Lakeside School

Teaching, learning, and working with generative AI is a focus in the Educational Excellence area of Lakeside’s strategic plan, Hope in Action: An Empowering Strategic Plan for Lakeside School. Learn more.

When ChatGPT and other artificial intelligence (AI) surged into the public sphere, I was skeptical. Very skeptical. After all, I still relish the moments when I can press pen to paper, whether journaling or taking notes, and see the strokes of my own penmanship, often in myriad colors. To me, there’s an authenticity associated with writing by hand, the visual of my own handwriting affirming that all the ideas and words are indeed mine.

So, learning that AI could be a writing partner (of sorts), or even that AI could write something for me, horrified me. It felt like the epitome of inauthenticity.

Then, a year and a half ago, I met Andrew Howard, a developer who had successfully launched numerous startups, some in the realm of education. Knowing the reputation of Lakeside and our college counseling program, he was eager for our team’s feedback on his newest vision, an AI-powered college counselor that could serve students in under-resourced schools that lack college counseling programs.

Over a few conversations, my perspective on AI began shifting. His vision would indeed serve countless students lacking college counselors. Yet, the more we fleshed it out, the more we started realizing how AI could help all students, including Lakesiders, in strengthening their college applications—in becoming deeply reflective teenagers who can articulate the meaning and the “why” behind their interests and values.

Last year, the college counseling team wrote a series of Inside Lakeside pieces on rethinking how students present their extracurricular activities in their applications. As we explained then, “credentialing” no longer makes students stand out; it’s devoid of personality and meaning. Instead, in these times of grade inflation and test-optional applications, it’s personality that makes students stand out.” If our students are to position themselves as the top applicants they deserve to be, then their applications need to convey some of their personality (most applications are fewer than two handfuls of pages, so it’s unrealistic to expect a student to convey their entire personality). But our students lead very busy lives: they spend so much time doing that they seldom reflect on the meaning behind what they do. Together, Andrew and I realized that AI could help students express authentic personality in their applications by guiding them toward insights about themselves.

While AI had once filled me with horror, it began filling me instead with hope.

Last January, our office launched Addie, the AI-powered college counselor, to help members of the Class of 2026 complete their introductory questionnaires, which typically take two to four hours. We had trained Addie to evaluate students’ responses for personality and thoughtfulness, and to prompt them for more information, when necessary (which was often!). A two-to-four-hour writing process quickly became five or six. While numerous students shared that Addie made their responses more thoughtful and deeper (and after reading their questionnaires, I strongly agree), they also shared that Addie felt more like a burden than a supportive tool amidst their very busy lives. For Addie to truly be useful to students in strengthening their applications, Andrew and I would have to reimagine how students could engage AI more efficiently.

This past spring, Andrew and his team proposed a new model: shorter conversations between students and Addie (15 minutes at a time) that could be scheduled at the student’s convenience, and that could occur by phone (Addie now talks!), text, or chatbot. These conversations would be available to the student and their counselor in raw and summary form, and once completed, Addie would aggregate and summarize students’ strengths, values, interests, personality traits, and more, across all conversations.

Currently, a group of juniors is piloting Addie 2.0, and I’m excited by what the students and I are discovering together. Most students are engaging with Addie on phone calls, some of which produce student responses totaling up to 10,000 words in 15 minutes—more than could be written in two to four hours in a traditional questionnaire—that are being summarized and aggregated to produce more insights into students. Many students multitask as they talk with Addie: one student shared that she often has her conversations while she’s folding her laundry, while another engaged Addie during car rides (of course, only when she’s in the passenger seat!) Students decide how and when to engage Addie, enabling them to fit the AI into their busy schedules and to engage Addie in the way with which they’re most comfortable (e.g., phone call, text, or chatbot).

Moreover, what all six of the students who recently met with Andrew and me shared was how much Addie made them think and reflect. One student explained how she told Addie about how much she loves walking her dog. When Addie asked why, the student responded that she loves the beauty of the outdoors. Addie then responded: “That’s so great. Tell me, what does beauty mean to you?” (That question is even very thought-provoking and challenging for me!) Another student recounted her conversation about a philosophy class she had really enjoyed, one that ultimately turned into philosophical banter that, in Addie’s executive summary of the conversation, revealed a variety of the student’s values and mindsets. A third student shared how Addie asked the simple question, “Why do you like hanging out with your friends?” which made her ruminate deeply, largely because in her busy world, she rarely has time to ponder this question.

As I listened to the students’ feedback and experiences, what I heard upended my initial fears. Addie had challenged each student to think more deeply, broadly, and interconnectedly about themselves than they were used to. It was, essentially, pushing each student to articulate their personality—the myriad thoughts, emotions, and behaviors that make them authentically themselves.

My fervent hope is that these students will be able to use these conversations with Addie—the executive summaries as well as the realizations these talks generate—to help make them unique college applicants whose personalities shine.

Of course, there are cons, and as we continue to develop Addie, accounting for these cons is paramount. Most of the students shared that they not only feel comfortable talking to Addie, but that they also are comfortable telling Addie private details of their lives they might not share with others (this is consistent with preliminary research on teenagers’ AI usage). A question we’re asking is “when is more comfortable too comfortable?” As a result, Addie is now being trained to alert me instantly if she hears thoughts of suicide or other self-harm, or stories of abuse or other physical or emotional harm. Additionally, there will be guardrails around how much and what topics students can engage Addie in. At its core, Addie is a tool to support students’ college process. It is neither their friend nor a companion of any kind—simply Google “people who fell in love with AI” and you’ll be deeply concerned—and establishing boundaries in Addie’s programming to prevent this from happening is incumbent upon our office and school. There are also numerous ethical and environmental concerns that mean Addie should be used with limitations.

Finally, Addie is neither a replacement nor a substitute for engaging with a Lakeside college counselor. While Addie’s capabilities will expand over time—her ability to scrape the internet and social media in mere seconds could eventually make her better at generating college suggestions than humans—she won’t be able to healthily support students through the emotional ups and downs of the college process; give in-depth essay feedback that accounts for the emotions, biases, and preferences of human admissions officers reading their applications; or even accurately and thoroughly tell students whether their applications are strong for specific institutions (most institutional priorities are never enumerated on the college’s website but are instead shared with college counselors, in person, at the numerous networking conferences we attend annually). In fact, if over time Addie can do certain tasks better than humans (such as making college suggestions), I hope that it enables our office to spend more time with students, focusing in greater depth on other elements of the college process.

Today, AI still makes me nervous. Its possibilities are immense, more than the human mind (or at least my mind!) can fathom. But I also see its benefits. My hope is that harnessing AI for these benefits, along with guardrails, will make students not only stronger college applicants but also more reflective, thoughtful, and complex human beings.

Ari Worthman is Lakeside’s director of college counseling. Reach him and other members of the team at info@lakesideschool.site.