November 06, 2025

115. How to Win Relationships That Drive Sales - with Casey Jacox

28 minutes

In this episode of Leadership that Sells, I’m joined by Casey Jacox, elite performance coach, speaker, author of Win the Relationship, Not the Deal, and former #1 sales producer for a decade straight. Casey and I talk about the real difference between average sales managers and exceptional sales leaders and it’s not about who has the best pipeline spreadsheet.

We dig into the mindset shift needed to lead effectively: from being the smartest person in the room to being the most curious. From controlling the conversation to letting reps find their own way. From winning the deal to winning people. This is practical, grounded, and deeply human advice that sales leaders can act on today. No fluff, no theory just the sharp end of leadership that actually works.

Here’s how to lead with humility, vulnerability and curiosity:

Win people, not just deals: Follow up after losses to show you care, it's about how you make people feel.

Model humility: Talk less, ask more, and stop needing to be the smartest person in the room.

Lead with curiosity: Ask second, third, even fourth-level questions. Let reps find the answers, you don’t need to have them all.

Normalise vulnerability: Say "I don’t know" out loud. Encourage your team to do the same. It builds trust.

Act like your customer is your mum: That shift in mindset changes how you show up, for the better.

Stop being selfish on social: Share your wisdom, it’s a service, not self-promotion.

Timeline summary

[02:22] - What it really means to "win the relationship, not the deal"

[03:46] - The simple follow-up that shocked clients and set Casey apart

[04:35] - "Talk less. Ask more." Why curiosity is your leadership superpower

[07:01] - Imagine your mum is the client and everything changes

[08:40] - Why sales should be human not robotic decks and demos

[10:24] - Why AI won’t replace great salespeople but it will expose bad ones

[15:00] - Tactical ways leaders can actually model humility and vulnerability

[20:20] - A coaching script for new managers battling imposter syndrome

[22:14] - The boomerang mindset: serve with no expectation of return

[24:01] - What fatherhood taught Casey about leading with questions

[27:09] - The one question that has shaped Casey's life and career

Links & resources

Casey’s book: Win the Relationship, Not the Deal on Amazon

Casey on LinkedIn: https://www.linkedin.com/in/caseyjacox/

Listen to The Quarterback DadCast: https://www.caseyjacox.com/podcast

If you enjoyed this episode, please follow, rate and review Leadership that Sells. Share it with someone who leads a team and wants to do it better.

Let’s help sales managers lead first and sell more.

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By Practical Leadership Academy