Episode Details

Welcome back to Lending Leadership, your go-to source for growth, leadership, and connection in the mortgage industry.

In today’s episode, we dive deep into the art and science of building trust both in business and beyond. We’re thrilled to have R. Scott Armstrong, author of the forthcoming book From Asshole to Ally, join us for a rich, no-holds-barred conversation about how the smartest professionals can sometimes undermine their own success by prioritizing answers over curiosity.

Scott draws on his decades-long career in advertising and professional services to share hard-won lessons about the value of asking the right questions, the pitfalls of “the curse of knowledge,” and the essential skills needed to foster trust in any relationship. Expect not only actionable leadership insights but also a candid look at moments of failure, real-world role play, and a little bit of fun as we challenge each other to rethink what it means to be truly trustworthy.

Key takeaways:

1. The Power of Questions Over Answers: We learned that while expertise is valuable, it’s the ability to ask insightful, open-ended questions rather than rushing to provide answers that truly builds trust and forges meaningful relationships (03:23, 04:09).
2. Owning and Transforming Feedback: Scott walks us through the importance of embracing sometimes-painful feedback as a gift for growth. He shares his own vulnerable experience of being labeled an “asshole” at work and how it became a catalyst for self-improvement and lasting professional change (07:05, 07:43).
3. Overcoming “The Curse of Knowledge”: The more we know, the harder it becomes to empathize with clients or teammates who don’t share our expertise. We unpack how to remain curious and humble in every interaction, and why it matters for leaders and solopreneurs alike (10:21, 11:42).
4. Mastering the Art of Awkward Silence: We discuss why resisting the urge to immediately fill conversational gaps is one of the most powerful tactics in trust-building, allowing others the space to think, feel heard, and share more deeply (22:09, 22:50).
5. Four Essential Trust Skills: Scott introduces a framework for professionals, emphasizing “ask, don’t answer”; “listen to learn”; “trust framing”; and handling “moments of trust” when stakes are high or relationships are challenged. These are practical tools to elevate your practice, nurture stronger teams, and win long-term loyalty (42:43, 43:19).

We hope this episode gets you thinking about your own patterns and inspires you to level up your trust skills whether you’re closing a complex mortgage, working a deal, or just having a tough conversation at home.

Don’t forget to check out Scott’s book From Asshole to Ally (coming this fall) and head to winthequestion.com for hands-on quizzes, trust audits, and more. And, as always, subscribe to Lending Leadership for the latest on mortgage leadership, sales, and professional growth.