A keyboard interface enables the efficient selection of one or more data items from a set of data items. The appearance of the keyboard interface can be dynamically generated and updated based on characteristics of the data items in the set. When a user selects a user interface element associated with a set of data items, the data items in the set can be evaluated to determine a number of keys to include in the keyboard interface as well as which characters are assigned to each included key. The number of keys and which characters are assigned to these keys can be determined by identifying a first character in each of the data items in the set. When the user selects a key, the keyboard interface can be updated in a similar manner but based on characters at a subsequent position in data items that matched the previously selected key.