How to Tactfully Challenge Your Boss (2 of 5)

Question from a reader: “Do you have a blog post on ‘How to tactfully challenge your leader or something like that?” Why, yes. Yes, I do. In fact, we have 5 now!


((Read part 1.))

I have been there. My boss asks me to do something that seems bad for business, for my team, or frankly, just sounds like a bad idea. I want to speak up (and my peers are counting on me to) but I am not sure how to approach my boss without the situation blowing up.

Every boss and every working relationship is different, of course, but I can offer five tips that helped me keep the peace while challenging the status quo so far in my career:

2 (of 5). Keep your emotions out of it. When your boss asks you to do something you think is stupid or not in your best interest, probably two things are happening. The first is, your boss likely struck a nerve that makes you feel intimidated by the request or demand (which probably means it will lead to personal growth–something we all react to with initial resistance). The other thing that happens is it becomes an interruption to your emotional comfort zone, which means you are going to feel emotional about it. The problem with acting on your emotions is they are sometimes misplaced or out of proportion to the actual problem.

We sometimes become irrationally mad at inanimate objects that do not act differently than they have acted before (I am prone to be angry at my phone when it runs slowly–something it sometimes does yet I am always surprised and angered by until I reign in my emotions). When I react emotionally, I am giving away my power and authority to random chemicals and inciting the other person to do the same. Soon, any actual conversation has ended and we are both only trying to out-emotion each another (whoever seems angriest wins). The actual problem is never solved. The only resolution is the contest of emotions is over and ultimately my boss has the trump card on that anyway.

You can not control or dictate the emotions of someone else but the calmer and cooler you remain the more you signal the other person to do the same and the more power you gain in the conversation.


Today’s Lesson: Some people think power is loud and boisterous. Power is the opposite. It is the quiet, calm collection of thoughts and precision placement of words and influence. Before any storm, there is always the Calm.

Tomorrow I’ll tell you what your boss can’t or won’t.



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