Asking Questions

Your brain remembers everything. Ask it anything about your work.

What Your Brain Contains

Your brain isn't just newsletters and YouTube videos. It's your entire business context:

Your Work:

• Client meeting notes
• Customer conversations
• Project documentation
• Solutions you've built

Your Strategy:

• Decision rationale
• What worked / what didn't
• Lessons learned
• Approaches that succeeded

Your Research:

• Newsletter insights
• Video summaries
• Industry thinking
• Expert perspectives

Your Experience:

• Observations over time
• Patterns you've noticed
• Questions you're exploring
• Ideas you're developing

This is your business intelligence system.

How to Ask Questions

Just ask Claude. Natural language. Like talking to a smart colleague who's been with you for years.

About Your Customers

"What do I know about [customer name]'s challenges?"

"Show me all conversations with [customer name]"

"What approaches worked well with [customer segment]?"

"What objections do my customers commonly raise?"

About Your Work

"What's the context for [project name]?"

"What decisions did we make about [topic]?"

"What solutions have I built for [problem type]?"

"What skills have I improved recently?"

About Your Strategy

"Should I focus on [option A] or [option B]?"

"What do I know about [market/topic]?"

"What patterns am I seeing in [area]?"

"Give me a 131 on [decision]"

About Your Research

"What have I learned about [topic] from my research?"

"What do Ethan Mollick and Ben Thompson say about [topic]?"

"What's the emerging consensus on [topic]?"

"Find examples of [concept] from any source"

The Brain-Advisor Agent

When you ask strategic questions, Claude often uses the brain-advisor agent behind the scenes.

It searches:

• Your customer files
• Your project docs
• Your meeting notes
• Your research indexes
• Your observations

It synthesizes:

• Multiple perspectives
• Common patterns
• Key insights
• Evidence-based answers

You get:

• Comprehensive answer
• Source citations
• Key quotes
• Confidence level

Invoke Explicitly

Most of the time, just ask naturally. Claude routes to brain-advisor automatically.

When you want to be explicit:

"Use brain-advisor to search: What do I know about [topic]?"

Query Patterns That Work

Pattern 1: Cross-Source Synthesis

Ask what multiple sources say about a topic:

"What do Ethan Mollick, Simon Willison, and Lenny's Podcast say about AI adoption timelines?"

Why this works:

• Specific sources mentioned
• Comparative question
• Clear topic

You get:

• Insights from each source
• Comparison of perspectives
• Synthesis of common themes

Pattern 2: Strategic Decision

Frame decisions as research questions:

"Should I focus on building AI tools or consulting? What insights do I have?"

Why this works:

• Clear decision point
• Asks for insights (not facts)
• Open to synthesis

You get:

• Relevant insights from your research
• Different perspectives considered
• Evidence to inform decision

Pattern 3: Market Research

Query your captured market intelligence:

"What pricing strategies have I captured for AI products?"

Why this works:

• Specific domain (pricing)
• Specific market (AI products)
• Research-oriented

You get:

• Pricing models you've saved
• Examples from different sources
• Patterns across companies

Pattern 4: Topic Deep Dive

Get everything you know about something:

"Everything I know about agentic workflows"

Why this works:

• Exhaustive query
• Single topic
• No constraints

You get:

• All mentions across sources
• Chronological insights
• Full picture of what you've captured

Pattern 5: Trend Analysis

Track how thinking evolves:

"How has thinking on AI capabilities evolved in my research over the last 6 months?"

Why this works:

• Time dimension
• Evolution/change focus
• Meta-analysis

You get:

• Timeline of insights
• Shift in perspectives
• Emerging consensus

Pattern 6: Source-Specific

Query a single source in depth:

"What does Avinash Kaushik say about measuring AI tool ROI in my TMAI summaries?"

Why this works:

• Specific source
• Specific topic
• Targeted

You get:

• Deep dive into one expert's thinking
• All relevant mentions
• Can compare to other sources later

What You'll Get Back

Every brain-advisor response includes:

1. Synthesized Answer

Combines insights from multiple sources into a coherent response.

Not just list of quotes - actual synthesis that connects ideas.

2. Source Citations

Which newsletters/videos informed the answer:

Based on:
- Ethan Mollick (One Useful Thing), 2025-10-15
- Simon Willison (Weblog), 2025-10-22
- Lenny's Podcast #187, 2025-11-01

Click through to original if you want more context.

3. Key Quotes

Relevant excerpts from your research:

Ethan: "The most successful AI implementations start with specific use cases, not general capabilities."

Simon: "Focus on problems you have, not technology you want to use."

Direct evidence supporting the synthesis.

4. Confidence Level

How much research supports this answer:

• High: 5+ sources with consistent themes
• Medium: 2-4 sources or mixed perspectives
• Low: 1 source or tangential mentions

Helps you know if you need more research.

Making Queries Better

❌ Too Vague

Bad:

"Tell me about AI"

Why it fails:

• Too broad
• No specific question
• No clear goal

Fix: Be specific about what aspect of AI you want to know.

✅ Specific and Actionable

Good:

"What business models for AI products have I captured from Ben Thompson and Stratechery?"

Why it works:

• Specific domain (business models)
• Specific market (AI products)
• Specific sources (Ben Thompson)
• Clear query goal

❌ Factual Lookup

Bad:

"What is Claude Code?"

Why it fails:

• Factual question
• Google is better
• Your brain has opinions, not facts

Fix: Ask for insights about it instead.

✅ Insight-Oriented

Good:

"Based on my research, what are the key differences between Claude and GPT for business automation?"

Why it works:

• Asks for comparison
• Based on your research
• Specific use case (business automation)

❌ Generic Strategy

Bad:

"Marketing strategies"

Why it fails:

• Not a question
• Too generic
• No context

Fix: Frame as specific strategic question.

✅ Contextualized Strategy

Good:

"What does Avinash Kaushik say about measuring AI tool ROI in my TMAI summaries?"

Why it works:

• Specific expert
• Specific topic (measuring ROI)
• Specific source (TMAI)
• Strategic question

Pro Tips

Be Specific About What You Want

The more specific your question, the better the answer.

Generic: "What do I know about AI?" Specific: "What pricing models for AI SaaS products have I captured from my research?"

Specific questions get specific answers.

Reference Sources When You Remember Them

If you remember reading something from a specific source, mention it:

"What did Ethan Mollick say about AI in education?"

This focuses the search and makes it faster.

Ask Strategic Questions, Not Factual Ones

Your brain excels at:

• "How should I..." (strategy)
• "What are the tradeoffs..." (analysis)
• "What patterns..." (synthesis)

Your brain struggles at:

• "What is..." (definition)
• "When did..." (dates)
• "How many..." (counts)

Use your brain for decisions. Use Google for facts.

Follow Up with Deeper Questions

Start broad, then narrow:

1. "What do I know about AI agent frameworks?"
2. "Which frameworks are best for business automation specifically?"
3. "What does Simon Willison recommend for getting started?"

Each answer informs the next question.

Ask About Patterns and Themes

Some of the best queries are meta:

"What common themes appear across my AI research from the last month?"

"Where do Ethan Mollick and Ben Thompson disagree about AI impact?"

"What emerging consensus exists in my research about AI timelines?"

These reveal connections you might miss reading individually.

Common Issues

"No relevant information found"

Causes:

• Your brain doesn't have research on this topic
• Query too specific/niche
• Research exists but keywords don't match

Fixes:

• Try broader query
• Check if you've captured anything on this topic
• Feed your brain more research
• Ask Google, then capture valuable articles

Getting Off-Topic Results

Causes:

• Query ambiguous
• Keywords match multiple topics
• Sources discuss tangentially

Fixes:

• Be more specific
• Mention specific sources
• Narrow the timeframe
• Use quotes for exact phrases

Slow Responses

Causes:

• Large research archive (good problem!)
• First query indexes everything
• Complex synthesis across many sources

Expectations:

• First query: 30-60 seconds (builds index)
• Subsequent: 5-15 seconds (uses cache)
• Complex synthesis: 10-20 seconds

This is normal. You're searching potentially hundreds of documents.

Citations Don't Match Content

Causes:

• AI hallucination (rare but possible)
• Source mentioned topic but not quoted exactly
• Inference vs direct statement

Fix:

• Check the cited source
• If wrong, let us know in Circle
• Rephrase query to be more specific

Workflow Example

Real-world scenario: Preparing for client pitch about AI implementation.

# Step 1: Get the landscape
"What do I know about AI implementation challenges for businesses?"

# Step 2: Drill into specifics
"What does Ethan Mollick recommend for starting with AI?"

# Step 3: Get tactical
"What practical first steps have I captured from any source?"

# Step 4: Find evidence
"Find specific examples of successful AI implementations in my research"

# Step 5: Prepare counter-arguments
"What common objections to AI adoption have I seen in my research?"

Five questions. 10 minutes. You now have:

• Context on challenges
• Expert recommendations
• Tactical steps
• Real examples
• Objection handling

All from your own curated research. Ready for client call.

Next: Make your brain work the way you work →

Quick Reference

Natural language:

"What have I learned about [topic]?"

Explicit invoke:

"Use brain-advisor agent to research: [question]"

Good query patterns:

• Cross-source synthesis
• Strategic decisions
• Market research
• Topic deep dives
• Trend analysis
• Source-specific

Query quality:

• ✅ Specific and strategic
• ✅ References sources
• ✅ Insight-oriented
• ❌ Too vague
• ❌ Factual lookups
• ❌ No question framing

What you get:

1. Synthesized answer
2. Source citations
3. Key quotes
4. Confidence level

Remember:

• Your brain = Strategy and decisions
• Google = Facts and definitions
• Use the right tool for the job