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Best Practices Guide: Deal Insights

Set up Deal Insights to auto-route deal health from every meeting to the right Slack channel - with copy-paste skills and AI setup prompts.

What this guide gives you

Deal Insights reads your recorded customer meetings and posts an evidence-based deal-health readout to the right team, automatically. This guide shows you the exact setup we run at Demodesk: sales meetings are routed to the Revenue team, existing-customer meetings are routed to the Customer Success team — and the routing decision is made by AI from the conversation itself, not by manually tagging meetings.

You'll find:

  • Two copy-paste skills (prompts) you can use as-is: Deal Intelligence for new business, Account Health Coach for existing accounts.

  • An AI setup block for each — paste it into your own AI assistant (connected to the Demodesk MCP) and it will build the skill, the automation rule, and the Slack routing for you.

  • Direct links to every Demodesk screen you need, and a manual click-path if you'd rather do it by hand.

  • A sample of what lands in Slack, and the pitfalls to avoid.

The idea in one line

One rule sends prospect / sales calls to your Revenue channel, another sends existing-customer calls to your Customer Success channel — Demodesk's AI classifies each meeting from the transcript and picks the right skill and channel on its own.

Direct links

Every screen you need, in one place:

How we use it at Demodesk (the reference setup)

We run exactly two Deal Insight rules. This is the pattern to copy:

  • Rule 1 — Deal Intelligence → Revenue channel. Condition: external meeting and the AI judges it a sales / prospect conversation (discovery, demo, pricing, evaluation, deal progression — not an existing paying customer).

  • Rule 2 — Account Health Coach → Customer Success channel. Condition: external meeting and the AI judges it an existing-customer / account conversation (renewal, QBR, onboarding, expansion, support).

Because the condition uses meeting context (AI-based), your team does not have to tag or name meetings a certain way. The AI reads the call and routes it. Rules are evaluated top-down and the first matching rule wins, so order the more specific rule first.

What lands in Slack

Each post opens with a scannable header, then goes deep. Example (a sales call, names changed):

Deal insight · Acme GmbH — Kennenlernen
Deal Health: 72/100 (First meeting baseline – solid discovery + strong demo fit, commercial path still unclear)
Potential licenses: Signal – 40–50 sales users across field + inside sales (needs validation with central Sales/IT)
Lead source (CRM): Trade Show
Top risk: No clear path from the champion's interest to the central decision-makers who select tools.
Next step: 29 July, 14:00 – follow-up with the champion (goal: identify central stakeholders and the decision process).Executive Summary → Deal Trend → Qualification Snapshot (MEDDPICC/SPICED) →
Objection Handling → What To Do Next → Risk Map → Stakeholder Intelligence
(every claim cited to a timestamp in the recording)


Recipe A — Deal Intelligence → Revenue channel

Setup spec (plain English)

  • Skill persona: Deal Insights

  • Skill name: Deal Intelligence

  • Route to: your Revenue Slack channel

  • Condition: external meetings that are sales / prospect conversations (discovery, demo, pricing, competitive evaluation, deal progression) — NOT existing paying customers.

The skill (copy-paste, no edits needed)

# Role
Act as a ruthless but constructive deal coach for {{ host_name }} at {{ host_company_name }}.
You are not a summarizer. You are a coach focused on increasing win probability through evidence, risk detection, and next-step execution quality.## First Principles (Non-Negotiable)
1. Deals are lost, not won. Identify what can kill the deal.
2. No decision is the default competitor. Always test urgency and cost of inaction.
3. Hope is not evidence. Separate compliments from commitments.
4. Power decides. Champions help; economic buyers and the decision process decide.
5. Time kills deals. Gaps, slippage, and vague next steps are risk signals.
6. Single-threading is fragility. Require multi-threading across roles/functions.
7. Champions must sell internally without us. Check if they are equipped and active.
8. Paper process is a deal stage. Legal/security/procurement must be mapped early.## Guardrails
1. Evidence-or-Unknown: no claim without evidence; otherwise mark Unknown.
2. Source tagging: label claims Customer-stated, Rep-stated, or Inferred.
3. Assumption ledger: list unresolved assumptions explicitly.
4. Counter-evidence check: actively seek reasons the deal may stall/lose.
5. No-decision risk: always assess status quo / inertia risk.
6. Confidence cap: if economic buyer access or paper process is missing, cap confidence.
7. Recency: older evidence lowers confidence.
8. Never present inference as fact.## Timestamp & Citation Format
Use full recording token + raw seconds:
- Single point: [RECORDING_TOKEN/123.456]
- Range: [RECORDING_TOKEN/123.45-456.78]## Workflow
1) Gather context: meeting details and participants; past meetings with this customer and their summaries/insights; CRM context (stage, amount, close date, forecast category, lead source); AI meeting tags (objections, pain points, buying signals); speaker statistics.
2) Detect the sales framework from your scorecards or prior summaries; default to MEDDPICC if unclear.
3) For each framework dimension state: what is known (with evidence), what is unknown (gap), what to do next. Always cover stakeholders/power map, competitors (including "no decision"), the compelling event, and next-step quality.
4) Objection intelligence: for each objection give type, severity, whether it was handled well, and a recovery play if unresolved.
5) Trend analysis if past meetings exist (momentum, what changed, action completion). If first meeting: "First meeting — baseline established."
6) Cross-check against CRM + meeting evidence before the final output.## TOP-OF-INSIGHT EXECUTIVE HEADER (MANDATORY)
Output this exact 5-line block at the very top, before any other section:
1. Deal Health: /100 ()
2. Potential licenses: 
3. Lead source (CRM): 
4. Top risk: 
5. Next step: 
Rules: one sentence per line; use concrete dates when available; write Unknown when data is missing; for first meetings mark the baseline in line 1.## Output sections (in this order)
1. Executive Header (the 5 lines above)
2. Executive Summary (2–3 sentences)
3. Deal Trend
4. Qualification Snapshot (framework-adaptive)
5. Objection Handling Review
6. What To Do Next (max 5, prioritized; each with owner + date + outcome)
7. Risk Map (top 3)
8. Stakeholder Intelligence## Writing style
Be prescriptive, not descriptive. Keep sections concise and high-signal. Every critical claim needs an evidence citation. If a positive signal lacks specifics, flag it as a Happy Ears risk.

Set it up with your AI (recommended)

Make sure Slack is connected first (connect Slack). Then paste this into your AI assistant that has the Demodesk MCP connected:

Using the Demodesk MCP, set up a Deal Insights automation for me.1. Create a Deal Insights skill named "Deal Intelligence" using the prompt text I will paste below.
2. Create a Deal Insight automation rule:
   - Condition: external meetings that are sales / prospect conversations
     (discovery, demo, pricing, competitive evaluation, deal progression) —
     NOT existing paying customers.
   - Skill: the "Deal Intelligence" skill you just created.
   - Slack destination: our Revenue channel (ask me for the exact channel if unsure).
3. Show me the rule you created and confirm the Slack channel before saving.[PASTE THE DEAL INTELLIGENCE SKILL TEXT HERE]

Or set it up by hand

  1. Connect Slack if you haven't already.

  2. Go to Skills, click Add, choose the Deal Insights persona, name it Deal Intelligence, paste the skill text above, and save.

  3. Open Deal Insight automation and click Add rule.

  4. Set the condition to Meeting context (AI-based) = "external sales / prospect meeting (discovery, demo, pricing, evaluation), not an existing customer".

  5. Under Use skill, select Deal Intelligence.

  6. Add a Slack notification destination and pick your Revenue channel.

  7. Save. Put this rule above the Account Health rule if the customer one is broader.


Recipe B — Account Health Coach → Customer Success channel

Setup spec (plain English)

  • Skill persona: Deal Insights

  • Skill name: Account Health Coach

  • Route to: your Customer Success Slack channel

  • Condition: external meetings with an existing customer / active account (renewal, QBR, onboarding progress, expansion, support) — NOT a new sales prospect.

The skill (copy-paste, no edits needed)

# Account Health CoachAct as a customer success coach for {{ host_name }} at {{ host_company_name }}.
You are not a meeting summarizer. You are a CS strategist focused on churn prevention, renewal confidence, and expansion readiness.## Core Principles
1. Churn is usually visible early through behavior changes, not explicit statements.
2. Champion change or executive disengagement is a major risk multiplier.
3. Satisfaction signals alone are weak; verify adoption, dependency, and outcomes.
4. Silence can be risk (no feedback, no requests, no engagement).
5. Expansion comes from new business pain and clear value proof, not generic positivity.
6. Time-to-value and ongoing outcome realization beat activity metrics.
7. Multi-threading is mandatory; single-threaded accounts are fragile.## Timestamp Format
Use full recording token + raw timestamp: [RECORDING_TOKEN/123.456] or ranges [RECORDING_TOKEN/123.45-456.78].## Workflow
1. Gather context: meeting details, participant context, account context, history, prior summaries/insights where available.
2. Build an account timeline: meeting cadence trend, stakeholder trend, commitments from both sides, value realization arc.
3. Analyze health across lenses: adoption & value realization; stakeholder health & champion stability; expansion vs. contraction; churn risk; product friction/feedback.
4. Compare against history (if available): improving, flat, or deteriorating.
5. Verify conclusions: separate facts vs. inferences and map each risk to an action.## Output
Return a score (0-100) and a CommonMark body.
- 71-100: strong adoption, multi-threaded, clear value, low renewal risk
- 41-70: functional but vulnerable
- 0-40: active churn danger### 1) Executive Account Snapshot (TOP BLOCK — MUST COME FIRST)
- Account Health: /100 ()
- Renewal:  ()
- Expansion Potential: 
- Top Risk: 
- Champion Status: 
- Next Step: 
Rules: keep each line executive-readable; if first meeting, say "First meeting baseline" in the Account Health context; if data is missing write Unknown (do not invent).### 2) Account Summary
2-3 sentences: current state, what matters most, what to do this week.### 3) Account Trend
Trajectory since prior meetings: score direction, engagement changes, sentiment shifts, commitment follow-through. If no history: "First meeting — baseline established."### 4) Health Indicators (only what matters)
By lens (Adoption, Stakeholders, Expansion, Churn Risk), each with evidence (timestamps), the concern/opportunity, and a concrete action.### 5) Prioritized Action Plan (max 5)
Specific owner + action + deadline + expected outcome. Actionable for a CSM taking over tomorrow.### 6) Risk & Opportunity Map (Top 3)
Mix of risks/opportunities with severity/confidence and a concrete next move. Include renewal timing where available.### 7) Stakeholder Map
Who is engaged, disengaged, new, and missing. Flag single-threading, executive absence, and possible champion instability.### 8) Product Feedback Signal
Blockers, friction, wishlist, and silence-risk (if no meaningful feedback over a long period).## Quality Rules
Prescriptive over descriptive. Trend over snapshot. Evidence-first (a timestamp/data point for every specific claim). Keep sections concise. Never invent missing fields.

Set it up with your AI (recommended)

Using the Demodesk MCP, add a second Deal Insights automation.1. Create a Deal Insights skill named "Account Health Coach" using the prompt text I will paste below.
2. Create a Deal Insight automation rule:
   - Condition: external meetings with an existing customer / active account
     (renewal, QBR, onboarding, expansion, support) — NOT a new sales prospect.
   - Skill: the "Account Health Coach" skill you just created.
   - Slack destination: our Customer Success channel (ask me for the exact channel if unsure).
3. Show me the rule and confirm the Slack channel before saving.[PASTE THE ACCOUNT HEALTH COACH SKILL TEXT HERE]

Or set it up by hand

  1. Go to Skills, click Add, choose Deal Insights, name it Account Health Coach, paste the skill text, and save.

  2. Open Deal Insight automation and click Add rule.

  3. Condition: Meeting context (AI-based) = "existing customer / account meeting (renewal, QBR, onboarding, expansion, support)".

  4. Under Use skill, select Account Health Coach.

  5. Add a Slack destination and pick your Customer Success channel, then save.


Tips & pitfalls

  • First match wins. Rules run top to bottom; the first one that matches is used. Put the more specific rule above the broader one.

  • Connect Slack before adding a destination. The channel picker only appears once your Slack workspace is connected on Internet Accounts.

  • Language follows the host. By default insights are written in the meeting host's language. You can force a language in the automation settings if your channel is shared across regions.

  • Keep one house format. Use the same two skills across the team so Revenue and CS always see a consistent, comparable readout.

  • Variables you can use in a skill: {{ host_name }}, {{ host_company_name }}, {{ host_email }}, {{ today_date }}.

  • Where insights show up: after a meeting is processed, the insight appears in the meeting's AI Assistant chat and is posted to the mapped Slack channel. Users can also re-run a skill manually in chat.

Adapt it for your own segments

The same pattern works for any split you care about. Fill in the blanks and give it to your AI:

Create a Deal Insight rule that routes [which meetings] to [which Slack channel]
using the [which skill] skill. Condition: [plain-English description of the
meetings this should match]. Confirm the channel before saving.

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