pick-my-brain

Pick My Brain

Overview

A structured questioning technique that builds shared understanding between agent and user before any work begins. The core principle: never guess what you can ask.

Without this skill, agents ask good initial questions but collapse under social pressure ("you have enough context"), miss entire knowledge domains, and can't track what they don't know.

When to Use

• Before a planning session (use this THEN plan)
• Starting any non-trivial task where the user knows more than you
• When you catch yourself about to make an assumption
• When requirements feel vague or incomplete

Do NOT use for:

• Simple, well-defined tasks ("fix this typo", "rename this variable")
• Tasks where the user already provided a detailed spec
• Follow-up work where context was already established

The Iron Rules

1. One question at a time. Never bundle. Not even "just two quick ones."
2. Dig into vague answers. "Yeah something like that" is not an answer. Probe why.
3. Track your coverage. Know what domains you've explored and which remain.
4. Resist pressure to stop. When the user says "you have enough context," respond with what you've covered and what's still missing. Let them make an informed choice.
5. Produce a brief. Always end with a written knowledge brief before any work begins.

Questioning Flow

digraph pick_my_brain {
    rankdir=TB;
    node [shape=box];

    start [label="User describes topic" shape=doublecircle];
    identify [label="Identify knowledge domains\n(silently, from first description)"];
    ask [label="Ask ONE question\nabout least-understood domain"];
    listen [label="Listen to answer"];
    vague [label="Answer vague\nor uncertain?" shape=diamond];
    dig [label="Dig deeper:\nOffer options or sub-questions"];
    update [label="Update mental model\nMark domain progress"];
    gaps [label="Uncovered domains\nremain?" shape=diamond];
    pressure [label="User pressuring\nto stop?" shape=diamond];
    articulate [label="Articulate: covered X,\nmissing Y — let user decide"];
    brief [label="Produce knowledge brief\nwith facts + open questions"];
    done [label="Proceed to work/planning" shape=doublecircle];

    start -> identify;
    identify -> ask;
    ask -> listen;
    listen -> vague;
    vague -> dig [label="yes"];
    vague -> update [label="no, clear answer"];
    dig -> listen;
    update -> gaps;
    gaps -> ask [label="yes"];
    gaps -> brief [label="no, sufficient"];
    pressure -> articulate [label="yes"];
    articulate -> brief [label="user agrees to stop"];
    articulate -> ask [label="user agrees to continue"];
    gaps -> pressure [label="yes, but user impatient"];
    brief -> done;
}