Session Types Reference
Guide for identifying brainstorming context and recommending appropriate methods.
Overview
Session Types Reference
Guide for identifying brainstorming context and recommending appropriate methods.
Session Type Detection
Listen for cues to identify the type of brainstorming session:
| Session Type | Typical Triggers |
|---|---|
| Product/SaaS Ideation | "app idea," "SaaS," "product," "build," "startup," "MVP" |
| Content Ideation | "newsletter," "article," "blog," "book," "chapter," "content" |
| Strategic Decision | "should I," "deciding between," "weighing options," "strategic" |
| Problem Solving | "stuck on," "can't figure out," "how do I," "challenge" |
| Creative/Artistic | "story," "design," "creative," "artistic direction" |
| Business Model | "pricing," "revenue," "business model," "monetization" |
| Positioning/Marketing | "differentiate," "positioning," "messaging," "audience" |
Recommended Methods by Session Type
Product/SaaS Ideation
Core questions to answer:
- What problem does this solve?
- Who specifically has this problem?
- Why would they choose this over alternatives?
- Can I build it? Should I?
Recommended methods:
- Jobs-to-be-Done — Understand the real need
- Audience Reality Check — Validate the target user exists
- Competitive Analysis — Map the landscape
- First Principles — Challenge inherited assumptions
- Pre-mortem — Identify failure modes before committing
Watch out for: Falling in love with the solution before validating the problem.
Content Ideation (Newsletter, Articles, Books)
Core questions to answer:
- What does my audience need to hear?
- What do I have unique insight on?
- What's the angle that makes this mine?
- How does this fit my larger body of work?
Recommended methods:
- Mind Mapping — Explore the idea space
- Audience Reality Check — Who specifically wants this?
- Forced Analogies — Find fresh angles
- SCAMPER — Vary existing ideas
- Telos Examination — Why does this content matter?
Watch out for: Writing what's easy instead of what's needed; chasing trends over building a body of work.
Strategic Decision
Core questions to answer:
- What are my actual options?
- What matters most in this decision?
- What am I assuming?
- What's the risk profile?
Recommended methods:
- First Principles — Clear away assumptions
- Weighted Scoring — Make tradeoffs explicit
- Pre-mortem — Test your leading option
- Steelman — Argue for options you're dismissing
- 10/10/10 — Check against time horizons
Watch out for: Deciding before actually exploring options; confirmation bias.
Problem Solving
Core questions to answer:
- What's the real problem? (Not the symptom)
- What have I tried?
- What assumptions am I making?
- What would make this easy?
Recommended methods:
- 5 Whys — Find the root cause
- Problem Reframing — Restate the problem multiple ways
- Inversion — What would guarantee failure?
- Forced Analogies — How do other domains solve this?
- First Principles — Strip to fundamentals
Watch out for: Solving the wrong problem; jumping to solutions too fast.
Business Model / Monetization
Core questions to answer:
- Who pays? For what value?
- What's the pricing psychology?
- How does this scale?
- What's sustainable long-term?
Recommended methods:
- Jobs-to-be-Done — What are they really buying?
- Forced Analogies — How do similar businesses price?
- First Principles — What is price really?
- Assumption Surfacing — What must be true for this model to work?
- Stewardship Frame — Is this pricing faithful/fair?
Watch out for: Underpricing; copying models that don't fit; leaving money on the table.
Positioning / Marketing
Core questions to answer:
- Who is this for? (specifically)
- What makes this different?
- What's the one thing to remember?
- Why should they believe me?
Recommended methods:
- Audience Reality Check — Get specific about who
- Steelman — Argue for competitors
- Inversion — How would I make this forgettable?
- SCAMPER — Vary the positioning
- Forced Analogies — How do non-competitors position?
Watch out for: Being everything to everyone; forgettable positioning; claiming differentiation that doesn't matter to the audience.
Session Energy Modes
Deep Exploration Mode
Characteristics: Long session, open-ended, divergent, willing to go down rabbit holes.
Approach:
- Use divergent methods freely
- Allow tangents (but park off-topic items)
- Don't rush to converge
- Embrace ambiguity
- End with synthesis, not decisions
Quick Progress Mode
Characteristics: Short session, focused, need to move forward, decisions over exploration.
Approach:
- Start with clear scope: "What decision do we need to make today?"
- Use convergent methods primarily
- Time-box divergent exploration (10 min max)
- Make decisions and log them
- End with next actions
Mode Selection: Connected vs. Clean-Slate
Connected Mode (Default)
Cross-reference other projects and existing work. Surface connections like:
- "This relates to your thinking on X"
- "You explored something similar in [project]"
- "This might conflict with what you decided about Y"
- "This could feed into your newsletter/book/other project"
Best for: Building on existing work, ensuring consistency, leveraging past thinking.
Clean-Slate Mode
No references to other projects or prior work. Fresh perspective.
Best for: Genuinely new territory, avoiding anchoring, testing ideas without baggage.
When to suggest clean-slate: When the user seems anchored on past approaches that aren't working, or when fresh thinking would benefit from starting over.