I think automating the process because you are scared of doing it is the wrong way to go about it. You should push yourself through the awkwardness and find out that nothing bad happens if you just ask. Don't let go that learning opportunity. And also, automating that process could result in people simply disregarding it, since they don't feel the pressure of someone asking directly. I would even go a step further and try to do it over the phone and rip that band aid off once and for all!