How to Tactfully Challenge Your Boss (5 of 5)

A friend asks: “Do you have a blog post on ‘How to tactfully challenge your leader?” Yep. I have 5!


Your boss asks you to do something that seems bad for business or bad for your team. You want to speak out but you are not sure how without the situation backfiring.

Every boss and every working relationship is different, but here are five tips that help me keep the peace while challenging the status quo:

((Read part 1part 2, part 3, and part 4.)) 


5 (of 5). Ask dumb questions. A “dumb” question is what I refer to as “a blatantly obvious question to which you already know the answer“. Pretend you have no idea why your boss is asking whatever he is asking and that you are somehow missing the point. Ask the dumbest question you can think of that will innocently challenge his proposal (probably something like, “Okay, but may I ask why?” or “Help me understand why we are… ” And consider following up with, “Okay, what can I do to help?”

Today’s Lesson: Sometimes asking dumb questions leads to great insights on both sides of the conversation.

I hope this series helped you find ways to politically and tactfully challenge the ideas you think might not lead to the best outcomes. If you want to keep the conversation going, share a story, or offer a tip of your own, be sure to comment on my FaceBook or Tumblr page, or via Twitter. Also, if you found value in the posts, be sure to share them or subscribe to the blog. Thanks for reading and sharing!