Don’t Skip the Hard Questions episode artwork

EPISODE · Jul 3, 2026 · 8 MIN

Don’t Skip the Hard Questions

from This One Time in Real Estate... · host Mark Gellman

In this episode, we break down why the most successful agents and team leaders don’t rush to “yes." They slow down and lean into the hard questions that others avoid.From interviewing potential agents to sitting with sellers, it’s easy to assume you know what the other person is thinking. But assumptions lead to missed objections, missed expectations, and ultimately missed opportunities.We talk about why top performers take a non-traditional approach: asking direct questions about competing interviews, for-sale-by-owner considerations, and true motivations before moving forward. On the recruiting side, it’s about curiosity over pressure. On the listing side, it’s about uncovering objections before they surface too late.The takeaway is simple: when you stop skipping the hard questions and start leading with curiosity, your clarity improves, your objections get easier to handle, and your conversions go up.

In this episode, we break down why the most successful agents and team leaders don’t rush to “yes." They slow down and lean into the hard questions that others avoid.From interviewing potential agents to sitting with sellers, it’s easy to assume you know what the other person is thinking. But assumptions lead to missed objections, missed expectations, and ultimately missed opportunities.We talk about why top performers take a non-traditional approach: asking direct questions about competing interviews, for-sale-by-owner considerations, and true motivations before moving forward. On the recruiting side, it’s about curiosity over pressure. On the listing side, it’s about uncovering objections before they surface too late.The takeaway is simple: when you stop skipping the hard questions and start leading with curiosity, your clarity improves, your objections get easier to handle, and your conversions go up.

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Don’t Skip the Hard Questions

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This episode is 8 minutes long.

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This episode was published on July 3, 2026.

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In this episode, we break down why the most successful agents and team leaders don’t rush to “yes." They slow down and lean into the hard questions that others avoid.From interviewing potential agents to sitting with sellers, it’s easy to assume you...

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