My solution involves a user configurable "tree" of questions/answers. The user (your manager/whatever) clicks through the tree until he reaches the end. This interface is shown (with your provided scenario) in the first three screenshots. For case 2b, the options to have a notes interface, which stores data in the server, is made available to be enabled for each question. The list of questions/answers is stored in a file and completely configurable by you, with an admin interface (shown in the fourth screenshot) allowing you to easily set up your own management flow. The ability to take notes can be turned on and off per question with a checkbox. Since configuration is based on a user-specified file, you can easily swap different sets of questions/answers in and out to suit different use cases.