[RPG] Is it possible to repeatedly give someone else the Help Action for an eventual Initiative roll

dnd-5ehelpinginitiative

Let's say Bob really wants Fred to act quickly for an eventual fight which they feel will come soon.

Can Bob repeatedly give Fred the Help Action for his eventual Initiative roll ("Stay focused! Stay focused! Stay focused!") in order to give Fred Initiative advantage when the encounter begins?

Best Answer

It's unlikely

What you are asking for is to be able to perform an action before combat begins. That's effectively granting a free, or even a surprise, round to that creature.

Whether you are using an Action to Help, to cast a spell, or anything else is still effectively granting a free action when no other creature gets one.

Surprise

This is really the only in-combat method for getting an opportunity to act before it really begins. However, in most combat situations this mechanic is unlikely going to get a chance to be used (and it's also after initiative is rolled.)

Repeated Help

Saying you go around every 6 seconds providing "help" to something just isn't realistic. You don't exactly know what you're helping someone to do. How are you helping them get a faster initiative? What are you specifically doing in the specific case of that combat? It's just not a normal way of acting and there isn't a way to constantly "help" someone in this manner.

When trying to figure out a way to work, do note that requirements for using Helping, or Working Together, on ability checks:

A character can only provide help if the task is one that he or she could attempt alone.

Moreover, a character can help only when two or more individuals working together would actually be productive.