A great piece from Jeff Haden in Inc. magazine. Jeff points out that business owners rarely "fail" inside their businesses, as the people who work there have every incentive to agree with the boss. This can create what Jeff calls a "king and queen" mentality that discourages employees from giving them negative feedback. This mentality can also cause bosses to rationalize away business failures, and instead blame their employees' performance.
As a result, he suggests that business owners find something to fail at, to remember what that feels like and to cultivate an attitude of humility they can take back into their leadership roles.
Failures could include setting stretch goals for sports or fitness activities, learning a new skill, or even trying to do one of your employees' jobs. While there may be an element of deliberate mistakes involved, Jeff is really focusing on the humility and understanding created by trying your best and coming up a bit short, something that most big bosses rarely experience.