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

James Whittaker


An image of the Microsoft logo.
Photo: SOPA Image/Getty Images

TThe 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.

Photo courtesy of the author.

The good aspects of working for Microsoft are very good, making repping the brand pretty easy.

This brings us to the present epoch under Satya Nadella who, against the odds, has revived the company’s mojo and returned it to prominence. He has accomplished this by abandoning the strategies of both his forebears. Microsoft is no longer a technology-forward or a sales-forward company. Nadella has embarked on a culture-forward vision, which presents some serious historical hurdles to clear. Namely: how does a company move toward a new version of itself when its ranks are replete with people who made their fame and fortune under the previous versions?

Nadella’s expectations have been made clear to everyone. Mandatory training has seen to that. He exhorts Microsoft to be a “learn it all” culture instead of a “know it all” culture. He warns Microsoft away from its “fixed mindset” and has hired a revolving door of consultants and evangelists (including a three-year stint as cultural attaché by yours truly) to help transition the company into a “growth mindset.”

Draw any Microsoftie into a discussion about terrible managers and you better hope you have some time on your hands.

It’s the right fight, as he should know. His long tenure at the company provided him with a front-row seat to the repercussions of Gates’ and Ballmer’s management styles. He witnessed the adolescence and maturity of the culture he is now so keen to end. Imagine watching a beloved child grow into someone you privately deplore, and you are partway to understanding his situation.

Nadella’s public fight against the old Microsoft is tacit recognition of the long shadows that both Gates and Ballmer cast. Each exited the company, but their legacies linger. Nadella contorts all he can to make this exact case without naming names, but this misses the point and delays the cure. When he implicates the know-it-alls, we all know who he is talking about. When our fixed mindset gets called out, we can all trace it to its source.

It’s hard to move past a shameful era with its icons providing cover for its continued practice.

Truth is, Gates and Ballmer are creatures of an era that few, most especially their successor, want to see return. Both were consummate know-it-alls, convinced that no subject, no matter how subtle, was a match for their intellect. No expert’s analysis was ever more prescient than their own. No competitor could possibly match the insights of their superior strategic minds. They specialized in snap decisions and dominating their subordinates. But chalking up the shouting, on-the-spot firings, and alleged chair-throwing as simply “leader’s passion” misses a greater point: They perpetuated their toxic behavior by surrounding themselves almost exclusively with leaders who emulated that behavior. Together, they created a management monoculture of cocksure masculinity that ensured every manager looked the same, sounded the same, and acted the same. This culture persists. Draw any Microsoftie into a discussion about terrible managers and you better hope you have some time on your hands.

Fast forward to today and the culpables still cannot be named. We dance around the sins of the past while keeping our heroes above the fray. Nadella’s internal culture-talks conjure images of a southern mayor disavowing racism while standing in the shade cast by a statue of Robert E. Lee. It’s hard to move past a shameful era with its icons providing cover for its continued practice.

Treating the culpables as untouchable sends a message to the current offenders that these behaviors are in bounds, and those who practice them suffer no lingering effects. It does nothing to stop the fiscal regularity of company-wide memos condemning ongoing sexism, racism, and bullying. It does nothing to stop the revolving door of the majority of new college hires leaving the moment their signing bonuses become permanent. It does nothing to stop the cycle of sucking up to those in power in an effort to gain power for oneself.

People who thrived under Microsoft’s toxic management style still hold power in discouragingly large numbers, and find plenty of hiding places in the shadow cast by Gates (Ballmer has shown the good sense to properly and fully abscond, indeed, his abdication was likely his single most valuable contribution to the company’s future). Those made-men (because they are exclusively of that gender) have each other’s backs. A know-it-all manager moves to a new product group and his know-it-all team follows him. A newcomer exposes a fixed-mindset executive and that executive’s fixed-mindset henchmen all rise to support him. Their herd immunity protects them from any serious attempts to change them. Emulating Gates and Ballmer made them wealthy and powerful and it’s going to take more than hallway culture posters, some online training, and the odd cheerleading hashtag like #MicrosoftLife to change that. It’s going to require a zero-tolerance policy on cultural malfeasance... past and present.

The people who have the most to gain from Nadella’s attempts at changing Microsoft’s culture aren’t just the newbies and youngsters. Microsoft has diversity at every level of the experience spectrum, thanks to a laudable legacy of welcoming every class of minority along with hoards of misfits and dreamers. This diversity is part of what made Microsoft such an enjoyable place to work.

However, welcoming diversity is mostly where it stops. All those square pegs are still trying to force their way into Microsoft’s round-hole management culture. The diverse class is persisting more than they are succeeding. Bill’s former favorites, still firmly entrenched under cover of his shadow, are seeing to that. When challenged, they simply invoke his name as a protective incantation, and, since Gates’ culpability remains unacknowledged, their spell succeeds.

This is a shame because when Microsoft does manage to break the made-man oligarchy, the result is often magic. Despite being behind in every single technology vertical that matters (and so far behind in some, like mobile and personal agents, that they threw in the towel), Microsoft is killing it. Revenue is up. Stock is up. Industry stature is up. The places where Microsoft finds itself thriving all have one thing in common: key made-men were pushed aside for better people.

This is the problem with the act-like-me, talk-like-me, think-like-me leadership monoculture: it doesn’t promote the best talent; it promotes the talent that most closely resembles those already in power. When those in power are swept aside in favor of candidates more in-line with Nadella’s new cultural vision, success quickly follows.

Take Amy Hood’s ascendency to become Microsoft’s CFO. No one knew her name. She wasn’t part of any known power circle or usual-suspects list. The decision was widely questioned via whisper campaigns inside the company. Those whispers have stopped. Indeed, few can recall the name of the made-man she replaced, and Hood is now regarded to be among the best CFOs in tech. She is the kind of atypical bet on talent, and talent alone, that moves the cultural needle.

It happened again with the transformation of the sales team. Ballmer’s man Kevin Turner was a chip off the old block. When he and Ballmer appeared together, it was difficult to tell where one of them stopped and the other started. Like Ballmer, Turner was an icon inside the company. Despite Microsoft’s innovation stagnation of the ’00s and early ’10s, his numbers always impressed. People inside the company joked he could sell dry air in the desert. The sales org kept printing money, quarter after quarter, year after year, despite having almost nothing exciting to sell. Insiders were convinced he was irreplaceable.

Leaders should reflect the ideals and values of those below them rather than those above them. Promoting those leaders is the fastest way to fix a company’s broken culture.

Those insiders were wrong. When Turner left, a renaissance occurred. New voices appeared. New ideas were finally listened to. New energy was created. The realization that it was Turner who was holding the sales org back took everyone by surprise. His aura wasn’t real, it was merely a reflection of Ballmer’s halo. There were better people, much better people, who were as good at what they do as Hood is at what she does. None of them would be doing it without the made-man cycle being broken.

But the biggest power transfer was created in the cloud group, currently the vanguard of Microsoft’s profit-and-shareholder-value brigade. Nadella himself ran this group and under his leadership, it was doing... ok, hitting its targets but dazzling no one. When he ascended to the CEO spot, junior, more qualified, and very unexpected people leapfrogged more likely candidates to replace him. The new bosses were people who wielded their picks, not during the Gates gold rush, but during the lean Ballmer years and still managed to occasionally strike gold. They labored when success was not a guarantee, so they never assumed it. What happened? They made Microsoft’s future. Nadella is a better CEO for having placed bets on them.

Changes at the top — not speeches, training or hashtags — make the most cultural impact. If you want real and lasting cultural change, sweep away the made-men who succeeded under the previous culture and promote the people who look, act, and think more like their employees than their managers.

This is a key point: Leaders should reflect the ideals and values of those below them rather than those above them. Promoting those leaders is the fastest way to fix a company’s broken culture.

My former skip-level manager, Qi Lu, another widely-regarded “magician,” who left Bing, thereby creating the circumstances for it to thrive, provides a case in point. Great ideas (and there were many) that bubbled up from the employees below him went nowhere. But the ineffective strategy passed down from above quickly became unquestioned law. Lu was a creature of his bosses and peers, not of his team. When the canopy of his fixed mindset was removed, new ideas found sunlight in which to grow. Alas that it was too late for Bing! The world would be a better place had someone given Google a proper run for its money. Instead, Microsoft’s made-men did little more than ensure Google’s monopoly.

Microsoft clearly understands it has a problem. If it didn’t, it wouldn’t be fighting such a public fight to reinvent itself.

It’s worth noting that cultural transformation didn’t happen in places, like Windows, where Nadella simply rearranged the made-men deck chairs. Instead of following his culture-change playbook, he simply swapped Windows’ made-men with Windows Phone’s made-men. The same people unable, over the course of a decade, to craft a winning strategy for mobile were suddenly tasked with crafting a winning strategy for the desktop. The unsurprising result is that Windows continues its tradition of boring, buggy software, and consistently fumbled updates. Made-men aren’t fixable, and the real talent in Windows, and the diversity of ideas it possesses, remains anonymously buried under layers of made-men above it.

If Windows was the only refuge for recycled failures — the wannabe leaders who energetically and emphatically backed Gates’ and Ballmer’s strategy that whiffed on the web, cloud, and mobile — Microsoft might be ok. But the residue of the past is thick in enough places that it is suffocating the culture of tomorrow.

Microsoft clearly understands it has a problem. If it didn’t, it wouldn’t be fighting such a public fight to reinvent itself. My message is simple: You can’t leave an outdated culture behind while continuing to worship its icons. The symbolic memorials of the people who got you into this cultural mess are an obstacle to getting you out of it. Like those statues of Robert E. Lee, their continued presence is homage to what made-men consider as better days.

The destruction of the leadership monocultures of Turner, Lu, Nadella, and whoever the hell that CFO was, demonstrates that the best people at Microsoft are the ones whose names no one knows and whose values reflect the future and not the past.

The future trajectory of Microsoft depends, in large part, on Nadella’s actual commitment to his publicly professed desire to create a more diverse and humble company. One can make a case, citing the examples above, that Microsoft is making progress. But my former female colleagues who reviewed this document in advance of its publication are unconvinced. None of them report feeling emboldened by the new Microsoft. They continue to withhold reports of discriminatory management practices. They relate stories of reports of abuse going unpunished and continue to fear reprisals for speaking out. In fact, multiple reviewers noted, independently, the irony that the only reason I am comfortable enough to speak out is that I am a “50-year-old white dude” and, thus, girded against reprisal from the body politic. So they remain silent when, in fact, they are among the voices Microsoft needs to hear the most. Apparently, Microsoft has dipped only a single toe in the river that flows to the future.

It’s time for a vigorous swim and the entire world should be encouraging Microsoft to take the plunge. At its core, Microsoft is a company that makes its money the old fashioned way: by creating products of value that people willingly part with their money to use. They stand as a bulwark against the data mongering and user exploitation that Google and Facebook see as the future of humanity.

The entire world has a stake in Nadella’s fledgling culture-forward strategy prevailing over the 40-year momentum of the made-men standing squarely in its way.

C’mon Microsoft. The world needs you.



James Whittaker

xFBI, xGOOG, xMSFT, speaker, writer, career guru. Chaotic good.