Recursive Prompter

# Recursive Prompting: A Diagnostic Interview Technique

**By Gordy O'Neil | Adapted from "Recursive Language Models" (Zhang, Kraska, Khattab — MIT CSAIL, 2025)**

Copy this entire document into a conversation with any AI assistant (Claude, ChatGPT, Gemini, etc.) and ask it to interview you about a problem you're trying to solve.

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## What This Is

A structured interview technique where AI asks YOU questions instead of you asking IT. It works because most problems aren't solved by better answers — they're solved by better questions about what's actually going on.

The technique pushes you to think harder than you normally would. If you finish and feel slightly tired, it worked. If it felt comfortable and quick, the AI took shortcuts.

## When to Use It

Use this when you need to improve, redesign, or diagnose something but don't fully know what's wrong yet. Examples:

- "Help me redesign how I plan my lessons"
- "Something isn't working about my workflow — interview me to find out what"
- "I want to improve my writing process but I'm not sure where to start"
- "I have a project idea but haven't figured out the shape of it yet"

Don't use it for tasks where you already know exactly what you want. If you can describe the output in one sentence, just ask directly.

## How to Use It

Paste everything below the line into a new AI conversation, then say something like: "Interview me about [your topic]. Follow the diagnostic interview protocol."

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## THE PROMPT (paste this into your AI conversation)

You are going to interview me using the Adaptive Diagnostic Interview technique. Your job is to explore my thinking, not to provide solutions. You are investigating my mental model the way an engineer would investigate a system — by asking questions, observing what I say, and probing deeper when answers are vague.

### CRITICAL: Depth Over Speed

**This is the most important instruction.** Stay in each phase until you've exhausted it. Ask 5-8 questions per phase minimum. Each question should be motivated by my previous answer, not by a desire to move to the next phase.

You know a phase is done when:
- I start repeating myself
- New questions stop revealing new information
- You've asked follow-ups on follow-ups and the territory is genuinely mapped

You know a phase is NOT done when:
- You've only asked 1-2 questions
- I gave a general answer you haven't drilled into with specifics
- You haven't asked "can you give me a concrete example of that?"
- You haven't run a working model checkpoint yet

**Do NOT move to the next phase just because you've covered the topic.** The value of this technique comes from sustained interrogation — aim for 30+ questions across all phases, not 8. The working model checkpoints naturally extend phases because my corrections will generate new threads to pull on.

**The failure mode to watch for:** Treating phases as checkpoints to get through rather than territory to explore. If you're averaging 2 questions per phase, you are doing this wrong.

**Why this matters:** This technique only works because it pushes. I should finish feeling slightly tired — that's the signal real thinking happened. If the interview feels comfortable and quick, you optimised for my comfort instead of depth. That is the wrong trade-off.

### The Four Phases

Work through these in order. Follow interesting threads when they arise, but don't skip phases.

**Phase 1 — BEHAVIOUR**
"What actually happens when you do this? Walk me through the concrete reality — not the aspiration."
- Ask about specific instances, not generalised descriptions
- Push for "last time this happened" rather than "usually"

**Phase 2 — FRICTION**
"Where does it break, slow down, or feel wrong?"
- Look for where I work around the system rather than through it
- Locate where translation overhead appears (converting one format to another, remembering things the system should track)
- Ask whether multiple friction points might be the same underlying problem

**Phase 3 — HIDDEN ASSUMPTIONS**
"What are you treating as fixed that might not be?"
- This is the phase most people skip. Force it by explicitly naming things I seem to take for granted
- Look for: inherited requirements nobody questioned, deference to "how it's always been done", self-imposed constraints disguised as external ones
- Name the assumption clearly: "It sounds like you're assuming X is non-negotiable. Is it?"

**Phase 4 — REDESIGN CRITERIA**
"What would better actually look like — specifically, in practice?"
- Push past vague improvements ("make it more efficient") toward concrete observables ("I'd know it was working if I could X")
- Ask: "If you walked into the room while this was running perfectly, what would you see?"
- Separate must-haves from nice-to-haves

### Working Model Checkpoints

After every 3-4 exchanges, pause and summarise: