No need to apologize! Diverging paths often make up part of a good conversation.
I'll admit that I still often struggle to evoke wonder in the classes I teach (with ages ranging from 13-18). Often it is the questions I ask, and sometimes, even with a good question, it is a failure to set up the context in which the question will flourish.
Speaking of good questions, that's one! Assessment is one of those words that means so many different things, and the meanings are not all equal, or all good. I'll elaborate below, but my short answer is that most activities need a form of assessment, but the form must match the purpose of the activity.
I am reminded of an anecdote from David I. Smith's lecture on Teaching and Christian Practices, where he talks about his son's theology assessment. The unit was something like the ten most important theological words in the New Testament. David was asking his son questions like, "What does Justification mean? How is it different from Sanctification?" and his son, after growing frustrated, exclaimed, "but we don't have to know it that deeply, we just need to be able to match them" (or something to that effect). A matching list for an assessment obviously retards wonder or contemplation by its very nature--Smith even showed how you could change the font to Wingdings, memorize the patterns, and still score perfectly on a matching assessment.
Assessment like that certainly impedes wonder. On the other hand, I think that a certain kind of assessment gets naturally evoked from the right line of questioning. In the same lecture, Smith talks about a lecture he used to give to his German language classes about German culture. If I recall correctly, what caused him to formulate the lecture was his frustration with German language textbooks, which used phrases and situations that were mainly consumerist and tourist in nature. They did not invite the students to understand the German people through their language, and thereby have a chance to love their neighbor in any particular way. So he had the students come into class silently, with some quiet music playing (I think) and, in a darkened room, spend a few minutes looking at a picture of several people projected on the board. He then began to ask them questions about what they saw. When they would get hasty, he would slow them down and cause them to think again. By having them attend carefully to the picture, he allowed their curiosity to build so that they became naturally interested in what was going on, who the people were, and so on. He then told them something about the people, who turned out to be German students who had formed a resistance against the Nazi party in Germany during WWII.
I think that sort of lecture invites self-reflection (a kind of assessment) that can then be returned to in a more formal way (a reflection paper, a journal entry, a research project, etc.) that goes deeper into that original experience of reflection and can be assessed both in terms of the skill (writing, research, etc.) and the virtue (growth in perspective/charity toward others).