How to Tactfully Challenge Your Boss (3 of 5)

From a former colleague: “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!


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

Every boss and every working relationship is different, of course, but I can offer five tips that help me keep the peace while challenging the status quo:

((Read part 1 and part 2.))

3 (of 5). Understand your boss might not necessarily agree with the instructions he or she is giving you either. If your boss is generally a bright person yet he is asking you to do something that seems counter to his personality or typical leadership style, he might be following directions, too. A good manager never lets his direct reports distinguish from the Company’s viewpoint and his own (because that is a sure-fire way to disenfranchise employees and pit them against their employer, as well as make the boss seem ineffective and powerless). Or he might understand how the Company is looking at it because he has information you are not yet privy to. That info might change your mind but he may not be at liberty to share it yet.

In all my years leading teams, I have never seen a strategy rolled out without the Company’s best interest in mind. Companies never come up with ideas to sabotage themselves (not intentionally). Front line workers and middle managers do not always see the big, long-term picture. Unfortunately, middle managers are stuck between both standing behind the Company and standing up for the Employee–it is a tough, unfair spot but that is why the best people in the company are usually there.


Today’s Lesson: Companies and bosses, like all people (which is what companies and bosses are made of) sometimes have to learn from their mistakes before they can grow again. You can challenge every decision you think is bad but remember you might not have all the information and you can always try trusting your boss first…

Tomorrow, I will give you a super-secret tip that will help you stand up in front of any crowd!