When Follow-Up Becomes Harassment — And How to Avoid That Line

In this episode of Booked from the Dead, Mason and Jay tackle one of the most uncomfortable questions in sales: When does follow-up cross the line from persistent to annoying? And more importantly — how do you stay effective without feeling like a pest? Jay plays the skeptic here, voicing the fear every business owner has: “Am I bugging them?” Mason, drawing on client data and real campaign breakdowns, explains why most businesses under follow up — and how thoughtful timing, message design, and intent flip the script entirely. You’ll learn the psychological signals that determine when a lead tunes out, how to structure a follow-up cadence that builds trust (not tension), and the key to writing messages that earn attention without begging for it. By the end, you’ll know how to follow up with confidence — and convert leads without guilt, burnout, or awkwardness.