There are two approaches, for drawing a live caricature, and I guess it would apply to other things too. There's the severed thumb approach. This is referencing the little trick you can do to make it look like your thumb is dissattaching and reattatching. You know the one. I imagine a little two year old being difficult at a family reunion or something and the silly old uncle sits beside him and shows him this trick and he sees it for the first time and is amazed and the uncle manages to keep the little rascal occupied for a while but this is more about how a fun older person is able to keep a young person entertained and engaged and occupied by staying ahead of their expectations. It's kind of like when one person can consistently beat the other at rock scissors paper. Anyway, we'll call it the severed thumb approach.  And it's a type of approach to entertainment. The other type I will call the Don Quixote approach. This approach you are seen from the outside. You're dreaming the impossible dreams and stabbing at invisible dragons. So the thumb trick approach is about having a carefully crafted thing and sort of coddling the audience. Taking them for a wild ride, every twist and turn of which is in your control. The Don Quixote approach is sort of experimental in a way. It's sort of surrealist. That's a better way to think of it. Grasping for things that you can feel at the periphery of your consciousness. So if you're sure that you have a thumb trick that will mystify your audience, do that, but if you suspect that it may be the other way around, Don Quixote will be the only way that you can entertain your audience directly. Indirectly, a thumb trick could work, but it would require that the audience be interested sort of anthropologically, as in, wow this method that you use for entertaining folks is really interesting.

Think about beginning artists. Imagine your very first live caricature. What if the very first person who sits for you is even remotely familiar with live caricatures. If you took the severed thumb approach and gave them a clean quick sketch with that cocky experienced "just leave it to me" type of attitude the customer will be insulted and disgusted at your utter arrogance and lack of skill, and that's why most beginners understand naturally that the approach in this type of situation has to be different. 

That's when you humble yourself and do your best and grasp for the unreachable. Stretching your mind doing the bestest best you've ever done, and you can acknowledge showmanship in whatever way but it cant be real showmanship because you don't have control of the audience.

But the point is this. For someone who can't see through the magic trick, enormous throbbing 100% souped up confidence and charisma will enhance the experience and the personal connection while the same approach for someone who can see through the trick is rather sad and disappointing. However, for someone for whom the trick wouldn't work, what would work is honesty and openness and experimentation and soul searching and mind stretching, and basically things that will strengthen you as a human and add power to your thumb trick.