instinctually, the first thing you think to yourself is "what do they like" which is a great start. step one is to make a list of all things that the gift recipient is interested in. now here's the twist, this list you've created is the list of things not to give your gift recipient.
that's right. don't get them what they are interested in. do not buy audio equipment for the audio lover, clothes for the shopper, computer stuff for the geek, music for the musician. you won't win.
let's pretend that your task is to buy a present for a guy who's a huge sneaker collector. knowing what's hot, what's about to come out, even the companies that are currently 'in' is quite the task for you to find out. then, you have to find out what are your gift receiving sneaker collectors opinion on these companies, styles, and other sneaker industry things. he's surfing sneaker blogs, posting on sneaker forums, and talking about sneakers to his sneaker friends every day. even buying accessories for his sneaker interest land you with a higher percentage of giving a dud gift because you just don't know. if you were to buy him something sneakers, he'll open them and give you that "thanks grandma, i love this sweater" smile.
step two is to think of things that you are an expert at. if there is something that is on your list that isn't on their list, then that's where you start to brainstorm ideas. i've got some real life examples here. my brother loves clothes and shopping for clothes. he'll go to the store and just browse when he has time to do so. given some free time this is the last thing i would ever do, the idea of just hitting up the mall is never anywhere close to an idea when my calendar has an open afternoon. he's the pro, i'm the oblivious one, and when he buys me a jacket, i don't even have to ask if it's what's hip now because i know that he's always in touch with what's hip.
when he opened the apple tv that me and my sister got him for christmas, he had no idea what it did. of course now he uses his apple tv a few times a week. he's not into technology stuff, but i sure am. it was a perfect present.
so let's recap here.
1.) list what the gift recipient is into.
2.) list out things you are interested in, that is not on list one.
3.) start from there brainstorming what to get them.
now there will be a time when this technique doesn't produce anything. and that's when i pull out my emergency step four.
4.) list out things i either always forget to buy, or hate buying.
some examples are towels, bottles of alcohol, and sweets. of course if all else fails go ahead and give the biggest gift cop out, a giftcard.