by 
We use assertiveness to get what we want. While there is no guarantee that we will always get what we want — as the saying goes — we catch more flies with honey than with vinegar. Following the script for assertiveness (DEAR MAN) has the highest likelihood for achieving the desired outcome.
It is helpful to keep other things in mind when deciding to speak up.
- Do we know clearly what we want? We have to be clear with ourselves about what we want from the other person so that we can communicate that clearly and concisely.
- Are we speaking to the correct person? For example, if it appears that a co-worker is receiving special favor, who is the best person to remedy the situation? Is it the co-worker or the supervisor?
- Is this the best time to have the conversation? If we are trying to talk to someone while they are busy with something else, we may not get the attention or consideration that we would like.
- Is there a difference of authority or power (teacher/student, parent/child, supervisor/employee)? An imbalance of power often changes the playing field. A person in a subordinate position may not be in a position to get what they want.
- What is the status of the relationship? Is it a new relationship? Is it tenuous? Is there a possibility that speaking up will damage the relationship?
- Is there unequal give and take in the relationship?
Many factors contribute to how strongly we ask for what we want. A wise person takes these into consideration when making a decision to speak up.
In the end, a good guideline is to ask yourself what is the most skillful and most effective approach to the situation. Also, consider how you will feel about yourself for speaking up or not speaking up. Decide what kind of a person you would like to be and act accordingly.