sales-coaching

Sales Coaching Skill

Structured frameworks for deal analysis, call coaching, and rep development.

Purpose

Enable continuous improvement of sales performance through win/loss analysis, call coaching, deal reviews, and skills development.

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Required Integrations

Setup: Connect these data sources to enable full functionality. Claude will prompt you to connect any missing integrations when you use this skill.

Data Sources

# SALES COACHING DATA SOURCES
# Configure the sources relevant to your coaching needs

# Enterprise Search (searches across all internal sources)
- source: enterprise_search
  connector: "{{GLEAN | MOVEWORKS | ELASTIC}}"
  data:
    - internal_docs
    - wiki_content
    - shared_drives
    - slack_history

# Call Recording & Conversation Intelligence
- source: call_recordings
  connector: "{{GONG | CHORUS | CLARI | WINGMAN}}"
  data:
    - call_recordings
    - talk_ratios
    - question_counts
    - topic_detection
    - sentiment_analysis
    - competitor_mentions
    - filler_words
    - next_steps_mentioned
    - monologue_lengths

# CRM & Deal Data
- source: crm
  connector: "{{SALESFORCE | HUBSPOT}}"
  data:
    - opportunity_history
    - stage_progression
    - win_loss_data
    - deal_notes
    - activity_history
    - pipeline_metrics
    - quota_attainment

# Sales Engagement
- source: sales_engagement
  connector: "{{OUTREACH | SALESLOFT | APOLLO}}"
  data:
    - email_metrics
    - sequence_performance
    - meeting_booked_rates
    - reply_rates

# Revenue Intelligence
- source: revenue_intelligence
  connector: "{{CLARI | AVISO | BOOSTUP}}"
  data:
    - forecast_accuracy
    - deal_scores
    - pipeline_health
    - rep_performance

# Learning Management
- source: lms
  connector: "{{LESSONLY | SEISMIC | HIGHSPOT | MINDTICKLE}}"
  data:
    - training_completion
    - certification_status
    - learning_paths

# Internal Playbooks & Docs
- source: internal_docs
  connector: "{{GOOGLE_DRIVE | SHAREPOINT | NOTION | CONFLUENCE}}"
  paths:
    - "/Sales/Playbooks/"
    - "/Sales/Win-Loss Analysis/"
    - "/Sales Enablement/Training/"

Output Destinations

# Where to deliver coaching outputs
outputs:
  # Always available - display in Claude UI
  - type: display
    enabled: true

  # Log coaching notes to CRM
  - type: crm
    connector: "{{SALESFORCE | HUBSPOT}}"
    actions:
      - add_coaching_notes
      - update_opportunity_notes
      - log_win_loss_analysis

  # Share insights with team
  - type: slack
    connector: "{{SLACK}}"
    channels:
      coaching: "#sales-coaching"
      wins: "#wins-channel"
      learnings: "#sales-learnings"

  # Save to enablement library
  - type: documents
    connector: "{{GOOGLE_DRIVE | SHAREPOINT | NOTION}}"
    destination: "/Sales Enablement/Coaching/"

  # Update LMS with identified skill gaps
  - type: lms
    connector: "{{LESSONLY | MINDTICKLE}}"
    actions:
      - assign_training
      - track_skill_gaps

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Instructions for Claude

IMPORTANT: Before executing this skill, you MUST validate the configuration above.

Pre-Execution Checklist

1. Check for placeholder values: Scan the YAML configuration for any {{...}} placeholders. These indicate required configuration that the user must provide.

2. Validate data sources: For each data source listed:

   • If a connector field shows {{OPTIONS}} format, ask the user which option they use
   • If URLs, paths, or names contain {{PLACEHOLDER}}, ask the user to provide actual values
   • Verify any required MCP servers are connected and available

3. Validate output destinations: For any output type beyond display:

   • Confirm the connector is available as an MCP server
   • Ensure destination paths/channels are configured (not placeholders)

If Configuration is Incomplete

Do not proceed with the skill. Instead:

1. List the specific missing or placeholder values found
2. Explain what each value is needed for
3. Ask the user to provide the missing configuration
4. Offer to help them set up the required MCP integrations

Example response when config is incomplete:

Before I can run this skill, I need some configuration:

**Missing values:**
- [List specific {{PLACEHOLDER}} values found]

**MCP connections needed:**
- [List required connectors not yet available]

Please provide these values, or let me know which data sources you'd like to skip.

Minimum Requirements

At minimum, this skill requires:

• Coaching context (deal review, skill gap, win/loss analysis)
• Rep or deal information
• display output enabled (always available)

Enhanced functionality requires:

• CRM for deal data and pipeline context
• Call recordings for conversation analysis
• Win/loss data for pattern recognition
• Sales methodology documentation

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Scheduling & Automation with Taizen

Automate this skill: Schedule recurring sales coaching tasks with Taizen. Create a free account to set up automated agents that run on your schedule.

How It Works

The Taizen MCP server accepts natural language requests to schedule agents. Simply describe what you want to automate:

Every Monday morning, generate a performance summary for each rep including
call metrics from Gong, win/loss patterns, and coaching priorities. Send to
#sales-management.

Taizen will:

1. Read this skill's definition to understand the capabilities
2. Create a recurring agent with your specified schedule
3. Execute the task and deliver results to your configured destinations

Example Natural Language Requests

Weekly Performance Digest:

Every Monday at 8am, generate weekly performance summaries for each sales rep
including call metrics, win/loss analysis, and coaching priorities. Post to
#sales-management and save to our Coaching folder.

Automated Call Coaching:

Whenever a new call is recorded in Gong, analyze it and send coaching feedback
to the rep and their manager if the talk ratio exceeds 70% or no next steps
were set.

Win/Loss Analysis:

When any deal closes (won or lost), automatically generate a comprehensive
win/loss analysis including call review and lessons learned. Post wins to
#wins-channel and save all analysis to our Win-Loss Analysis folder.

Monthly Skills Assessment:

On the 1st of each month, run skills assessments for all reps based on their
call data from the past month. Identify strengths and development areas, and
notify managers of their team's results.

Setting Up Taizen Automation

1. Create Account: Sign up at usetaizen.com
2. Connect MCP: Add the Taizen MCP integration in your Claude settings and authenticate
3. Connect Gong/Chorus: Link your conversation intelligence platform
4. Schedule Agent: Describe your automation in natural language
5. Taizen Reads Skill: The agent receives this skill's full definition to understand what it can do

Technical Details

When scheduling via Taizen MCP, Claude will:

1. Read this SKILL.md file to get the full skill definition
2. Call Taizen MCP with the skill content included

Parameter	Description	Example
task	Natural language description of what to do	"Generate weekly rep performance summaries"
schedule	When to run (cron or trigger)	"every Monday at 8am" or "when call is recorded"
skill_content	Object containing primary skill and referenced skills	See structure below
outputs	Where to send results	"Slack #sales-management, Google Drive"
team	Which team/reps to analyze	"Enterprise sales team"

skill_content structure:

skill_content:
  primary:
    name: "sales-coaching"
    content: "<full content of this SKILL.md>"
  referenced:
    - name: "product-context"
      content: "<full content of product-context SKILL.md>"

Note to Claude: When a user asks to schedule this skill with Taizen, read this entire SKILL.md file and pass it as skill_content.primary. Also read any referenced background skills (like product-context) and include them in skill_content.referenced.

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Coaching Modes

1. Win/Loss Analysis Framework

Structured analysis of closed opportunities:

Win Analysis

• What were the key factors in winning?
• Which messages/value props resonated?
• Who were the champions and how did we engage them?
• What competitive dynamics existed?
• What can we replicate?

Loss Analysis

• What were the primary reasons for losing?
• Where in the process did we lose momentum?
• What objections went unaddressed?
• What would we do differently?
• What can we learn?

No-Decision Analysis

• Why did the prospect go dark or delay?
• What signals did we miss?
• How could we have created more urgency?
• What qualification gaps existed?

2. Call Coaching

Review and coach on specific calls:

Talk Patterns

• Talk-to-listen ratio
• Question frequency and quality
• Monologue lengths
• Engagement signals

Discovery Quality

• Depth of questions
• Pain uncovered
• Business impact quantified
• Next steps secured

Objection Handling

• How objections were addressed
• Missed opportunities to probe
• Effective responses to replicate

3. Skills Assessment

Framework for manager-rep coaching conversations:

Skill Areas

• Discovery & qualification
• Value articulation
• Objection handling
• Negotiation & closing
• Account management
• Pipeline management
• Executive engagement

4. Deal Coaching

Real-time guidance on active opportunities:

• Deal qualification assessment
• Strategy recommendations
• Next best action
• Risk identification
• Resource deployment suggestions

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How to Use This Skill

Invoke with natural language describing what you need:

Win/Loss Analysis

• "Analyze the deal we won at Acme Corp - what worked?"
• "Do a loss analysis on the TechCorp opportunity - why did we lose?"
• "Review our win/loss data against Competitor X over the last quarter"
• "What patterns do you see in our lost deals this quarter?"

Call Coaching

• "Coach me on my discovery call with Nike yesterday"
• "Review Sarah's demo call with Stripe - what feedback should I give her?"
• "Analyze my last 5 calls - what should I work on?"
• "What are the common issues you see in our team's discovery calls?"

Rep Coaching Sessions

• "Help me prepare a coaching session for Sarah - focus on discovery skills"
• "What should I focus on in my 1:1 with Mike? Pull his recent data"
• "Create a development plan for a new rep struggling with objection handling"
• "Analyze the team's performance this month - who needs coaching on what?"

Deal Reviews

• "Review my deal strategy for the IBM opportunity"
• "What are the risks in my current pipeline?"
• "Help me prepare for our weekly deal review - pull my top 5 deals"
• "Is the Acme deal qualified? What gaps do we have?"

Team Analysis

• "What skill gaps does our team have based on call data?"
• "Compare top performers to the rest of the team - what are they doing differently?"
• "What training should we prioritize for the team?"

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Output Format

Win/Loss Analysis

## Win/Loss Analysis: [Company Name] - [Outcome]

**Analysis Date**: [Date]
**Data Sources Used**: [CRM, Gong, etc.]

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### Deal Overview

| Attribute | Value |
|-----------|-------|
| Company | [Name] |
| Deal Size | [Value] |
| Sales Cycle | [Days] |
| Outcome | [Won/Lost/No Decision] |
| Close Date | [Date] |
| Rep | [Name] |
| Competitors | [Who else was involved] |

### Key Factors in [Outcome]

**Primary Reason**:
[Main factor that determined the outcome - from CRM notes and call analysis]

**Contributing Factors**:
1. **[Factor 1]**: [Details with evidence from calls/notes]
2. **[Factor 2]**: [Details with evidence]
3. **[Factor 3]**: [Details with evidence]

### Process Analysis

*Based on call recordings and CRM activity:*

| Stage | What Happened | What Worked | What Didn't | Call Evidence |
|-------|---------------|-------------|-------------|---------------|
| Discovery | [Details] | [Positives] | [Negatives] | [Specific call moments] |
| Demo | [Details] | [Positives] | [Negatives] | [Specific call moments] |
| Proposal | [Details] | [Positives] | [Negatives] | [Specific call moments] |
| Negotiation | [Details] | [Positives] | [Negatives] | [Specific call moments] |

### Conversation Insights

*From Gong/Chorus analysis:*
- **Total Calls**: [Count]
- **Average Talk Ratio**: [%]
- **Key Objections Raised**: [List]
- **Sentiment Trend**: [How it changed over time]
- **Competitor Mentions**: [What was said]

### Stakeholder Analysis

| Stakeholder | Role | Sentiment | Impact on Deal |
|-------------|------|-----------|----------------|
| [Name] | [Role] | [+/-/Neutral from call sentiment] | [How they influenced] |

### Lessons Learned

1. **[Lesson 1]**: [Actionable takeaway]
2. **[Lesson 2]**: [Actionable takeaway]
3. **[Lesson 3]**: [Actionable takeaway]

### Recommendations

- **For this account**: [If applicable, next steps]
- **For similar deals**: [How to apply learnings]
- **For the team**: [Broader implications]

### Clips to Review

*Key moments from call recordings:*
- [Call name] @ [Timestamp]: [What happened - good or bad example]

Call Coaching

## Call Coaching: [Rep Name] - [Call Type]

**Call**: [Call name/account]
**Date**: [Date]
**Duration**: [Length]
**Data Source**: [Gong/Chorus]

---

### Call Metrics

| Metric | This Call | Rep Average | Team Average |
|--------|-----------|-------------|--------------|
| Talk Ratio | [%] | [%] | [%] |
| Longest Monologue | [seconds] | [seconds] | [seconds] |
| Questions Asked | [count] | [avg] | [avg] |
| Filler Words | [count] | [avg] | [avg] |
| Next Steps Set | [Yes/No] | [%] | [%] |

### What Went Well

1. **[Strength 1]**: [Specific example with timestamp]
2. **[Strength 2]**: [Specific example with timestamp]

### Areas for Improvement

1. **[Area 1]**:
   - What happened: [Specific example @ timestamp]
   - Suggestion: [How to improve]
   - Example response: "[What to say instead]"

2. **[Area 2]**:
   - What happened: [Specific example @ timestamp]
   - Suggestion: [How to improve]

### Discovery Quality Assessment

| Element | Status | Evidence |
|---------|--------|----------|
| Uncovered Pain | [✓/✗] | [Quote or lack thereof] |
| Quantified Impact | [✓/✗] | [Quote or lack thereof] |
| Identified Decision Maker | [✓/✗] | [Evidence] |
| Understood Timeline | [✓/✗] | [Evidence] |
| Clear Next Steps | [✓/✗] | [Evidence] |

### Objection Handling Review

| Objection | How It Was Handled | Better Approach |
|-----------|-------------------|-----------------|
| "[Objection]" | [What rep said] | [Improved response] |

### Coaching Conversation Guide

Questions to ask in your 1:1:
1. "What do you think went well on this call?"
2. "At [timestamp], the prospect said [X]. How did you interpret that?"
3. "If you could redo the [section], what would you do differently?"
4. "What support do you need to improve [skill area]?"

### Recommended Training

- [Specific training module related to identified gaps]
- [Practice exercise suggestion]

Rep Coaching Session

## Coaching Session: [Rep Name]

**Period**: [Time period reviewed]
**Manager**: [Your name]
**Data Sources**: [CRM, Gong, etc.]

---

### Performance Overview

| Metric | Actual | Target | Trend |
|--------|--------|--------|-------|
| Quota Attainment | [%] | [%] | [↑/→/↓] |
| Pipeline Coverage | [X]x | [Target]x | [↑/→/↓] |
| Win Rate | [%] | [Team avg %] | [↑/→/↓] |
| Average Deal Size | [$] | [Team avg $] | [↑/→/↓] |
| Sales Cycle | [days] | [Team avg] | [↑/→/↓] |

### Skill Assessment

*Based on call recording analysis:*

| Skill Area | Rating | Evidence | Priority |
|------------|--------|----------|----------|
| Discovery | [1-5] | [From call analysis] | [H/M/L] |
| Value Articulation | [1-5] | [From call analysis] | [H/M/L] |
| Objection Handling | [1-5] | [From call analysis] | [H/M/L] |
| Closing | [1-5] | [From call analysis] | [H/M/L] |
| Account Management | [1-5] | [From activity data] | [H/M/L] |

### Conversation Quality Trends

*From Gong/Chorus over [time period]:*
- **Talk Ratio Trend**: [Chart or summary]
- **Question Frequency**: [Improving/Stable/Declining]
- **Discovery Depth**: [Assessment]
- **Objection Handling**: [Assessment]

### Strengths to Leverage

1. **[Strength 1]**: [Evidence] → How to leverage more
2. **[Strength 2]**: [Evidence] → How to leverage more

### Development Areas

1. **[Area 1]**:
   - Evidence: [Specific examples from calls]
   - Impact: [How this affects results]
   - Development plan: [Specific actions]

2. **[Area 2]**:
   - Evidence: [Specific examples]
   - Impact: [How this affects results]
   - Development plan: [Specific actions]

### Action Plan

| Action | Timeline | Support Needed | Success Measure |
|--------|----------|----------------|-----------------|
| [Action] | [When] | [What help] | [How to measure] |

### Coaching Questions for 1:1

Use these to guide the conversation:
1. [Question about self-assessment]
2. [Question about specific deal/call]
3. [Question about goals]
4. [Question about obstacles]
5. [Question about commitment]

### Recommended Training

- [ ] [Training module 1] - addresses [skill gap]
- [ ] [Training module 2] - addresses [skill gap]

### Follow-Up Plan

- **Next Check-In**: [Date]
- **Focus Areas**: [What to review]
- **Metrics to Track**: [What to measure]

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Automation Options

When configured with integrations, this skill can:

1. Post-call coaching - Automatically generate coaching feedback after calls
2. Win/loss triggers - Auto-generate analysis when deals close
3. Weekly rep digests - Summarize call metrics and coaching opportunities per rep
4. Skill gap detection - Alert managers when patterns indicate training needs
5. Best practice library - Auto-tag and save great call moments for training