Speaking Truth to Power: Reflections on My Career at Microsoft
Former Microsoft engineer James Whittaker talks about how CEO Satya Nadella can fix the deeply flawed company
The only easy answer to the question “what was it like working at Microsoft?” is “Which one?” My on-again, off-again Microsoft career spanned three different versions of the company, each deeply inspirational and tragically flawed in its own unique way. As it once again struggles to reinvent itself, the Microsoft of the future is being weighed down by the ghosts of its past.
The Microsoft of the ’90s, with Bill Gates calling the shots, was a technology-forward company, fast-paced, ambitious, and unapologetically capitalistic. It was a beast, number one in nearly every genre that mattered, dreaded by its partners, feared by its competitors, and alternately loved and hated by its users. Raw ambition and single-minded drive for dominance pervaded the company, from senior leaders on down to individual contributors. Working for Microsoft during the ’90s was an intellectual rush, wrapped in the opulence of runaway personal wealth. Microsoft was the shit and they knew it.
The Microsoft of the 2000s, under Steve Ballmer, was almost exactly the opposite. Bruised and battered by the consent decree handed down by the Department of Justice for the very same ambition that brought it to dominance, Ballmer’s Microsoft was sales-forward and cautious. It was either gazing at its own Windows-shaped navel or nervously clutching its pearls at the approach of Google in its rearview mirror. This inattention to anything resembling the imaginative or innovative caused it to hemorrhage talent, flatline its stock, bore its customers, and miss (or at least be very late to) the next three technology megatrends — web, cloud, and mobile — on the trot. It was an era of hand-wringing and coming to grips with a profitable but uninspired slide into irrelevance.
The good aspects of working for Microsoft are very good, making repping the brand pretty easy.