Ken and I are running around stressed trying to get ready to go to France. I walked into Ken's office today to see him typing on his precariously balanced laptop, intently concentrating with his tongue sticking out of the corner of his mouth. What was he doing? Copying bookmarks to the laptop. How? By hand, by retyping every URL.
Ken's a smart guy and a professional software engineer. But he's not a Windows hacker. So when he needs to do something odd on the Windows box he patiently does what he knows will work. In this case, retyping 100 URLs.
After showing him where the Favorites folder was and how to mail himself a zip file, we pondered what had gone wrong. It's simple, really. Other than asking someone how would you ever figure out how to do something weird like copy bookmarks from one computer to another?
We can solve this specific problem with a tool like Google Browser Sync. But in general how do we make software obvious to use, both for its intended purpose and for the weird little things you need to do once a year?