At the end of the day, both Apple and Microsoft have given up advantages to each other.
Despite offering a range of enterprise capabilities for some time, Apple didn't make a significant push for the enterprise market until recently. Most people see Apple's partnership with IBM as the first major public commitment to iOS as an enterprise platform. Likewise, Apple delayed its entry into the larger tablet or two-in-one device market - a.k.a. the types of tablets that can replace laptops -- long after Microsoft and other companies had launched products.
In contrast, Microsoft moved forward aggressively with business-oriented tablets with Windows 8 and the early Surface models. Those moves included a few missteps, including the ARM-powered devices that weren't capable of running legacy apps.
Although Microsoft moved pretty quickly in that area, it trailed Apple significantly in embracing the mobile arena as a whole. Windows Phone was a radical departure from the earlier Windows Mobile, it initially shipped without major enterprise features, and it has not surprisingly struggled to gain market share. This allowed the iPhone to dominate the enterprise smartphone market and provided a halo effect and toe hold for other Apple products, including the iPad, in business.
Whether the iPad Pro manages to be a hit with business users, either in general or in specific fields like design, remains to be seen. It does seem likely, however, that if Apple had targeted this market a couple of years earlier, it could have had a better shot at edging out some of the competition from Microsoft.
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