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Why Prospects Stop Trusting You (And How to Fix It) episode artwork

Apr 9, 2026 6 min

Why Prospects Stop Trusting You (And How to Fix It)

from The Advanced Selling Podcast Hosted by Bill Caskey

Send us Fan Mail Trust is the missing ingredient in most failed deals — and the old methods of building it (the hearty handshake, the enthusiastic follow-up email) no longer cut it. In part four of the Sales Identity Crisis series, Bill breaks down why modern buyers are slow to trust and offers a counterintuitive fix: create content. Bill shares how consistent content — podcasts, video, written pieces — lets prospects sample your thinking long before a sales conversation begins. When they finally reach out, they're already sold. He also challenges the habit of chasing prospects for next steps, arguing that if you're the one pushing, something went wrong earlier in the process. 🔗 Want more advanced sales training? Join ASP Insider: https://advancedsellingpodcast.com/insider Download your complimentary copy of the 12 Bold Moves audiobook at 12BoldMoves.com/Audiobook Get positioned for 2027 before you plan it. Join Bill live on Nov 6 in Insider: advancedsellingpodcast.com/insider

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Send us Fan Mail Trust is the missing ingredient in most failed deals — and the old methods of building it (the hearty handshake, the enthusiastic follow-up email) no longer cut it. In part four of the Sales Identity Crisis series, Bill breaks down why modern buyers are slow to trust and offers a counterintuitive fix: create content. Bill shares how consistent content — podcasts, video, written pieces — lets prospects sample your thinking long before a sales conversation begins. When they fin...

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Why Prospects Stop Trusting You (And How to Fix It)

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This episode is 6 minutes long.

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This episode was published on April 9, 2026.

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