This paper presents our latest work on assisting AMS (application management service) clients or accounts to generate effective cross-skill training plans. Specifically, we aim to answer the following two questions: 'Whom to train?' and 'What to train?', both of which are very critical to training plan generation. To achieve this goal, we first analyze a given account's service request data and identify a set of candidate categories (which indicate skills) for each account consultant to be trained upon, then we measure the following three important metrics: the importance of each such category, consultant's resource utilization, and the temporal correlation between such category and the categories that the consultant can already handle. Finally, we present all measurements to the account team allowing it to generate very flexible cross-skill training plans based on various goals. So far, we have applied this tool to a couple of real AMS accounts, and have received some initial yet encouraging feedback.