When we wrapped up the first Leading Lady internship program last summer, I wasn’t sure if we’d do it again. I mean, it was amazing—don’t get me wrong—but running an internship program takes intention, energy, and a whole lot of trust. But then I thought, what if we made this a regular thing?
Spoiler alert: we did it again, and it was one of the best decisions I’ve made for my business.
So if you’re a woman entrepreneur wondering how to get the support you need, build your team with intention, or just curious about what goes on behind the scenes here at Leading Lady—pull up a chair. This one’s for you.
Why We Brought on a Second Round of Interns
After our first internship experience over the summer, I knew we were onto something special. The energy it brought to The Collective, the projects we were able to accomplish, the way it pushed me to be a better leader? I wanted more of that.
So we did it again. This time, we brought on three incredible women: Catherine, a graduating senior at Towson University studying Business Administration with a concentration in marketing; Madison, a student at Anne Arundel Community College majoring in Human Services who’s transferring to continue her studies in social work; and Molly, who’s been managing a coffee shop for seven years while figuring out her next career move.
The Projects That Made This Round Special
Over their four months with us (four months! Can you believe how fast that flew by?), these ladies tackled some pretty big projects. I interviewed them about it for a recent podcast episode.
One of the projects the interns worked on was a party to celebrate the finale of the We Lead book series—a three-volume series featuring stories from women entrepreneurs. They had it catered, created a signature cocktail and mocktail, and brought together 30 attendees to honor the authors. They knocked it out of the park.
Catherine lit up when she talked about the book launch party. “The planning that went into that—it was stressful in the right ways, but it was overall just a fun event,” she said. “We really got to plan everything from the ground up.”
Madison’s favorite part? Getting exposure to so many different types of businesses. “I didn’t realize that there were so many women entrepreneurs, especially within The Collective,” she shared. “It was beautiful being able to see high-achieving women and meet them firsthand.”
She got to work on her communication skills too—something she admitted she tends to hold back on. “Being able to really work on my communication and communicate with the ambassadors every day helped a lot,” she said. “I really looked forward to doing that.”
And Molly? She dove into research projects with one of our ambassadors, Elizabeth, helping find sponsors for the Wellness Rebranded podcast and connecting it to our community. (Trust me, Elizabeth is heavy on the research side, so Molly got pulled into a whole world she didn’t even realize existed.)
What They Learned About Real Business
Some of the biggest lessons for the interns came from the most unexpected places.
When I asked them what was really hard about being an intern, Catherine jumped right in: “All of us have different schedules. So we all had to be very on top of communicating with each other, even outside of work.”
She’s right. I will die on this hill—organizations cannot thrive if they don’t have a strong communication structure. If you can’t communicate with your team, especially when you’re overlapping schedules, things fall through the cracks. There are misunderstandings. Balls get dropped.
That’s real-world, hands-on experience right there.
Madison brought up something I think every entrepreneur can relate to: the challenge of balancing multiple priorities. “When you work a Collective meeting, you’re here for four hours, but all those four hours are taken up,” she explained. “So that’s a whole day out of your work week. Trying to break it up so that the ambassador work could still get done by the deadlines—that was really difficult.”
And that’s entrepreneurship! We’re all juggling a lot of things. Learning how to manage competing priorities while staying calm? That’s a skill that will serve them for the rest of their careers.
The Magic of Creating Space (Yes, Even the Snacks)
Part of the interns’ responsibilities included keeping The Collective stocked—and I’m not talking about just grabbing whatever’s on sale. We have six different types of creamers. Specific brands of coffee. Little Kinder Buenos for our members who love them. (And yes, toilet paper with scalloped edges. People still laugh about it, but tell me it doesn’t make you smile just a little bit.)
But here’s why it matters: when you have 80 members coming in and out of a coworking space, you’re thinking about the experience each woman has when she walks through that door.
Madison put it beautifully: “It’s like you’re really paying attention to what your members and your community prefer. When I go somewhere and they have my favorite little snacks, it makes me feel so seen. It makes you feel appreciated. It makes you feel heard. Like you’re meant to be here, meant to be in this space.”
That’s exactly it. Every detail—from the drinks to the products in the bathroom to the flowers on the tables—is purposeful. I want every woman who walks in here to feel like the anxiety just melts away a little bit.
What It’s Really Like to Work With Me
I asked my interns what was hardest about working with me. And they didn’t hold back.
“You like certain things a certain way,” Catherine said. “Me and Madison, our first time grocery shopping, we were like, oh my goodness, what if AliceAnne doesn’t like this?”
Fair point. I am particular. But here’s why: as a woman entrepreneur, I really relate to my members. When they come into this space, I want them to know that I did the research to get them the most excellent products, the most thoughtful experience.
Madison added something that made me think: “You guys have already made a system within your community. Having to jump into these unspoken rules you have—it’s like you guys have some telepathic ways going on.”
(For context: Aubrey and I have worked together for 21 years. We have a language between us that’s just eyeballs at this point.)
But here’s what I appreciated about these three—they have inclination. That’s not something you can teach. That’s something you either have or you don’t. And each of them demonstrated the ability to read the room, figure out what needed to be done, problem-solve, and support us. Even when I wasn’t always great at communicating my vision clearly. (I’m working on that, I promise.)
I’m also not a micromanager. Once I’ve assigned something to someone, I trust that they can do it—or they’re going to come to me with questions if they need support. As I told them: if I’m quiet, that’s good. If I’m talking a lot to you, then I probably don’t like something.
The Culture We’re Building Together
When I asked the interns to describe what happens at a Collective meeting, their answers reminded me why I do this work.
Madison’s response gave me chills: “My first day at a Collective meeting, I looked at AliceAnne and said, wow, this is just a really big community hug. It just feels like a very welcoming space. Everyone’s sharing their own experiences. It’s really just about having other women that have gone through similar things that you can rely on and look to for support.”
That’s exactly what I wanted to create. The Collective is the community I needed as a business owner—a space where I could say, “Hey, this is hard. How did you do this?” or “Can you tell me how you got to that next level?” or just “I’m having a really hard day. I want to burn it all down and start a knitting club at home.”
(Don’t tell me you haven’t had those days too.)
Catherine, who worked our La Cadena meetings—that’s our Spanish-speaking collective—described it this way: “I love seeing Latina women business owners come together and build this friendship, this big community of helping each other.”
She gave a perfect example: “If I was a business owner and I met someone who’s also a business owner, but I’m not really good at marketing or certain tactical skills—but this person might be very good in those areas—I think it’s good that we connect so I can ask questions, and they can do the same for me.”
That’s it. That’s the whole point.
Their Biggest Takeaways
I asked each intern for their biggest takeaway, and their answers were all different, and all powerful.
Catherine: “I’ve discovered that there is a community for women who have businesses. It does exist. I never knew this was a thing—it never crossed my mind. I think it’s amazing that you exist and that you’re willing to help others navigate their businesses.”
Madison: “Learning that healthy work environments do exist. I’ve had a lot of roadblocks with my different jobs over the years. It has never been a good experience—I’ve always been in a toxic work environment. This was a breath of fresh air knowing that there are people that truly do care about you, that are understanding.”
(That one broke my heart a little. And made me even more grateful she had a positive experience here.)
Molly: “Honestly, confidence building. In many ways. A big one for me is being able to make decisions. Here we had to make a decent amount of decisions by ourselves.” She laughed and added, “You were just pushing us out of the nest. We gotta fly.”
Yes. Yes, you do.
Would They Become Entrepreneurs?
I had to ask: after seeing behind the scenes—including my many meltdowns—do they think entrepreneurship is for them?
Catherine said yes without hesitation. “I would love to own my own business one day. Not sure what, but I like the flexibility. I can work from home on a Monday if I want to. I can be in France if I want to and working.”
(And then she said she might be a Collective member someday. I’m holding her to that.)
Madison was more hesitant. “I do not think I can handle the stress levels,” she admitted. “You made it look really easy, but I know you’re just a very strong woman. I think I would get super overwhelmed.” But then she added something important: “If I was definitely passionate about something to an extent where I felt like people need this in their lives—maybe I could. But I’d have to find my little niche.”
And Molly? She’s dreaming of a flower coffee shop. (Someone said we should go into business together. Stay tuned, listeners.)
What This Means for You
So there you have it—why our internship program continues to be one of the most powerful things we’re doing at Leading Lady.
If you’re a business owner wondering how to get the support you need, consider this: mentorship and internships aren’t just about delegating tasks. They’re about building culture. Developing leaders. Creating a pipeline of people who understand your vision and can carry it forward.
And honestly? They make you better too. These women pushed me to communicate more clearly, trust more fully, and remember why the details matter.
If this gave you ideas, or if you’re curious about starting something similar in your own business, I’d love to hear from you. Reach out—I do read and respond to every email personally.
And if you know someone who might be a great fit for a future internship cohort, send them our way. You’re not just part of my business—you’re part of the heart behind it.
Ready to Be Part of Something Like This?
Here’s what I want you to know: everything you just read about—the community hugs, the women supporting each other, the healthy work environment that made Madison feel seen for the first time—that’s not just for interns. That’s what we’re building every single day inside the Leading Lady community.
Our next round of interns will be working alongside our Collective members, learning from our ambassadors, and soaking up the energy of women entrepreneurs who show up for each other. And I’d love for you to be one of those women they get to meet.
If you’re a woman entrepreneur in the Annapolis area craving that in-person connection—a space where you can ask the hard questions, celebrate the wins, and know that someone has your back—The Collective or La Cadena de Éxito might be exactly what you’re looking for. It’s where the magic happens. (And yes, there are snacks. So many snacks.)
Not local? The Hub is our virtual membership where you can tap into this community from anywhere. Weekly coaching calls, ambassador connections, resources to help you grow—all without the commute.
Here’s your next step: Join my free Facebook community to get a taste of what we’re all about. Or follow along on Instagram where I share behind-the-scenes glimpses of life at The Collective—interns, flowers, scalloped toilet paper, and all.
And if you’re not sure where you are in your business journey or what kind of support you actually need, grab our free Strategic Planning Wheel. It’ll help you see the bigger picture and figure out your next right step.
You’re not meant to do this alone. None of us are.
