deal-coach

/octave:deal-coach — Deal Coaching

An interactive coaching skill built around the Resonate → Elevate → Compel sales methodology. Choose your output mode — role play, coaching microsite, coaching deck, or interactive quiz — and get coaching grounded in deal context AND your actual GTM messaging.

Three Stages:

Stage	Focus
Resonate	Understand and resonate with the buyer
Elevate	Confirm the fit and elevate the opportunity
Compel	Deliver the value and compel the buyer to action

Three Coaching Outputs per Stage:

Field	Type	Purpose
Buyer Mindset	String	Where the buyer's head is — psychology, fears, motivations
Value Propositions	Array	Which value props to deploy and why they fit this stage
Talking Points	Array	Specific things to say, grounded in deal context

This skill reads five coaching reference files at runtime:

• references/frameworks.md — Resonate / Elevate / Compel: Buyer Mindset + Value Props + Talking Points
• references/coaching-agents.md — 3 coaching agent personas + 2 cross-stage + scoring rubrics
• references/stage-mapping.md — Buyer's Journey → coaching stage mapping + inference rules
• references/html-templates.md — HTML section/slide templates per output mode
• references/messaging-narratives.md — How coaching grounds in GTM context

If reference files are not found, fall back to general coaching methodology and note the limitation.

How this differs from /octave:train:

• /octave:train is generic sales training (objection handling, personas, product knowledge)
• /octave:deal-coach is methodology-specific — every output is structured around Resonate/Elevate/Compel, scored against coaching rubrics, and coached by stage-specific agents

How this differs from /octave:meeting-prep:

• /octave:meeting-prep produces a strategic battle plan for an upcoming meeting
• /octave:deal-coach produces training and coaching materials organized around the three coaching stages

Usage

/octave:deal-coach
/octave:deal-coach [company domain or name]
/octave:deal-coach --mode [roleplay|microsite|deck|quiz]
/octave:deal-coach --stage [resonate|elevate|compel]
/octave:deal-coach [domain] --mode roleplay --stage elevate

Examples

/octave:deal-coach
/octave:deal-coach acme.com
/octave:deal-coach --mode roleplay
/octave:deal-coach acme.com --mode microsite --stage compel
/octave:deal-coach --mode quiz --stage resonate
/octave:deal-coach acme.com --mode deck --stage elevate

Instructions

Follow these steps precisely. Do not skip or reorder them.

---

Step 1: Choose Output Type (CT-1)

If the user specified --mode, use that. Otherwise, ask:

AskUserQuestion({
  questions: [{
    question: "What kind of deal coaching output do you want?",
    header: "Output Mode",
    options: [
      {
        label: "Role Play",
        description: "Practice a coaching-backed conversation scored against Buyer Mindset, Value Props, and Talking Points. 8-12 exchanges, then a scorecard."
      },
      {
        label: "Coaching Microsite",
        description: "Self-contained HTML coaching page organized around Buyer Mindset / Value Propositions / Talking Points — with deal context, priority actions, and stage-grounded messaging."
      },
      {
        label: "Coaching Deck",
        description: "Slide presentation walking through the coaching framework for a specific deal, with stage-specific content and talk tracks."
      },
      {
        label: "Interactive Quiz",
        description: "Test coaching methodology knowledge with deal-grounded scenarios. Scoring breaks down by Resonate/Elevate/Compel."
      }
    ],
    multiSelect: false
  }]
})

Store the selected mode for routing in Step 5.

---

Step 2: Identify Deal Context (CT-2)

Determine if coaching should be grounded in a specific deal or run in generic/practice mode.

If the user already provided a domain, name, or email, skip to 2b.

2a. Ask for deal context

AskUserQuestion({
  questions: [{
    question: "Should this be grounded in a specific deal, or do you want generic practice?",
    header: "Deal Context",
    options: [
      {
        label: "Specific Deal",
        description: "Ground coaching in a real account — uses CRM data, findings, events, and your playbook to make coaching deal-specific."
      },
      {
        label: "Generic Practice",
        description: "Practice the methodology with library-level data only (personas, playbook, proof points). No specific account context."
      }
    ],
    multiSelect: false
  }]
})

If Generic Practice: Skip to Step 2c.

If Specific Deal: Ask for the company domain or contact email:

AskUserQuestion({
  questions: [{
    question: "What company domain or contact email should I research?",
    header: "Company",
    options: [
      {
        label: "Enter domain",
        description: "e.g., acme.com"
      },
      {
        label: "Enter email",
        description: "e.g., jane@acme.com"
      }
    ],
    multiSelect: false
  }]
})

2b. Gather deal-specific context

Run these MCP tool calls to build a complete picture. Run independent calls in parallel:

Company & CRM Context (parallel):

enrich_company({ domain: "<domain>" })
find_crm_records({ domain: "<domain>" })
find_crm_activities({ domain: "<domain>" })
generate_crm_context({ domain: "<domain>" })

Library Context (parallel):

search_knowledge_base({ query: "<company name> OR <industry>" })
list_findings({ domain: "<domain>" })
list_events({ domain: "<domain>" })
list_all_entities({ entityType: "persona" })
list_all_entities({ entityType: "competitor" })
list_all_entities({ entityType: "proofPoint" })

Playbook (after knowledge base search returns):

get_playbook({ oId: "<matched_playbook_oId>" })

If any tool call fails, note the gap and continue. Coach with available data and flag missing context.

2c. Generic practice mode context

For generic mode, gather library-level data only:

search_knowledge_base({ query: "playbook" })
list_all_entities({ entityType: "persona" })
list_all_entities({ entityType: "competitor" })
list_all_entities({ entityType: "proofPoint" })

get_playbook({ oId: "<default_playbook_oId>" })

2d. Load coaching reference files

Read the references needed for the inferred or selected stage:

Read: references/frameworks.md
Read: references/stage-mapping.md
Read: references/coaching-agents.md
Read: references/messaging-narratives.md

If generating HTML output (microsite or deck), also read:

Read: references/html-templates.md

---

Step 3: Infer Coaching Stage + User Override (CT-3)

If the user specified --stage, use that and skip to Step 3b.

3a. Infer stage from signals

Use the weighted inference algorithm from references/stage-mapping.md:

Signal	Weight	Source
CRM deal stage	40%	find_crm_records → map to Resonate/Elevate/Compel
Conversation findings	30%	list_findings — pain points (→Resonate), competitor mentions (→Elevate), ROI/budget (→Compel)
Deal activity patterns	20%	list_events — discovery call (→Resonate), demo (→Elevate), proposal (→Compel)
Time in stage	10%	Days in current stage vs. expectation

For generic practice mode: Skip inference. Let the user choose:

AskUserQuestion({
  questions: [{
    question: "Which coaching stage do you want to practice?",
    header: "Stage",
    options: [
      {
        label: "Resonate",
        description: "Understand and resonate with the buyer — discovery principles, building trust through understanding"
      },
      {
        label: "Elevate",
        description: "Confirm the fit and elevate the opportunity — disrupt status quo, differentiate on value, build credibility"
      },
      {
        label: "Compel",
        description: "Deliver the value and compel the buyer to action — business case, Why Now, champion enablement"
      }
    ],
    multiSelect: false
  }]
})

3b. Present inference and allow override

Confidence calibration: CRM absence is a data hygiene issue, not a deal health signal. If CRM data is missing but activity signals are strong, redistribute the CRM weight across other signals.

Present the inference:

STAGE INFERENCE
===============
Stage: [Resonate / Elevate / Compel]
Confidence: [High / Medium / Low]
Buyer's Journey Phase: [Phase Name]

EVIDENCE
--------
CRM Stage (40%): "[Stage Name]" → maps to [Stage]  [or "No CRM record — data gap, not deal gap"]
Findings (30%): [Key signals]
Activities (20%): [Key activities]
Time (10%): [Assessment]

Then confirm:

AskUserQuestion({
  questions: [{
    question: "Does this stage assessment look right?",
    header: "Confirm Stage",
    options: [
      {
        label: "Yes — proceed with [Stage]",
        description: "Generate [selected mode] coaching for [Stage]"
      },
      {
        label: "No — let me pick",
        description: "Override the inference and choose a different stage"
      },
      {
        label: "Show all stages",
        description: "See all 3 stages with descriptions before choosing"
      }
    ],
    multiSelect: false
  }]
})

If user picks "No" or "Show all stages," present the full stage list (same as generic mode above).

3c. Stall detection

If time-in-stage signals indicate a stalled deal (>2x expected time), add stall diagnosis:

STALL DETECTION
===============
This deal appears stalled at [Journey Phase].
Time in stage: [X] days (expected: [Y] days)

Root Cause Hypothesis: [Stage] gap
- [Explanation of why this stage gap is likely the root cause]
- [Specific evidence from findings/activities]

Recommendation: Focus coaching on [Root Cause Stage], not the nominal CRM stage.

Route to the root cause stage's coaching agent, not the nominal stage.

---

Step 4: Route to Coaching Agent (CT-4)

Based on the confirmed stage, activate the appropriate coaching agent from references/coaching-agents.md:

Stage	Coaching Agent	Focus
Resonate	Resonance Coach	Discovery principles (wide, deep, high), trust building
Elevate	Elevation Coach	Case for Change, Value Framing, differentiated value, proof points
Compel	Compel Coach	Business case building, Why Now Case, champion enablement

Cross-stage agents (available as supplements):

• Negotiation Strategist — Available when stage is Compel and negotiation dynamics surface
• Objection Handler — Available at any stage when objections surface in findings

Load the agent's persona, coaching criteria, scoring rubric, and grounding instructions from the reference file. Use the grounding map from references/messaging-narratives.md to connect the agent's outputs to the seller's Octave library data.

---

Step 5: Generate Output (CT-5)

Branch based on the output mode selected in Step 1.

---

Mode 1: Role Play (RP-1 through RP-4)

RP-1: Setup the Scenario

AskUserQuestion({
  questions: [{
    question: "What kind of role play do you want?",
    header: "Scenario",
    options: [
      {
        label: "Single Stage Practice",
        description: "Practice one stage ([Stage]) in a focused 8-12 exchange conversation"
      },
      {
        label: "Full Journey Simulation",
        description: "Walk through Resonate → Elevate → Compel in sequence, simulating the full buying journey"
      }
    ],
    multiSelect: false
  },
  {
    question: "How difficult should the buyer be?",
    header: "Difficulty",
    options: [
      {
        label: "Friendly",
        description: "Buyer is open and receptive. Good for learning the coaching framework."
      },
      {
        label: "Skeptical",
        description: "Buyer pushes back moderately. Tests methodology under pressure."
      },
      {
        label: "Hostile",
        description: "Buyer is resistant, dismissive, or aggressive. Tests advanced skills and composure."
      }
    ],
    multiSelect: false
  }]
})

If in specific-deal mode, identify the buyer persona from entities gathered in Step 2. If generic, let the user choose from available personas:

AskUserQuestion({
  questions: [{
    question: "Which persona should the buyer represent?",
    header: "Buyer Persona",
    options: [
      // Dynamically populated from list_all_entities({ entityType: "persona" })
      {
        label: "[Persona Name]",
        description: "[Persona title/role — from entity data]"
      }
      // ... up to 4 personas
    ],
    multiSelect: false
  }]
})

RP-2: Load Stage-Specific Intelligence

Load the coaching agent's rubric and grounding map for the selected stage.

For deal-specific mode, map all Octave data to coaching output fields using references/messaging-narratives.md.

For generic mode, use playbook-level data to create a representative scenario.

Prepare buyer behavior rules based on stage:

Stage	Buyer Psychology	Behavior Rules
Resonate	Exploratory, guarded	Shares surface problems, tests whether seller digs deeper. Friendly: volunteers info. Hostile: one-word answers.
Elevate	Status quo defender / comparison shopper	Resists change, references competitors. Friendly: open to new perspective. Hostile: "We've been doing fine for years" / "Your competitor does that too."
Compel	Analytical, needs numbers, risk-averse	Asks about ROI, pushes back on vague claims. Friendly: engages with data. Hostile: "Those numbers don't apply to us" / "Now is not the right time."

RP-3: Run the Role Play

Set the scene:

See mode-output-templates.md for the role play scene setup template.

Then begin as the buyer persona:

• Play the buyer with stage-appropriate behavior (see table above)
• Adjust resistance based on difficulty level
• Drop stage-relevant cues that a well-trained seller should pick up on
• Friendly: give verbal rewards when the seller executes methodology correctly
• Skeptical: push back on weak points but yield to strong methodology
• Hostile: resist aggressively; only yield to excellent execution
• Allow natural conversation flow — don't force every principle or beat
• After 8-12 exchanges, signal wrap-up: "I think we're running short on time..."

For Full Journey Simulation:

• Start at Resonate and progress through each stage
• After each stage, pause: "Good — let's fast-forward. [Context for next stage]."
• Score each stage independently, then provide a cumulative scorecard

RP-4: Coaching Scorecard

After the role play ends:

See mode-output-templates.md for the full coaching scorecard template with stage-specific talking points rubrics.

After the scorecard:

Want to:
1. Run this role play again (same stage, same difficulty)
2. Try a harder difficulty level
3. Practice the next stage ([Next Stage])
4. Practice objection handling for this stage
5. Get a coaching microsite for this stage
6. Switch to a different output mode
7. Done

---

Mode 2: Coaching Microsite (MS-1 through MS-3)

MS-1: Style Selection

Reference the style preset system from skills/deck/references/style-presets.md.

Each coaching stage has a default style preset:

Stage	Default Preset	Rationale
Resonate	soft-light	Exploratory, calm, trust-building
Elevate	midnight-pro	Urgency, disruption, bold contrast
Compel	executive-dark	Business gravitas, financial seriousness

Present the default with option to override:

AskUserQuestion({
  questions: [{
    question: "The default style for [Stage] is [preset name] ([rationale]). Want to use it or pick a different style?",
    header: "Style",
    options: [
      {
        label: "[Default Preset] (Recommended)",
        description: "[Preset description]"
      },
      {
        label: "Pick a different style",
        description: "Choose from available presets"
      },
      {
        label: "Auto-pick from brand",
        description: "Extract colors from the company's website and generate a custom theme"
      }
    ],
    multiSelect: false
  }]
})

If user picks "Pick a different style," present mood-based preview options (follow the pattern from deck/SKILL.md Step 4).

MS-2: Generate Content Outline

Before generating HTML, present the content plan:

See mode-output-templates.md for the microsite content outline template with full structure, design principles, and Octave sources block.

MS-3: Generate HTML

Use templates from references/html-templates.md to generate a self-contained HTML file.

Content grounding rules (from references/messaging-narratives.md):

• Every Value Proposition must reference specific playbook messaging — never generic claims
• Every proof point must cite a specific library entity, appear inline in the section it supports, and include a usage note (deploy now / save for later / already shared)
• Every Talking Point must be grounded in the deal context (if available) and connected to the Buyer Mindset
• Every objection response must be grounded in the specific decision the buyer is making — not generic competitive objections
• Use "perspective-shifting question" framing — collaborative, not adversarial
• This is a selling tool — orient language around advancing the deal

Structural rules:

• Header + Deal Brief is NOT collapsible — full-width gradient hero with deal stats
• Priority Actions, Deal Activity, and Journey Map are collapsible <details> with +/− toggle
• Sections 01-06 (07 if MEDDPICC included) are collapsible <details> elements
• ALL collapsible sections start COLLAPSED by default (no open attribute)
• The Play is NOT collapsible — full-width gradient footer
• No duplicate content between sections
• Evidence goes inline (not standalone)
• Do NOT use framework labels as visible headers in Talking Points (e.g., "The Shift", "The Stakes"). Use practical deal-specific language. The framework informs content structure internally.
• Do NOT include both "Elevate" and "Evaluate" badges in the header — use "Coaching Stage: [Name]" only. The Journey Map section explains the buyer journey mapping.

Content density limits:

Section	Limit
Header + Deal Brief	Company info + 4-6 deal stats + coaching stage badge + deal-specific subtitle
Priority Actions	Exactly 3 actions
Deal Activity	3-6 timeline entries (key events + "Next" entry)
Journey Map	3 phases (Resonate/Elevate/Compel), each with generic explanation + deal-specific context
Stage Assessment	3-4 evidence cards + confidence calibration
Buyer Mindset	Mindset narrative + 3-5 buyer signals + adaptation guidance
Value Propositions	4-6 props with evidence inline and usage notes
Talking Points	4-6 talk tracks (strategic point + quote + evidence) organized by conversation flow
Objection Handling	3-5 objections grounded in buyer's decision frame
Next Stage Preview	1 transition checklist + next agent preview
Deal Gaps (MEDDPICC)	8 elements + gap-to-action mapping (if included)
The Play	1 strategic sentence + 1 concrete action

Output location:

.octave-deal-coach/
  [company-kebab]-[stage]-[YYYY-MM-DD]/
    [company-kebab]-[stage].html

Example:
.octave-deal-coach/acme-corp-elevate-2026-03-03/acme-corp-elevate.html

For generic mode, use practice instead of company name:

.octave-deal-coach/practice-resonate-2026-03-03/practice-resonate.html

After writing the file, open it:

open "[file path]"

---

Mode 3: Coaching Deck (DK-1 through DK-3)

DK-1: Style Selection

Same as MS-1. Use stage-appropriate default presets.

DK-2: Generate Slide Outline

Present the slide outline for approval. Slide content varies by stage:

Resonate (~7 slides):

1. Title Slide — "[Company] — Resonate" + stage badge
2. Stage Context — Deal position, buyer's journey phase, buyer mindset assessment
3. Buyer Mindset Deep Dive — Awareness level, trigger, constraints, adaptation guidance
4. Discovery Principles — Go wide, go deep, go high — applied to this deal
5. Value Propositions — Stage-appropriate props with deployment guidance
6. Talking Points — Discovery questions and conversation starters with listening cues
7. Next Steps — Transition checklist to Elevate

Elevate (~9 slides):

1. Title Slide — "[Company] — Elevate" + stage badge
2. Stage Context — Deal position, competitive landscape, buyer mindset
3. Buyer Mindset Deep Dive — Status quo attachment, change readiness, evaluation mode
4. The Case for Change — The Shift → The Stakes → The Possibility for this deal
5. Differentiated Value — What's unique AND important to this buyer
6. Value Propositions — Value Framing examples (Product → Buyer → Executive voice)
7. Talking Points — Case for Change talk tracks + differentiation delivery
8. Proof Points — Evidence grid with deployment guidance
9. Next Steps — Transition checklist to Compel

Compel (~9 slides):

1. Title Slide — "[Company] — Compel" + stage badge
2. Stage Context — Decision dynamics, stakeholder positions, buyer mindset
3. Buyer Mindset Deep Dive — Decision process, champion strength, detractors, risk appetite
4. Before vs. After — Side-by-side with quantified delta
5. Value Chain — Capability → workflow improvement → business outcome → financial result
6. Value Propositions — ROI-focused props with quantified outcomes per stakeholder
7. The Why Now Case — Business urgency + personal urgency
8. Talking Points — Business case narration + champion enablement scripts
9. Next Steps — Decision pathway and timeline

Present outline and ask:

Generate this deck?
1. Yes — generate
2. Adjust slides
3. Change style
4. Start over

DK-3: Generate HTML Deck

Use slide templates from references/html-templates.md for a self-contained HTML file with scroll-snap slide architecture.

Viewport fitting rules (from deck/SKILL.md):

• ALL font sizes use clamp() — never fixed px
• ALL spacing uses clamp()
• Strict content per slide: Title = 1 heading + 1 subtitle; Content = 1 heading + 4-6 bullets; Grid = max 6 cards
• If content exceeds limits, split into additional slides
• overflow: hidden on every .slide
• Media queries at 700px, 600px, 500px for short viewports

Animation:

• Staggered entrance via Intersection Observer
• .animate-in class with opacity + translateY
• nth-child stagger delays
• Respect prefers-reduced-motion

Navigation:

• Keyboard: ArrowDown/Up, Space, PageDown/Up
• Scroll snap for touch/trackpad
• Progress bar + nav dots
• Print: page-break-after: always, remove snap

Output location:

.octave-deal-coach/
  [company-kebab]-deck-[stage]-[YYYY-MM-DD]/
    [company-kebab]-deck-[stage].html

After writing, open in browser:

open "[file path]"

---

Mode 4: Interactive Quiz (QZ-1 through QZ-4)

QZ-1: Choose Quiz Type

AskUserQuestion({
  questions: [{
    question: "What type of coaching quiz do you want?",
    header: "Quiz Type",
    options: [
      {
        label: "Stage Recognition",
        description: "A buyer says X — which coaching stage? Tests your ability to diagnose where a deal is."
      },
      {
        label: "Methodology Application",
        description: "You're in [Stage] — what's the right Buyer Mindset, Value Props, and Talking Points approach? Tests methodology knowledge."
      },
      {
        label: "Talk Track Completion",
        description: "Buyer says [objection/question]. Using the coaching methodology, what's your response?"
      },
      {
        label: "Full Review",
        description: "Mix of all categories covering Resonate, Elevate, and Compel. Comprehensive assessment."
      }
    ],
    multiSelect: false
  },
  {
    question: "How many questions?",
    header: "Length",
    options: [
      {
        label: "Quick (5 questions)",
        description: "Fast check — 5-10 minutes"
      },
      {
        label: "Standard (10 questions)",
        description: "Thorough assessment — 15-20 minutes"
      },
      {
        label: "Deep (15 questions)",
        description: "Comprehensive review — 25-30 minutes"
      }
    ],
    multiSelect: false
  }]
})

QZ-2: Load Quiz Material

Load coaching content from reference files. If deal-specific, ground questions in actual deal data. If generic, use playbook-level data.

Build question bank by category:

Stage Recognition:

• Present a buyer quote or scenario → ask which stage
• Use findings and CRM data for realistic scenarios
• Include red herrings (scenarios that seem like one stage but are actually another)

Methodology Application:

• Name a stage → ask for the right approach
• E.g., "You're in Elevate. What are the three beats of the Case for Change?"
• E.g., "A buyer says they're evaluating competitors. Which coaching output fields should you focus on, and what goes in each?"
• Include application questions that test Buyer Mindset → Value Props → Talking Points mapping

Talk Track Completion:

• Present a buyer statement → ask for the methodology-backed response
• E.g., "Buyer: 'We're happy with what we have.' Using the Elevate methodology, what do you say next?"
• Score on methodology adherence AND natural delivery

Full Review:

• Mix all categories
• Weight toward the selected/inferred stage
• Ensure coverage across all three stages

QZ-3: Run the Quiz

Present questions one at a time:

QUESTION [N]/[Total]
Category: [Stage Recognition / Methodology Application / Talk Track Completion]
Stage: [Resonate / Elevate / Compel]
[If deal-grounded: "Based on your [Company] deal"]

[Question text]

[For multiple choice: Present 4 options]
[For open-ended: Ask the user to type their response]

After each answer:

[Correct / Partially Correct / Incorrect]

[Brief explanation referencing specific coaching elements]
[If deal-grounded: How this applies to their specific deal]

Score so far: [X]/[N]

QZ-4: Quiz Results

See mode-output-templates.md for the full quiz results template with breakdowns by stage, dimension, and category.

After results:

Want to:
1. Retake this quiz
2. Take a quiz focused on your weakest area ([Stage])
3. Practice a role play for your weakest area
4. Get a coaching microsite for your weakest area
5. Try a different output mode
6. Done

---

Step 6: Delivery + Next Actions (CT-6)

After delivering any output, offer iterations:

For Role Play and Quiz: Next actions are included in RP-4 and QZ-4 above.

For Microsite and Deck: After opening the HTML file, present:

Coaching [microsite/deck] generated and opened in your browser.

File: [file path]
Company: [Company Name or "Generic Practice"]
Stage: [Resonate / Elevate / Compel] — [Stage subLabel]
Coaching Agent: [Agent Name]
Style: [Preset Name]

Want to:
1. Practice this stage with a role play
2. Add MEDDPICC deal gap analysis [if not already included]
3. Move to the next stage ([Next Stage]: [subLabel])
4. Try a different output mode for this stage
5. Regenerate with a different style
6. Done

If the user picks option 3 (next stage), return to Step 3b with the next stage pre-selected and flow through Steps 4-5 again.

---

Output Directory

All HTML outputs go to .octave-deal-coach/ in the project root:

.octave-deal-coach/
  [company-kebab]-[stage]-[YYYY-MM-DD]/
    [company-kebab]-[stage].html            # Microsite
  [company-kebab]-deck-[stage]-[YYYY-MM-DD]/
    [company-kebab]-deck-[stage].html       # Deck

This directory should be in .gitignore.

---

MCP Tools Used

Research & Enrichment

Tool	Purpose
enrich_company	Company profile, industry, tech stack, strategic context
find_crm_records	Deal stage, amount, close date, pipeline position
find_crm_activities	Recent interactions — calls, emails, meetings
generate_crm_context	AI-synthesized CRM narrative

Library — Fetching

Tool	Purpose
get_playbook	Full playbook with value props, messaging, positioning
get_entity	Individual entity details (persona, competitor, proof point)

Library — Searching

Tool	Purpose
search_knowledge_base	Find matching playbooks, guides, research
search_resources	Find relevant resources (docs, presentations)
list_all_entities	List personas, competitors, proof points, references
list_findings	Objections, pain points, competitor mentions from conversations
list_events	Deal history, stage changes, activity timeline

Content Generation

Tool	Purpose
generate_content	Generate supporting content if needed

---

Error Handling

No CRM data found: "I couldn't find CRM records for [domain]. I'll proceed with library-level data only. Stage inference will rely on findings and events. You can also manually select a stage."

No playbook found: "No matching playbook found. I'll use general coaching methodology without playbook-specific grounding. Talk tracks will reference the framework but won't include your specific messaging. Consider running /octave:library to check your playbook setup."

No findings/events: "No conversation findings or events found for [domain]. Stage inference will rely primarily on CRM stage. For more accurate coaching, ensure conversation data is synced to Octave."

Reference file not found: "Could not load [reference file]. Falling back to general coaching methodology. For full coaching, ensure reference files are in skills/deal-coach/references/."

Stage inference low confidence: "I'm not confident about the coaching stage — multiple stages scored similarly. I'd recommend selecting manually. Here are all options: [present all three stages]."

MCP connection failed: "Could not connect to Octave. Check your connection with /octave:workspace. Deal coaching requires Octave MCP tools for deal context and library data."

HTML write failed: "Could not write the HTML file. Check that .octave-deal-coach/ is writable. Try: mkdir -p .octave-deal-coach"

---

Related Skills

• /octave:train — Generic sales training (role play, quiz, guided learning) without deal coaching methodology
• /octave:meeting-prep — Strategic meeting battle plan as HTML
• /octave:deck — General-purpose slide deck builder
• /octave:pipeline — Deal coaching and pipeline management
• /octave:enablement — Sales enablement materials (cheat sheets, objection guides)
• /octave:battlecard — Competitive intelligence and battlecards
• /octave:research — Account and person research