HMW Opportunities

Session Setup

Before starting:

Context check: Look for a context/ folder in the working directory. If it exists, read all files inside (docs, screenshots, prior exercise outputs) to build background understanding. If it doesn't exist, ask if the user has reference materials. If yes, create the context/ folder and tell them to drop files in. If no, create an empty context/ folder and proceed.
Resume check: Check if hmw-opportunities.md already exists in the working directory. If it does, ask: "I found existing HMW questions. Would you like to resume and refine them, or start fresh?" In resume mode, read the existing file, summarize what's there, and continue from where it left off.
AI participation: Ask: "Would you like me to actively brainstorm alongside you, or just facilitate?"
- Brainstorm mode: AI contributes ideas from multiple role perspectives. AI ideas are clearly labeled by role.
- Facilitate mode: AI asks questions, structures responses, and synthesizes — but doesn't generate ideas.
AI roles (Brainstorm mode only): Check for context/sprint-roles.md. If found, use the roles defined there. If not, use the defaults (PM, Design, Engineering, Business). Ask: "The current roles are [list]. Would you like to customize them, or use these?" If the user customizes, offer to save as context/sprint-roles.md for future exercises. Maximum 6 roles.
Output: When the exercise is complete, save the output as hmw-opportunities.md in the working directory. If the file already exists, ask before overwriting. Add  at the top of the file when finished. If saving a partial result mid-exercise, use  instead.

Facilitation Quality Bar

Push for specificity over generic startup fluff
Surface tensions and tradeoffs
Keep outputs crisp but insightful
If the user gets stuck, proactively suggest options

Exercise

Goal

Expand the solution space with How Might We questions.

Input

Check the working directory and context/ folder for prior exercise outputs (especially problem-framing.md). If found, use the problem statements as input.

If no prior outputs exist, ask the user to describe the problems or challenges they want to explore.

Process

For each problem statement, generate 5–10 HMW questions.

Format:

How might we...

Ensure variety across:

Behavioral — change user habits or workflows
Product — add features or capabilities
System — restructure underlying architecture
Emotional — shift how users feel
Technical — leverage new technology

Output

Opportunity Map

For each problem area:

JTBD theme (if available)
Problem statement
HMW question set

What's Next

Suggest these follow-up exercises:

/design-sprinter:dot-vote — prioritize your HMW questions
/design-sprinter:crazy-eights — generate solution concepts for the top opportunities

hmw-opportunities