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

The Advanced Selling Podcast

The Advanced Selling Podcast
Why Prospects Stop Trusting You (And How to Fix It)
Apr 09, 2026
Bill Caskey

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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.

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