Add spice then oil, or oil then spice?
Well, this is rather complex. Let me break it down in two parts:


Oil on the meat vs. oil in the pan
There are two advantages to oiling your meat instead of pouring oil in the pan: Less splattering and typically less oil used overall.
But keep in mind which oils you use: For frying / searing you want something with a high smoke point. Leave your extra virgin for cold or only slightly warm uses.
Oil or spices first
Your meat should be dry before you put it in the hot pan or you will end up with possibly painful splatters, or at least a lot of extra cleanup (see 1.). So you should always dry your meat, e.g. with paper towels. This will mean your spices are less likely to stick to the surface. Oiling the meat first helps the spices to adhere better, rubbing them in or just sprinkling doesn't make much of a difference.