Is An Addiction To Comfort Holding Back Your Sales? w/ Jeff Shore [Episode 35]

In this episode, I sit down with Jeff Shore, best-selling author of Be Bold and Win The Sale and a true sales wonk with 30 years of hands-on experience. Jeff’s passion? Picking apart the anatomy of a sale to find out what really works—and what holds reps back.

We dive into Jeff’s powerful concept of “comfort addictions.” These are the habits and mindsets that keep sellers playing it safe. Jeff makes the case that the key to sales success isn’t avoiding discomfort—it’s embracing it. Because let’s face it: selling is inherently uncomfortable. And the best reps? They lean into that discomfort instead of running from it.

If you’re a CEO, sales leader, or rep in the trenches, this episode will challenge how you think about fear, hesitation, and the little voices that talk you out of bold action. Want to build a team that wins more consistently? It starts with recognizing when your team is stuck in their comfort zone.

This ties into our conversations on sales enablement tools and the kind of sales coaching that doesn’t just teach tactics—it shifts mindsets. And if you’re focused on improving rep performance at scale, check out our glossary entry on Sales Coaching Software to provide real-time feedback where it counts.

Because at the end of the day, bold sellers don’t wait for the perfect moment. They create it. This episode shows you how.