Asking a difficult question, regardless of the setting, can be a tense moment. When it comes to asking the tough questions, there are a few things you should do to be prepared before you start talking. One of the worst things you can do in a sensitive situation is to come in unprepared. Take a moment to understand the process of how to ask a difficult question and you will get better results than you expected.
Things You'll Need
Wait at least 72 hours before asking the question, if the situation allows you to. This will give you ample time to prepare to ask the question and it can also give you time to calm down if the situation involves high emotions.
Design a two column table on a piece of paper and give one column the heading of "Pros" and the other the heading of "Cons."
Fill in each side of the table with what you perceive to be the consequences of asking the question. In some cases, a difficult question could be something that changes your life and the other person's life for a long time. It is good to see the pros and cons of asking the question written out so you can contemplate them. If there are more cons than pros, then it may not be time to ask the question.
Research the topic of the question by using reference materials in the library or information found on the Internet. If you feel the need to ask someone's advice, do not reveal that you are contemplating asking a difficult question. Ask general questions that can help you get your answer. Discussing a sensitive topic with others before discussing it directly with the person you have the issue with can sometimes backfire. If the situation works itself out, but the person finds out that you were discussing the issue with others before you discussed it with her, then the anger that you felt you had avoided may suddenly become a factor.
Ask the question immediately once you feel that you have sufficiently researched the topic and considered the consequences. If you are facing the person you need to ask and you begin to delay asking the question, you may get cold feet and never ask at all. For example, if you are getting ready to ask a girl to marry you the best way to do it is to prepare to ask the question and then, when you are faced with the moment of asking her, just ask right away. If you have done the preparation work as outlined above, you are already prepared for the potential consequences.