Have a checkbox in a Potential that, when checked, sends an e-mail?

We want to create a Potential by hand, and then once we find out the needs of our customer, send them an e-mail with questions that they need to fill out.  Sometimes those questions will be ABC, sometimes, XYZ.  So we would want to automate the sending of those e-mails from the Potential as much as possible.

Could this be done with Creator, Automation, Workflows...anything that can reach into the Potential itself?

Thanks!