Disagree with Your Boss and Live to Tell About it
January 16, 2015 Fast Company Leadership Blog | by Bill Rosenthal, CEO, Logical Operations

Imagine your boss gives you a directive that sounds really absurd. You’re afraid that following orders could cause a customer to leave, hurt the company’s reputation, or even break the law.

You may not like it, but it’s part of your job to protect your boss from self-inflicted harm. There is a right way and a wrong way to do it, though. Here are six guidelines:

1. DO SOME RESEARCH

Maybe in the grand scheme of things your boss’s idea isn’t so awful. You don’t have all the information the decision was based on, after all. Before you object make sure you're not opposed to the idea because you're adversely affected by it, and don't assume the decision's wrong until you understand it fully.

2. SHOW RESPECT

Some bosses want to be challenged because it fosters creativity and guards against group-think. But not all do. Tailor your response accordingly.

With even the most congenial boss, you should never say, "That wouldn't work." Avoid barrier words like "disagree" or "no" either. Most of all don't react angrily when you're given the assignment. Try to understand your boss's thinking first. Ask questions with a degree of deference that fits the company's culture and your relationship with your boss. There's a huge difference between, "This is going to lose that customer for us," and, "How is this going to affect that customer?"

If you agree with your boss's objective but not the implementation plan, be enthusiastic about the objective—and endorse whatever parts of the plan that you like. To negotiate successfully you have to be seen as an ally, not an obstructionist.

3. KEEP ASKING QUESTIONS

Socrates advised his students to ask a series of questions that can help the other person rethink assumptions and become open to new ideas. Use Socratic questioning to help your boss reevaluate the idea and, at the same time, help you understand what your boss wants to accomplish. Confirm that you understand by paraphrasing what your boss said. Take notes. Ask for permission to present a detailed implementation plan and make a date to present it.

4. DEVISE A BETTER ALTERNATIVE

Create a plan that will meet your boss's objective but avoid the problems that you foresee. Anticipate the resistance your plan might encounter up and down the line in the company. Try to consider everyone's personal motivators as well as the business ones involved. Talk out the plan with a trusted advisor who can spot weaknesses. Don't get so wedded to the plan that you minimize evidence that it might not work. Prepare concise, persuasive answers to questions about the plan that you'll likely be asked.

5. PRESENT THE PLAN

Begin with the bottom line: the outcomes that your boss identified, using your boss's own language. Save the details for later. Nobody wants a data dump, especially a busy boss. Rehearse the presentation so you can make it without using notes. Keep rehearsing; you'll find that with each iteration you can eliminate unnecessary content.

Present with confidence and enthusiasm. Use self-assured body language. Change your voice volume and pitch to emphasize your important words and phrases. Make unflinching eye contact; avoiding eye contact can signal you're unsure about what you're saying. Avoid non-words like "um" and "ah," which are also signs of insecurity.

6. BITE THE BULLET

Let's say you've done everything right but your boss won't budge. You can't back down if ethics would be compromised. Absent that, though, it might be best for you to suggest that you test the plan. Be sure your test is objective—and be a good loser if it's you who has to back down. You don't want your boss to think that you're moving ahead begrudgingly.

Just remember: Every point of view is reasonable to the person who holds it, successful persuasion depends on the other person's trust in the persuader, and persuasion never happens when the message is unclear. Keep these principles in mind whenever you have to disagree with someone. Observe them carefully if that someone is your boss.

Bill Rosenthal has headed employee education businesses since 1986 and is CEO of two sister companies: Communispond provides virtual and traditional classroom training for improved communications and sales. It has served 350 of the Fortune 500 companies since its founding in 1969. Logical Operations, Inc., founded in 1982, offers more than 4,600 titles in its skills training curriculum library that spans six major business categories. It serves businesses, government, commercial training centers and academic institutions.