I need to teach my supervisor about web development/design. Something that covers best practices, what is front-end development, the different technologies involved, theory, etc. Something easy and quick to read. I think i may hand it to her and tell her I really enjoyed it and hope she finds it useful. Something that won’t make me come off as an *******. Can anyone recommend anything?
I’ve been around for a while; I was a student for many years (and found myself in the same situation as you, with a hopeless teacher), and I was even a teacher myself for 10 years. My advice: get a new supervisor. 
At best, you’ll be waiting a long time for the teacher to get up to speed. At worst (much more likely) ego will get in the way, and you’ll be penalized for insubordination (whether overtly or by subterfuge).
Sigh. Well, I hope those aren’t the only options. It’s certainly frustrating because I’m not a wiz-kid in the field but I know I should lead the web development initiatives in my workplace. My supervisor simply isn’t greatly involved in the field. Perhaps you’re right. I’ll keep that in mind.
Ah, when you said ‘supervisor’, I immediately thought ‘college supervisor’ or something similar. In the workplace, perhaps you have more options. Just have a sit down with the supervisor and start to speak about web standards and how important they are. If she shows interest, refer her to some good articles on the subject. But really, if you show you are on top of all this, it might increase your value to the business, and you can train them to rely on you to handle this sort of thing. I’ve found that, over time, a few people I’ve worked with have ended up letting go of their out-dated ideas and realizing that they should just let someone else handle web-related things.
I agree, encourage your supervisor to use you as an on site knowledgeable person. build your own website the right way is a good one. I still remember the first time someone used the example of a computer being like a desk. a harddrive is like a file cabinet, its where all your files and folders are. examples like this will keep items understandable. It takes time to stay up and compare the different options, which is where you can help out. Be the go to person, include them but include them with the right kind of examples. When you start talking about front-end and technology you are getting into some more technical information. LOL just a few months ago was trying to explain difference between domain name and hosting to a person. (street address vs building helped).
I will continue trying to explain to my supervisor that I’m knowledgable. Unfortunately I think she’s ignorant to the point that she doesn’t understand or know the scope of my knowledge and I haven’t necessarily known hers either.
So can anyone recommend any books? At least something covering web design best practices?
Without talking with her its hard to recommend a where to start book. The most helpful I have found are the dummies or idiots series. When I share this story people will do a well if she did it and it worked, maybe I will try it. Back when I really started into computers a friend loaned me this Excel book, had to be 3" thick. Barely made it thru chapter 1 and lost it. So picked up a dummies book, it gave me the base terminology. So when I went back to that thick book, was able to understand the whole book. It is all about terminology and those books do a good job of teaching the terminology on a subject.
Sometimes its good to ask a different question. Would it maybe work to set her up with a web consultant or web firm? Businesses bring in outside experts all the time and do as they say. You would look for a firm willing to include you, more a we offer text website updates for this amount, but I think you have someone on staff that can do it more cost affordable. Then as you are included she may rely more on you. Do remember the firm will need to be paid for their time. So don’t expect them to pass all work back to you.
My recommendation will be WordPress because it is easy to install, easy to use and best of all it is free! It comes with themes you can choose from and customize. When your supervisor gets more experience it will be easy to design the website from scratch. Just search for “WordPress website tutorial” in Google.