Explorations in Critical Thinking in the Face of AI
My job is to widen college and career access for young people who are furthest from opportunity. I came into the AI Together Community of Practice (CoP) with Lead by Learning with the understanding that our students are going to have to be prepared to work, think, and have relationships in a world that is AI-saturated. So, educators need to know how to support that process, instead of sending them out only with traditional reading, writing, and calculation skills that won’t help them thrive.
However, I joined the Community of Practice with Lead by Learning hesitantly. Previously, my only experience focusing on AI was a very unhappy one, screening students’ capstone papers for AI-generated text. In Oakland public schools, all seniors complete a 10-page Capstone research paper, an action project, and a public presentation. All the teachers at the school are involved in Capstone paper and presentation grading. Whole school Capstone grading also pushes us to align across content areas and grade levels in Capstone skills such as critical thinking and formulating an argument with valid evidence. When students skip the scaffolds teachers use to guide them through their research, analysis, and writing process, and just feed their topic to AI, they bypass the competencies that Oakland has established as qualifying students for graduation. This left me asking: Are these competencies still relevant?
In our semi-annual pathway advisory board meetings with industry professionals, we ask this of leaders in the fields connected to our students’ pathways. What are the skills that make people successful in this field? Our industry partners say: we’re looking for people who can reason, explain, establish purpose, and connect with others. AI can help with technical skills, but those are easily learned. The real thinking and relating capacities are not, and AI is not helping people in this critical area.
In joining AI Together, I wanted to explore the potential of AI to support student learning and challenge myself to not just reject it as a barrier to student reading, thinking, and writing. Since I was working on organizing summer opportunities for students, I started out with a hypothetical prompt on Chat GPT, focused on students who weren’t going to do one of the many internships we connect students with.
I’d like to offer high school students an engaging set of self-guided materials to support math literacy and reduce summer learning melt. It would be great if students could engage in these activities with family members — younger siblings, parents and grandparents, so that the whole family has the opportunity to connect in math literacy activities. Perhaps there could be a scavenger hunt kind of component, involving family members in exploring their community (Oakland, California) as part of their engagement with this mathematical experience. I have in mind math literacy that is empowering, helping people make sense of their world along the lines of Paulo Freire and Bob Moses.
Chat GPT surprised me. It foregrounded the framing in liberatory pedagogy that I was looking for, and outlined activities and conversation starters focused on gentrification, environmental justice, wage analysis, food justice, and transportation, for example:
- Is time a form of wealth?
- Who has the longest commutes?
- How does commute time affect health or family life?
I liked what it generated. But what astonished me as a first-time Chat GPT user was how effectively it addressed MY proclivities. It commented: “You’re building something that treats Oakland youth as intellectuals. That’s very much in the lineage of Bob Moses — not remediation, but liberation.” The affirmation of my intention was touching. It made me realize how easily AI can substitute for a partner in dialogue – or a friend. How long had it been since I had a conversation about liberatory pedagogy with anyone?
I was stunned by AI’s ability to zero in on my interests and values, and to respond to me using language that rang true for me. It made me wonder how it might substitute for a friend for lonely young people. I wondered: Is there any value in schools making use of AI’s dialogic capacities to re-learn and re-teach productive conversations?
In the AI Together Community of Practice, we discussed the value of dialogue in productive use of AI – going back and forth to hone in on the right input and output. I am interested in seeing if, in educational use of AI, dialogue can be better crafted to support critical thinking and to widen perspectives.
After that initial experiment, I turned to the practical challenge I wanted to focus on: How can I use AI to support organizing resources for students, teachers, and families – without sharing student data? Claude AI helped me with organizing opportunities for students, which enabled me to get opportunity announcements out to the school community in a more timely way, so that more students could participate in internships, workshops, and other opportunities. This builds students’ sense of connection to school, Google Classroom, and teachers as a resource for their livelihood.
Moving forward, I will probably continue to use AI for organizational support, and I’ll explore AI’s dialogic capacities as mentioned above. I am more committed than ever to keeping any student data off AI platforms. I am still just as concerned about student reliance on AI, and I will continue to look for ways to shift that. Meanwhile, it is sustaining to me to be in dialogue with other educators about the forces that threaten teaching and learning and how to support students’ independence of mind, creativity, and well-being in the face of that.

Shanti Elliott is the Linked Learning Pathway Coach at Skyline High School in Oakland, supporting teachers and students to connect classroom learning with real-world applications.
Before moving to Oakland, Shanti worked in Chicago schools for 20 years, teaching English and leading civic engagement. She also taught in the School of Education and Social Policy at Northwestern University.
Shanti’s work focuses on education for social change through community-school partnerships, anti-racist pedagogy, and broadening political awareness. Shanti has written for a wide range of publications, from Folklore Forum and The Slavic Review to Schools Journal. Her book, Teaching and Learning on the Verge: Democratic Education in Action, was published by Teachers College Press in 2015.
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