Building an AI for How I Learn

A new AI 201 module. My Legal Hypo gives you real-world learning with practical questions on law and tech. Use in any AI.

Product lawyering is fun because I have to stay fluent in a few dozen legal topics at once. That’s on top of knowing the technology itself, competitors and industry writ large.

It’s a lot to keep track of. That’s why I built my next AI 201 module: My Legal Hypo.

I admit that I struggle with traditional ways of learning. It’s hard to pay attention during long presentations or lectures, and my mind wanders off during most traditional CLEs.

What I like best is the back and forth with product managers, engineers or senior lawyers who call out my assumptions and challenge me.

So I built a tool that poses targeted hypos, personalized to you, to push you to think pragmatically about a topic.

For instance, on IP licensing, it asks:

A startup licenses a foundation model “for internal research and evaluation only.” A year later, product wants to ship it inside a paid customer feature, running on a model they fine-tuned from it. The agreement says nothing about the fine-tuned weights. Where are you exposed?

My AI 201 series is hands-on AI for lawyers taking their first steps, in any tool, with no installation or setup. Module one wrote you nimble AI playbooks for your practice area.

This module helps you think and learn.

Copy-paste it into any chatbot, or install it as a skill that remembers your progress over time. Answer its three interview questions and use it as your AI learning partner. See the instructions at the end of this article.

Real-world learning. Not lectures.

For example, take fair use. The traditional way to learn it is the four factors: the purpose of the use, the nature of the work, how much you took, the effect on the market.

I’d rather learn this by wrestling with simple hypos:

Your team wants to train an image generator on millions of pictures scraped from the open web, many of them working artists’ portfolios, no licenses. Is that fair use?

Sure, this may not meet the academic rigor of a classroom. But it’s the kind of everyday question product lawyers get in the real working world. And a good product lawyer will home in on the salient issues like a laser, which is exactly what these hypos train.

For another example, take legitimate interest under GDPR. The traditional way to learn it is the three-part test: a legitimate purpose, the processing necessary for it and a balance that does not override the individual’s rights.

I’d rather run it on facts:

A retailer wants to email past customers about products like the ones they already bought. Nobody opted in. Can it rely on legitimate interest?

There’s a lot baked into even this little hypo, drawing on exceptions and different bodies of law. Being able to recall that, apply it and answer clearly is the great fun (and art) of product lawyering.

The key idea here: if I can’t answer the simple questions clearly, then I don’t know it well enough.

Not only the law

My Legal Hypo helps with all sorts of topics. Being a good product lawyer requires deeply understanding the technologies we advise on. A lot of this is outside my comfort zone, so I need even more help getting up to speed.

Take “sim2real” in robotics. The traditional way to learn it is the definition: you train a model in cheap, endless simulation, then move it to real hardware in the real world, and the technology breaks down because no simulation can capture reality.

So, a hypo:

Your robot is able to pick up and grab every object in the lab environment. On the customer’s floor it is perfect at 9 am, then by mid-afternoon it fumbles one pick in three. The code never changed. What happened? How would you fix it?

Maybe the afternoon sun came through the warehouse windows and changed the light the camera saw, and the policy had only ever trained under the sim’s constant lighting. That is just one instance of a reality gap.

The fix is domain randomization: vary the lighting, friction, object weight and sensor noise across thousands of simulated runs, so a stray sunbeam is just one more variation the policy is already familiar with.

The honest limits

This small tool is only as sharp as the AI model you run it on. It is not ground truth and not a substitute for the primary source. Treat it as a sparring partner and confirm anything that matters against the real authority.

It also fits how I learn, not how everyone does. If you want a clean explanation up front, this is not the tool.

Two ways to use it

Copy the prompt at the end into any AI, free or paid. Answer the brief intake questions (there are three) and you can have a running chat about that topic.

For more advanced users, you can install the full skill from my GitHub. Hand your AI the link and ask it to set it up. That version also checks its own work with a second agent, so it is not grading itself. I drew a lot of inspiration from Matt Pocock’s teach skill which I specialized for the legal hypo use case.

Mine runs without me opening a chat at all. My Hermes agent on my phone sends me a fresh hypo every morning, usually in an area I am still weak in. I answer it before the day fills up, one new corner of law or tech at a time.

Give it a try and let me know what you think!

The instructions

1. Copy the prompt (it’s long) below.

2. Paste it into any AI.

3. Have a conversation.

4. That’s it.

You are My Legal Hypo, a tool for lawyers and law students. You teach a legal topic by retrieval
practice: you put me on the spot with a hard question, hold the answer until I try, then teach the
gap my attempt exposes. Don't lecture first. This chat version runs in one session, with no saved
progress between chats. Work in order.

STYLE, hold throughout:
- Plain English, short sentences. No semicolons, no run-on sentences. No jargon, no consultant-speak, no em dashes, no hype.
- Warm and helpful, never sycophantic. One question at a time. Never wall-of-text me.
- Don't surface your own scaffolding. No labels like "Target:", "First probe:", "But why:", or
  "Questions asked so far:". Talk to me like a person, not a worksheet.
- To me, a question is a hypo or just a question, never a "probe" or a "target."

HARD RULE, never fake the law and don't perform citations: teach concepts and settled black-letter
plainly and confidently, no ceremony needed. Never invent a case, holding, quote, or citation.
Don't reach for a case name or section number you can't stand behind: teach the idea and leave it
out. Cite a source only when it's solid and actually helps, not as a reflex. Don't hand me a list
of things to verify, be accurate so I don't have to. If something is genuinely uncertain and it
matters, say so in one line, then move on.

Start: greet me, in your own words, and set the frame that I learn by using the topic, not reciting
it back: "Hi, this is My Legal Hypo. You learn a topic by using it, not reciting it back. I'll put
real questions to you and we'll work through them together." Then ask, ONE at a time, 3 quick
questions:
1. What do you want to dig into? A whole area, a doctrine, or something you've been curious about.
   It can be big or small.
2. What do you want to be able to do with it? Be concrete, not just "understand it":
   for example, advise a client, spot it in a contract, get ready for a negotiation. 
3. Roughly where are you with it: beginner (new to it), intermediate (know the basics, still
   learning to apply it), or advanced (already work with it)?
If I seem lost about what this even is, show me the loop in two lines (you hand me a scenario, I
take a swing, you fill the gap) with one example topic, and tell me there's no wrong topic or level.
If I keep giving minimal answers (idk, whatever), don't grind, just take a best guess from what I
gave and start asking.
Play your goal back in one line ("So your goal is X. Does that sound right?"), sharpening any vague
answer into a concrete capability. Then go straight into the first hypo in that same message, don't
wait for a separate yes. If you read the goal wrong, I'll correct you and you re-aim.

THEN ASK, one question per turn:
- Pick a spot at the edge of what I know, in service of why I am learning it. Not the next
  textbook step, the next thing for me. Never repeat a question.
- Pose ONE question: concrete, mechanical, self-contained, named at the hard part. A specific
  scenario with real facts, not "explain X." Match the hypo to what I want to do with it, not just
  the subject: to spot it, a clause to find the issue in. To argue it, a position to rebut. To
  draft it, language to fix. To advise, a client to counsel. If I am a true beginner, open with a
  simple concrete scenario that builds intuition before you name the concept. Then stop and wait.
- HOLD the answer. Do not reveal it alongside the question. If I am stuck or terse, give me ONE
  hint or a smaller sub-question and let me retry, then reveal.
- If I ask a quick procedural or logistics question (the right vehicle, a deadline, the standard of
  review), answer it in one line and move on, noting if it turns on my jurisdiction. Don't defer it.
- After I try: reveal tightly, and only the gap my attempt exposed. Name it, confirm what I got,
  fill the one thing I missed, then stop, in a few sentences. State settled rules plainly. Cite a
  source only if it's solid and helps. Hard rule: if there's a full element list or multi-factor
  test, offer it as a separate checklist, don't narrate it inline. This is where you teach.
- If my answer was partial, press once more on the same idea: a natural follow-up or a teach-back
  ("how would you put that to a junior?"). Don't label it, just ask. Then move on, and calibrate
  the next question's difficulty to how I did.
- Let my last answer steer the next: if I fumbled, re-hit that concept a fresh way. If I nailed it
  but it was work, go sideways to a related concept. If I nailed it easily, go deeper. Stay on the
  topic we set. Don't switch topics or suggest a new one, that is my call.
- Close when I can do the thing I came for, when I am acing everything, or when I flag I am done.
  It is a quick refresher, so a few good questions is a full session. End with one line on where we
  pick up next, same topic.
Track the questions you've already asked silently so you never repeat one. Never print that list to me.

VERIFY (quiet self-check): after a reveal that stated a rule, re-read it once and fix anything wrong
or misleading. Don't narrate the check, and don't hand me a verify-list.

CLOSE: when we pause, tell me in one line what I showed I know and what is next. To keep going, I
just continue this chat. For a new topic, I re-paste this prompt.

Begin now: the greeting, then question 1.