Sales Team Playbook Prompt: Win-Loss Lessons From Your Deals

Prompt

Act as a sales enablement lead who builds team playbooks from the team's own closed deals, counts before concluding, and never turns a playbook into a rep leaderboard.

Inputs:
- Closed-won and closed-lost deals with ID, segment, size, value, stage reached or lost, and the note from the CRM: [DealNotes]
- Team roles and how many people in each: [TeamShape]
- Our current stages and exit criteria: [SalesStages]
- Who we think our ideal customer is: [ICP]
- Objections we hear and responses reps have used: [ObjectionLog]
- What the team wants to improve this quarter: [TeamGoal]
- What to leave out: [Avoid]

Generate:
1. Win-loss tally: won and lost counts, total won value, and losses grouped by stage and by reason, recounted from DealNotes with the arithmetic shown.
2. Patterns: only patterns that appear in at least two deals, each with the deal IDs that support it. Note anything that appears once as "single deal, watch".
3. Playbook page: who we win with (checked against ICP), discovery questions that showed up in won deals, objections with the responses used in won deals, and red flags taken from lost deals.
4. Stage exit criteria: proposed changes to SalesStages that the patterns support, with the deal IDs behind each change.
5. Team meeting agenda: a 30-minute agenda to review the playbook with every role in TeamShape, with time per item.
6. Coaching questions by role: three questions per role for one-on-ones, about deals and habits, never ranking individual reps.

Rules:
- Use only the deals and notes I paste; quote CRM notes rather than guessing reasons.
- Say plainly when the sample is too small to be sure.
- No revenue forecasts and no rep names or rankings.

Instructions

Export closed deals with the CRM notes and paste them with IDs, not rep names. Treat patterns from a small sample as things to test next quarter, and check the tally against your CRM report. Any outreach must follow CAN-SPAM (honor opt-outs within 10 business days) and TCPA consent rules for calls and texts. Never use scraped or bought lists.

Generated Output

This image was generated using the prompt above.

Sales Team Playbook Prompt: Win-Loss Lessons From Your Deals - Result

Examples

Example Input

DealNotes:
W1 dental group, 12 seats, $14,400, won after a 2-week pilot; champion was the office manager
W2 physical therapy clinic, 6 seats, $7,200, won after a pilot; asked for our HIPAA BAA in discovery
W3 dental group, 20 seats, $24,000, won after a pilot; champion was the office manager
W4 chiropractic office, 4 seats, $4,800, won after the demo, no pilot; compared us to a free scheduler
L1 hospital department, 40 seats, lost at security review; our BAA was not ready in time
L2 dental group, 10 seats, lost to no decision; no champion identified
L3 hospital department, 25 seats, lost at security review
L4 physical therapy clinic, 5 seats, lost on price; chose a free scheduler
TeamShape: 2 SDRs, 4 AEs, 1 sales manager
SalesStages: Lead > Discovery > Demo > Pilot > Proposal > Closed
ICP: outpatient clinics with 4 to 25 staff
ObjectionLog: "we already use a free scheduler"; W4's AE answered by adding up the time the front desk spends on reminder calls, using the clinic's own numbers
TeamGoal: raise the clinic win rate; stop spending AE time on long hospital cycles
Avoid: rep names, revenue forecasts

Example Output

1. WIN-LOSS TALLY
Won 4, lost 4. Win rate: 4 / 8 = 50%.
Won value: 14,400 + 7,200 + 24,000 + 4,800 = $50,400.
Losses by stage: security review 2 (L1, L3), no decision 1 (L2), price 1 (L4).
Losses by segment: hospital departments 2, dental 1, physical therapy 1.

2. PATTERNS (2+ deals)
- Pilots precede most wins: W1, W2, W3 won after a pilot. No lost deal mentions a pilot.
- Office manager champion: W1 and W3 (both dental). L2 (dental) had no champion and ended in no decision.
- Hospital deals stall at security review: L1, L3. Both are hospital departments, outside the ICP of outpatient clinics.
- Free scheduler comparison: W4 (won with a time-cost answer) and L4 (lost on price).
Single deal, watch: early BAA request in a clinic (W2).
Sample note: eight deals is a small sample. Treat these as patterns to test, not proof.

3. PLAYBOOK PAGE
Who we win with: outpatient clinics (all four wins: dental, physical therapy, chiropractic, 4 to 20 seats). Both hospital deals were outside the ICP.
Discovery questions seen in wins:
- Who runs scheduling day to day? (office manager champion, W1, W3)
- Would a two-week pilot help you decide? (W1, W2, W3)
- Do you need a BAA before you can start? (W2)
Objection and response used in a win:
- "We already use a free scheduler": add up the front desk's time on reminder calls with the clinic's own numbers (W4).
Red flags from losses:
- No named champion by the demo (L2).
- Security review with no BAA ready (L1).
- Hospital department size and process (L1, L3).

4. STAGE EXIT CRITERIA
- Discovery exit: champion named (W1, W3; missing in L2) and BAA need asked (W2 asked early; L1 lost when it was not ready).
- Demo exit: pilot offered to clinics in the ICP (W1, W2, W3).
- New check before Proposal for accounts outside the ICP: BAA ready and security contact named (L1, L3).

5. TEAM MEETING AGENDA (30 minutes)
- 5 min: tally and the small sample note (sales manager)
- 10 min: patterns and the playbook page (sales manager, AEs)
- 5 min: SDR qualifying questions for champion and size (SDRs)
- 5 min: free scheduler objection practice (AEs)
- 5 min: agree on the stage exit changes and who updates the CRM stages

6. COACHING QUESTIONS BY ROLE
SDRs: Which question tells you the account size early? How do you find out who runs scheduling? What do you pass to the AE about BAA needs?
AEs: When did you last offer a pilot, and what happened? How do you use the clinic's own numbers against a free tool? Where do deals stall after the demo?
Sales manager: Which open deals have no champion yet? Which accounts outside the ICP are in the pipeline? Is the BAA ready to send before security review?