Unusual Suspects: Microsoft’s Brad Smith on Making the Rare Leap from GC to President

In 2015, Brad Smith joined an exclusive club, becoming one of only a few General Counsels to be appointed as President of a multi-billion-dollar company. We look at how his legal background is helping Microsoft navigate a world that’s spinning faster than ever before.

In the complicated world of corporate leadership, the journey from General Counsel (GC) to CEO has often remained elusive. Our research shows that just 5% of GCs believe their role offers a clear path to becoming CEO. It’s perhaps one reason why so few even aspire to take the helm: Less than 5% of GCs told us that they hoped to become CEO, compared to 62% of Chief Operating Officers.

Yet, as those who have made the leap demonstrate, a GC background brings significant benefits—particularly as the world begins to spin faster than ever before and business issues become increasingly tangled. One pioneer in this space is Brad Smith, a former GC and Microsoft’s President and Vice Chair.

Every year I've had a different job… and if there's a thread that runs throughout the 30 years… it has been trying to help Microsoft and others, including our customers, navigate through this ever-changing landscape.”

I am happy I have a law degree, and there are days when I actually use it. But mostly I'm dealing with a much broader swath of questions. That continual broadening of different intellectual disciplines and functions…defines the role I play at Microsoft today, but also what is needed in the world of business… [as we try] to deal with the complexity of the world in which we live.”

Brad Smith
Former GC and Microsoft’s President and Vice Chair

Brad began his in-house career with Microsoft in 1993, having previously been a partner at the law firm of Covington and Burling (where he is reportedly still remembered as one of the firm’s first attorneys to insist on having a personal computer on his desk).

He first headed up the tech giant’s European legal and corporate affairs team, taking successively more senior roles before being named GC in 2002. In a rare move, he was made President in 2015—a title that had not existed at Microsoft for over a decade.

Today, Brad leads a team of 2,000 business, legal, and corporate affairs professionals across 54 countries, spearheading the company’s work (and representing it publicly) on some of the most pressing questions facing the tech sector today, including AI, cybersecurity, privacy, competition, sustainability, and even immigration. It’s on these particular issues that Brad’s legal background continues to pay dividends.

A changing paradigm

Traditionally, GCs have been perceived as the guardians of compliance, risk mitigation, and legal strategy—capabilities that have not always been prized as highly as traditional CEO skill sets around operational and strategic excellence.

Yet as the corporate landscape and CEO role evolves, perspectives around GCs’ suitability for the top job are shifting. Increasingly, organizations and their boards recognize the unique strengths that GCs can bring to the table.

Jennifer O’Connell, who helps global organizations identify and assess GCs, puts it well when she says that GCs have “very honed muscles” when it comes to navigating complexity and mitigating appropriately against risk. She also describes GCs as the “conscience of the company,” combining commercial instincts with a strong moral compass. “These characteristics are being given more weight than ever before and will increasingly help set GCs apart from their ExCo peers,” she says.

Brad demonstrated many of these strengths when he negotiated a historic anti-trust settlement with the US Department of Justice—a high-profile case that led to a media frenzy and ultimately Microsoft changing its business practices. Since that trial, Brad has continued to spearhead the industry to assume more responsibility and has called for governments to move faster to address the challenges that new technologies create. 

A decade ago in Silicon Valley, people stood up and proudly said, ‘We believe in moving fast and breaking things,’ and then eventually, the rest of the world said, ‘You know, I think you all are breaking more than you should,’" 

The industry has gone through a shift, I would argue is still going through a shift, in having to accept the responsibility that is being foisted quite rightly upon it. And the interesting thing about Microsoft is we had to go through that before others. We're not necessarily, and we never necessarily were, the smartest kid in the class, but we had to enroll in this school before others did.” 

Brad Smith
Former GC and Microsoft’s President and Vice Chair

Today, these same characteristics will undoubtedly help Brad deliver on Microsoft’s promise to be carbon negative by 2030—something he describes as a “moonshot,” given the rise of Gen-AI, an energy-intensive technology that is now being adopted at a scale unimaginable when Microsoft made its climate pledge in 2020. 

Brad remains committed to the goal, not least because it is the right thing to do—and is confident about finding a way through the complexity, whether that’s purchasing semiconductor chips that run on carbon-free energy or building data centers out of greener steel or concrete. 

True to his background, Brad believes that it will be regulations and accounting principles that will drive the most change, including the Corporate Sustainability Reporting Directive, which not only applies to companies headquartered in Europe but also global organizations that have a presence there—either in terms of employees or revenue. 

Watch what happens in Brussels. Watch the rules…We're all going to have to snap to that.”

Inspecting trees, analyzing forests 

While the potential advantages of elevating GCs into senior business leadership roles are clear, challenges persist. GCs may run into preconceived notions about their suitability for the role—and have to work harder to win over hearts and minds—at least at the start of their transition. 

For example, our research shows that one of the biggest differences between CEOs and GCs is their risk appetite—with CEOs typically more adventurous than GCs who prefer adherence to rules. 

There may also be extra legwork to broaden their skill set and proficiency in areas such as finance, operations, and marketing, to meet the diverse demands of the senior leadership positions that they will now oversee as CEO. 

Ultimately, however, leadership is about thriving in complexity, whether it’s through partnerships with regulators, working across borders with different governments, or simply focusing on growing a fast-paced, highly competitive business. For Brad, adopting a learning mindset and systems thinking has been critical to his success in the role—and something he seeks to foster in others. 

I spend a significant part of every day trying to develop and augment the skill in everyone around me, including myself, because you better not forget your own ability to keep trying to get better"

The phrase I find myself using frequently right now is people need to be able to do two things really well: They need to be able to inspect the trees, and analyze the forest. If you analyze the forest without inspecting the trees, you don't really know what you're talking about. But if all you can do is inspect the trees, there is a real limit to your ability to contribute analytically.”

If there's a frustration I sometimes find, it's when I get reports that are like tree inspection reports. Here is a report and it describes 10 trees. And I'm like, ‘That's great, but what about the forest?’ And then somebody says, ‘Well, let me tell you about another 10 trees.’” What you're making me do is become the forest analyzer. Everybody has to be good at both of these things. And analyzing the forest is fundamentally, in my view, at least in part, an exercise in identifying patterns.”

Brad Smith
Former GC and Microsoft’s President and Vice Chair

So, while GCs have not always shone brightly on succession radars, this may begin to change. 

Historically, the characteristics of a CEO have largely been at odds with the characteristics of a GC”  “Yet in the increasingly more global, complex and more highly regulated geopolitical environment that organizations now operate in, a GC’s ability to cut through the chaos is giving them an opportunity to elevate themselves in ways they have arguably not had the opportunity to do before. And, of course, every so often, a rare individual like Brad comes forward and proves just what is possible if you look beyond your usual suspects.” 

Jennifer O’Connell
RRA Global Legal, Regulatory, and Compliance Practice Leader