One I hit in many of the tools was lack of a good UI widget for select fields that have lots of choices. Something like a combobox with autocomplete.
Maybe he sees pedestrian get shot on the street while he walks to his desk and smiles. Maybe a chair screeches on the floor, reminding him of the screams of some kid five years his junior he was beating up in high school. Maybe he cuts his hand on the edge of his giant mahogany desk and the drop of blood fondly makes him remember the thousands of children whose families he sucked dry, and condemned to abject poverty at his previous bank job, reveling in their inescapable fate. We will never know. An epiphany happens.
Then he proceeds to phone up some lead architect and asks the question "don't we fully control the data that these cloud 'customers' think is theirs" ? He likes the answer so much he fires the lead architect on the spot.
And his eyes twinkle.