After facilitating a conversation the other day with a group of managers, I went back to review something I wrote back in 2009 in a book titled Know What You Don't Know. The managers asked me how one can dissent in the most persuasive and constructive fashion, particularly in situations where they feel as they the leader may not want to hear an opposing viewpoint.
Know your audience: Learn about the person you are trying to persuade. Present your arguments in a way that fits that person’s preferred mode of processing information.
Understand the history: Determine who will feel most threatened by your attempts to shine a spotlight on a particular problem. Avoid placing blame on that person; focus on how to improve the situation.
Seek allies and build coalitions: Strength resides in numbers. Find others who will support your viewpoint. Present a united front.
Work through key confidantes and gatekeepers: Identify the individuals who have the ear of the person you ultimately must persuade. Seek them out and try to bring them onboard first.
Focus first on divergent thinking: Remember that your near-term goal should not be to persuade everyone to adopt your view immediately. Begin by simply trying to encourage people to think differently about the situation at hand.
Present alternative solutions: Do not just point out the problem; offer a series of possible solutions. Make it clear that you want to help fix the problem.