A computerized personal assistant, comprising: a natural language user interface, NLUI, including a microphone and a speaker; a skill discovery machine configured to communicatively couple to a computer database including a plurality of available skills for the computerized personal assistant, wherein the computer database defines, for a candidate skill: an assistive action defined by instructions executable by the computerized personal assistant to perform an operation to assist a user, wherein the assistive action comprises: gathering and outputting information and/or multimedia content; recording information for later retrieval; communicating with at least one other user; controlling electrical and/or mechanical appliances; or interacting with a cooperating computer service or device; a reference context previously associated with the assistive action; and a complementary help action previously associated with the assistive action, wherein the complementary help action is defined by instructions executable by the computerized personal assistant to output a predefined response to educate the user about the assistive action; and wherein the computerized personal assistant is configured to: recognize a current context of the user; operate a previously-trained machine learning classifier to assess a match confidence for the candidate skill, the match confidence indicating a quality of match between the current context and the reference context, including assessing a higher match confidence for the candidate skill based on the candidate skill having a relatively lower utilization frequency by the user, compared to other available skills of the plurality of available skills; execute the instructions defining the assistive action responsive to the match confidence exceeding a predefined match confidence threshold; and execute the instructions defining the complementary help action responsive to the match confidence not exceeding the predefined match confidence threshold. a natural language user interface, NLUI, including a microphone and a speaker; a skill discovery machine configured to communicatively couple to a computer database including a plurality of available skills for the computerized personal assistant, wherein the computer database defines, for a candidate skill: an assistive action defined by instructions executable by the computerized personal assistant to perform an operation to assist a user, wherein the assistive action comprises: gathering and outputting information and/or multimedia content; recording information for later retrieval; communicating with at least one other user; controlling electrical and/or mechanical appliances; or interacting with a cooperating computer service or device; a reference context previously associated with the assistive action; and a complementary help action previously associated with the assistive action, wherein the complementary help action is defined by instructions executable by the computerized personal assistant to output a predefined response to educate the user about the assistive action; and an assistive action defined by instructions executable by the computerized personal assistant to perform an operation to assist a user, wherein the assistive action comprises: gathering and outputting information and/or multimedia content; recording information for later retrieval; communicating with at least one other user; controlling electrical and/or mechanical appliances; or interacting with a cooperating computer service or device; a reference context previously associated with the assistive action; and a complementary help action previously associated with the assistive action, wherein the complementary help action is defined by instructions executable by the computerized personal assistant to output a predefined response to educate the user about the assistive action; and wherein the computerized personal assistant is configured to: recognize a current context of the user; operate a previously-trained machine learning classifier to assess a match confidence for the candidate skill, the match confidence indicating a quality of match between the current context and the reference context, including assessing a higher match confidence for the candidate skill based on the candidate skill having a relatively lower utilization frequency by the user, compared to other available skills of the plurality of available skills; execute the instructions defining the assistive action responsive to the match confidence exceeding a predefined match confidence threshold; and execute the instructions defining the complementary help action responsive to the match confidence not exceeding the predefined match confidence threshold. recognize a current context of the user; operate a previously-trained machine learning classifier to assess a match confidence for the candidate skill, the match confidence indicating a quality of match between the current context and the reference context, including assessing a higher match confidence for the candidate skill based on the candidate skill having a relatively lower utilization frequency by the user, compared to other available skills of the plurality of available skills; execute the instructions defining the assistive action responsive to the match confidence exceeding a predefined match confidence threshold; and execute the instructions defining the complementary help action responsive to the match confidence not exceeding the predefined match confidence threshold.