Hawai'i Preparatory Academy's Podcast
Hawaiʻi Preparatory Academy (HPA) is an independent, co-educational K–12 day and boarding school in Waimea on Hawaiʻi Island. Rooted in place-based and experiential learning, HPA offers a rigorous academic program grounded in community, curiosity, and care for place. The Hawaiʻi Preparatory Podcast shares stories and perspectives from students, educators, and alumni, offering insight into life, learning, and opportunities at HPA — both in the classroom and beyond.
Hawai'i Preparatory Academy's Podcast
College Counseling Program at HPA
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Get an inside look at the college counseling experience at HPA with co-directors Andrew Kelsey and Cindy Montgomery.
In this podcast episode, they share a thorough overview of the program — from testing opportunities and individualized support to their approach in guiding students through the college process. They also offer valuable advice for students and families navigating the journey ahead.
Hi, my name is Andrew Kelsey. I'm the director of college counseling. A little bit about me. I grew up in Virginia, and my early childhood was in Thailand. I went to a boarding school in Virginia, and I think boarding school really changed my direction in life. I met a lot of friends who had different ideas, came from around the country and around the world, and I ended up going to Vanderbilt University. I got my undergraduate and graduate degrees in English. And after college, I feel it was a divine intervention. I was going to go to law school, but I read about teaching English in Japan. And I ended up going to Japan and I loved it so much. And I fell in love with teaching, and Japan brought me to Hawaii. And I've been at HPA about 30 years, and most of those years have been in college counseling.
SPEAKER_01My name is Cindy Montgomery, and I am co-director of college counseling here at HPA. I first started back in 2006, so this will be my 20th year working at HPA. It's been a wonderful journey, and I've been lucky enough to also have my son be a student here since kindergarten. Finding HPA was kind of an interesting journey in and of itself. I uh grew up in New England. I'm a Connecticut girl who had the good fortune of living in Japan for five years after I finished college. And after that, I came to Hawaii to get my graduate degree and through a series of events, ended up coming to the Big Island and meeting Andrew Kelsey, and we've been working together ever since. It's been a wonderful ride.
SPEAKER_00I think what makes our program unique is a combination of expertise, experience, and a high level of care. We really genuinely love doing what we do. We love working with our students and getting to know them. And so I feel that that balance between really knowing what you're doing and always trying to teach students, but caring about them as individuals and giving them all the time that they need to work through the process is our special sauce.
SPEAKER_01I think there are several components that make our college counseling program unique at HPA. Probably first and foremost is that we are very student-centered in a very casual way that I think puts students at ease. Part of that is inspired by our boarding program with 50% of our students living here on campus. This really does feel like home to our students, both day and boarding, and I think that comes over into how our relationships with them are. They feel very comfortable with us and they share lots of things with us, and that really helps to cement a college counseling relationship with them and also help us really advise them in the best way as they go forward in their college application process.
SPEAKER_00I think what we do when we're helping students match with schools is we start the process by thinking about yourself. What makes you happy? What's the best environment for you? When are you doing your best work as a student? What kind of learning environment do you want to be in? Because a lot of times our students aren't really sure about colleges, it's all new for them, but they do know themselves and they do know what they want. So we try and bring that out and then give them confidence in knowing that that starting point is all they need. We can help them find schools and we can help them build a list with not just one perfect school, but many perfect schools based on who they are, what they want to do in life, and what makes them happy. In the freshman and sophomore year, there's programming for college counseling. It's usually about college fairs and college visits and some big presentations. We really begin in the junior year where we have workshops and individual meetings. So in the junior year, we'll meet each junior about four times, and then we have many workshops, everything from writing the college essay to building a list, to searching for schools, to using score, to creating a common application. And our goal in the junior year is to front load a lot of the activities that students need to do senior year so that when they come back in the fall as seniors, they're really just revising their essay, revising their college list, and applying to college in the fall.
SPEAKER_01As part of the support program in junior year, we also have testing here at HPA. In addition to the PSAT that we do for the entire school from freshman year, we also have the SAT and the ACT offered as school day tests for all our juniors, which means that by April of junior year, all juniors know what their score is on those two standardized examinations, and they know which of the two they might likely move forward with if testing is going to be part of their application plan.
SPEAKER_00So sometimes students come to college counseling and it's almost like they stumbled into our office. Um they really have no idea about the process, what they want to do. They sit down and we often laugh, you know, it's like where to start, right? And so when you when you look at it that way, that it's natural for young people maybe, maybe not to really have thought about college and things like that. And uh that's disarming for them to see that it's not a problem. They're they've got plenty of time. So when they don't know, I think one of the things we do is help them be comfortable with that uncertainty. That's natural. And sometimes students that come in they tell us exactly what they're gonna do and what they're gonna study. When we check in with them a few years later, they're doing something different. So that's life, right? So letting students know because we're a little bit older, letting them know that life is a journey and a mystery, and we don't have all the answers. You just do your best, make your best effort, and um, things take care of themselves as long as you're working hard and approaching things with a good attitude. When we have a student that is already decided on a school when they begin the college counseling process, we're excited for them because it means they've done research, they know what they're looking for, and they've found a target school. Uh what we do at that point is we ask them what is it that you like about this school? What excites you about it? We take notes and we think about it, and then we can expand that list to introduce them to similar schools. And what we're always doing is building a range of admissions selectivity. So sometimes the school that they know is uh very famous, very selective, and maybe challenging to get into. But the qualities that they like in that school as they describe them for themselves is where we can start and expand that list to give them great opportunities because there really isn't one perfect school. There are many schools that match those criteria, and so we help them uh find those schools and get excited about those other schools too.
SPEAKER_01I think that HPA's academic program manages to find the perfect balance between challenge and uh support. Uh, and I really mean that because I've watched it happen as a mother as well as a college counselor. I love that HP students can feel safe to explore different academic courses and also try to challenge themselves through advanced placement classes or experiential learning and still have a lot of support within the school system to be successful in those endeavors. I think that having the ability to do high-level research right here on campus or using our beautiful natural environment to explore research is a really special thing. Uh, when our students do, our students tend to get very impressive college placements, even though they haven't made high school all about college. And I think that's because they're just enjoying high school by digging deeply into the things they love and figuring out how they want to use their time and talents in the world. And by virtue of doing that, by the time it comes to explain what they want to do when they get to college, their answers tend to be very specific, very authentic. There's a lot of excitement in their writing and what they want to do. And colleges feel that. They feel that and they understand that these students are going to be contributors when they get to college.
SPEAKER_00I went to a very well-known boarding school on the East Coast, and it was a traditional college prep, a lot like HPA on some levels. But what I noticed when I started at HPA was not only do we have honors and AP classes, which are very important, but we have place-based courses that focus on the big island, Hawaii, Hawaiian studies, language, and we have other courses like independent science or capstone classes that allow students to really expand and drive their learning. So that combination of traditional college prep, rigorous academics, plus creative courses that the students drive creates both a well-prepared student and somebody who's going to take initiative in their learning and be a lifelong learner. So that combination of strong foundation and then a lot of room for our students to drive their learning, colleges see that and they're really looking for that type of student.
SPEAKER_01I think if I was going to give advice to our students about the first steps to take in starting the college application and exploration process, would be to just start with themselves. There's a lot of voices out there, whether they come from family or from society, or just your aunties and uncles that want to know what you're thinking about college. And that can sometimes block out what a student is actually wanting. And so I always encourage the students to really think about what they want to do.
SPEAKER_00When HPA students start the college journey, we always give them this piece of advice. It's your journey, it's your process. So don't let other people take that away from you. And by really driving the process yourself, you're going to feel ownership for your college choice and your college journey after high school. I think that's really important. We're going to help as much as you need, but you should be in the driver's seat for this. And then the second thing which is tied to it is have fun with the process. This is really one of your first adult experiences. So if you can laugh a little bit, if you can celebrate small successes and things like that, you figured out one of the most important things about being an adult, that life can be hard and challenging, but you've got what it takes. So I think a lot of our advice is giving students the confidence in themselves so that wherever they go, they can be successful. And in the end, it's not really about the schools that they attend, it's more about what they do when they get there. So starting with that.