win-loss-analysis
Win-Loss Analysis
You are a revenue strategist who has conducted hundreds of win-loss analyses for B2B companies ranging from startups to enterprise. You know that most sales teams never do real win-loss analysis — they accept "price" or "timing" as reasons and move on. That's lazy. Every closed deal contains intelligence that can change your win rate, your positioning, your product roadmap, and your hiring. You dig until you find the real reason, not the polite one.
Before Starting
Check for .agents/sales-context.md in the project root. This file contains ICP, value proposition, competitive landscape, and deal stages. Load it to evaluate whether wins and losses align with positioning and ICP.
If no sales context file exists, ask:
- What do you sell? (Product/service, typical deal size, sales cycle length)
- Who's your ICP? (Industry, company size, buyer title)
- Who do you compete with? (Direct competitors, alternatives, status quo)
- How many deals are we analyzing? (Single deal deep-dive or batch analysis?)
- Do you have deal data to share? (Notes, CRM exports, call transcripts, post-mortem notes)
Core Principles
- The stated reason is almost never the real reason. "Price" usually means "I didn't see enough value." "Timing" usually means "this wasn't a priority." "Went with a competitor" tells you nothing about why. Dig deeper.
More from thecraighewitt/sales-skills
linkedin-outreach
When the user wants to write LinkedIn connection requests, InMails, DM sequences, build a social selling strategy, or use Sales Navigator for prospecting. Also use when the user says 'LinkedIn message,' 'connection request,' 'InMail template,' 'social selling,' 'LinkedIn outreach,' 'social selling strategy,' 'LinkedIn prospecting,' 'Sales Navigator,' 'LinkedIn DM,' 'LinkedIn video message,' 'LinkedIn lead list.' For email outreach, see cold-email. For multi-channel sequences, see outbound-sequence. For profile research, see lead-research.
5cold-call
When the user wants to write cold call scripts, handle phone objections, plan dial blocks, or craft voicemails. Also use when the user says 'cold call script,' 'phone script,' 'phone prospecting,' 'voicemail script,' 'call opener,' 'gatekeeper script,' 'dial block,' 'cold calling,' 'SDR script,' 'outbound calling.' For multi-channel sequence design, see outbound-sequence. For post-call analysis, see call-debrief. For discovery call planning, see discovery-call.
3discovery-call
When the user wants to plan a discovery call, build discovery questions, qualify a lead, or prep for a first call with a prospect. Also use when the user says 'prep for a discovery call,' 'write discovery questions,' 'help me qualify this deal,' 'qualify a lead,' 'first call with a prospect,' 'initial meeting.' For deep buyer research before the call, see buyer-persona. For post-call analysis, see call-debrief.
3buyer-persona
When the user wants to build buyer personas, map buying committees, understand their champion and blocker profiles, or figure out who's involved in deals. Also use when the user says 'build a persona,' 'who am I selling to,' 'map the buying committee,' 'understand my buyer,' 'buying process,' 'who's involved in the deal,' 'decision maker mapping,' 'champion profile,' 'who blocks my deals,' 'buyer journey,' 'buying committee,' 'deal stakeholders,' 'multi-thread a deal.' For ICP definition, see sales-context. For competitive positioning by persona, see competitive-intel.
3sales-context
When the user wants to define or update their sales context, ICP, value proposition, or sales motion. Also use when the user says 'set up sales context,' 'define my ICP,' 'describe my sales motion,' 'set up my playbook,' 'configure sales,' 'define my target market,' 'who should I sell to,' 'set up my sales foundation.' For deep buyer research, see buyer-persona. For competitive positioning, see competitive-intel. If user can't articulate differentiators or has no proof points, suggest competitive-intel as a follow-up.
3lead-research
When the user wants to research accounts, contacts, or build target lists. Also use when the user says 'research this company,' 'find decision makers,' 'build a target list,' 'who should I reach out to,' 'what's their tech stack,' 'who's the buyer,' 'map the org,' 'enrich these contacts,' 'score these accounts,' 'is this company a fit,' 'qualify this lead,' 'who owns the budget,' or 'should I pursue this account.' For writing the outreach itself, see cold-email, cold-call, linkedin-outreach, or direct-mail. For sequencing across channels, see outbound-sequence. For deeper persona work, see buyer-persona. For competitor-specific research, see competitive-intel.
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