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Bossing around: Choose words wisely around your boss

Do you have a solid working relationship with your boss?
For your sake, that relationship hopefully is built on the pillars of trust and hard work, along with mutual respect between the two of you.
And, of course, a little bit of biting your tongue on your part perhaps.
The subordinate and boss relationship can turn sour quickly if you, the worker, feel the need to say certain things to your boss that, in hindsight, probably wasn't the best career choice.
Exactly why you take liberties on what you say to your boss can't always be pinpointed. Maybe you feel overconfidence in your relationship with your boss and see the two of you as close enough to brutally honest. Then again, your talent might be justified, but even that doesn't give you the kind of outlet where you can say anything you want.

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Take for instance the idea behind questioning your boss about a decision, particularly one that they do a million times throughout the course of a year and is relatively second nature to your boss. They'll probably not appreciate that sort of questioning attitude but instead would rather you save the feedback for a new project that truly needs more than just your boss' voice.
One of the more controversial lines you can debate saying to your boss is "I don't know."
Some argue that the "I don't know" is more of an admission of being honest and wanting to learn. The better option, however, is to assure your boss that you'll be doing research or finding an answer to that question you don't know. Saying "I don't know" also can be viewed as you throwing up the white flag and walking away from a challenge.
The same could be said for "There is a problem we need to discuss." Bosses are faced with problems on a daily basis, so you telling them that a problem is either here or brewing is the exact opposite of what they want to hear. Instead, you can broach the subject of the problem, but come up with a way to fix it.
Then, your boss will appreciate the feedback and once again look to you as their go to person. But even that namesake doesn't guarantee you'll have free reign on what you're permitted to say.

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