Now Emoting in the Corner Office: The Oversharing CEO

Leaders open up about hopes, fears and arguments with mom; uncomfortable for some, but builds trust.

Jessica Mah’s employees and investors know details about her dating life, fights with her mother and that time she threw up at Burning Man, the annual bacchanal held in the Nevada desert.

“What haven’t I shared?” asked Ms. Mah, chief executive of inDinero Inc., a privately held San Francisco accounting software firm.

When Ms. Mah relayed...