Reading Datasheets?

I'm new to this as well. As I've had to learn things quickly I've adopted this "workflow":

1. Make sure you can actually get the part you want to read up on. I recently almost ordered a PCB that relied on a part central to it's design (an SMD antenna) which was not available anywhere I looked.
   
2. Find reference designs with google (similar applications of a similar device to what you're trying to do)
   
3. Verify relevant electric properties (i.e what currents it can handle etc, the interesting parameters will vary from part to part) for you design
   
4. Look at the pin out explanations (for a mCU you'll want to check things like verifying it has support for the IO you need etc) to verify it supports what you need and expect
   
5. Look at the available packages it supports, and I also learned it's a good idea to verify it uses the most common pin layout for common parts (SOT-23 transistors for instance, some odd ball parts will not be in the common configuration)
   
6. Google everything you're unsure about, or ask a friend, or ask a forum - such as this one :) I'm sure I'll post many questions here.
   
   

For me, it's been really helpful to view reference designs and tutorials/explanations on youtube.

I also have more than one CAD installed in case I want to reference an open source project or something like that.

Last point I learned when doing my latest project was to try to find my exact part when I place the symbol in the schematic. For the aforementioned project, I drew the schematic first, then had to go over and figure out exact parts and values. Let me tell you - it was no fun.