Andrew Wintner Interview

In times of great change, a transition in leadership can always be difficult to adjust to. At WESS, we’ve gone through a number of transitions in a short time, one of the most notable being the arrival of a new principal. Over the past few weeks, many of us have had the chance to get to know our new principal, Andrew, as we've seen him around the hallways and throughout the school. In this interview, we’ll take a closer look at his vision for WESS and the exciting changes he has in store for the future. From his personal background and experiences to his aspirations for the school community, Andrew shares insights on what drives his leadership and how he aims to foster a dynamic and inclusive environment for students and staff alike. Read on to hear firsthand about his approach to education, leadership, and the road ahead for WESS.

What are qualities at WESS that you easily adapted to? 

I think some of the qualities that were easy to adapt to are things that I wholeheartedly believe in such as expeditions and crew and being on a first-name basis with teachers. I think there's a lot of student-centered ideology. That's been really easy for me to grapple with because I believe in it wholeheartedly. 

What are some qualities that you may have had a harder time getting used to?

I'm not gonna make a whole lot of friends with this one, but I think what's been hard for me to adapt to is … bathroom culture, timeliness to school.. timeliness to class once in school, and I might as well go for it, right, for having the conversation… I don't as a principle, I don't condone cursing. I understand cursing.. I don't understand the amount of, like , ostracizing language that I hear on a given day. That is deeply harmful and hateful by nature. 

Students have often seen you outside in the halls during passing periods and at the end of the day. What have you learned or noticed about WESS during these times?

Best students in the five boroughs. You are all like these wonderful, unique people. I just think your stories are very interesting to me and it brings me great joy to hear them. I also think you're a uniquely capable group of young people. I've been at a lot of schools where it's not a knock on those schools, but it's like, we need to do X, Y, and Z and then it never gets done. and like, here it's like, we need to do X, Y, and Z, and then there's like 50 students who are willing to do X, Y, and Z to get it done. So it's humbling to be part of that. 

Is there any advice you received early in your career that you still use today?

There are two quotes that I think deeply, deeply, deeply influenced me and they basically mean the same thing. One of them, my mom, used to tell me this and it's not her saying, but it's a saying that she'd always pass on to me: No one cares how much you know until they know how much you care. Meaning you could be the smartest person in the world, but if people don't think you actually care about their well-being, you're never gonna be able to pass that intelligence on. And then another thing that's been really deeply influential to me is a Maya Angelou quote, and I'm gonna misquote it here, but it’s basically “People will forget what you tell them people will forget what you teach them, but people will never forget how you make them feel.” So I just think like, my general vibe as a human being is to spread joy and I think like that's what I want to continue to bring to the space as much as possible. 

Do you think outward-bound schools successfully prepare students for post-secondary life as much as other schools do?

I think it's a different way to approach students for postsecondary life, right? And I think I believe in it, and that's why I'm here. I think just like anything else, the reason Outward Bound works at WESS is because it's done well, whereas Outward Bound in itself isn't the thing that prepares students for postsecondary life, it's the successful implementation of it. So, like, this school is amazing because of the teachers, the families, and the young people that comprise it, and Outward Bound is an outlet to make sure that their genius is centered. Another quote that I love is “Good instruction is good instruction is good instruction,” Which means the most important thing that will drive your post-secondary readiness is strong teachers. I think that's true whatever school level or program you are in. I think Outward Bound is a great way to bring out teacher creativity to support students, and I think it's fun too. 

During COVID, we stopped doing some of the fieldwork, and I know we are kind of back to some fieldwork now, but we haven't done a ton of it, so now that COVID is mostly behind us, are there plans for bringing fieldwork back?

The answer is yes. I think what we're trying to do is streamline the process of each grade, getting the same amount of fieldwork, whether you're in 6th grade or 12th grade. Not that they are the same expeditions, but the number of times that you have to showcase your learning by doing field work and then doing POLs and expeditions need to be equitable across the grades. So we’re thinking about how we outlined the different expeditions and fieldwork that's happening by each grade and kind of creating a vertical map to make sure you're not doing the same thing twice and to make sure that it gets slightly more difficult each year so it feels like what you're doing in 12th grade is more difficult than what you were doing in 11th grade, 10th grade, and so forth. But the short answer is yes, we’re going to reprioritize our roots in EL and Outward Bound and make sure that the expeditions happen, and fieldwork prior to that. 

We know that the AP curriculum is super strict and different from the Outward Bound Curriculum, so how do you plan to align the curriculum so students are prepared for AP exams while also continuing to learn in the WESS way? 

There is not one answer, right? It's not like I can say this one sentence and it's going to be the thing that happens, but I think it comes back to this idea that good instruction is good instruction is good instruction, and I do think that as a community, we do have the capacity to take the best parts of being an AP for all school and the best parts of being an Outward Bound school and make sure that we get to marry those two together. So, you're getting the rigor and structure of AP with the rigor and structure of Outward Bound in a way that is beautiful. The thing that's tricky is, as we all know, the college board has very specific things that you need to teach in very specific signposts of when you need to learn them. So I think, just transparently, WESS and many other Outward Bound and AP for all schools are figuring out how to navigate that because we want to make sure that we support teachers and implement an AP for all curriculum that is Outward Bound by nature. 

What's one thing about your background that might surprise the students in WESS?

I don't know. I guess I really don't know what my image is, so I don't know what would surprise people. One fun fact is I did a 50-mile race through the Grand Canyon. Another fun fact for me is I spent three weeks in a Czech hospital; maybe that's not fun, but it was interesting. 

What's your favorite school tradition, and how do you plan to keep it alive or change it?

Yeah, what do you guys think of no-school Fridays? I'm just kidding. My favorite school tradition I do is something I want to do at WESS and is also something that I used to do at school pride days, where there is a school day where everyone wears their WESS gear. I’m not trying to mute individuality, I'm not trying to mute creativity, I'm not trying to take away anyone's fashion, but I do think that the one thing that everyone who walks through these doors in the morning has in common is that we are a part of the WESS community and I think it's really powerful and beautiful to see everyone come together around a common cause, which is supporting WESS. I'm not saying WESS is perfect, not saying WESS can't grow, not saying everyone even loves WESS, but I think that the way that you start to build school spirit is by starting to have some of those outward things. Some other things to put on people's radar.  I think there's a great need in this school for us to have grade-wide town halls, crew lessons, whatever you want to call them, but I think there needs to be a time about once a month when everyone is coming together, not to be like lectured or told rules but to have fun as a grade team and get to know people and do things that bring joy to the space. The last thing I’ll say is that I am a very competitive person, I do think it's kind of fun to have a competition across crews, like I know there's a crew Olympics. This is my last one, and this is not a this year thing, maybe not even a next year thing, can you guess what we had between passing periods instead of bells? Music. Each crew would get to pick 5 songs they wanted to hear in the space, so your crew would pick a Monday song, and then like you get one week a year. It's just a way to express identity. The issue and the only downside of this is sometimes it creates a little too much energy in the hallways when we’re trying to reduce it. I think it's a great way to celebrate identity, and also, music is fun right?

If you could describe WESS in three words, what would they be?

Intelligent, caring, unique 

How do you think technology will impact the way schools operate in the next decade?

I think technology is always constantly evolving. I think technology is something that should not be shied away from. it's something that should be taught into, right? I'm just a firm believer that we can tell people to put their cell phones away, but the real thing that we need to do is teach people why it's not healthy to be on their cell phones 24/7. I think there is responsible use of technology. In terms of AI, I think a lot of people have strong feelings about AI and I'm not here to try to switch anyone's opinion, but I just think in times of any great revolution or change, it's often met with fear and met with “this is so different than what we are used to.” So to not support young people in knowing how to use AI feels like an undue hardship to you all, right? It wouldn't be fair to say we are preparing people for post-secondary life and not talk about probably the hottest educational issue that is out there right now. I think there are appropriate ways to use AI and I think there are inappropriate ways to use AI, just like there are appropriate ways to use the internet and inappropriate ways to use the internet. So to me, it's not so much that AI is a good or bad thing. It needs to be implemented with clear expectations of how you use it. and I think one thing I can share with you is there are a lot of really passionate people internally at WESS that are working on a very clear AI policy, so it's not just some wishy-washy thing. Like there are some classes where you can use AI to write your essay, and there are some classes where you can't. I think there needs to be clear parameters to center student thinking. I will say I do worry about how I don't want genius to be muted and uniqueness to be squashed by AI. This all goes back to the education piece, like how do we give AI prompts so it brings out our own voice and gives us a draft, and then we can take the draft and build on. so it's amplifying our work rather than just taking our work away from us. 

In your opinion, what is the biggest challenge students face today and how can we work as a community to address it?

I think I say this all the time, I'm so happy I didn't have social media when I was your age. I think it makes life just way more difficult in so many different ways, like from social anxieties to fearing that you might say the wrong things at the wrong time in a way that is really harmful and has a large impact on you and your community. I think it's also really not safe. I think sometimes people perform on social media and do unsafe things they wouldn't normally do if it wasn't being broadcasted to the rest of the world. I also think just the way that people interact behind the cloak of social media, meaning they feel emboldened to say things they might not say if they didn't have that platform to do it, is really hateful and harmful and spreads a lot of malcontent through middle school and high school. The other thing I would say is, this is a good and bad thing, when I was growing up, I didn't have all the information of the internet at my fingertips right? So, I think that that power comes with great responsibility and sometimes I feel like it must be really hard to be a young person and know “I can just look something up online” or use AI to figure this out. It brings up a ton of pressure to you all because I think there's an expectation that you have all this information that maybe is unfair. 

This is more my projection on my own personal experience, but I do think there's a lot of pressure on high schoolers in particular for what their post-secondary life is going to be like, and I do worry that I want people at WESS to enjoy WESS and love high school and love the experiences in the memories and they're learning in classes. I'm not saying to not have a rigorous program to support your post-secondary life, but I worry if all we're doing is using high school as kind of a springboard to post-secondary life that it might just pass us by. I think in high school when I was coming up it was just different, I didn't even know that I had a transcript until I applied to college. It wasn't the same thought process as these are things that are going to help you when you're applying to college which I think was good and bad. I think there's probably a happy medium in between where we can look ahead to the post-secondary while still enjoying life here. 

What do you think and hope students will remember about their time at WESS when they graduate?

I think there's a lot of things people will look back on and have enjoyed, but I think coming back to the Outward Bound piece, I think one thing that makes WESS very unique is like, I hope they remember their expeditions. I hope they remember the fieldwork they did. I hope they remember how it felt when they were doing a Presentation of Learning in front of people and there was an audience. I hope those are the things they remember. I also think there's a great pride in graduating from WESS because it's a 6 to 12 school,  and a lot of people have essentially grown up at WESS, if that makes sense. They've matured from middle schoolers to high schoolers to post-secondary life. We all know how different a 6th grader is versus a 12th grader, so hopefully, they'll remember maturing at WESS, coming-of-age for lack of a better term. 

While change can be stressful, especially change in administration, this interview really showed us how prepared Andrew is to help WESS grow into the best version of itself. We thought Andrew’s responses to our questions showcased how prepared and eager he is to support WESS and start a new chapter of growth for our school. His responses to our questions emphasized how prepared he is for the role and his investment in our community. As a small school, WESS is very tightly bound to our core values, and it is clear that Andrew has joined our community prepared to stick to what is important to WESS. As a 6 through 12 school, we often face a unique set of challenges, and it is clear that Andrew is prepared to overcome obstacles that would not necessarily be found in other middle schools or high schools. The constant battle between education and technology like AI has become a more mainstream problem in recent years, and when we asked Andrew about his plans to integrate this new and upcoming technology, his response about acknowledging AI as something that can no longer be ignored by schools demonstrated to us how he is ready to take on these new situations. The world can be a scary place, and it is evident that Andrew is aware of these struggles and is prepared to make WESS a safe space where every student will be valued. We found this interview incredibly insightful and insightful in Andrew’s plan for WESS’s future. We are excited to see what's in store for this new chapter of our school.