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I don’t like the optional Flanking™ rule in the 5e DMG. Not only is it a kind of flavorless way to get advantage, something we want to be careful with, since advantage doesn’t stack and I want it to be reserved for specific fictional positioning stuff, or conditions. (A lot of YouTube DMs have proposed using +1 or +2 for flanking instead of advantage for this reason.)
It’s also finickily defined. Drawing lines, counting hexes etc. It’s meant for minis, and I’m more into “theater of the mind”–style fighting.
Here is what I like instead.
“Flanking” (as opposed to Flanking™):
then you are “flanking” and you can use your “Striking unnoticed from behind” ability (as it’s called in B/X p B10, renamed “Back-stab“ in OSE) or Sneak Attack ability (5e) if you have it.
(This isn’t the only way to get that ability—you can also get it by hiding, for example; having advantage basically. But, this kind of “flanking” doesn’t give advantage; it’s just another, non-advantage way to get Sneak Attack a.k.a. Back-stab.)
“WTF?” dear reader might ask now. “Isn’t that just normal 5e PHB Sneak Attack conditions?“ That’s right.
My thinking is that it takes a character having Sneak Attack (or abilities like Sentinel (5e)) to explicitly & consistently mechanical benefit from this “flanking” setup.
For normal champions, knights, rangers etc please go ahead and describe how you are striking at the enemy’s turned back or whatever you do (in a way that makes sense with the fictional positioning) since if you do manage to injure them, it matters where you hit them, because Oh, Injury!, even though the dice&numbers to hit them is just a normal attack against AC.