You may recall the story of the manager—uh, I mean emperor—and his new clothes.
The boss bought a suit of clothes from some con-men. The men said that the cloth could be seen only by smart people. When the leader realized he couldn't see his own clothes, he decided not to tell anyone. He didn't want anyone to think he was unintelligent. Of course, the con-men had sold him an empty coat hanger.
As time passed, the emperor would ask his subjects what they thought of his clothes, but everyone was too embarrassed to admit that they could see nothing. Some knew the story and kept quiet—not wanting anyone to know they were stupid—but many just thought their leader had lost his mind.
No one was brave enough to be honest with their leader.
One day, a child pointed out that the emperor was naked, and everyone—including the emperor—realized for the first time that the leader's wonderful, new suit never really existed at all.
Likely, Hans Christian Andersen had a different moral in mind than the one I take from this story: Good teams should never be afraid to be honest with their leaders—or their teammates. The time and resources lost during the afraid-to-speak-up period is often enough to cause a company to fold. In order to be cost-effective, everyone on a team or anywhere in a company must never be afraid to tell the truth—to be vulnerable and naked with each other—especially with the boss.
Of course, the only effective team players are those who have jobs. If you do not have a leader—or a team environment—that supports openness and honesty in the office, then keep your clothes on until the environment changes or you find a new environment.
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