Prep For Life: A Conversation Between CEO Diahann Billings (VI) And Board EVP & Secretary Sue Meng (XV)

When Prep for Prep’s new CEO Diahann Billings (VI/Grace Church, Poly Prep, Yale) JD, Columbia, who stepped into the role in August 2025, sat down with Board EVP and Secretary Sue Meng (XV/Brearley, Harvard) MA, Oxford; JD, Yale, it was both a conversation and a reconnection. Years ago, Diahann served as Sue’s college counselor, helping her craft the essays that would take her from Brearley to Harvard and beyond. Today, the two Prep alumnae reflect on how their shared beginnings shaped their paths and how Prep for Prep’s mission continues  to guide their work and leadership. Both are lawyers by training, leaders by instinct, and products of a community that saw their potential early and never stopped investing in them. What follows is a condensed version of their conversation.

Diahann: Law school is maybe one of the best things  I did. I love the way it helps me to think, to organize, look at fact patterns, figure out what we’re trying to solve for. 

Sue: Practicing as a young lawyer was incredibly good training. You’re constantly playing different roles, trying to figure out things that are often above your head, knowing that eventually, you’ll figure it out. The lesson it teaches you is if you put your mind to it, there’s no problem you can’t solve. 

Diahann: Absolutely, I couldn’t agree more. When I am dealing with folks, I can tell who has a “get it done, figure it out” mentality. The first time I realized I had that in me was in the Preparatory Component. 

Sue: Prep was the first time I really had to bust my balls.  I had little marks on my shoulders from how heavy those backpacks were. 

Diahann: I remember running with the backpack. It seemed like I was always trying to run to get to Trinity  on time. It was a challenge, but early on, you realize  you can do something really difficult. 

Sue: It wasn’t just academically challenging, it was socially the most fulfilling time I have found in my life to date. It was the first time I was surrounded by kids who were like me, not just in terms of being academically inclined, but also who weren’t afraid to talk about things. In fifth or sixth grade, people made fun of me because I went  to extra school, but I was doing extra school with all my best friends. 

Diahann: I wanted to get to extra school. I really had to grow quite a bit academically, but immediately, I felt like, “I get this community. I get these people and they get me.” 

Sue: At eight years old, I told everybody, “I’m going to Harvard or Yale.” It was Prep that gave me the path to actually get there. It started with people like Ms. Mulvey [a Prep for Prep admissions counselor], who told my mom, “Sue is a Brearley girl.” She was right. That decision was obviously pivotal in my life. 

Diahann: For me, it was Gary Simons [Prep for Prep’s founder] and my Prep college counselor, Kim Wilson. Grace Church and later Yale were exactly right for me. This set of adults at Prep truly knew me and saw me.  You need folks to invest in you for the long term to help you see yourself in a different light. 

Diahann: Some folks second-guess Prep kids because we’re not looking at those standardized test scores alone. I would bet you money that you and I, our test scores probably weren’t the highest, but our IQ scores were probably great. Our partner schools understand that  we can see what’s possible. 

Sue: Now there are all these books, studies, etcetera,  on how grit is such an important factor in resilience  and a predictor of success in life. We had grit. The fear of being kicked out of the program was a really huge motivator for me. I was like, “That can’t happen to me. I’m putting the pedal to the metal.” 

Diahann: Right. I was like, “This is hard, but I’m doing this. I am not getting dropped.” 

Opening Doors 

Sue: Almost every single one of my summer internships was arranged through Prep. I did the Experiment in International Living after my 10th grade summer and returned as a counselor. Prep arranged for me to  intern at Paul Weiss the summer after my junior year.  It’s probably one of the reasons I went to law school. Through Prep, I had deeper, richer, and more varied experiences than a lot of my classmates at Brearley. 

Diahann: One of my summers in college, I was accepted as a White House intern. I had no idea where I was  going to live, how I was going to eat. I didn’t know if it was possible. Prep helped me figure out how to make it actually happen. 

Sue: You had this incredible set of resources available to you and people who always had your back in a way that someone who just goes to independent school without a program like Prep behind them really doesn’t. To me, it felt like a huge privilege.

Sue: There are very few things in my life where I’ve been affiliated with something for decades. There’s something very special about Prep. It’s probably the longest relationship I’ve had with any institution, period. 

Diahann: We call it “Prep for Life.” We’re comprehensive with a capital C. I’m not sure there’s any part of my career that Prep hasn’t touched. It shaped my commitment to education and public service. I get to wake up every day and do something I’m passionate about. 

Sue: Prep was the tipping point, the moment that changed everything that came after. Prep opened all these doors  to me that otherwise wouldn’t have just remained closed, I wouldn’t have known there were doors in the first  place. I achieved the Harvard and Yale dream. Thank you,  Prep for Prep. 

Sue: It was so important to see role models like you  really blaze through doors. To me, you were a giant in my Prep world. 

Diahann: I was equally overjoyed and also not surprised when someone said, “You know, the new chair of Brearley’s Board of Trustees is Sue Meng.” To your point, young people are going to have dreams like we had that are things they don’t even know exactly how to express or articulate. But it’s easier for them, because they can say, “I want to be a Rhodes scholar,” and a lot of them will because you are. Hopefully, we are helping them dream bigger.