If you are like most people, you do not have enough routine one-on-one discussions about your work with your boss on a regular ongoing basis, every day or every week, before anything goes right, wrong or average on your work for that boss.
Most managers and non-managers alike are so busy all day every day juggling their various responsibilities at work that they don't make time for a regular schedule of management conversations: I mean routine one-on-ones between you and your boss to discuss your work for that boss at any given time; to plan, clarify expectations, attend to resource needs, review progress, and make adjustments.
Instead, most management conversations occur on-the-fly or ad hoc: Maybe in the middle of a group meeting, even if many of the people present at the meeting don't need to be part of that particular conversation; or on widely distributed group emails; or sudden random emails and voicemails; or in passing; or when the boss has a nervous moment; or you have a nervous moment, or when there is a big problem that suddenly comes to your attention or the boss's attention. All of a sudden the boss can no longer avoid her management responsibilities and springs into action. By that point, of course, both you and the boss have a very difficult task on your hands. It would be like if you and your boss were trying to go out and take a ten mile run together when you were both completely out of shape.
I call this phenomenon -- not enough routine one-on-one management time -- "management on-the-fly."
There is no systematic logic to management on-the-fly. The only alternative though is for you to get in the habit of having regular one-on-one management conversations with every boss you answer to at any given time, so that you can discuss the work you are doing with each boss on an ongoing basis.
That means you need to make time every day (or every other day or once a week) to manage your boss. Whether your boss realizes it or not, you and that boss need to build a regular management dialogue together. So take the initiative. Start scheduling regular one-on-one management conversations with your boss. If you have more than one boss, start scheduling regular one-on-one management conversations with every boss.
Make it a habit.
Things will go better. I promise you, things will go better.