A computer-implemented method of personalizing a conversation assistance audio device, the method comprising: presenting a user of the conversation assistance audio device with a set of simulated audio environments played back at the conversation assistance audio device, the set of simulated audio environments comprising at least two simulated audio environments, wherein each simulated audio environment in the set of simulated audio environments comprises audio playback at a substantially identical background noise level and at a signal-to-noise range between -5 dB and 20 dB; receiving feedback from the user about each simulated audio environment in the set of simulated audio environments; adjusting at least one audio setting at the conversation assistance audio device based upon the feedback from the user and known audio characteristics of the set of simulated audio environments and the conversation assistance audio device, wherein adjusting the at least one audio setting comprises selecting the best-fit audio setting for the conversation assistance audio device based upon the feedback received from the user, once feedback is received across a threshold number of settings at distinct sound pressure levels; providing an interface for receiving the feedback from the user, wherein the interface comprises at least one actuatable mechanism for adjusting the at least one audio setting on the conversation assistance audio device, and wherein the interface is located on the conversation assistance audio device or a computing device connected with the conversation assistance audio device; wherein the at least one actuatable mechanism comprises a volume adjustor; wherein the at least one audio setting on the conversation assistance audio device is adjusted in response to the user modifying the at least one actuatable mechanism on the interface; the method further comprising scaling the adjustment to the at least one audio setting on the conversation assistance audio device based upon a scaling factor; wherein the scaling factor comprises an inference between audio characteristics of each of the simulated audio environments in the set of simulated audio environments and a model of real-world audio characteristics. presenting a user of the conversation assistance audio device with a set of simulated audio environments played back at the conversation assistance audio device, the set of simulated audio environments comprising at least two simulated audio environments, wherein each simulated audio environment in the set of simulated audio environments comprises audio playback at a substantially identical background noise level and at a signal-to-noise range between -5 dB and 20 dB; receiving feedback from the user about each simulated audio environment in the set of simulated audio environments; adjusting at least one audio setting at the conversation assistance audio device based upon the feedback from the user and known audio characteristics of the set of simulated audio environments and the conversation assistance audio device, wherein adjusting the at least one audio setting comprises selecting the best-fit audio setting for the conversation assistance audio device based upon the feedback received from the user, once feedback is received across a threshold number of settings at distinct sound pressure levels; providing an interface for receiving the feedback from the user, wherein the interface comprises at least one actuatable mechanism for adjusting the at least one audio setting on the conversation assistance audio device, and wherein the interface is located on the conversation assistance audio device or a computing device connected with the conversation assistance audio device; wherein the at least one actuatable mechanism comprises a volume adjustor; wherein the at least one audio setting on the conversation assistance audio device is adjusted in response to the user modifying the at least one actuatable mechanism on the interface; the method further comprising scaling the adjustment to the at least one audio setting on the conversation assistance audio device based upon a scaling factor; wherein the scaling factor comprises an inference between audio characteristics of each of the simulated audio environments in the set of simulated audio environments and a model of real-world audio characteristics.