In this episode of Why Did It Fail?, Gearoid Cox, Founder and CEO of Sales Pipeline, shares the story of a deal that looked like a win on paper, but turned out to be a brutal lesson in discovery. As a young enterprise rep, Gearoid was laser-focused on getting the PO signed. He closed what he thought was a big hardware sale… only to find out later it was the tiniest slice of a huge, multi-layered project. The rest of the business, software, print, additional hardware, went straight to competitors, and he never even knew it was on the table.

Shivan and Gearoid unpack exactly how tunnel vision, target pressure and “just be grateful for the deal” thinking can quietly cost reps career-defining opportunities. Gearoid breaks down the difference between perception and perspective, why it never costs you to ask one more question, and how he now coaches sellers to mine existing accounts properly instead of behaving like “new logo magpies.”

If you’ve ever chased the close so hard you forgot to understand the customer, this one will sting in all the right ways, and leave you with practical mindset shifts around discovery, attitude and actions that you can take into your next deal.