When you look at this cup and read its label, you simply see what has been printed and what it may mean; however, this layout can allow for open interpretation simply due to its design execution. The text could be viewed as “Leadership for Learning Awards” but what does it enforce with confidence its real meaning? Will you understand that this is an award for Leadership for Learning with 100% confidence? What would happen to its meaning based on subtle emphasis?
Consider this: maybe the recognition means that there is leadership to create or emphasize for more learning awards; or that there is leadership to give learning awards. Sure you may argue that there is the best meaning for this phrase and the previous two are incorrect simply based on common practice within the known audience, but should you ensure the certainty for all by design? Why not create a clear message with a considered care and responsibility for that message?
Say that this recognition is an award for people with the leadership for learning. To help clarify that message, style the word “Awards” so it has a distinguishing visual identity. Think of the Gestalt principles. They are basic explanations of how we view and organize that information to evaluate and assess it in a quick manner. There are several common principles; one author identified 15. In any case, the basic principles such as
Similarity
Proximity
Good Form
and maybe even Common Region
would indicate how we see and read this information on the cup.
Maybe with a little design work, we can group the words to title the award for recognizing Leadership for Learning instead of creating a layout that could be some Learning Awards pushed with a momentum by a leader. To organize this understanding, we style the words to make groups. There are a multitude of arrangements; here are four that I thought could clarify the meaning.
(1) Initial caps for the award title over a wide-spread style for the word. 
(2) All caps footed on a foundation.
(3) A small variation of #1. 
(4) All caps for all words, but setting the relationship by size.
Design when used effectively provides clear communication but beyond that a sense of style that presents a polished experience backed by care and pride for the production of this message.