You are trying to analyze or evaluate questions, problems, claims and the like. It's not as easy as it looks. There are numerous inputs into the process and a number of traps, or fallacies, that you can fall into. It takes time to learn to do it, but the time is well invested.
If you can make use of this process, you will make better decisions.
Purpose: What are you doing? What are you trying to evaluate or analyze? Can you state it clearly, without fuzziness and/or excess generality? If you want good examples of unclear statements, listen to campaigning politicians. Their campaign promises are usually so vague as to be worthless. Also - what they promise may actually be impossible or infeasible to deliver, but that may be hard to see at first because of the lack of clarity. Uncritically believing the statements made by campaigning politicians can be extremely hazardous.
Evidence: What evidence do you have available? Along that line, you might apply two properties of measurement: Precision and Accuracy. To say that someone's weight is "over 180 pounds" is not precise; it might be 181, 200, 220, and so on. If you say someone's weight is between 145 and 155 but it is really 130, that is not accurate, although its precsion is reasonable.
Assumptions: What are you taking to be true without proof. How will these assumptions affect your conclusion? This is important: Most decisions or evaluations involve some assumptions. When you are trying to make a difficult decision, try writing down your assumptions. This may take practice. Try to evaluate the effect your assumptions have of the outcome. Try to understand, for each assumption, what happens to your conclusion if that assumption is wrong. Evaluate cost and/or consequences both ways.
Biases: You probably have some internal biases that might affect the conclusion. What are they? Did the bias make you ignore some important evidence? Did bias drive some assumptions? Do you have any vested interest in the outcome? Can you look at the problem from several different angles?
Conclusions:What do you finally conclude? What logic did you use to get there? Does it make sense? Is it consistent with the real world?