Unless you are a natural contrarian who loves being on the opposite side of almost any issue, chances are you don’t relish arguing or disagreeing with your boss. Some folks are so emotionally uncomfortable with conflict that they avoid such disagreements altogether.

There are times, however, when you just seem to know you should say something about how a boss behaves, does things, or concerning what they are about to do. A good friend and colleague of mine refers to this as “speaking truth to power”. Being a part of an organization sometimes means having the courage to put your personal and organization’s best interest ahead of any discomfort you might feel in challenging authority.

What makes open disagreement with the boss difficult is the uncertainty regarding how the disagreement will be interpreted. And you can generally disregard the fact that the majority of bosses will tell you “let me know exactly what you think”.

Many bosses respond to disagreement in a mature, reasonably objective way. Others see opposition as a direct challenge to their authority. For still others, disagreement often translates into something like “oh, so you think you are smarter than me” . For an immature boss lacking in self-confidence, opposition can seem far more threatening than constructive. The better your handle on the bosses personality and temperament, the better your odds of success,

When you do decide to speak up, stay calm and avoid accusations. Be constructive, come armed with facts not opinions. Be direct and to the point. Avoid loaded adjectives and remain mindful of the power imbalance when talking to the boss.

My military friends advise sticking to the two “yes but” rule; two is all you get. Because the boss must live with the consequences of their decisions, ultimately they get to have the final word. Have your say but know when you have said enough. Knowing when to let it go is perhaps the single most important key to disagreeing with authority if you wish to be taken seriously when you next decide to speak up.

If your disagreement is met with an angry or emotional response, you have probably made your point. Give your boss time to cool down and think about what you had to say. Remember, emotional outbursts are not a product of rational thinking and cannot be reasoned with. Do not respond in kind.

In the end, winning is not the point of disagreeing with your boss. Speaking truth to power is.

UPDATED April 2026

Categories: Exercising Responsibility, Managing & Leading, Managing People

Tags: advice for managers, effective management and leadership, effective managers and leaders, management advice, Managing & Leading, managing up, Self-Management