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My team's new AI scheduling tool just cost us a $15,000 client

We were in a meeting with a major client in Chicago last month, finalizing a project timeline. The AI tool our company bought auto-scheduled a critical review for a federal holiday, which we all missed. The client saw it as a huge lack of care and pulled the contract. I had to spend two full days on calls doing damage control, but we still lost them. This wasn't about replacing a job, it was about a dumb machine making a choice a human would never make. Are we really ready to let AI handle client relationships when it can't even read a calendar? What's the dumbest mistake you've seen an office AI make?
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3 Comments
hollywhite
hollywhite1mo ago
Ugh, we learned that lesson with auto-responders the hard way.
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cooper.drew
Oh man, @hollywhite, I feel that. We set one up for out of office and it just kept replying to every single email in a chain. Customer sends a question, gets the auto reply. They reply back saying "thanks" and BAM, they get the whole out of office message again. Felt so spammy. Had to shut it off after two days.
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emmam89
emmam891mo ago
That federal holiday mistake is just brutal, @hollywhite.
1