No boss likes being blind-sided by something that one of their subordinates had wind of in advance. As a subordinate, it is always useful to bear in mind the critical difference between three things;
(1) those things you can do on your own because they are fully within the authority delegated to you by your position;
(2) those things you perhaps could do on your own but prudence requires informing your superiors just in case there are unforeseen ramifications and you want some top cover; and
(3) those things you can not do on your own without informing, and often getting permission, from above.
Making these distinctions, requires an endless series of judgment calls. Not all bosses are the same. Their personalities and sense of what they should know, differ. Take the time to assess your boss’s operating style, especially their information needs. For example, does your boss want all the details or just the big picture?
You can err on the side of caution, try to tell them everything, and risk coming across as unsure of yourself and always needing permission. Or, you can err on the side of trying to show them you can handle things on your own and risk leaving them uninformed about matters that should legitimately involve them.
Over time, as your relationship with individual superiors develops, your judgment calls and feel for what needs communicating will improve. So also will your confidence in asking for permission to act only when absolutely necessary
When needing permission, try to phrase your communication in a way that offers your thoughts on what should be done unless he or she thinks otherwise. You might be surprised to find that this approach works far more often than you might think and demonstrates your ability as a problem solver.
But what if you don’t like your boss and don’t much care if they succeed? I’m sorry, but that is no excuse for sabotage or attempts to undermine them by keeping them in the dark. Over time, you will only hurt yourself. Doing the right thing is important even when you dislike your boss. So keep them informed.
UPDATED April 2026
Categories: Exercising Responsibility, Managing & Leading, Managing People
What Best Mnagers Know & Do 
Mr. Busch, You provide some very useful and insightful stuff. I’ve subscribed to your blog and look forward to future posts.
Thank you for the discussion. I took for granted that employees knew what to communicate to their boss, especially seasoned employees but am learning everyone has not developed that skill. The last paragraph about “liking” a leader is critical because while an employee may think they are hurting their manager by withholding information it is more likely than not they are hurting themselves.