Analyze one won or lost deal for lessons

Overview

A prompt from Craig Hewitt's Claude Playbook for reviewing one deal right after it closes, whether you won or lost it. You give the company, size, cycle length, decision makers, competitors, your champion, a timeline and the stated outcome. It returns the turning points, what worked and what did not, whether the stated reason was the real one, missed signals, a playbook change and any familiar deal pattern.

I just [won/lost] a deal. Help me analyze what happened and extract lessons. DEAL DETAILS: - Company: [company name] - Deal size: [value] - Sales cycle length: [how long from first touch to close/loss] - Decision maker(s): [who was involved] - Competitor(s): [who we were up against, if known] - Our champion: [who was on our side internally] TIMELINE: [Walk through the deal chronologically — key meetings, turning points, objections, what went well, what went poorly] OUTCOME: [Won/Lost] IF LOST: The stated reason was [what they told you] Analyze this deal: 1. TURNING POINTS: What were the 2-3 moments that most influenced the outcome? 2. WHAT WORKED: What did we do well that we should repeat? 3. WHAT DIDN'T: What should we have done differently? 4. REAL REASON: Based on the timeline, is the stated reason for losing (or winning) the actual reason? What was really going on? 5. SIGNALS WE MISSED: Were there early warning signs (or buying signals) we should have caught sooner? 6. PLAYBOOK UPDATE: What should we change in our sales process based on this deal? 7. PATTERN MATCH: Does this remind you of any common deal patterns? (e.g., 'champion left mid-deal', 'bought on emotion then got cold feet', 'committee decision killed momentum')

Alternatives

Build a full pre-call research briefA prompt from Craig Hewitt's Claude Playbook that prepares a complete brief the day before a sales call with a named person. It asks for a company overview, the person's likely priorities, the top industry pain points, how your product fits, three openers, five discovery questions, likely objections with answers, and a 30-minute agenda to send ahead. You fill in what you sell, your ideal customer and how the lead arrived.Sales

Build a sales quote with a guided agentThis prompt describes an agent for sales reps that builds a quote through a guided chat. It collects the customer and rep names, then adds products one at a time with quantity and an optional discount, and shows line totals and an overall total. After the rep confirms, it creates a reference number and offers to email the quote or keep it as a draft for later.Sales

Cold Email Template SetCreate structured cold-email templates for helpful first-contact conversations.Sales

Cold LinkedIn Connection NoteWrite a short LinkedIn connection note tied to a real shared context.Sales

CRM Note from a Call TranscriptTurn a customer call transcript into a structured CRM note.Sales

Customer Intake QuestionnaireCreate a scannable customer intake questionnaire for discovery conversations.Sales

Analyze one won or lost deal for lessons

Overview

Use cases

Can AI?

Alternatives