This article describes proposed content of an online toolkit for users of the work system modeling method (WSMM), an extension of the work system method (WSM), which was developed to help business professionals understand IT-reliant systems and collaborate with IT professionals. A summary of work system theory (WST) and WSM provides a background. A two-dimensional design space for modeling methods illustrates WSMM's context. Two limitations of WSMM imply the need for a toolkit that overcomes those limitations. An auto rental example is used to illustrate a series of modeling, analysis, and design modules related to different stakeholder purposes. Most of the modules reflect components of Word documents used as outlines to produce over 700 management briefings, mostly by MBA and Executive MBA students, between 2003 and 2017. A concluding section summarizes the main ideas, explains how the use of different modules based on the work system metaphor flexibly supports systems analysis and design, and identifies challenges for future research.

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