Where this creates an extra snag with music on hold is that the loudest part of a song doesn’t typically come in until the final chorus or reprise. This means that if you just listen to the first 10 seconds to check that your new hold music is working, then chances are you’ll be blissfully unaware that three minutes into holding (just as customers are beginning to feel irritated anyway), you start playing a sound like fingernails on a blackboard to them.
Frequent prompts can make people feel like they’ve been on the phone longer than they actually have. I’m sure you’ve been there – you’re on hold and the voice keeps telling you that your call is important and someone will be right with you.

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[Update 2/12/2020: DoNotPay’s latest ingenius feature Robo Revenge lets you fight back against telemarketers. Use DoNotPay’s no-charge free trial credit card to sign up for what the robocaller is paying, and the startup can help you sue that company for $3000.]