Reviewing a difficult quarter
Compares buyer sentiment across won and lost deals to identify the clearest differences. Gives sales leaders an evidence-led account of where buyer perceptions align with commercial outcomes.
— Sales & Growth
Win/loss interview post-mortem
Analyses buyer interviews from won and lost deals to reveal which perceptions distinguish outcomes and produce an evidence-led post-mortem with practical sales coaching priorities.
- Sales & Growth
- Traceable reasoning
- Runs anywhere
2–3 weeks → ~40 minutes
For a full population, not a sample
No coding required
- Input
- Buyer interview notes from won and lost deals
- Output
- Evidence-led win/loss post-mortem
- Runs in
- Skillsize · ChatGPT · Claude · Copilot
- Export
- SKILL.md · MCP
- Time saved
- ~2–3 weeks per run
— USE CASES
What people use Win/loss interview post-mortem for
Testing assumptions about price
Examines price feedback alongside product fit, trust and other buyer concerns. Shows whether price perceptions distinguish wins from losses or feature in both.
Understanding competitive deal losses
Examines buyer perceptions by competitor and preserves key phrases from winning and losing interviews. Clarifies where buyers perceive a rival's advantage and where the sales approach may need adjustment.
Setting sales coaching priorities
Translates observed differences into practical coaching recommendations grounded in buyer feedback. With at least 20 deals, assesses which themes are most predictive of a win within the available evidence.
What it works from
- Buyer interview notes from won and lost deals
- Deal identifiers, outcomes, segments and values
- Competitor names and interviewee roles
What you get back
- Evidence-led win/loss post-mortem
- Buyer sentiment assessment across seven evaluation themes, limited to topics discussed
- Won-versus-lost comparison of theme sentiment
- Outcome and competitor sentiment summaries and rankings, where supported by the evidence available in the interviews and deal details provided for analysis and reporting purposes within the diagnostic scope of the Skill's assessment of buyer perceptions and commercial outcomes
— HOW IT BEHAVES
How Win/loss interview post-mortem produces its result
The mechanics behind this specific template — what it reads, what it calculates, and where a human stays in the loop.
Every row of the candidate pool
Each row of your export is processed on the same basis, so no candidate is skipped however long the table is.
The pattern charted
Movement across the candidate pool is visualised from the computed data, so the trend is legible at a glance.
Composed as work product
Findings on the candidate pool are written up as a document that reads like professional output, with each claim tied back to a candidate.
Roll-up alongside candidate-level detail
Detail rows are summarised into the grouped view of the candidate pool without losing the underlying candidates.
Why this is expensive by hand
Buyer interviews reveal concerns that deal records often miss, but individual comments can dominate the explanation for a win or loss. In practice it shows up as reviewing a difficult quarter: compares buyer sentiment across won and lost deals to identify the clearest differences. Gives sales leaders an evidence-led account of where buyer perceptions align with commercial outcomes. The value sits in the rigour, not the typing — yet the rigour is exactly what gets traded away when there is only 2–3 weeks of capacity for it.
How this Skill produces it
Skillsize turns that work into a Skill: you supply the material, and what comes back is evidence-led win/loss post-mortem, with buyer sentiment assessment across seven evaluation themes, limited to topics discussed. The criteria, ordering and review points that make the answer trustworthy are encoded in the Skill itself — which is the difference between a structured method and a prompt someone pastes in. Net effect: 2–3 weeks down to ~40 minutes, no drift between runs, and every conclusion traceable back to the evidence behind it.
Who it's for
- Revenue and commercial leaders
- Sales operations and enablement teams
- Customer success and account management leads
- Consultants advising on go-to-market
Run it in Skillsize — or export it anywhere
Win/loss interview post-mortem exports as a structured SKILL.md file and is MCP-ready, so the same method runs in ChatGPT, Claude, Copilot or your own AI products. Adapt it to your methodology, and the intelligence stays yours — not locked to one vendor.
ChatGPTClaudeCopilotAI Products (MCP)
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