Comprehension is an organic and dynamic process. To speak in a Zen way, we cannot really determine where we are going in our meditation, because when comprehension hits you, it is like lightning. It is the psychological flavor of the new. To reach this state, you have to follow the hunches of your heart. If you feel there is something you absolutely need to understand about a given situation in your retrospection that you cannot ignore, you have to follow that.
Many students look for an intellectual way of explaining meditation. This is good in the beginning, but a road block later for the aspirant. Meditation is learning how to use your consciousness, not your mind. My recommendation, however, is that you learn to observe yourself in meditation, since that is what it really is: a deepened state of self-remembrance. You might begin by analyzing your three brains, your reactions to impressions in the day, the nature of those impressions, etc. There are guidelines, or better said, principles, as Adnaley referenced from The Revolution of the Dialectic, but no checklist about how to go about meditation.
The following, however, might get you started in the right direction: concentrate your mind on that scene and your reactions until you grasp, comprehend or experience something new about that situation: it can be an image, a sound, a feeling (superior emotion), an idea (superior intellect) or might even be more abstract than that. What the process of meditation entails is seeking information. Right now, our minds are already filled with information, but it is subjective, mechanical and cluttered. Real insight is the magic of the consciousness, and it will hit you like an eureka moment. The next step after having this experience is not to get identified, but to keep inquiring with your consciousness about what your heart longs for you to know.