For my first iteration I came up with a few areas that might be appropriate points for the persona to interact with learners and created a set of icons using our brand shape language.

We really liked the idea of having this feature be an ever-present part of the platform that learners could chat with if they had a question or would prompt learners where they needed nudges. Because the feature would be overlayed on all types of content it needed an icon set that wouldn't blend in with the rest of our brand, so I tried using a 3-tone gradient which would be sure to stand out.

We defined different alerts and message types this feature might need to represent, such as a reminder or encouragement. Using only our shape language it became difficult to represent all of these ideas so I also tried iterations using shapes and lines, which turned out to be a lot easier to understand visually.

After all of these icon explorations we felt the fully personified smiley icons were the most successful for a few reasons. They helped connect the user with the emotion of the message and as a series created the feeling of a mentor or peer helping you out through your course.