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Job shadowing was a career exploration activity for students. It was relevant at different phases of career development, namely school level, to look at new career options and to explore opportunities within a selected career. Shadowing provided awareness about the daily routine and nuances of a selected career by associating with a professional. It facilitated synchronisation with an organisation's work culture and provided on the job experience. Shadowing provided opportunities to develop relationships with professional workers and to gain information on available options without any liability or obligation. Similarly, reverse shadowing had been traditionally utilised in various company operations. Business families had adopted this approach to gather knowledge as well as insight into different fundamental business aspects. In reverse shadowing, a person from managerial/leadership level gained information from a key junior staff member about critical business processes. CEOs that invariably focused on macro issues could use reverse shadowing to also have a micro view of their business. This facilitated innovation, decision-making and direct access to how things worked at the front end. Would the strategy of shadowing at workplace be able to chisel business success?