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Reports in Hindsight transform your deal data into actionable business insights through AI-powered analysis. This guide walks you through the complete process of creating, customizing, and sharing reports that drive strategic decision-making.

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Before You Start

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Prerequisites

  • At least 10-15 deals in your Hindsight database for meaningful analysis
  • Deals with sufficient context (CRM data, call transcripts, notes, or summaries)
  • Clear business questions you want your report to answer

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Types of Questions Reports Can Answer

  • Win/Loss Analysis: What factors drive successful deals vs. losses?
  • Competitive Intelligence: How are we performing against specific competitors?
  • Product Insights: What features are most requested or create friction?
  • Sales Performance: How effective are our sales processes and methodologies?
  • Market Trends: What patterns emerge across different segments or time periods?

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Step 1: Define Your Dataset

  1. Go to the Reports tab in your Hindsight dashboard
  2. Click Create New Report to open the report builder

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Apply Strategic Filters

Think carefully about what data will answer your business question: Deal Status Filtering
  • Closed Won + Closed Lost: For comprehensive win/loss analysis
  • Closed Won only: To understand success patterns
  • Closed Lost only: To identify failure modes
  • Open Deals: For pipeline health and current trends
Time Period Selection
  • Recent data (30-90 days): For current market conditions
  • Quarterly analysis: For performance reviews and planning
  • Year-over-year: For trend analysis and strategic planning
  • Custom ranges: For specific campaign or product launch periods
Segment Focus
  • New Business: For acquisition strategy insights
  • Expansion/Upsell: For growth strategy analysis
  • Renewal: For retention and customer success insights
  • Specific Products: For product-specific market intelligence

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Sample Dataset Configurations

Executive Win/Loss Review 
Status: Closed Won + Closed Lost
Period: Last Quarter
Segment: All segments
Competitive Analysis 
Status: All deals
Period: Last 6 months  
Segment: New Business
Competitors: Top competitors
Product Feedback Analysis 
Status: All deals
Period: Last 3 months
Segment: All segments
Product Line: Specific product

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Step 2: Configure Your Columns

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Default Fields

  • Decision Drivers: Key factors influencing deal outcomes
  • Competition: Competitive factors and mentions
  • Features: Product capabilities discussed or requested
  • Metrics: Deal size, timeline, and quantitative data
  • Summary: Contextual insights about deal outcomes

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Adding Custom Fields

Enhance your analysis by including relevant business context. This includes any of your synced CRM fields and other Hindsight-generated insights. Account Properties
  • Company size (employee count, revenue)
  • Industry vertical
  • Geographic region
  • Customer segment/tier
Deal Properties
  • Sales rep and team assignments
  • Deal source (inbound, outbound, referral)
  • Product line or solution type
  • Implementation complexity
Custom Answers
  • Specific qualitative insights you track
  • Champion identification
  • Budget authority confirmation
  • Technical evaluation results

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Column Selection Strategy

  • Start comprehensive: Include more fields initially, then refine
  • Match your questions: Ensure columns support your analysis goals
  • Consider correlations: Include fields that might reveal unexpected patterns
  • Balance detail vs. clarity: Too many columns can dilute insights

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Step 3: Generate and Review

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Create Your Report

  1. Review your dataset configuration in the preview table
  2. Verify you have sufficient deal volume (10+ deals minimum)
  3. Click Create Report to begin AI analysis
  4. Download the CSV if you want to review raw data

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Understanding the AI Process

The AI analyzes your dataset through several stages:
  1. Data Synthesis: Reviews all deal information and context
  2. Pattern Recognition: Identifies trends and correlations
  3. Insight Extraction: Generates specific findings and recommendations
  4. Report Structuring: Organizes insights into logical sections

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Initial Report Review

When your report generates, look for:
  • Data coverage: Confirms the right deals were included
  • Insight quality: Specific, actionable findings vs. generic observations
  • Evidence backing: Claims supported by deal examples and data
  • Logical structure: Clear flow from overview to specific insights

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Step 4: Customize Your Analysis

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Prompt Customization

Before generating, you can modify the AI prompt to focus on specific areas. Try adding specific sections to the report outline in the prompt: Standard Win/Loss Prompt 
Analyze this dataset for overall win/loss patterns, competitive factors, 
and sales execution insights. Focus on actionable recommendations.
Competitive-Focused Prompt 
Focus specifically on competitive dynamics. Identify which competitors 
we're losing to, why we win against others, and messaging gaps.
Product-Focused Prompt 
Emphasize product-related insights including feature requests, 
objections, and competitive product comparisons.
Sales Process Prompt 
Analyze sales methodology effectiveness, deal progression patterns, 
and coaching opportunities for the sales team.

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Step 5: Refine and Extend

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Conversational Follow-Up

After your initial report, continue the analysis: Ask Specific Questions
  • “What are the top 3 objections in lost deals?”
  • “How do win rates differ by company size?”
  • “Which features are mentioned most in closed won deals?”
Request Different Perspectives
  • “Analyze this data from a sales coaching perspective”
  • “What would a product manager need to know from this data?”
  • “How should marketing adjust messaging based on these insights?”
Drill Down on Findings
  • “Show me specific examples of the pricing objections mentioned”
  • “Which deals exemplify the competitive wins against [competitor]?”
  • “What’s the common thread in deals that mention [feature]?”

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Iterative Improvement

Refine your report through multiple iterations:
  1. First pass: Get overall patterns and high-level insights
  2. Second pass: Focus on specific findings that need deeper analysis
  3. Third pass: Extract actionable recommendations and next steps
  4. Final pass: Prepare insights for specific stakeholder audiences

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Step 6: Share and Act

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Save to Reports Library

  1. Give your report a descriptive name and tags
  2. Add it to your Reports Library for future reference
  3. Share via URL

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Best Practices for Ongoing Success

Reports are most valuable when they become a regular part of your business rhythm. Start with simple analyses and gradually develop more sophisticated approaches as your team becomes comfortable with the insights and their applications.
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