What to Do When Your Boss is Wrong?

I recently was reading a Harvard Business Review article about “supporting a decision you don’t agree with.” The article was helpful, and offered the reader wise counsel in advocating that workers should not undermine their boss’ decision. They’re both on the same team after all!


But, this got me wondering: What about when the boss is wrong? Bosses are human after all, and all humans are prone to making mistakes. So what happens when the boss is entirely wrong, and you the worker can see it, yet the boss wants to move forward anyway? To be sure, this goes beyond “supporting a decision you don’t agree with.” I am referring to big initiatives, where the very survival of the organization may hang in the balance. What do you do then?


For starters, respectfully challenge the decision. If anyone I lead is reading this, I want noise, albeit in a respectful tone! “Your idea sucks,” is harsh, but it may be necessary. It would be better to say something like “here is where your idea may run into trouble” —and then name the potential obstacles. The point is that you need to speak up! And not just once. The leader had better fully understand your point of view, its merits, and your concerns around the direction they—the leader— intend to go. The most unhelpful thing you can do for your organization is be quiet in the moment, and play “armchair quarterback” later. Know-it-alls in hindsight are not helpful whatsoever.


Speak up in the moment!


But what if the boss still does not listen? Dan Coyle shares an example of this in The Culture Code (yes, this book again!). The story is of Dave Cooper, and his now famous “Seal Team 6’s” capture of Osama Bin Laden. You’ll have to read the story yourself in the book. The short version, goes like this: The higher ups ordered Cooper to use a new kind of stealth helicopter for the mission to capture Bin Laden. The problem? The chopper had never been used in combat! Cooper challenged authority, but command was insistent. Instead of blindly obeying the order, or denying the order, Cooper did something altogether different by preparing his men for every conceivable thing that could go wrong with the helicopter. In fact, as Coyle shares, they practiced “downed helicopter drills” so many times that his men started sarcastically joking about running even more drills. The result is amazing. (Go buy the book!)


What do you do the next time something similar happens in your organization? For example, the boss is insistent on using a certain supplier that you suspect will fail. You respectfully voice your concern to no avail. Do you sit back and watch, or like Cooper, or do you help the team do “drills” in anticipation of the challenge to come?


Leaders always take ownership of the problem!


Leaders are always out to help others succeed, no matter the cost to their own ego!


This leads us to one final reminder before closing: Respectfully voicing your opinion and planning for contingencies are positive behaviors of any culture. Sitting around and gossiping about how stupid management is —regardless of how true that sentiment may be —is not. As Dr. Henry Cloud has said before, “I do not understand people who pee in their cereal and gripe because it tastes bad!”


Bosses are often wrong. Challenge them respectfully. Create contingency plans that will serve the organization.


Just don’t pee in everyone’s cereal.

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