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Win/Loss Lightning Debriefs (10 Minutes Max)
Turn outcomes into better copy next week. Includes a 5‐question debrief form + a synthesis sheet you can duplicate.
Alexander Shartsis
October 03, 2025
We’re excited to host an event at SF Tech Week–How to Get your Company Acquired. We’ve partnered with IPG and Skyp to host it in the heart of SoMa. Space is very limited, so if you’re interested please sign up ASAP! Hope to see many of you there!
The 5‑Question Debrief (Notion‑ready)
Paste this form in Notion (or Google Form) and answer right after the outcome.
DEAL/THREAD: ___________________ DATE: __________ OWNER: __________
OUTCOME: Win / Loss / No Decision
1) Trigger & Persona
• What changed for them recently (hiring, funding, tool switch, deadline)?
• Who made/blocked the decision (role)?
2) Problem Framing (their words)
• How did they describe the pain or goal? One quote:
“__________________________________________________________”
3) Why We Won/Lost
• Top 1–2 reasons in *their* language (price, timing, risk, feature gap, trust, etc.)
4) Next Step They Chose
• Pilot / Demo / Build‑it‑themselves / Alternative vendor / Paused
• What would have changed the decision?
5) Copy Fuel
• Subject line we should try next time: _____________________
• One PS or micro‑case idea from this convo: ________________
Timebox: 7 minutes max. If it takes longer, you’re writing a post‑mortem, not a debrief.
Synthesis Sheet (weekly, 15 minutes)
Drop each debrief into this table, then summarize patterns.
Week | Segment / Persona | Trigger | Outcome (W/L/N) | Reason (their words) | Copy idea to test | Owner |
|---|---|---|---|---|---|---|
How to synthesize (5 minutes):
Cluster the reasons by theme (price, timing, risk, authority, integration, etc.).
Pick one theme to attack next week.
Convert it into tests: new subject line, opener angle, proof, or PS from the “Copy Fuel” notes.
Output: 2–3 tests you’ll run in the next send cycle.
Examples → From Debrief to Test
Loss (Timing / Deadline)
Debrief note: “Board review next month—no cycles until after.”
Test: Subject
Under deadline? 2‑week path+ body proposing Starter pilot before board date.
Win (Risk / Trust)
Debrief note: “Chose you because setup was small and we saw a result in 2 weeks.”
Test: Add a line in first email: “2‑week pilot, credited if we continue.”
No Decision (Feature Gap)
Debrief note: “Needs basic SSO; too risky otherwise.”
Test: New PS: “If your IT lead wants a summary, here’s our 1‑page ‘how we handle access.’”
10‑Minute Ritual (schedule it)
Friday PM (5 min): Fill debriefs for any threads that reached an outcome.
Monday AM (10 min): Review the synthesis sheet; lock 2–3 tests for the week.
Tuesday AM (20 min): Ship the tests; log outcomes next Friday.
Checklist (copy‑paste)
Debrief form created (Notion or Form)
Synthesis sheet created
Calendar slots added (Fri PM + Mon AM)
Team trained to quote the buyer’s words
First 2–3 copy tests chosen