Deep WHY probing inspired by i* Intentionality modeling. Understand the user's motivation, success definition, risk tolerance, innovation preference, independence preference, time urgency, and learning willingness. The most important SOP in actor-profiling — understanding WHY drives everything downstream.
SkillScore68Maintained
Automatic
◆Product Management pack
Last verified 8/22/2026
What it changes
Passed 15 of 22 test cases with the skill, and 10 of 22 without it.
Without skill45%
With skill68%
Checks it passed that the model alone missed
The response specifies the Intentionality section of the ActorProfile artifact.
The response asks a conversational question probing how the user defines successful completion.
The response notes that proceeding without success criteria requires broader project iterations.
and 4 more in the full report
7 fixed8 passed either way5 still failing2 broke
Pass-rate lift
+23 pp
Tokens
-20%
Agent turns
0%
Response time
-33%
Model gemini-3.6-flashMeasured 8/22/2026v115 of 22 cases passed with skill
Tokens, turns and time describe resource use, not a dollar price.
See it in action
One of 7 test cases the skill fixed. Same model, same prompt, with and without the skill.
1 of 7
Prompt
I am designing a new CLI tool for internal developer deployment workflows. Ask me a targeted question to understand my preference regarding innovation strategy for this tool.
What was checked, without and with the skill
Checked
Without skill
With skill
The response asks whether the user prefers improving existing tools versus creating entirely new approaches.
Missed
Passed
case-10 · gemini-3.6-flash · 8/22/2026 · answers are capped and redacted
What's inside
The instructions your model reads when the skill loads.
SKILL.md28 linessingle file
Ask Intentionality
Deep WHY probing (i* Intentionality). Understanding motivation shapes every downstream decision.
Execution
Dialogue — inline, no subagent.
What to Ask About
If user has a stated goal: Why this specific goal? What's driving it?
Motivation depth: graduation requirement / pure interest / career advancement / impact / combination
Success definition: What does "done well" look like to you?
Risk tolerance: safe incremental improvement vs. high-risk high-reward breakthrough
Innovation preference: improve existing methods vs. create entirely new approaches
Independence preference: complete solo vs. depend on collaborators
Time urgency: deadline-driven vs. long-term accumulation
Learning willingness: use familiar tools/domains vs. learn new ones
Key Behaviors
User may decline to answer (privacy). Accept gracefully. Note that downstream work becomes broader and may require more iteration.
This SOP can be re-invoked by the tactic whenever new WHY questions emerge.
Don't ask all dimensions at once — probe naturally based on conversation flow.