I am assuming that the person failed the field tasking 5 times not the weapons handling.
I will disagree with Garbageman on that fact does have to turn out well. I don't believe that it has to be completed to pass BUT you must show that you knew what was asked and what your mission was and most importantly that you led the task to its completion. The process (or format) has to be followed but they are looking at your leadership as well.
Some components to consider: leadership ability, ability to work under pressure (time constraints), ability to work with others (can you lead and folow), oral and written expression (your written orders and delivery of the orders) and care and attention to detail (safety, external considersations).
The format is straight forward and can be filled out easily but to control your syndicate (approx 8 pers) is critical. Depending on when you do your task, you must keep them motivated (esp. when sleep deprived and the last day of tasks), make sure they're comfortable (before your task starts and you're doing your estimate, get some food into them and get them in the shade or out of the wind) and during your task, don't be scared to be the hardass (if your sentry pers are standing together BS'ing, get them focused on their job).
Good advice that I was given early on in BOTP is to deliver your orders so that somebody in the next site (ie. instructor
) knows that you're the one in charge. If your voice is soft and wavering, its not effective. If your assertive and have the attention of your syndicate or section, then they are listening and taking in what you are saying.
My 2 cents before tax. Hope it helps.