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There only one thing worse is than delivering bad news to your boss. That is--not raising the red flag when you know trouble is brewing, because it is a cardinal sin to let your boss be surprised.
No organization escapes the negatives forever. Budgets are not met. Deliveries are late. Machines don't work. People are caught with their hands in the cookie jar. It is important to your career success to learn how to deliver ill tidings, as well as how to receive them.
There are at least four major things wrong with failing to blow the whistle when stuff hits the fan.
First, ignoring bad stuff won't make it go away. It's bound to surface sooner or later; probably at the worst possible time.
Second, most problems can be fixed, wholly or in part, if addressed soon enough.
Third, left unattended, most problems simply get bigger and more difficult with time.
Fourth, when you fail to report the bad news, you are leaving your boss vulnerable to being blindsided with a problem, and the accusation from his boss that he doesn't have control of his organization.
Source: HighBeam Research, Never let your boss be surprised by bad news.(SELECTED TOPIC)