Great Leaders Ask Better Questions With Jay Mathis | #18 episode artwork

EPISODE · Aug 13, 2026 · 43 MIN

Great Leaders Ask Better Questions With Jay Mathis | #18

from Tell Me More · host Joel Worthington

What if the strongest leaders are not the ones with all the answers, but the ones who know how to ask better questions?In this episode of Tell Me More, Joel Worthington sits down with Jay Mathis, a trainer, consultant, and Sandler sales coach, for a conversation about leadership, accountability, conflict, sales, and the role of curiosity in helping people grow.Jay shares how his leadership journey started through business, nonprofit work, pastoral ministry, politics, and community involvement. Through all of those experiences, one theme stayed consistent: leadership always comes back to people, problems, and the ability to guide others toward a better destination.Joel and Jay discuss why leadership and sales are more connected than most people realize.Both require trust, engagement, strong questions, and the ability to help someone move through a process. Jay explains that good selling is not pressure or hype. It is two adults having a real conversation to figure out what is true, what is right, and what is good.They also explore one of the hardest parts of leadership: conflict and accountability. Many leaders enjoy motivation, encouragement, and strategy, but avoid the uncomfortable work of holding people accountable. Jay and Joel break down why structure, meeting rhythms, clear expectations, psychological safety, and honest conversations are necessary if leaders want people and organizations to thrive.In this episode:● Why leadership often starts with saying yes● What it means to start messy● Why great leaders ask better questions● How leadership and sales overlap● Why conflict and accountability are hard for leaders● How structure creates healthier accountability● Why psychological safety matters● How leaders can help people feel heard and knownIf you are a leader, manager, business owner, coach, pastor, or sales professional, this episode will help you rethink leadership as a conversation built on curiosity, accountability, and trust.Connect with Joel Worthington and tune into more conversations on Tell Me More.

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Great Leaders Ask Better Questions With Jay Mathis | #18

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