear. In fact, that's usually how it is. Um, and so um, yeah, I think that's important for other leaders to hear that again, when we tell, you know, like you say, everyone loves a comeback story. And so when we tell the story, it can get reduced to, you know, this these really hard events happened, hard decisions were made, things started to turn around, and off, you know, off we go. Um, but in reality, it's like the squiggly line um graphic that I know a lot of leaders see where it's like my path, what I thought my path would look like and what it actually looks like, definitely living that in the day-to-day.

SPEAKER_01 10:52

Oh, yeah. Never a straight line, is it? I'm curious. You said you don't feel isolated, but you feel lonely. Like, how do you define the difference?

SPEAKER_00 11:02

I think isolated is where maybe for me, you don't really know who to call or who to talk to. Um and like I said, I've I've done a lot of intentional work to cultivate that for myself. Um, you know, I have colleagues and mentors and friends. Um, I have a therapist, you know, like I have this sort of way to make sure that I don't get isolated. And at the same time, as a leader, there's decisions that you have to make that you can crowdsource, you can process, you can weigh the pros and cons. But at the end of the day, you're the one who has to sit with that decision and make that decision. And it's really you. Um, and that can feel lonely. You know, sometimes I wish I had a co-CEO. So we can we made this decision together. Um, and it's been an important part of my leadership journey to know, okay, this is my decision to make, and it's really important, and I'm going to, you know, weigh everything in making that and communicate as much as I can as soon as I can. Um, I've been thinking about um, well, I've been really into the show, The Diplomat. I don't know if you've ever watched that on the show.

SPEAKER_01 12:21

I haven't watched it yet.

SPEAKER_00 12:22

It's a great, yeah. It's a great leadership show. Okay. Um, but they were talking about, you know, in politics and, you know, when decisions get to the president's desk, they're often 4951, meaning, you know, it could go either way and there's no great answer, and you have to choose, you know, there's a a good argument for either way. Um, and that really is to me, not that I'm comparing myself to presidential aspirations, but that is what leadership is about. Because if it were an easier or more clear decision, it would never make it to your desk. It would never make it to you because some of your other amazing, more capable staff would have already made the decision. And, you know, we have a culture of really empowering leaders to make decisions on their own. And so those are the moments where it really does feel lonely.

SPEAKER_01 13:18

And with that 5149, you're just gonna make half the people mad no matter what you decide. Right. And then you feel that's where the loneliness comes in, where it's just like you can't make everyone happy.

SPEAKER_00 13:31

Right. And a lot of responsibility because it will have impact for the young people we work with and for our staff. And so, you know, I just have this desire for folks to know like I do not take this lightly, like I know my decisions have impact. And sometimes I can get into over-justifying or over-explaining, and that's when I know I'm kind of out of my integrity because I really try to hold the process and share as much as I can about the process during the time in which I'm making a decision.

SPEAKER_01 14:07

Yeah. And a lot of staff in the, you know, the organizations I'm working with or my client organizations are always asking for more transparency, more transparency. And how do you handle that? Because it's, you know, like you said, there's some things aren't ready yet for to be shared because they're sensitive issues. How do you handle this call for higher transparency from your team when you want to give it to them, but you have to like wait for a certain point?

SPEAKER_00 14:38

Oh gosh. I mean, I think so much of what you're describing is like the human experience, right? Like we always feel like we'll feel better if we have the information sooner or more of it, even if it's bad news. Um and that actually, in my experience, hasn't been the case. And I've learned, I think, by sharing too much too early around like, well, I'm here's all the things I'm considering, and here's all the possibilities that we that could happen. And then staff feeling like, oh my God, like something big could happen and it could really impact me, but I'm not gonna know what the outcome is for a while. Um, and there's a lot of reasons that you can't share, especially personnel-related decisions, HR um related um decisions. And so I think that um how I handle it is I try to make myself available. So going to like team meetings, staff meetings, um, and hear from staff like what information do they feel they're missing? Because a lot of times you're like, oh, I can actually answer that or share that. Um and also just create opportunities where I can invite people to check assumptions with me or check concerns with me. Um because sometimes it just the rumor mill will get going and it's not actually, you know, I can actually say, well, that's not something on the table for consideration. Um but I really think that um what I'm able to share with staff is that we are working really hard to turn things around and restabilize, and um we're going to have an all hands call every month, which is something new that we've decided to do, which has helped a lot for information sharing. Um we've created processes like an anonymous feedback form that has a little QR code. My team loves a good QR code that they can they can um input questions, concerns, and it really helps just create that flow of information. And sometimes I think when people want transparency, it's that they don't actually know how to get their questions in front of the leader, and so create opportunities for that, and just you know, being transparent, you know, I say like I can share, I want to share as much as soon as I can. And I need you to trust me that you know I can't share everything. Um I think a lot about communication with you all, and it's really important to me.

SPEAKER_01 17:21

That's awesome. I I think that what leaders can sometimes forget is in when staff are calling for transparency, they probably each have different questions to ask. And it kind of, as you were talking, made me think about like parenting, where you know, you can't share everything with your kids as they're growing up, it's not age appropriate. But they will ask questions, and when they're ready to know, they'll ask you a direct question. And if you can answer that then, that just continues to build trust. So it's almost like the call for transparency is way too vague. And you can kind of share back as executive director and say, Um, you know, what I've seen in the survey or what people are asking for is more transparency as we're, you know, we're navigating the messy middle right now. Please give me your questions either directly in my office or through this anonymous um avenue or channel that you've set up. That is really important, easy thing to do, and you will get more questions than you would have thought because some people are afraid to ask questions for fear of being, I don't know, misunderstood or or it will be used against them. The anonymous feedback form is really powerful. And, you know, put a QR code to it and it gamifies the whole thing, makes it more that's a great point, Marsha, about the messy metal.

SPEAKER_00 18:49

I think that, you know, sometimes you can just get in reactivity mode and and reactive and go about solving problems that you're actually you're not clear on what the problem is you're trying to solve. And transparency is a great example of like, okay, well, staff said they need transparency, so we're gonna do A, B, and C. And then staff are like, that's not what we wanted at all. And that doesn't like satisfy our desire. Um, and so really like taking that step, which is slowing down, to say, what does better look like? Um, tell me what better would look like, tell me what more transparency would look like. We had um, we were getting a lot of feedback. I was getting a lot of feedback around staff wanting more leadership presence, which I think is common for nonprofits that have direct service programs. Um, and it's really hard. That's also very vague. What does that mean? Do you want me sitting like in your space for one day every month? And like, so then we tried that, and staff were like, I'm sorry, what are you doing here? Like, you know, um, and so really it was like, okay, try that. Like, now let's have a conversation. Like, what would actually feel meaningful? And it was, I think it's really them just having a chance to have informal conversations with me, to float questions, to give me feedback in an informal way. Um, and I learn a lot during these these times where I'm I'm hanging out with staff and programs.

SPEAKER_01 20:20

That's cool. Do you have um like a specific name for it or anything?

SPEAKER_00 20:26

No, we don't. That's a really good uh that's something we should because we also love a good good branding, good name. We call our all hands meetings one together calls. Um, but I should think about it a little more and ask them.

SPEAKER_01 20:39

Yeah, ask them to do like a little competition.

SPEAKER_00 20:42

Yeah, yeah. I think we're finding our group with it more and more. And it's also like when I get to see young people over in our project.

SPEAKER_01 20:48

Yeah, too. Yeah, yeah. And so you've told us about kind of like when you came in and where you started, which was we'll call that the beginning for lack of a better word, because it was started way before you. But let's say it was your beginning. Now you're in the messy middle, figuring it out on a day-to-day basis, or not at the end. Do you have any advice for other leaders who are in this same kind of messy middle space and the the end feels a little bit too far or too vague? How do you approach like your day-to-day life as you're, you know, um recalibrating towards that ideal future?

SPEAKER_00 21:29

I think it really is breaking things down into smaller chunks. Um, and you know, one of the biggest pieces of advice that we say a lot, because we have to remind ourselves to celebrate the wins, um, to really acknowledge when you when you see things shift. Um, like when we first started doing these all hands, these monthly all hands one together uh meetings, it was kind of clunky and rough and And staff were like, what is this for? Like, do we get to have a conversation or do we get to air our questions? Or we don't really understand. You know, and we started to say, like, well, this is for information sharing and transparency. And I said to the team, like, it's like a podcast, not a talk show. Like, we're sharing, you know, with you. And this is like, because they were like, well, we don't know what things are happening and shifting. And then just, you know, the last couple of times it's felt like, wow, we're really finding our groove. We have sort of a routine with these meetings. And, you know, we share wins and celebrations and birthdays and updates, you know, around the organization. So, you know, and it's not perfect, but we're celebrating, you know, that it's better and that it's a place of community for staff. And I also think, you know, when you're in, you know, like you've talked about the beginning, I would say the hopeful beginning, the messy middle. And yeah, we're not, we're not through it yet. Um, but I would say that it is really as a leader, identifying what are the things that you know you need to move forward, regardless of the outcome of this period of time. And so for me, you know, I have like three things that I feel that I'm uniquely positioned to move forward. And no matter what the outcome for Together is, like getting these three big strategic things moving in a good direction will benefit the mission and the organization. And so that really helps me as a leader to have a filter of what I say yes to and what I say no to. And then it also helps with transparency and communication with staff because, you know, as an ED or a CEO, you're, you know, you're getting a lot of feedback around the spaces that you are in and the spaces that you are not in. Um, and so I say to the team, like, this is what I'm basing my decisions around, you know, the spaces that I'm in and the spaces that I'm not in. And I think a lot about that because people internally always want more of you, and people externally always want more of you. And so you have to not only make those decisions, but I think communicate the why behind them. Um, and we have an amazing staff. I love your um work around like intergenerational work, a lot of Gen Z employees, and they really want the why. Um, that's really important. And so communicating that, having your anchors as a leader, knowing what you're working on. And then I think, you know, sometimes it is just another CEO told me when I was in a really difficult period, and I was just like, I don't know what even to do next. And she was like, do the thing that's right in front of you and just keep doing that until you start to find more of a rhythm to your days. Um, and so, you know, it's like getting up and putting on your tennis shoes in the morning, which makes it easier to walk out the door and go for a walk, um, even though you can't imagine going for a walk. Um, it just feels too hard. So just like I think those small things of how do you what needs to be done today um doing it, and it starts to create that momentum. Um so I think don't underestimate like the small things um that you can do each day to move it forward. Um, so those are, yeah, some of my big pieces of advice for other leaders.

SPEAKER_01 25:35

Annie, thank you so much. I I just needed all those reminders today. And I hope everyone listening can really take this in and know that they're not alone and feeling lonely is part of the job. It is normal, so there's nothing wrong. But reach out and make sure that you have peer support. On that note, I am launching a mastermind in the fall for a small group of executive directors and CEOs who want to feel a little less lonely as they're going through this work. We don't have all the answers for everything's gonna turn out, but I love what you just said about just doing the next right thing in front of you. And if you're feeling alone and isolated a lot, please, you know, reach out to me. I can connect you with people, and um, and we'll make sure that that leadership is less lonely than it should be. Annie, thank you so much for sharing your story and your tools for success, and you're doing an amazing job. Um, thank you for that for the work you're doing in the world.

SPEAKER_00 26:44

Yes, thank you, Marsha, for having me and for the work you're doing in the world. It's really important. Thank you.

SPEAKER_01 26:52

Thanks for listening to today's episode of Nonprofit CEO Spark. If you're ready to turn burnout into boundaries and build a healthy, happy culture where everyone, including you, can thrive. Visit culturecares.com to learn how I support nonprofit organizations like yours. If this episode brought you value, share it with a fellow leader navigating stress and overwhelm. And remember, you are meant for great things and you don't have to burn out to prove it. Until next time, keep leading with courage and confidence.