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This supplement is to accompany the case. These vignettes are based on a fictional organization, Starling Systems, in which Jack Swain, Starling’s COO, has been selected by the company’s board of directors to replace the recently departed CEO. Jack must deal with four challenging situations in his early days as CEO. The first involves managing a difficult conversation with Robert Cortez, Starling’s senior vice president of finance, who was also vying for the CEO position. Jack cannot use title or compensation to convince Cortez not to leave so must somehow come up with alternate reasons to compel this valuable management team member to stay. The second vignette deals with Jack’s revelation based on a conversation with Starling’s recently department director of business development that the company’s vice president of sales may be mistreating his employees. The third vignette finds Jack in a sticky situation where he has offered the COO position to an outside candidate, and he now must explain to his vice president of operations, currently serving as interim COO, why she was not offered the position. Finally, Jack must deal with infighting between his top performing customer service representative and his newly-hired vice president of customer service. This supplement is part of the Stanford Graduate School of Business free case collection (visit www.thecasecentre.org/stanfordfreecases for more information on the collection).