Careers are often described as if they can be mapped out in advance, with each step building neatly on the last. But during a recent Silfen Leadership Series conversation at Columbia Business School, Shelley Stewart III ‘12, Senior Partner at McKinsey & Company, offered a different perspective: some of the most consequential decisions are made without a clear end in mind.
In a discussion hosted in partnership with the Bernstein Center for Leadership and Ethics and moderated by Malia Mason, the Courtney C. Brown Professor of Business at CBS, Stewart reflected on a career that has moved from Wall Street to entrepreneurship to the upper ranks of global consulting. Today, as a Senior Partner, Global Leader of Reputation and Engagement, and leader of the firm’s insights and ecosystems, which includes McKinsey’s Institute for Economic Mobility, his work helps organizations unlock potential in markets and communities too often overlooked.
The throughline of Stewart’s story is not a carefully constructed plan, however. Instead, it is a series of decisions, often made at moments of uncertainty, that reshaped his trajectory, and ultimately defined his approach to leadership.
Building Through Experimentation
Stewart began his career in sales and trading at JPMorgan, drawn in part by the conventional signals of success that often guide early professional decisions, like financial upside, prestige, and momentum. But the experience quickly became more complex than those initial motivations suggested. Working through the global financial crisis exposed him to the fragility of institutions and the unpredictability of markets, offering an early lesson in how quickly even well-established systems can shift.
In the aftermath of the crisis, Stewart made an entrepreneurial leap, co-founding a private investment firm. The move reflected both ambition and an instinct to capitalize on disruption.
“There was a lot of disruption—a good time to go try something,” Stewart said.
Yet even as the firm gained traction, Stewart began to question the long-term implications of his path. While at Columbia Business School, where he balanced the demands of running a firm with the intensity of the MBA experience, he came to a realization: his expertise was becoming too narrow.
That recognition marked a turning point. Rather than doubling down on a successful but increasingly specialized track, Stewart chose to step away without a clearly defined next step.
Stewart noted that career clarity often follows action, not the other way around. His path underscores the value of experimentation for leaders, especially early in their careers, as progress is rarely the result of a perfectly constructed plan. More often, it emerges through iteration.
Knowing When to Pivot
For Stewart, the decision to exit his firm was a deeply personal inflection point. Walking away meant relinquishing financial upside, as well as a professional identity he had worked to build.
Despite the outward markers of success, Stewart found himself without a clear roadmap. During the conversation, he shared one moment in particular where his father offered a grounding perspective, reminding him that prior achievements did not eliminate the need to make thoughtful decisions about what came next. In this way, he argued, success does not remove uncertainty but instead reframes it.
“I wanted to go to a place that would build resume equity over time, because I didn’t know what I wanted to be. And then two, someplace that wouldn’t pigeonhole me—someplace where I could see lots of sectors, lots of functions, and have a lot of option value,” Stewart said.
What made the pivot possible was a willingness to confront sunk costs and reassess direction honestly. Many professionals remain in roles or trajectories not because they are the best fit, but because they have already invested so much in them. Stewart’s decision to pivot reflected his prioritization of long-term growth over short-term continuity.
This mindset also acknowledges a reality that is often underemphasized in discussions of leadership: the role of timing and luck. Stewart recognized that his career benefited from both. But rather than diminishing his achievements, that acknowledgment highlights an important leadership capability, the ability to position oneself to take advantage of opportunity when it arises.
That combination of self-awareness, adaptability, and humility ultimately enabled Stewart’s transition into consulting, where he would go on to build the next phase of his career at McKinsey & Co.
Leadership at Scale
At McKinsey, Stewart’s role has evolved beyond the technical foundations of his early career. As leader of the firm’s global Reputation & Engagement function, he operates at the intersection of strategy, communications, and institutional trust, shaping how one of the world’s most influential organizations engages with external stakeholders.
The scope of his role spans more than 65 countries and encompasses everything from marketing and publishing to broader public engagement. Stewart noted that his work today is less about executing within a defined domain and more about influencing how the firm shows up in the world.
That shift is perhaps most visible in his role as founder and chair of the McKinsey Institute for Economic Mobility. The initiative reflects a broader view of leadership that extends beyond firm performance to address systemic challenges. Focused on expanding access to economic opportunity, the institute connects research, policy, and practice in an effort to better understand and improve mobility outcomes.
For Stewart, this focus is not abstract. It is informed by both professional experience and personal perspective, reinforcing the idea that leadership at the highest levels increasingly requires engagement with issues that sit outside traditional business boundaries.
Today’s leaders are expected not only to drive organizational success, but also to contribute to broader societal conversations by shaping narratives, influencing systems, and engaging with complexity at scale. For the next generation of business leaders, Stewart’s message is that leadership is less about mapping out every step, and more about building the capacity to navigate whatever comes next.
