No two days at Latin School of Chicago are the same for Shelley Greenwood—and that’s wonderful, says the assistant head of school. Greenwood leads in the areas of student life, athletics, diversity/inclusion, development, and more—a mix of responsibilities that she says are eclectic and exciting, she says.

“I wouldn’t change it for anything,” says Greenwood, who’s been with the 1,200-student pre-K-12 school for 28 years.

Along the way, being open to new opportunities (and willing to put on new hats) has been key, she says. Now, she’s taken on the role of chairing the 2021 CASE-NAIS Independent Schools Conference—all online for the first time—in January.

Here, she shares her perspective on leading a collaborative advancement team, her best career advice, what keeps her motivated, and more.

How did you make your way to advancement and your role now at Latin School of Chicago?

I’m assistant head of school at Latin, working with our head of school Randall Dunn. A big part of my work has always stayed really grounded in the advancement area, though my path to advancement was definitely not a traditional one. My first administrative role was in enrollment management at Wayland Academy in Beaver Dam, Wisconsin, U.S., where I’d been a student and a faculty member. I came to Latin School of Chicago in 1993 as director of admissions and financial aid.   

When Latin School moved to what we called at the time institutional advancement, we moved under the guidance of Frank Hogan, who was the head at Latin at the time (a CASE Robert Bell Crow Memorial Award winner) and just a really big believer in the advancement model and keeping the umbrella pretty wide. So right from the get-go, our advancement program encompassed the traditional area of development and alumni relations, but with communications, admissions, financial aid, and enrollment management all full partners in the advancement model.

So now, within advancement at Latin, my umbrella has gotten even broader. I have direct reports working in student life; diversity, equity and inclusion; and athletics. Together, we talk a lot about how collectively we work to advance the mission of Latin, and how our different areas support that mission and what we need from each other to do our best efforts. As eclectic as that may seem, I wouldn’t change it for anything. It has opened up avenues of thinking and support for every area under that umbrella, and truly been a gift for the traditional areas of development, alumni relations, and communications.

What do you love most about the work?

It’s fun; it’s eclectic. One day is never anything remotely close to the day before. After 40-plus years now working in schools, that’s what I need to stay feeling engaged and vital, and to continue with my own learning.

What’s the thing that you’ve accomplished that you’re really proud of there?

It’s the advancement model, to be very honest. We have an extremely diverse group of areas and a diverse group of individuals with who bring their perspective and lenses to conversations. Sometimes those conversations are hard, but it’s the way that we work together to unpack them and facilitate the overall mission of the school that brings us back to together. I’m proud of facilitating that group of highly talented, highly opinionated, highly passionate individuals. There’s a lot of mutual respect. That’s what I’m most proud of: keeping that going for almost 25 years now.

How has your team been able to stay connected during COVID-19?

Well, obviously, good old Zoom has played a huge role. We’ve tried to hold on to certain practices and routines and traditions that were in place before and respect the need for those. Initially, we thought, well, maybe we should just sort of meet on an as-needed basis. Well, that went out the window in about two weeks. We craved the routine. So I’ve kept my one-to-one with my individual directors, we kept her every other week meeting with the entire assistant heads group, we have actually increased our senior leadership time from where it was last year.

What’s some of the best career advice you’ve received along the way?

Be open to new opportunities. Don’t be afraid to get engaged with a task or a role that you might not believe you’re perfectly prepared for. If you would have told me 40 years ago what I would be doing today, I would have said, “No way,” right? But people just gave me chances and I was lucky enough to be in schools that had that kind of ethos, if you were willing to put in the work and be willing to add a hat (because in independent schools you rarely sunset anything, you just keep adding!).

Also, certainly, finding mentors along the way. They can come from really different places, but find someone who can help you with your own personal and professional growth. I’ve been fortunate to be influenced by leaders at other schools or fellow CASE volunteers and CASE staff.

Don’t be afraid to ask for help. Be a learner, just like our children are in our schools. Be open to that growth mindset and different opportunities that can come your way.

Speaking of new opportunities, this year’s CASE-NAIS Independent Schools Conference will be all online. What do you what are you looking forward to about it?

The thing I am the most excited about is how accessible it’s going to be. It really, really excites me that for an unbelievably reasonable investment, you could have anyone that you wanted in your school community have access to participate in this online conference. For instance, my athletic director is going to be there, my director of diversity, equity, and inclusion is going to be attending the conference, my director of enrollment management is going to be there.

I think it’s huge for us to link arms right now around the work of schools and to be partners and to be supportive of each other’s work and to reinforce the connections of what we do.

I love the format; it feels manageable. People can work in the morning, and then at noon, log onto the conference and enjoy some great professional development and networking. I think the timing is perfect. It’s nice to be able to start the year off with it. I really do believe that it’s going to make a positive impact for all of us.

Do you have something interesting you like to keep in your workspace?

I have a photo that reminds me of a really special gathering from last December. It’s a photo that one of my direct reports turned into one of those great photo magnets: a picture of the eight of us successfully at the conclusion of our escape room outing, which is what we decided to do for the holidays. We did solve it in time and got safely out of the escape room, but it’s this wonderful photo of this extraordinary group of people. Every time I look at it, it centers me about what I do. In that setting, you learn about yourself and your team—and I love that our team was up for it. That’s one of my favorite things in my office.