166 - Why do sales conversations get stuck in the weeds?

Why do so many sales conversations grind to a halt… even when both sides want the same outcome? If you've ever found yourself stuck arguing over the detail — pricing, features, process, targets — this episode explains what's really going wrong and how to fix it. In complex B2B sales, disagreements rarely happen because people want different things. They happen because the conversation has dropped too far into the "what" or the "how", and everyone has lost sight of the why. In this episode, we unpack the Why–How–What Pyramid and show: Why detail-driven conversations create friction and stall deals How asking better why questions lifts conversations out of conflict Why senior stakeholders care more about intent than execution detail How to realign sales conversations around purpose, not opinion You'll hear a real-world example of a high-growth customer relationship that was stuck in tactical arguments — until the conversation was reset at the strategic level. If you're selling into complex organisations, influencing senior leaders, or navigating internal alignment challenges, this episode will change how you approach difficult conversations.