While in combat, I am a wizard with a hawk familiar from the Find Familiar spell. I have been trying to send my hawk to give the help action by being a distraction. My DM has been making me roll for the hawk (performance or perception) for it to be a distraction in order to give the help action. If it fails, my hawk is not allowed to give the help action that turn.

For the Help Action the definition is "You can lend your aid to another creature in the completion of a task. When you take the Help action, the creature you aid gains advantage on the next ability check it makes to perform the task you are helping with, provided that it makes the check before the start of your next turn.

Alternatively, you can aid a friendly creature in attacking a creature within 5 feet of you. You feint, distract the target, or in some other way team up to make your ally's attack more effective. If your ally attacks the target before your next turn, the first attack roll is made with advantage."

Should he be making me roll for the hawk to be able to help? Do I need to be a successful distraction to say I want to use the help action?

RAW, no, your hawk does not have to roll to take the help action. Taking the help action is what makes you a successful distraction. You don’t have to roll athletics to take the dash action.

That said, in my game, I houserule that you do need to pass an ability check (DC 10) to help another character on their ability check. I do not do this with the combat usage of the help action, but I can imagine a DM house ruling like this. It’s poor form to spring it on you with no warning though.

A roll is not required by default, however the DM is entitled to introduce rules such as these at their discretion. A familiar using the help action constantly is common, but often considered a cheesy exploit, so I don't blame the DM for nerfing it a bit.

RAW no, the help action just works.

I'm not a big fan of house rules like these. The help action already has a roll, it is the advantage roll of the helped ally. This is like if you had to succeed a concentration check to cast a spell or an athletic check to make an attack.

The familiar help strategy is only OP if the DM lets it be by giving the familiar plot armor, when responded to appropriately the player (you) is gambling 10GP on 1 or 2 help actions, which is fair.

That's true. If the familiar is treated like an actual target, then if the player tries to use it in combat, it will be expended pretty quickly. Either way, it shouldn't be able to provide the help action continuously for free.

Quote from Memnosyne >>

That's true. If the familiar is treated like an actual target, then if the player tries to use it in combat, it will be expended pretty quickly. Either way, it shouldn't be able to provide the help action continuously for free.

 Why not? Wouldn't it depend on what kind of creatures you are using it against?

Quote from Wysperra >>

Quote from Memnosyne >>

That's true. If the familiar is treated like an actual target, then if the player tries to use it in combat, it will be expended pretty quickly. Either way, it shouldn't be able to provide the help action continuously for free.

 Why not? Wouldn't it depend on what kind of creatures you are using it against?

Sure, context matters. The Help Action is most commonly used in the context of a humanoid helping another humanoid, which is not only equipped to perform the same tasks, but is capable of understanding and anticipating the needs of the creature it's helping. By comparison, an Owl has an intelligence of 2, can't speak, can't attack, doesn't have hands, and no practical skills other than perception and stealth.

RAW doesn't make a distinction between different creatures' capacity for rendering aid, but common sense says that there is a significant difference between a Tiny stealth fluff ball and a fully functioning adult humanoid. In combat against an average small beast, sure, an owl is a compelling distraction, but against the average guard, drake, goblin, or honey badger, that owl isn't either not going to matter, or isn't going to stick around for long. Allowing the owl to provide continuous advantage without in-game costs, consequences, or considerations would represent a major oversight.

Warlock Pact familiars are obviously better, but would still be a valid target.

Partially agreed. What I meant was the PC can use the familiar as much as they want with the understanding that the monster might attack and kill the familiar.

Even a kraken can get distracted for one round by an owl =) [ref: Clash if the Titans]