How to Disagree with Your Boss-and Win

Published: Jan 24, 2019
Modified: Mar 25, 2020

By Kevin Daley

A midlevel manager—let’s call her Laura—gets a directive from the boss that she thinks is ill-advised. Laura concludes that the plan won't achieve the desired results. It will increase costs or demoralize employees or cause customer dissatisfaction. Whatever the problem is, Laura is aware that because it’s the boss’s plan, she has to deal with the situation with a degree of sensitivity.

There’s a right way and a wrong way to disagree with the boss and win an argument. Laura realized it was necessary to cool off before confronting the situation. She waited a day—but the course she took was the wrong one. She walked into the boss’s office and told him the plan won't work. "Of course it'll work," the boss replied.

"I want to redesign the plan," Laura said.

"No," answered the boss.

Laura reflected on all this later. She realized that she had caused her boss to become defensive and that she had to change her approach. She asked the boss for a meeting where she could ask some questions to help her understand the plan better. They set a date and time.

Laura went to the meeting with a pen and notepad and asked the boss what he wanted to achieve with his plan. The boss described his objectives. Laura then asked a series of questions to clarify her understanding of the objectives. To be certain she understood correctly, she paraphrased the goals. She then told her boss she could achieve the objectives and asked for permission to come back with a plan later that week. The boss agreed. The story has a happy ending. The boss accepted Laura’s plan and she began implementing it later that day.

Here are some lessons Laura gained from this experience, in the form of do’s and don'ts that can help you disagree with your boss and win.


  • Come out and say you disagree with the boss’s plan. Avoid use of the dreaded word "but," which might make it appear that you're negating everything the boss had said. Instead, use the word "suggest"—it’s a magic word in this kind of dialogue, because no boss bristles at a suggestion.
  • Let your emotions come into play. Wait a while before presenting an alternate plan. Ask for a meeting to discuss the boss’s objectives.


  • Start that meeting by asking what the boss wants to achieve and the reasons for these goals. Ask open-ended questions to probe further. Paraphrase to make sure you understand. Thank the boss for the information and set a date for presenting your plan.
  • Make sure your plan links to the boss’s critical needs, including the personal ones as you understand them.
  • Visualize yourself in the boss’s shoes. Appreciate what’s good about the boss’s roadmap. After all, your goal is to have your plan accepted, not to prove the boss wrong.
  • Open the meeting by giving the boss the floor. You won't get the attention you need until the boss invites you to speak. Present your plan enthusiastically. Make it clear that the intention of your plan is to achieve what the boss wants. Start with the bottom line, not how you'll implement the plan. Fill in the details only if you're asked for them. Keep it short; the boss is busy.

Whatever you may think of your boss, you can’t advance your career without him or her on your side. Good communications skills with all the people you work with are essential for building your career. The way you present yourself to your boss—indeed, to everyone you work with—will affect your ability to do your job well and the way you're viewed as a professional.

About the Author(s)

Kevin Daley is founder and chairman of Communispond, Inc., a communication skills training firm. He is the author, with Laura Daley-Caravella, of Talk Your Way to the Top, published by McGraw-Hill. Contact him via