But what if you are right? There are a number of ways to effectively challenge your boss. How to Respectfully Talk to Your Boss About Your Workload Provide Evidence You’re in a Jam. 5. A strong argument is one that uses facts over opinion. Remember, you should still remember your place within the hierarchy of the company, and you’re certainly going to cross a boundary if you talk back to your boss in a way that is dismissive, patronizing, sarcastic, or outright insulting. //-->. If your goal is to convince your boss they're wrong, then it’s not going to be a productive discussion. Obviously writing ‘he or she’ throughout would make for an inelegant article, sacrificing readability to appease some rabid bra-burning lesbians. If you can accept your boss’s authority, it will go well with you.