How To (Constructively) Disagree With Your Boss

The best teams thrive on productive disagreement. Here’s how to plead your case respectfully.

How To (Constructively) Disagree With Your Boss
[Photo: Flickr user John Haslam]

Whatever your feelings toward your boss, the fact is that he or she got to that position because of some combination of experience, expertise, and training. In other words, they earned it. That doesn’t mean you’ll always agree with the decisions your boss makes. Sometimes you’ll even be certain your boss is wrong–either on something small and harmless or much more consequential.


So how do you challenge your boss respectfully and productively? It can be daunting to point out a difference of opinion to someone we report to. Many of us simply aren’t great communicators when it comes to those in higher positions.

But with a little effort and tact, you can disagree with your boss in a way that’s respectful and gets things done.

Build Trust

Trust is at the center of all good employee-employer relations. Without it, there’s virtually no hope you can persuade your supervisor that your own view of things might be better than theirs. That trust is a two-way street, and you have to do your part to earn it.

Keep to your project deadlines. Go the extra mile when there’s an opportunity to. Make sure your performance is consistent. You want to demonstrate over time that you’re a reliable part of the organization. It will show your boss not only that you respect her and can meet her expectations for you, but that you’re considerate. Show you care about your working relationship, not just your work. You’re a team working together, not at cross-purposes.


Let The Small Stuff Slide

Just as your boss has been placed in his role for certain qualifications, you’ve been placed in yours because he knows you can do it. But when you approach him about trivial matters, you send the message that you’re losing sight of the big picture–which can convey incompetence or a lack of initiative. Keep in mind that your boss is busy. He’d probably rather focus on more important issues and wants you to do the same. So pick your battles.

Say It Tactfully

Tact, as Benjamin Franklin put it, is about “remembering not only to say the right thing in the right place, but far more difficult still, to leave unsaid the wrong thing at the tempting moment.”

When it’s time to disagree with your boss, the way you express it can make all the difference. If you hedge and apologize too much, you won’t be taken seriously. But if you’re too confrontational or arrogant, the effort can backfire that way as well. Instead, be calm, focused, clear, and firm when you speak. Keep the issue in the foreground, and make sure your boss knows it isn’t personal.

In some cases, your boss might have really made an obvious mistake. Don’t bring it up publicly. Confer in private and point out your view of the issue. Never make demands or embarrass your boss, or you’ll have thrown out all the trust and respect you’ve worked so hard to build.


Get The Timing Right

Timing and tact go hand in hand. You need to be sensitive about your boss’s personality before diving in. Maybe you know his mornings are especially busy, so you’ll wait until the afternoon to confront him. Maybe your boss simply doesn’t take criticism very well. Consider scheduling a short meeting so you’re guaranteed a few minutes to talk it through. This way you can both prepare mentally and emotionally for the conversation, rather than trying to sort it out on the fly.

Understand What’s At Stake

There’s nothing worse than an employee who acts like a know-it-all but doesn’t have the facts straight. One way to keep your cool and composure is to be confident about your grasp of the issue you’re raising. Keep the conversation focused so it doesn’t become a heated argument about something else.

While you’re brushing up on the facts at hand, anticipate your boss’s counterargument. What might have led her to the position you disagree with in the first place? How can you use that knowledge to persuade her to see it differently? Drill yourself on the strongest answers to the questions your boss might ask. Gather resources and data to back up your case and make it more credible.

Know When To Back Down

Not all arguments can be won. There’s a time and place for everything, and this time might not be yours. If your boss refuses to consider your argument, respect his decision and make sure he knows he still has your full support.


Your graciousness in accepting defeat will shore up the trust that allowed you to disagree in the first place. How you respond might even lead him to reconsider his decision later on or to seek our your input on another issue in the future.

You’ll be able to stand out for the right reasons, making yourself a valuable part of the team. In fact, the best teams thrive on productive disagreement. If you can get that right, you won’t just be making a contribution to your team. You’ll be showing you have what it takes to become someone else’s boss when the time comes, too.

James Richman is a business author, and much of what he writes about is based on his own experiences–both good and bad–as the CEO of the globally recognized and trusted online technology company 1stWebDesigner.