As FLS said, knowing the speed and acceleration capabilities of the plane-set helps a lot.
But I might also add to this discussion that there is a big SA (Situational Awareness) component to this. Watching the cons around you and seeing how they are maneuvering is really the best way to judge their energy state. A simple way of thinking about this is to ask "what did they last do?" Did they just dive? - then they are relatively fast. Are they at the top of a zoom climb? - then they are relatively slow. Did they just turn hard? - then they just decelerated from whatever speed they had.
So, if you are going to start your "chase" (engage the con) after one of these examples, you can probably tell before you engage whether or not you have chance of catching them, because it is more about YOUR current speed (E-state, really) vs. their current E-state. Then knowing both of your acceleration and top speed capabilities helps with determining if your timing will be right (if you have enough time to get to them before they get their energy greatly exceeding yours).
The slowest plane in the game can "catch" the fastest plane in the game, IF they time it right. Good situational awareness plays a big role in determining if you can do that, though.
I wanted to throw that into the discussion, because thinking of it as an SA question, in addition to aircraft capability, may be helpful too I believe.
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Ryno