I've found that having them find their outbound heading on the DG and holding their pointer finger and a thumb up to create the teardrop area(left hand hold, left hand teardrop and vice versa for a standard hold) helps them visualize the entry the best (basically inside the TD area is a teardrop, below the thumb is a direct and the upper half of the DG not in the TD area is a parallel). I've also had some who did best by drawing it on their kneeboard and figuring out the best entry that way, but most do quite well with the D.G. method.
I tend to favor the drawing method, mostly because it teaches the visualization of the hold and shows how the AIM entries actually make sense. If you, for example, teach what the AIM entries are (without the numbers) and draw the holding pattern and the airplane's relationship to it on a board, most students will invariably select an entry just like the ones in the AIM and from approximately the same angles. They just make sense. That's in part why holds on a moving map are so easy - you hardly need the GPS prompt for type of entry.
Here's "Hold southwest of the VOR on the 220° radial, left turns. Maintain 8000. Expect further clearance at 0000Z." You are arriving from the northest. "Copied" by drawing instead of by writing. I thing the entry is obvious just looking at it.
I'm not against the thumb, pencil, whatever on the DG method but I think it bypasses understanding of the hold in favor or a mechanical device.
But I admit to a lot of bias. If you are familiar with the related pencil-on-the-DG method, there are actually two versions of them, one that uses the inbound course for reference and one that uses the outbound. I was taught one of them during my instrument training (don't ask which) but ran into a CFII in my first IPC who insisted it was all wrong and I
must change to the other one. Yeah, I should have told him he was an idiot but what the heck did I know? He screwed me up so much I could never use either one of them again.
I realize the thumb method doesn't suffer from the same issue; a meting that required you to turn your hand upside down would be practically unworkable. But the result of my experience was finding the drawing method and I because biased against any of the mechanical ones. I do use teach them though, if the drawing method make no sense to the student. People learn differently and a CFI's job is to teach in a way the student understands.
(BTW, the other outgrowth of that experience was the comment I sometimes make that the single worst thing a CFI can do is force a pilot to change a technique that works just because the CFI likes another one better)