Computer-implemented functionality is described herein for assisting a user in interacting with an environment. In one implementation, the functionality operates by: determining that a particular user is within a prescribed proximity to an electronic sign, or will be in prescribed proximity to the electronic sign, based on sensor information provided by one or more sensors within the environment; determining an identity of the user; determining at least one destination of the user based at least on calendar information; providing directions to the destination(s), to provide unfiltered direction information; optionally filtering the unfiltered direction information with respect to restriction information (e.g., privacy information, security information, etc.), to produce filtered direction information; composing sign information based on the filtered direction information; and sending the sign information to the electronic sign for presentation by the sign.