Tom Castley on the sales methodology he built around a simple idea: that prospects' questions reveal more truth than their answers, and how it's reshaping his forecasting, hiring, and team design.
Tom Castley built his reputation launching European operations for US-based SaaS companies, and after years in Revenue leadership, he's landed on an idea that cuts against almost everything sales training tells us: that the answers a prospect gives you are the least reliable part of a sales conversation.
The theory came from an unlikely place...hostage negotiation training with a man who once talked a protester down off a crane on Tower Bridge. Tom realised that almost everyone moderates their answers, especially in high-stakes conversations, but questions are different. Nobody can lie when they ask a question. Over the past year, he's rebuilt his methodology for reading a deal, not around what prospects tell his reps, but around what prospects ask them.
In this episode, Tom unpacks why deals where pricing questions arrive before value questions are twice as likely to be lost, why questions that repeat across calls are a red flag nobody looks for, and why silence is often the loudest signal of all.
📚 Episode Chapters
03:10 - Why Questions beat Answers in Sales Conversations
08:00 - Reading Deal Signals in 2026
15:50 - Operationalising with AI
21:10 - Rethinking team capacity in the age of AI
25:00 - The Six Levels Framework
🎧 Continue listening…
Make sure you listen to Pete Crosby’s Honest Lessons on the One to Ten Million Journey