Vivian Giang has written a useful article for Fast Company about how to disagree effectively with your boss or other senior leaders in your organization. She draws on the expertise of Priscilla Claman of Career Strategies, Inc. Giang provides several recommendations:
1. Know Your Boss' Decision-Making Style
Are they influenced by data and formal analysis? Do they worry about how their decisions affect interpersonal relationships? In short, you need to know what type of argument or presentation will be most influential with your boss. Speak and make your case in a format and style that will make the most impact with that person.
2. Recruit Credible Allies
Don't go it alone. Find others who can rally behind your argument and stand with you. Perhaps they can even join you in making the case to your boss or other senior leaders. Or, perhaps, you can identify the leader's confidante or trusted adviser. Make your case first to that person, as they may be your best channel for presenting a constructive dissent and persuading your boss to listen carefully.
3. Identify Your Baggage
Consider your past experiences and your reputation/track record. Now put yourself in your boss' shoes. What will they automatically assume about you and your argument? What will they expect of you? If you can recognize any baggage that you may bring to the conversation, you can anticipate roadblocks and objections much more effectively.