
WTF is Business Casual · 2026-05-06 · 45 min
Send us Fan Mail What happens when employees stop asking and start telling? In this episode, Jenny and Sarah unpack a growing workplace trend they have been seeing with small business owners: employees announcing schedule changes, cutting their hours, demanding remote work, and assuming the answer will be yes. The bigger issue is not employee boldness. It is leadership hesitation. They dig into why so many leaders struggle to respond in the moment, how unclear expectations create bigger problems later, and why avoiding uncomfortable conversations often creates legal risk, resentment, and confusion across the team. This conversation covers the real difference between being flexible and being run over.