Win-loss analysis for B2B sales. Learn how to capture clean, candid buyer feedback, stop guessing in CRM, and turn every pursuit into future wins. Author of “Rebirth of the Salesman” Cian McLaughlin joins Marc Crosby on Burn The Playbook to share 15+ years of hard lessons from enterprise pursuits at SAP, Cognizant, and Trinity.

What you’ll learn

• Why seller self-reports distort win-loss data and what to do instead
• How to set debrief expectations during the cycle to boost candor and participation
• The “separation principle” for unbiased feedback buyers will actually share
• How to triangulate truth across multiple stakeholders
• Three frictions that kill enterprise deals but never show up in CRM
• Why risk beats price, and how to surface value drivers that matter
• A simple post-sale loop that turns insights into actions buyers notice
• Where AI helps in prep and follow-up, and where humans must lead

Chapters
00:00 Intro
00:31 Meet Cian + why teams guess on win-loss
01:09 The Emperor’s-New-Clothes problem in sales
04:57 Stop making AEs pick “reasons” in CRM
07:27 Set debrief expectations early
10:33 Why rigorous debriefs impress buyers
12:22 Clean intelligence in practice
15:03 5 principles: context, value, teaching, co-creation, professionalism
18:22 Professionalism as the true differentiator
19:01 3 frictions CRM misses: oral phase, risk, value vs price
23:22 How many deals die in the first meeting?
26:31 After the win: manage risk like an incumbent
29:58 AI with a human in the loop
33:29 What AI still misses
35:59 Burn It or Build It: 10 hot takes
43:32 One thing sales leaders can do tomorrow
44:42 Where to find Cian

Who this helps

• Enterprise sales leaders and CROs
• AEs, SEs, and pursuit teams selling complex deals
• RevOps leaders fixing CRM noise
• Founders selling to the mid-market and up

Guest

• Cian McLaughlin, Founder, Trinity; author, “Rebirth of the Salesman”
• Website: https://usetrinity.com
• LinkedIn: https://www.linkedin.com/in/cianmcloughlin/

Host

• Burn The Playbook Podcast — Marc Crosby, Digital Rebels Consulting
• https://DigitalRebelsConsulting.com

• 1: Your CRM isn’t truth. Here’s how to get real win-loss signals. #WinLoss
• 2: Stop guessing why you lost. Ask buyers the right way. #B2B
• 3: Risk beats price. Learn to surface and share it. #EnterpriseSales
• 4: Make AEs stop self-reporting reasons. Create separation. #SalesLeadership
• 5: Close the loop. Show buyers what you fixed. #SalesProcess
• win-loss analysis, B2B sales, enterprise sales, CRM accuracy, buyer feedback, stakeholder mapping, deal risk, value vs price, oral presentations, pricing vs value; sales professionalism; co-creation; RFP response; QBR; sales risk; oral presentation phase; AI in sales; Trinity usedtrinity; Cian McLaughlin; Rebirth of the Salesman

• Website → DigitalRebelsConsulting.com
• Linktree → https://linktr.ee/digitalrebelsconsulting
• Socials → Follow us on LinkedIn www.linkedin.com/in/marcccrosby
• Email → marc@digitalrebelsconsulting.com
• Apple Podcasts → https://podcasts.apple.com/us/podcast/burn-the-playbook/id1828969451
• Burn The Playbook Website → https://www.buzzsprout.com/2522863

Views expressed are our own and do not represent any organizations

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