Not possible without
extremely complex event branching or custom plugins. If you're not already a truly expert user of RPG Maker, don't attempt it.
However, you can have a single animation (like swinging the sword slightly up) use movement in
Yanfly's Action Sequences to
move the user to a position where it looks like they are aiming at their target. For example, if the animation is swinging the sword slightly up, then you'd want to move "Henchman" to a spot slightly below (and to the left of) the target he is aiming at, and then take the swing. Yanfly's Action Sequences allows you to do that.
By the way, your signature picture is adorable!