I have ADD and I thought it would be useful to point out that there is a difference between ADD and ADHD. Not everyone is diagnosed with hyperactive disorder in addition to attention deficit. From my readings, many adults do not know and are never diagnosed with ADD/ADHD. It's still one of those things that people haven't accepted, just like giving ritalin to many kids. IMO, it's probably over diagnosed in children and under diagnosed in adults. I am not a doctor though.
As for meds, I take Ritalin SR. I took Concerta for about a year and eventually it started to do nothing for me. Even upping the dosage helped none. I'm on a lower dose of Ritalin SR and it works a lot better. I still have issues with motivation, but I think those are less related to ADD then to just not wanting to start something. Ain't apathy great? :-) There is a definite difference when I don't take meds. Lack of concentration, lose focus easily, etc. Any little noise or motion caught by my eye will distract me.
One thing I haven't seen mentioned is that there is a symptom called hyperfocus. So, not only can one with ADD become distracted by things, but the same person can also become extremely focused on one thing, and no minor thing will distract that person. At work, the whole distraction thing can keep me from getting something done, but once I get so focused on something that nothing distracts me, I can go hours. So there are definitely pros and cons to it.
As for telling your boss, I say try and judge how he/she will react to it. I've told mine as well as my very close coworkers and friends. Whether they believe it's a true disorder or not aside, they know and some have told me when they see improvements or vice versa. If your boss is open to these kinds of things, then I would tell him. May make things easier and he may point things out along the way.
As for your parents and siblings, they can react different ways. My mom is a teacher and actually set me up with a psychologist who comes to her school for the testing and diagnosis. She kept telling me to look into it for about two years. My sister, dad and step-mother all feel the opposite. That I don't have ADD, that I don't need meds, etc. They don't see the difference that occurs when I take the meds. So no matter who you tell, there will be people who are on both sides of the fence.
Lastly I'll close with this... I've found that alcohol has the "same" effect that the Ritalin has. It seems the Ritalin will speed up the slow parts of the brain, where as the alcohol will slow down the fast parts of the brain. Just a personal observation.
Good luck with the diagnosis. One good thing out of it is that you can tell people you take stimulants that are derivatives of speed or other narcotics. Just something I like to joke about. Oh, and my doctor has no red tape, that I know of, to deal with. I just have to pick up a new prescription each month. Oh, and don't take it on weekends if you don't need it. Your body will become accustomed to it and won't have the same effects. (How's that for a bunch of random thoughts?)
-Chris