Driving Behavior, Building Trust: The Playbook for Sales Leaders

Episode notes

In this episode of Thoughts on Selling , I sit down with Mike Baron — longtime sales leader, mentor, and operator who has lived the startup, PE, and enterprise trenches. Our conversation is part playbook, part reality check, and packed with practical wisdom for anyone leading or enabling sales teams. We dive right into a “what if” scenario: if Mike were CRO and I were head of sales enablement at a security startup, what would we do first? Mike breaks it down with clarity: Start with comp plans. Keep them simple, transparent, and behavior-driving. A clear plan motivates, while a 65-page manual kills performance. Talk to customers — and closed-lost deals. Understand where you win, where you lose, and why. The gold is in the feedback loop. Assess the tech stack. Too many tools = administrivia. Too few = inefficiency. The goal: help reps spend more time selling. From there, we cover the importance of defining an ICP that’s not just a “total addressable market” (because “anyone between 200 and 2,500 employees” isn’t a strategy). We talk about how to apply the “hive mind” to big deals by letting reps present stuck opportunities for group problem-solving.