It all depends on your dog. Most can get by with having it done by the groomer when they get their haircut. Some of our clients come in between grooming a to have us express them also. Some dogs never need the expressed and come in always empty.
Just make sure when you do it, to be careful not to over attempt or squeeze to hard, you can injure your dog and cause gland leakage. I always give my self a 3 attempt rule. If I haven't gotten anything out after 3 tries, I tell the owner to take them to the vet.
It's possible that either your dog is scooting because hair has overgrown and is causing tickling, or you are not in the right area. Some dogs anal glands full higher, some lower and some further back.
I remember when I first was learning how to groom (I was 17) it took me a week before i successfully expressed glands, and my mom makes fun of me still because I came home that day all excited. I think my problem was I was afraid to hurt the dogs so I wasn't squeezing hard enough.
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