Determine the purpose of your question. Ask yourself what piece of knowledge you hope to gain by the answer. Questions can be broken down into six categories: what, why, how, who, when and where.
Determine whether your question is a thinking question. For example, if the question can be determined through a cursory inquiry on a popular website, the answer may be a few keystrokes away. Otherwise, write down the question.
Analyze the word usage of your question. Formulating a successful "thinking" question involves proper selection of adjectives. For instance, "best" often results in misleading answers. Different criteria determine what is best. The best hotels in Miami may involve price, luxury, proximity to the beach or a combination thereof. In that case, determine the criteria and use them in your question.
Assess whether your question automatically results in another question. If so, try to combine both questions into in a single inquiry. However, do not force a synthesis if the question loses its intent.
Determine your motives for asking the question. Thinking questions may be asked for other reasons besides desire for knowledge. For instance, questions may be a means of expressing one's own beliefs. Other "thinking" questions may be asked with the intention of "tripping up" the answerer. Consider whether the forum is an appropriate location for such questions. A vigorous debate between colleagues may be an acceptable situation, but the Q&A segment of a formal academic lecture may not.
Ask your "thinking" question. Speak clearly and articulately. If you feel intimidated, e-mail will work as an appropriate method of inquiry.