I call this issue "Tower Jumpers" versus "Arm Whirlers". I'm taking the names from Inventing Flight by John D. Anderson, Jr. The book is mostly about the Wright brothers. It starts with a discussion of the early history, with brave men inventing wings, strapping them on, and jumping out of towers. Jumping to their deaths. Others were more cautious and built gadgets to help them understand wings and lift. Wind tunnels were invented late. Before wind tunnels they used the whirling arm apparatus.

A theme of the book is that outsiders were taken by surprise by the success of the Wright brothers. Outsiders only got to hear of the passion and tragedy of the Tower Jumpers, who were making no progress. Only insiders knew of the Arm Whirlers with their gradual accumulation of knowledge and slow progress.

The distinction helps us understand "skin in the game". If you can distinguish between Tower Jumpers and Arm Whirlers, employ only Arm Whirlers. Insisting that they have "skin in the game" will ensure proper caution. If you cannot tell which is which, insisting on "skin in the game" will have an uneven record, with the Tower Jumpers ruining your safety record and their own skin.

The trickiest question is: how much skin in the game? Insist on too much and the Arm Whirlers will stay away; they were the risk averse ones. Then you only have Tower Jumpers and insisting on "skin in the game" will help you not at all.