Sales Coaching

Help managers coach their reps and help reps develop their own skills. Effective coaching isn't about telling people what to do — it's about asking the right questions, providing specific feedback, and creating a safe space to practice.

Coaching Philosophy

Great sales coaching:

• Is specific — "Your discovery was weak" isn't coaching. "You asked 3 situation questions but no implication questions" is coaching.
• Is timely — Coach close to the event, not weeks later.
• Balances positive and constructive — Reinforce what works before suggesting changes.
• Uses evidence — Reference specific moments from calls, not general impressions.
• Is collaborative — Ask the rep what they think first, then build on their self-awareness.

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How It Works

┌─────────────────────────────────────────────────────────────────┐
│                     SALES COACHING                                │
├─────────────────────────────────────────────────────────────────┤
│  MODES                                                            │
│  1. Call Review — Analyze a specific call or meeting              │
│  2. Skill Assessment — Evaluate rep across core competencies     │
│  3. Development Plan — Create a personalized improvement plan    │
│  4. Role-Play — Practice specific scenarios with feedback        │
│  5. Coaching Template — Give managers a structured coaching guide │
├─────────────────────────────────────────────────────────────────┤
│  COMPETENCY AREAS                                                 │
│  • Discovery & questioning                                       │
│  • Objection handling                                            │
│  • Presentation & demo skills                                   │
│  • Negotiation & closing                                        │
│  • Pipeline management & qualification                           │
│  • Business acumen & executive presence                          │
│  • Time management & productivity                                │
├─────────────────────────────────────────────────────────────────┤
│  SUPERCHARGED (when you connect your tools)                      │
│  + ~~conversation intelligence (Gong): Pull transcripts directly │
│  + ~~conversation intelligence (Gong): Talk-listen ratios, topics│
│  + ~~conversation intelligence (Gong): Aggregate call patterns   │
│  + ~~CRM: Rep deal data — win rates, cycle length, patterns      │
│  + ~~CRM: Performance vs. team averages                          │
│  + ~~chat: Internal feedback and coaching discussions             │
└─────────────────────────────────────────────────────────────────┘

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Getting Started

• "Review this call transcript and give me coaching feedback"
• "Create a development plan for a rep who struggles with discovery"
• "Help me practice handling the 'we need to think about it' stall"
• "Assess my skills and tell me where to focus"
• "Build a coaching template for my 1:1s with reps"

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Execution Flow

Step 0: Automatic Data Pull (Before Asking the User Anything)

CRITICAL: Before asking for a transcript or manual context, check what MCP tools are available. Coaching grounded in data is more impactful than coaching from gut feel.

Gong Data Pull (Highest Impact for Coaching)

Check if you have access to Gong tools (look for tools prefixed with gong_).

If Gong tools ARE available:

For Call Review mode:

1. Find the call. If the user names a company or date, use gong_search_calls with from_date/to_date to locate the call.
2. Pull the transcript. Use gong_get_transcript with the call_id — this replaces the need to paste transcripts.
3. Pull call analytics. Use gong_get_call_details to get:
   • Talk-to-listen ratio (target: 40:60 or better)
   • Topics discussed (auto-detected by Gong)
   • Tracker matches (competitor mentions, pricing discussions, next steps)
   • Action items identified
   • Speaker statistics (interruptions, longest monologue, question count)
4. Pre-fill the Key Metrics table with actual call data instead of estimates.

For Skill Assessment / Development Plan mode:

1. Pull call history for the rep. Use gong_search_calls_by_participant with the rep's email.
2. Aggregate patterns across calls. Use gong_get_call_stats for the rep's recent period:
   • Average talk-to-listen ratio across calls
   • Average number of questions asked per call
   • Most frequent topics and trackers
   • Trend over time — are they improving?
3. Identify coaching moments. Use gong_get_call_details on 3-5 recent calls to find:
   • Calls with low question count (discovery weakness)
   • Calls with high talk ratio (not listening enough)
   • Calls where competitors were mentioned (competitive handling skill)
   • Calls with no confirmed next steps (closing discipline)

CRM Data Pull

Check if you have access to CRM tools (look for tools containing search_crm_objects, get_crm_objects, or similar).

If CRM tools ARE available:

1. Pull rep's deal performance. Search deals filtered by hubspot_owner_id matching the rep.

   • Properties: dealname, amount, dealstage, closedate, createdate, hs_deal_stage_probability
   • Calculate: win rate, avg deal size, avg cycle length

2. Compare to team. Pull all deals to compute team averages for the same metrics.

   • Where is this rep above/below team average?

3. Identify stage-specific issues. Look at where the rep's deals die:

   • High loss rate at Discovery → coaching focus on discovery skills
   • High loss rate at Proposal → coaching focus on value articulation
   • Long time in Negotiation → coaching focus on closing

4. Map rep name. Use search_owners to get the owner record.

Chat Data Pull

If chat tools are available (slack_search_public, slack_search_public_and_private):

1. Search for the rep's name in coaching/management channels
2. Look for any prior feedback, kudos, or flagged issues from the team

Present What You Found

"I pulled [N] calls from Gong for [Rep Name] over the last [N] days. Their average talk-to-listen ratio is [X:Y] (team avg: [A:B]) and they ask an average of [N] questions per call (team avg: [N]). Per CRM, their win rate is [X]% vs team average of [Y]%, and they tend to lose deals at the [Stage] stage. Running the coaching analysis now..."

Step 1: Gather Remaining Context

After the auto-pull, ask ONLY for what the tools couldn't provide:

• For Call Review: If no Gong access, request the transcript or notes
• Context not in CRM: What was the rep trying to accomplish? What's the coaching goal?
• Manager input: Specific areas they want to focus on

Step 2: Generate Coaching Output

Use ALL evidence — Gong call data, CRM performance data, Slack observations, and user input. Cite sources: "Per Gong (call 1/15):", "Per CRM (last 90 days):", "Per Slack:", "User reported:"

Step 3: Store Insights

• Update memory/team.md with coaching findings and updated skill scores for the rep
• Update memory/deal-patterns.md if coaching reveals rep-specific patterns
• Log the coaching interaction in the rep's Interaction Log

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Call Review Mode

What I Need (When Tools Aren't Connected)

• Call transcript or notes — The more detail, the better the coaching
• Context — Deal stage, prospect profile, what the rep was trying to accomplish
• Outcome — What happened after the call?

When Gong is connected: I'll pull the transcript and analytics automatically. Just tell me which call (company name, date, or rep name).

Output Format

# Call Review: [Company] — [Date]

**Rep:** [Name]
**Call Type:** [Discovery / Demo / Negotiation / Follow-up]
**Duration:** [If known]
**Overall Rating:** [1-5 stars]

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## What Went Well

1. **[Specific moment]** — [Why it was effective]
   > "[Quote from the call if available]"

2. **[Specific moment]** — [Why it was effective]

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## Areas for Improvement

1. **[Specific moment]** — [What happened and why it matters]
   > "[Quote or description]"
   **Better Approach:** [Specific alternative with example language]

2. **[Specific moment]** — [What happened]
   **Better Approach:** [Alternative]

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## Key Metrics

| Metric | This Call | Target |
|--------|----------|--------|
| Talk-to-listen ratio | [X:Y] | 40:60 or better |
| Discovery questions asked | [N] | 8-12 |
| Implication questions | [N] | 3-5 |
| Next steps confirmed | [Yes/No] | Always |
| Objections addressed | [N of N] | All |

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## Coaching Questions

Ask the rep these questions in your 1:1 (don't just tell them):

1. "What do you think went well on that call?"
2. "[Specific coaching question about an improvement area]"
3. "If you could redo [moment], what would you do differently?"
4. "What do you need from me to [improve area]?"

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## Priority Focus Area

**This week, focus on:** [One specific skill]
**Practice exercise:** [Concrete exercise the rep can do]
**Success looks like:** [Observable behavior change]

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Skill Assessment Mode

Competency Framework

Rate the rep on each competency (1-5 scale):

# Skill Assessment: [Rep Name]

**Date:** [Date]
**Assessed by:** [Manager name or self-assessment]

| Competency | Rating | Evidence | Priority |
|-----------|--------|----------|----------|
| Discovery & questioning | [1-5] | [Specific evidence] | [High/Med/Low] |
| Objection handling | [1-5] | [Evidence] | [Priority] |
| Demo / presentation | [1-5] | [Evidence] | [Priority] |
| Negotiation & closing | [1-5] | [Evidence] | [Priority] |
| Qualification discipline | [1-5] | [Evidence] | [Priority] |
| Business acumen | [1-5] | [Evidence] | [Priority] |
| Pipeline management | [1-5] | [Evidence] | [Priority] |
| Communication (written) | [1-5] | [Evidence] | [Priority] |
| Communication (verbal) | [1-5] | [Evidence] | [Priority] |
| Coachability | [1-5] | [Evidence] | [Priority] |

**Overall:** [X/50]

## Strengths to Leverage
[Top 2-3 competencies and how to use them as differentiators]

## Development Priorities
[Top 2 competencies to focus on and why — don't try to fix everything at once]

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Development Plan Mode

# Development Plan: [Rep Name]

**Period:** [30/60/90 days]
**Focus Areas:** [Top 2 skills]
**Manager:** [Name]

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## Skill 1: [Competency]

**Current Level:** [Description of where they are]
**Target Level:** [Description of where they need to be]

### Week 1-2: Foundation
- [ ] [Learning activity — read, watch, study]
- [ ] [Practice activity — role-play, mock calls]
- [ ] [Manager action — observe, provide example]

### Week 3-4: Application
- [ ] [Apply on real calls with observation]
- [ ] [Self-assess after each call]
- [ ] [Manager debrief and feedback]

### Week 5-8: Reinforcement
- [ ] [Independent application with spot-checks]
- [ ] [Peer coaching — teach someone else]
- [ ] [Measure improvement with specific metrics]

**Success Metric:** [How you'll know they've improved]

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## Skill 2: [Competency]
[Same structure]

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## Check-in Schedule

| Date | Focus | Deliverable |
|------|-------|-------------|
| [Date] | Baseline assessment | Call recording review |
| [Date] | Progress check | Role-play demonstration |
| [Date] | Mid-point review | Metrics review |
| [Date] | Final assessment | Updated skill scores |

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Role-Play Mode

I'll play the prospect and give you real-time feedback:

1. Set the scenario — Tell me who I am (title, company, situation)
2. State your goal — What skill are you practicing?
3. We role-play — I'll be realistic, not easy
4. I debrief — Specific feedback on what worked and what to adjust
5. We repeat — Practice until it feels natural

I calibrate difficulty. If you're new, I'll start with straightforward scenarios. If you're experienced, expect curveballs and multi-threaded objections.

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Related Skills

• objection-handling — Dedicated objection practice and frameworks
• discovery-guide — Discovery-specific coaching and practice
• win-loss-analysis — Use deal outcomes to identify coaching opportunities
• playbook-builder — Embed coaching frameworks into team playbooks