Example Prompts

Real-world examples of effective questions to ask Brief Chat.

Last updated: November 25, 2025

Brief Chat works best when you ask specific, contextual questions. Here are real examples of prompts that work well, organized by use case.

Strategic Planning

Big Picture Questions

What are our biggest product risks right now?

  • Analyzes roadmap, customer feedback, and technical debt
  • Identifies gaps between strategy and execution

How aligned is our roadmap with customer feedback?

  • Cross-references Linear roadmap with Fireflies/Fathom transcripts
  • Highlights misalignment or validation

What features are most requested but not built yet?

  • Searches customer calls and support conversations
  • Compares against shipped features in GitHub/Linear

Feature Prioritization

Comparison & Trade-offs

Compare the impact of building X vs Y

  • Analyzes customer mentions, usage data, and technical complexity
  • Provides evidence-based recommendation

What's the smallest thing we could ship to test this hypothesis?

  • Reviews current architecture and feature scope
  • Suggests MVP approach

What dependencies are blocking our next release?

  • Checks Linear/Jira for blocked tickets
  • Identifies critical path issues

Customer Research

Understanding Your Users

What pain points do enterprise customers mention most?

  • Searches Fireflies/Fathom transcripts
  • Groups by theme and frequency

Show me the top themes from recent customer calls

  • Analyzes last 30 days of call transcripts
  • Ranks by mention frequency

Who are our happiest customers and what do they have in common?

  • Combines PostHog behavior data with customer calls
  • Identifies success patterns

Velocity & Operations

Team Performance

How long does it typically take us to ship a feature?

  • Analyzes Linear cycle time
  • Shows average and distribution

What's our bug-to-feature ratio in the last quarter?

  • Queries Linear/Jira for issue types
  • Calculates ratio and trend

Which team members are overloaded right now?

  • Checks GitHub commits and Linear assignments
  • Identifies bottlenecks

Decision Support

Decision History

What decisions have we made about pricing?

  • Searches Brief's decision log
  • Shows chronological decision history

Show me all documented trade-offs for the mobile strategy

  • Finds decisions tagged with "mobile" and "trade-off"
  • Displays rationale and context

What did we decide about authentication last month?

  • Time-scoped decision search
  • Includes who decided and why

Follow-Up Questions

After any initial answer, drill deeper:

Get More Detail

  • "Tell me more about that third point"
  • "Explain the reasoning behind this recommendation"
  • "What are the counter-arguments?"

Request Evidence

  • "What evidence supports this?"
  • "Show me specific quotes from customer calls"
  • "Which customers mentioned this?"
  • "What's the data behind this claim?"

Validate Confidence

  • "How confident are you in this answer?"
  • "What else would you need to be more certain?"
  • "Are there gaps in this analysis?"

Explore Alternatives

  • "What if we did X instead?"
  • "What are we missing?"
  • "What's the opposite perspective?"

What Works Well

✅ Specific Questions

Good: "What do customers say about our onboarding flow?" Better: "What pain points do SMB customers mention about onboarding in the last 30 days?"

✅ Using Exact Names

Good: "What's the status of that new feature?" Better: "What's the status of Project Phoenix?"

✅ Time-Scoped Questions

Good: "What did we ship?" Better: "What features did we ship last quarter?"

✅ Context-Rich Prompts

Good: "What should we prioritize?" Better: "Given our focus on SMB customers and limited eng resources, what should we prioritize next quarter?"

What Doesn't Work

❌ Vague Questions

Bad: "How are things going?" Why: Too broad, no clear answer

Better: "How is our sprint velocity trending over the last 3 months?"

❌ Questions Outside Your Data

Bad: "What's the weather?" Why: Brief has no web access

Bad: "What's Notion's pricing strategy?" Why: Brief only knows YOUR data

❌ Real-Time Status Checks

Bad: "Is Linear down right now?" Why: Can't check external service status

Better: "When was the last time we synced with Linear?"

❌ Questions Requiring Unconnected Data

Bad: "What do Salesforce leads say?" (if Salesforce not connected) Why: Can't access unconnected data

Better: First connect Salesforce, then ask

❌ Future Predictions

Bad: "Will we hit our Q4 goals?" Why: Can analyze trends but not predict future

Better: "Based on current velocity, are we on track for Q4 goals?"

Advanced Prompt Patterns

Context + Question + Format

Given our focus on SMB customers, 
what features should we prioritize next quarter? 
List the top 3 with evidence from customer calls.

Comparison with Criteria

Compare building feature X vs Y. 
Consider: customer demand, technical effort, strategic fit.
Show me evidence for each.

Time-Scoped Analysis

Analyze our decision-making speed in Q3. 
How long from first discussion to logged decision?
What's slowing us down?

Tips for Better Prompts

- Specific gets actionable answers - General surfaces unexpected patterns

  1. Start specific, get general when exploring

- Use project names, feature names, customer segments - Brief searches your actual content

  1. Reference your exact data

- "Show me the data" - "What supports this?" - Gets traceable answers

  1. Ask for evidence

- Don't try to ask everything at once - Build on previous answers

  1. Use follow-ups

- Time, resources, team size - Gets more realistic recommendations

  1. Mention constraints

What's Next?

Ready to improve your prompts further?