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How Margaret Motto empowers students to find the right fit

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Margaret Motto always saw herself as a helper, but she didn’t always know where that path would lead her. Now, as the college and career counselor at Pierson High School, she focuses on helping students reflect on who they are and what they want to be—not just for their college applications, but for life.


Tell me a little bit about where you grew up and the role education played in your childhood.

So I grew up on the North Fork here, and my mom was a high school math teacher. Interestingly, she has a master’s degree in physics, while my father had an eighth-grade education. They met at a Catholic singles dance. He passed away when I was very little, and my mom had to raise five kids by herself.

I knew education was important because my mom was a teacher, and because she was a single mom, I wanted to make her proud. I think it was hard for her, but she taught us the value of knowing your purpose, your job. My job was to be a student, so I tried hard. Plus, I enjoyed school—I was the kid who volunteered to read, and I liked to participate and stuff. I’m one of those geeky people who walks into Staples and smells the notebooks, and it’s like, “Oh! The possibilities!” That’s how I feel about school, and I still take classes for fun.

Did your mom inspire you to become an educator?

No, but she’s the reason why I’m here. The truth is, I never wanted to be a teacher. I didn’t see education as a career option, even though I often found myself in positions where I’d be leading a class or program or explaining something to somebody else. But being a teacher wasn’t my shtick, and I actually don’t think I’d be great in a classroom every day. I always saw myself as a helper; I just didn’t know how to make that work in a school until the opportunities fell in line.

I went to the College of the Holy Cross, a Jesuit school in western Massachusetts, and I joined the Jesuit Volunteer Corps when I graduated. It really felt like a way to give back and be a woman for other people, so I moved to San Antonio, Texas, and helped run a social services office that provided food, clothing, and support. I especially liked working as a youth counselor there, but I didn’t know what that meant. After, when I was thinking about what I wanted to do with myself, my mom said, “Well, why don’t you go to grad school?”

So I went to grad school in New York City to become a counselor. I was on the fence about whether to do a mental health track or a school counseling track, but my mom encouraged me to specialize in school counseling and get the certification. So I did. I worked in career counseling at Siena College and Fordham University for a few years, and this position came right when I was thinking about using my certification. But if you asked me when I graduated from high school whether I’d come back and work in my hometown—no! That wasn’t me; I wanted to go and see and do. But I feel like you end up where you’re supposed to be, and I’m so thankful for my mom. She’s a pretty special lady.

Providing guidance: “I can’t ever tell a kid what to do,” says Margaret. “I always say, ‘I advise, you decide’—but if you ask my opinion, I’ll tell you my opinion.”

What does the guidance counseling office look like at Pierson?

We’re a school counseling office that has a college counselor and a high school counselor. The office has morphed in the eight years I’ve been here, but the high school counselor and I have a great relationship. I meet the students in ninth grade in a college and career prep class, and then the high school counselor and I will work together. It’s so great to bounce ideas off somebody else, and I’m lucky to have him.

How would you draw the distinction between the different kinds of counselors in high schools? I imagine it’s probably a pretty common point of confusion.

The high school counselor is looking to advise students on their time here—getting the most out of high school, squeezing all the water out of the sponge. As the college counselor, I focus strongly on post-high school planning. My counterpart wants to make sure they graduate, and I want to make sure that they think about what’s beyond high school. I don’t really care what that is: If they want to go to work, if they want to join the military, whatever it is they want to do, I’m more than happy to support them. But I want them to have a plan. Everybody needs to have a direction so they find something fulfilling.

Whatever it is they want to do, I’m more than happy to support them. But I want them to have a plan.

A lot of kids go off to college and then come back. It’s too expensive, maybe they should have taken a year at community college, maybe they should have done an apprenticeship instead. And that breaks my heart. So I ask the students to think about who they are and who they want to be. A lot of high school is about posing, like doing something because your friends are all doing it, and I try to get them to do some self-reflection: What do you want to do? Where do you want to be? It’s when we can get to that deeper conversation that I can help them find the right fit and get to the right place.

Because of how our office works, students get to sort of reintroduce themselves when I work with them one-on-one in eleventh grade. It’s nice to know that you have the ability to reinvent yourself, and I think the whole world should know that you don’t have to be a label somebody else gave you. You can be whatever you want to be. And if there’s only one person who tells you that, I want to be that lady.

A school by the harbor: Pierson is located in Sag Harbor, a historic village in the Hamptons. Although the area is famous for its luxury homes and properties, the population that lives in Sag Harbor year-round includes both higher-income and lower-income families.

Walk me through what a typical day looks like for you.

There is no typical day in guidance! As a counselor, I don’t have a schedule. I have a contract that says I have to be here at certain times, but a typical day consists of doing tasks I need to get done and seeing students in between. The fall is usually very busy with appointments for me, and leading up to college applications, it’s insane. School starts on September 6, and on September 8 I’ll have a college application night in the auditorium for parents and students.

In the mornings, I can usually find a spot to make a cup of coffee and look at my calendar, even if I have to get in early to do it. I might go to a classroom, depending on what’s going on, and I also do one-on-one appointments. The benefit of being in a smaller school is I meet with every senior at least twice, and other students can come in when they want. I’ll go over their college lists, connect them to researching schools that might be a good fit, help organize the materials that go out to colleges, things like that. I spend a lot of time writing letters of recommendation.

What percentage of the graduating class do you usually write letters of recommendation for?

I write a letter for every single student. Most colleges require a teacher endorsement as well as a counselor endorsement, which goes along with a statement from the high school—the percentage of our kids who go to college, our average SAT score, that we’re an IB school, that kind of thing. I create the school profile and documents, and then I plug in the information for each student, like their ranking and their classes. And then I write the actual letter. It’s all on the computer now, which is different from when I went to school.

Good letters of recommendation are not regurgitations of a resume; the colleges and scholarship committees already get those. I want to be able to tell a story about a student and include anecdotes that really reflect who they are. That’s why it’s so important for me to spend time with the kids and get to know them. People sometimes assume that I have a template for recommendations, but I don’t. I’m sure my letters all sound similar, but that’s because they’re in my voice. I want my letters to be personal, and that requires building trust.

Picture yourself in college: Over the summer, Margaret asks recent grads to send her photos of them on their new campus. Then, she shares the photos at college application night in the auditorium. “When they see photos of graduates at places like the University of Hawaii, Queens College, Sterling College, they can say, ‘Hey, maybe that could be me.’”

How do you go about establishing that trust, especially when you’re working with so many students?

Listening plays a huge part, and so does remembering things. And I share my own experiences and vulnerabilities, too. For example, I’m terrible with names, especially with the freshmen, and when it happens I’ll just be honest and say, “I’m sorry, I forgot your name.” Telling the truth is always easier than making up a lie, and not every experience is a great one.

I also don’t judge. When a kid comes in and tells me that they saw someone doing this drug at a party, or that their boyfriend cheated on them—they’re sharing something very personal, and I make sure they understand that I’ll keep it confidential. There are certain rules that counselors have to follow and I’m a mandated reporter, but they can tell me about what’s going on in their lives. When you establish that with one student, they’ll tell their friends. Then you’ll get three kids in your office, and all of a sudden you have a lunchtime crew of kids who come in during lunch and just want to hang out.

That’s awesome, and I want more time where I can just sit and be like, “Why do you doodle on your shoes?” “What’s your cat’s name?” I’m such a chatty person it can be hard to tell sometimes, but most of counseling is listening. If you listen for the right things and you ask the right questions, you’ll find that kids desperately want to talk. And you’ll hear from them.

On the flip slide, what are some of the challenges to connecting with your students?

So many things compete for students’ attention. Even when they’re not in school, they have very rigorous schedules, and where we are geographically doesn’t always help. I had a girl a couple of years ago who was a competitive Irish step dancer, and she had practice almost an hour away every day. She loved it, and there was no way you could take her away from it. But between their schedules and things like electronics, it can be really hard to say, “Well, could you contemplate your college application essay a little more?”

It can also be hard to get the right message across to the student who doesn’t participate in clubs or have an activity after school. Like, don’t do volunteer work because it looks good on a resume; do volunteer work because you like it and because it’s helping someone else. But the kids will see me and think that I’m telling them to volunteer or join a club or get a job because it’ll help with college applications, when it’s really about preparing them for life. Getting them to understand that preparing for life is a good thing—that’s the challenging part.

If you listen for the right things and ask the right questions, you’ll find that kids desperately want to talk.

What happens if that message doesn’t make it through?

I’ve had hard cases when a student doesn’t graduate and there’s nothing I can do. I can’t do the work for them. I can’t show up to school for them. This is their job; I already went to school. But—and I think everyone who works with teens can relate to this a little bit—they don’t always realize that there’s more than just the here and now. That there are more important things than having the right sneakers, going to the right party, getting replies to their texts. And when they don’t see that, they don’t always make great choices, and it’s sad because I don’t know if they’ll follow through in the future.

Sometimes students will fail a test or their SAT score won’t be so great, and that’s okay. I always say, it’s not really failure unless you give up. Kids don’t always appreciate the message, but I try to reach every single one of them. I want to show each of them kindness and positive regard, even if the student isn’t kind to me or doesn’t want my help. I want them to feel care, even if they reject it.

Coming together: Despite their different backgrounds, students at Pierson often bond over shared activities. “There are times when it’s hard or confusing, like when it comes to affording college or class trips, but they grow up together. They find a happy medium,” Margaret says. “The thing that unifies these kids is that they all need emotional support, no matter how much money they have.”

Sag Harbor is in an area known for its wealth, but you also have a lot of students who come from disadvantaged situations. How broad is the spectrum of needs across the families you work with?

Sometimes the higher-income, higher-education families will have certain expectations. I had a student a few years ago whose family was really focused on Dad’s alma mater, even though it was pretty clear that she wasn’t going to get in. My mentor, who was actually my own college counselor in high school, said to me, “Be as supportive to the student as possible and engage the family in data.” And that was the key. I shared the acceptance rate and the average test scores; of course that wasn’t all she was, but we needed another plan. I think that helped provide validation for the student, too—knowing that a lot of people didn’t get in to that school, no matter what her parents expected.

Be as supportive to the student as possible and engage the family in data. That’s the key.

And then you have the students who don’t have that familial support, where I’ll never meet the parents. I’ll send them everything that their kids get, because I want them to have that information, but will they read it and pay attention? The higher-income families, they read it all. But the lower-income families don’t always know what to do or how to help. And while the wealthier families often have one parent at home, the parents who work in landscaping or other blue-collar jobs get home significantly later than their kids. Texting can help, but it isn’t always possible for them to be involved in the same way.

Empowering students to be themselves: Despite Margaret’s role, families at Pierson sometimes hire private consultants for college applications. “I’ve seen a lot of essays that were not written by students. I’ll be like, ‘This doesn’t sound anything like the student I know. Where’d this come from?’” Margaret says. “It’s supposed to be their story, but it’s been manipulated by someone else. I want the kids to be authentic. I’m not a big ‘Fake it ‘til you make it’ person; I’m more ‘Be you and strive to be better.’”

Earlier, you talked a little bit about using computers for recommendation letters. How else do you use technology during the day?

I finally gave in to the tech guys last year and got two monitors for my office, and that’s very much an aid. I use Naviance, which is a electronic system that helps students search for colleges and keep track of their application materials. I look up a lot of information and read a lot of blogs. Google Docs is a gift, especially since the Common App will be integrating with it this year. And I keep Google Calendar open since that’s where everything is layered in—time in the computer lab, college visits, community meetings.

I’ll have Remind open, too, which helps me with planning. I love that I can set up everything in advance if I want, because I’ve got a lot going on. I might have fifty some-odd colleges coming to visit this semester, but if I schedule all of my messages now, I’m all set.

How did you first learn about Remind?

My sister teaches high school English at my alma mater, and she’s also the musical director there. Since I have some history with theater, I help out with whatever she needs. A few years ago, she was using Remind to communicate with the cast, and I really got to know the kids in a different way. I was like, “How come I don’t have this?” And she was like, “I don’t know, why don’t you?” That’s when I started using it.

At first, I felt a little stiff. I sent very simple messages, like “Come to the meeting.” Now that I’m a few years in, I’m so much more comfortable. There’s really no one right way to do it—I’ve hit send too early on a couple of messages, but there are so many right ways to use Remind. Kids love it when I do emojis, for example, so I try to be a little cheeky when I send them stuff. And what I love is sending pictures, because sometimes those really are better than words. I’ll send a picture of me standing in the computer lab by myself to remind them of application workshops, PDFs of scholarship applications, things I see when I visit college campuses. I hate to think of myself as marketing, but in a sense, that’s what I’m doing. I’m trying to keep them focused so they can get their stuff done.

Relationships are paramount: “I love when I can see something in a student that they might not have realized was there,” Margaret says. “There was one kid who’d had trouble at the beginning of high school, and he didn’t really think he was going to go to college. But then I saw him eating lunch with a group of kids who were non-native English speakers, and it turns out that he was helping them with their vocabulary and really looking after them, even though nobody seemed to be looking out for him. I thought it was amazing that he didn’t give up on them, so I didn’t give up on him—and he texted me this summer that he’s going on to college-level work at the community college.”

Have you noticed any changes in the way you interact with students and parents?

It’s changed everything. I’m somebody who could very easily live and breathe this job, but I have a life outside of school that I like. Remind lets me meet the kids where they are—they have access to me in a way that’s more comfortable for them, but I can have my own time. I used to be the person who was like, “Ugh, stop invading my space!” But this doesn’t feel like an invasion of space. If I get that text from a kid when I’m on the ferry home at the end of the day, even when I’m tired or have stuff to do in my own life, I will respond. If it can wait, I don’t need to reply. I don’t know how I would have done this job without this technology.

Being able to communicate with families directly is great, too. Parents often have several phone numbers in our school data system, so they won’t get texts from the school if their landline is listed as their primary number. And it’s helped with setting up appointments. Before, if a parent was frustrated or distressed and wanted to see me, they had to call the school and wait to be connected to my office—and I might not have gotten their message for hours. But if they text me, I’ll see it. And chances are I’ll reply and say “I’m free at noon,” or whatever it may be.

You mentioned that you’re especially busy in the time leading up to college application deadlines. How does communication play a role in getting students to that finish line?

I’ve always had a personal goal of getting every kid to apply to at least one school by winter break, but a few years ago, the number was only at 50 percent. I remember sitting down with the principal and trying to figure out was going on, if it had something to do with my communication style. But by December 1 last year, I had more than 80 percent of the class apply to a school, and that was so rewarding. I was so proud of us.

I really believe that Remind helped with that. It’s shocking how well it worked, and I’m hoping it’s the same this year. It just makes my life easier, and it makes the process easier for the kids, too. I always tell the students to get their applications done so they can enjoy their senior year. Imagine going back to visit yourself in your last year of high school—when your application is out of your hands and you don’t have the answers yet. It’s just such a good exhale. And now you can enjoy the senior stuff: your clubs, your activities, your job, whatever it is you’re doing. Enjoy it, savor it, and we’ll deal with the results when they come in.

The kids have access to me in a way that’s more comfortable for them, but I can have my own time.

Right—there’s so much going on at this point their lives. What do you hope that your students get out of your time together?

I hope they feel empowered. I think about my mentor, Joyce, who passed away this summer—she was a wise woman who supported me not just in high school, but throughout my life. She helped steer me to my college, she was the one who mentioned the Volunteer Corps to me, and when I called her to tell her that I got this job, she said, “Come over.” She was just a force to be reckoned with, and wow, did she teach me things about college counseling.

But what I learned from working with Joyce that I hope I can pass on to the students is this: You are in control. You can seek the answers by asking questions about who you are and what you want to be, even when it’s hard or scary. I want the kids to embrace these questions and feel empowered to make great life choices, because there’s some place for everybody.


Interview by Taylor Chapman, who previously taught Spanish at a high-poverty high school in North Carolina. Photography by Patrick Michael Chin.