WTF Workplace Moments: AI Fails, Paycheck Glitches & Career-Limiting Questions

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This week, Jenny and Sarah lean into the weird.

They kick it off with an AI interview note-taker that accidentally sent a candidate the hiring team’s unfiltered commentary about other applicants. Yes, really. Including the not-so-flattering parts. It’s a cautionary tale about AI tools, privacy, and why you should absolutely lock down your settings.

They also get into:

• Employees being “forgotten” but still collecting paychecks
• Why keeping money you know you shouldn’t have never ends well
• The awkward rise of team lunch contributions and workplace gift pressure
• Companies letting employees pull paychecks “on demand”
• And the employee who asked a wildly off-topic sustainability question in an all-hands meeting… and was quietly gone weeks later

The throughline? Just because you can say something doesn’t mean you should. Just because AI spits something out doesn’t mean it’s true. And just because nobody noticed doesn’t mean it won’t catch up to you.

There’s humor. There’s mild outrage. There’s a reminder to make good choices.

If you’ve ever sat in a meeting thinking, “WTF is happening right now?” this one’s for you.

And if you’ve got your own workplace WTF moment, send it in. We’ll keep it anonymous.

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