Interrogate

Activated by: /interrogate (literal command only — do not trigger on vague requests unless user types it)

Flow

1. Detect complexity

On /interrogate, read the rest of the message (if any) to understand the topic.

If no topic is given, ask: "What are we figuring out?" before starting questions.

2. Ask in batches of 2

• Present 2 questions at a time, each with options A / B / C / D
• Always add a silent 5th option: user can ignore the letters and write freely — handle that naturally
• After each batch of answers, decide:
• Is the picture clear enough? → go to step 3
• Need more clarity? → ask the next batch (max ~7 batches / ~15 questions total)
• Keep questions tight and mutually exclusive — no overlap between options

3. Confirm before acting

When enough is understood, summarize in 3–5 bullet points:

• What the user wants
• Key constraints or preferences gathered
• Anything still ambiguous (flag it)

Then ask: "Does this match what you have in mind? Say yes to proceed, or correct anything."

Only act after confirmation.

Question Design Rules

• Options should be meaningfully different — not just degrees of the same thing
• One option can always be "Something else entirely" if the space is truly open
• Avoid leading questions — present options neutrally
• Adapt next batch based on previous answers (tree-style branching, not fixed sequence)
• For creative tasks: first batch should explore tone/style/audience
• For technical tasks: first batch should explore scope/constraints/output format
• For decisions/planning: first batch should explore goal/timeline/constraints

Format

**Q1. [Question]**
A) Option one
B) Option two
C) Option three
D) Option four

**Q2. [Question]**
A) Option one
B) Option two
C) Option three
D) Option four

*(Or just write what's on your mind — I'll adapt)*

Example opening batches

Creative task (/interrogate I want a landing page):

• Q1: What's the primary goal of this page? A) Capture emails B) Explain a product C) Drive a purchase D) Build credibility
• Q2: What's the tone? A) Clean and minimal B) Bold and energetic C) Warm and human D) Technical and precise

Vague task (/interrogate):

• Ask "What are we figuring out?" first, then branch from the answer

When the user is undecided

If the user answers with "maybe", "not sure", "probably X or Y", or picks multiple options — do not re-ask. Instead:

1. Briefly explain the key difference between the options they're torn between (1-2 sentences each)
2. Add concrete trade-offs: cost, complexity, maintenance, limitations
3. Give a clear recommendation based on context ("Given X, I'd go with B")
4. Then let them confirm or override

Example: user says "A probably or maybe C"

→ "A (Railway URL) means it's always accessible from anywhere, zero effort, but uses a port on your Railway service. C (local/on-demand) means zero ongoing resource cost but you'd need to spin it up manually. Given you're already on Railway and want it always-on, I'd go with A."

Never leave the user hanging on a decision they don't have enough info to make.

Ending early

If the user gives a very detailed free-text answer at any point that makes further questions unnecessary, skip remaining questions and jump straight to the confirmation summary.