I spent a weekend recently with my Grandma Betty (my mother's mother) in Columbus, Ohio. Betty has had a computer since her 80th birthday (we bought her a blue and silver Macintosh G3 if memory serves) and her grandchildren have kept her up to date with newer models (and moved her to PCs), wireless networks and color printers.
She is not the world's most sophisticated Internet user, but I learned a lot from watching her use her computer. She opened an email from an old friend asking for a donation to a charitable cause. She read it and told me she was willing to give them money but she didn't know how to do it. Why not? Because the person didn't make it easy for her. No link for a one-click contribution. Lucky for him, she cared enough to ask me to figure it out for her.
Whenever possible, make things one click. To make an appointment. Give a clickable phone number at the top of every page of your website so it works easily on a cell phone.
Think about everything you do from the perspective of the USER. Make it simple. Don't send someone a Google doc. You are assuming they have a Google account and know how to go and fetch it. Not a good assumption.
When you send someone a document (like a contract) make sure you give it a name that will make sense to the recipient. Don't send me something called "Deborah document." I won't have any idea it's from you. Call it "XYZ Co Contract for Deborah 8.1.13." Or something else that makes sense once I receive it.
Keep the Grandma Betty Rule in mind and you'll always find the simplest and most straightforward presentation of your information.
Oh---and she'd kill me for publishing that picture of her without showing you how beautiful she really is, so here's another photo of my wonderful Grandma. Hope I age as well as she has!