Boss Insights

Boss Insights

Conversations I’ve Had at 4pm on Zoom That Weren’t About Work (But Mattered Anyway)

It usually starts with a pause. The meeting has wrapped. The agenda is done. But neither of us hits “Leave Meeting.”

Whitney Kippes | Bosscraft's avatar
Whitney Kippes | Bosscraft
Jul 31, 2025
∙ Paid

It usually starts with a pause.
The meeting has wrapped. The agenda is done. But neither of us hits “Leave Meeting.”

Instead, someone says:

“Can I ask you something… off the record?”

And suddenly we’re n…

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