# How to Win at School With AI - Right Now By Wes Pomeroy. Published August 31, 2026. https://wespomeroy.com/writing/how-to-set-up-an-ai-tutor/ Last week I wrote about [seven chronic gaps in how school works](https://wespomeroy.com/writing/ai-tutor-for-students/), and what you can finally do about them. Enough of you asked how it's built, so here it is. This is easier to follow if you think of it as hiring a tutor. Not as a metaphor. It's the closest description of what you're setting up, and it tells you what to do at every step. Some of this depends on having a transcript of the class. I recommend a Plaud Note Pro. Check with your school about whether they allow it, and if they don't, push back. If a school cares more about its students than about its own liability or its own learning curve, it will allow it. ## Step One: Hire the Tutor Get Claude Cowork, and get at least a basic Pro subscription. That's the hire. That's your tutor. ## Step Two: Make Sure the Tutor Can Remember The power of AI doesn't come from one good session. It comes from session upon session - a system that remembers what you decided, what you prefer, what you already covered, what you tried. So ask yourself how much help a tutor would be if you got rematched with a new one every time. Every session starts with them learning your background from scratch. They have no idea what you worked on together, what you already struggled with, or which approaches worked. That's what you have by default. That's what you have to fix. What needs to carry from one session to the next: - What was covered - What was discussed - What methods were tried - What the challenges were - What worked, so it can be repeated I couldn't find anything off the shelf that did this reliably and had the rest of what I needed, so I built my own. It's called [BooBridge](https://boobridge.com), and the site walks you through the setup. Or use something else. The point isn't my tool. You need memory that holds from one session to the next, and now you know what to look for. ## Step Three: One Project Per Class In Cowork, set up a project for each class you want to focus on, and turn BooBridge on for it. Or enable durable memory some other way, if you found a different method in Step Two. One per class, deliberately. Chemistry gets its own tutor with its own memory. So does History. Each subject has different needs, and keeping them apart means each project stays on the specifics of that class instead of getting diluted across everything. The memory stays down to what's actually necessary. ## Step Four: Establish the Baseline Everything a real tutor would ask in a first meeting: - What is this class? - What's the syllabus, and what's going to be covered? - What days does it meet? - What are the expectations around tests and homework? - Where can class materials be found? - Where can grades be found? - Is there extra help available? - Who else is in the class? Anything you'd pick up in the first few days from the teacher or from paying attention. The context of the class, its focus, what resources exist. All of it goes into the project. Upload documents. Point it at websites. Scan things in, paste things in, type them in, or just talk it through. However you get it there, get it there. You only do this once, and the more thorough you are, the better everything downstream gets. Context is the work. ## Step Five: Feed It, Every Class Every single class, put in as much as you can. - A text transcript of the class - The classwork - The homework - Any graded classwork or homework that comes back - Your notes - Your classmates' notes Anything that gives insight into what got covered that day. Graded work is what makes the pattern-spotting possible - knowing what kind of material gives you trouble, instead of just which test went badly. Every day, find the fastest way to gather that material and get it into the project for that class. ## Step Six: Figure Out How You Actually Learn Now the material's in there. When it's time to do homework or study for a test, ask the tutor to prepare a study guide, and then experiment with what form it takes. Maybe it's flashcards. Maybe a little interactive quiz on a web page. Maybe a podcast. Maybe something that reads aloud and highlights along the way. Maybe it explains the concepts as an analogy to a video game, or to anything else you already know cold. Try things. Find out what works for you, in this subject. This is where the memory pays off. Once you find out that flashcards do nothing and the quiz format works, that gets remembered, and you're not re-running the same experiment every week. ## Step Seven: Put It to Work You've got the material and you've got the formats. Here's what you actually do with it. - **Catch up on what you missed.** Ask what got covered while you were lost, or absent, or writing down the last thing the teacher said. - **Get it explained another way.** Ask for the same concept as an analogy, a diagram, a conversation, or in plainer language, until one of them lands. - **Grade your own attempt.** Do the homework, then have it check your work and take you through the parts you got wrong. Keep going until you have it. - **Get quizzed.** Have it test you on the material, then test you again on whatever you missed. - **Find the weak spots.** Point it back at graded classwork and tests, and have it show you what needs strengthening before the next one. - **Find the pattern.** Ask where you're consistently having difficulty, and have it adjust both the study approach and the format accordingly. That last one is what makes this different from a study guide. Every week, the system gets better at teaching you specifically. ## Do It Anyway This is early. It's not turnkey, it's not polished, it has rough edges and frustrations, and it's more manual than it should be. Do it anyway. What's on the other side of that work is the list I wrote about last week. A class you can replay at your own speed instead of getting one pass at it. The same lesson in whatever form finally makes it stick. A question you can ask four times without spending the room's time or having anyone remember you asked it. A record of what you actually struggled with, week over week, instead of a report card that shows up too late to change anything. A student who uses this has an advantage over a student who doesn't, and that gap is going to widen. A parent who waits is costing their kid time nobody gets back, and that goes double for a kid with special needs, where the distance between how school teaches and how that kid learns is the problem in the first place. Nobody would deny a student a library, or the internet, or a calculator. This is no different. Be on the right side of history on this one. I know you probably don't like AI. Most people don't. It's uncomfortable. If you have questions or concerns, ask me, privately if you'd prefer.