Tasting a cigar is a contemplative process. Much like tasting anything (e.g. Food, wine, etc). I can discern flavor when I eat/drink something. In my case, it "popped" for me when someone challenged me to describe what I tasted in a single malt scotch. I tasted a citrusy flavor (kinda like an orange) along with some floral "smells" (notes/tones). It was an impression I got when I closed my eyes and really thought about what I was tasting.

Similarly with cigars. No always, but sometimes I pick up a leather kind of taste - or woodsy... Sometimes I do taste my impression of prunes, or plums (LFD chisels do that for me). I definitely taste spiciness quite often in the more full bodied cigars. Lighter cigars are much more subtle and really hard to describe. Of course you know - I've been told we did not buy a cigar because it tasted like prunes or chocolate... LOL

But I would not get hung up on it. Smoke what you enjoy and enjoy what you smoke!