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Leading with Humanity: Why Historical Thinking Will Drive the Future of the Tech Sector



By his mid-thirties, Rishi Jaitly boasted a resumé that would be the envy of any aspiring tech leader: Head of Public-Private Partnerships at Google and YouTube, Vice President for Asia Pacific and the Middle East at Twitter, co-founder of a venture capital firm whose investments in a range of startups brought powerful new technologies to the developing world.


But what had empowered Jaitly’s success in the tech sector, he realized, was not deep technical expertise, nor was it that traditional management credential, the MBA—he had neither. Rather, it was the historical training that he had first received as a Princeton undergraduate—and the passion for history and the humanities that he had cultivated in the years since, including as an expatriate, fueled by a sense of “awe and wonder” about the world and the wider human experience within it.


Now, as founder of the Virginia Tech Institute for Leadership in Technology, which offers the United States’ first executive credential in the humanities, Jaitly hopes to bring those same skills and sensibilities to other tech leaders—and, ultimately, to build a movement around the importance of humanistic perspectives to the future of the tech sector. For Jaitly, this work is not only pragmatic; it is also a moral calling: ensuring that tech leaders fulfill the larger civic and social purpose of the work they do, especially as they navigate the complexities of technologies like artificial intelligence.


Saybrook spoke with Jaitly about his career journey, what he has witnessed about the power of historical thinking for business and tech leaders, and why he believes that such capabilities will be the “superpower of the future.” Our conversation has been edited for length and clarity.


Saybrook: How did you begin integrating historical and humanistic perspectives into your leadership roles in the tech sector? And how did that evolve into the work you’re currently doing at Virginia Tech?


Jaitly: I got my undergraduate degree in history. But that was not an inevitable choice. I came to Princeton thinking I would study the sciences and become pre-med, but I grew attached to a message emanating from the university’s leadership at the time, which was, “Study what exhilarates you. Study what gives you intellectual joy, and that will pay dividends in the long run.” It was a tough decision because the culture I grew up in and the culture around me were telling me to “study functionally,” but I trusted in what I heard from the university and in my inner voice.


Fast forward a number of years into my career in technology. I’d be sitting in meetings at big tech companies or as an entrepreneur or in venture capital, and even though I was succeeding in those worlds, I often felt a bit different from others in the room. I would look to my left and see a bona fide business-credentialed person, and look to my right and see a bona fide technically-credentialed person. On some level, I felt like I didn’t belong. The experiences I carried with me (including from the non-profit sector), the way I asked and answered questions, the ideas I presented, certainly the way I wrote, felt like they were coming from another place.


There was no way to express that identity, really. There was no way to explain how someone like me was now flourishing in these technology companies, developing product ideas, motivating engineers, leading acquisitions, closing deals. There was no language available, I felt, to frame the skills and sensibilities that were allowing me to thrive.


That changed when a friend of mine from Google, Scott Hartley, wrote a book in 2017 called The Fuzzy and the Techie: Why the Liberal Arts Will Rule the Digital World. For the first time, I felt like what had been an underground feeling surfaced above ground. I realized it was OK to say, and essential to acknowledge, that the liberal arts and the humanities—and more pointedly, my training in history—had been fueling me in a variety of tech contexts. Not just the hard skills, but the broader, seemingly softer sensibilities.


So that led me to say, “I can’t just sit with this epiphany. I need to be an advocate for this path.” At first it was sort of a side hustle, but in the last year, that has become the primary thrust of how I spend my time: “How do we make this humanistic identity, experience, and sensibility more accessible to all people, including in the tech world, across the educational and experiential life cycle?”


Saybrook: Are there specific moments in your career where you saw historical thinking—the skills and sensibilities, if not the subject matter knowledge—drive decision-making in the tech sector?


Jaitly: My first foray into the technology world was as a speechwriter for Google’s then-chairman and CEO, Eric Schmidt. My training in history gave me skills around storytelling and language—distilling information into narratives, using narratives to arrive at the essence of a matter—that helped me succeed in that role. So, from the outset, there was a very direct line between my historical skills and the way I navigated the tech world.


Then, in the 2000s, and I was living abroad for the first time in New Delhi, where I was working for Google and helping evangelize the Internet among government officials across South Asia. They felt threatened by the content that Google hosted on platforms like YouTube, blogs like Blogger, and social networks like Orkut, believing it had the potential to spark civil unrest. I recall visiting YouTube.com one evening only to find it completely censored. Part of my job was to negotiate the reopening of these platforms in these markets.


Other companies entering these markets, it seemed to me, were more transactional, focused on short-term results when interacting with the region’s public institutions. I tried to operate differently, with a sense of deep curiosity about where these government officials in countries like India, Pakistan, and Bangladesh were coming from. I tried to express empathy not only in how I spoke to them but also in how I listened to what they told me about why they felt threatened by these technologies. My goal was to get to the core of the disagreement and the context that had shaped it, to build relationships and understanding, and ultimately to devise solutions that took a long-term view of the role that new technologies might play in the story of these countries.


This was particularly important during moments like the 2008 terrorist attacks in Bombay. I testified in front of the Indian parliament, whose members were concerned that terrorists were using Google Earth and Gmail to plan attacks. It was a volatile time. Having that training in history allowed me to be more sensitive and human than others in my shoes might have been.


Saybrook: Beyond your own career, how have you seen other tech leaders or firms leverage historical or humanistic thinking to their benefit?


Jaitly: One thing I’ve noticed at a lot of tech companies is how the most effective leaders rely on the power of storytelling to motivate teams, sharpen objectives, and drive morale.


Part of doing that is situating what they’re doing within a longer-term, bigger-picture view of the arc of history. When I was at Twitter, I noticed that [co-founder] Jack Dorsey and a lot of the other executives would talk about Twitter in terms of the history of expression and publishing. We would often talk in serious business meetings about Twitter as a realization of Gutenberg's vision of the printing press. That was a serious clarifier and gravity creator in terms of recruiting talent, driving our ability to do deals, and talking to brands, governments and public figures.


To me, these were “aha” moments around the power of historical storytelling in driving business outcomes. I saw that power at other firms as well—describing their innovation in the context of a wider arc of how payments or travel occurred decades ago and how they occur today, for example. I think, particularly for rank-and-file employees and for stakeholders in external partnerships, people want context. They want to know where they sit in the larger human story. That may not be a conscious feeling. But, in practice, I found it to be a really powerful way to realize desired outcomes and fulfill the essential human need to belong.


I sometimes used similar strategies myself. Inspired by Bill Shore’s book The Cathedral Within, I would tell my teams stories about cathedrals whose builders never lived to see their finished products, which took centuries to complete. But by anchoring their understanding of their work within a larger historical arc, they remained inspired to build enduring, purposeful structures.


Now, with that said, it was and still is critical for the walk and talk to be in stride. At tech companies, there’s a tendency to become quite poetic about products and their capacity to change the world. When used thoughtfully, historical analogues can help you describe the power and promise of your innovation, but they can also instill the humility to reflect on the unintended consequences or drawbacks of prior innovations and how that might guide our thinking today.


Saybrook: Obviously there is a huge conversation going on around generative AI. How can leaders leverage historical and humanistic skills to make better use of AI?


Jaitly: I think these tools dramatize the importance of asking the right questions and taking the long view. The field impacted most by generative AI in the last six months has been technology itself. Computer scientists no longer spend nearly as much time solving computational problems as they did a year ago. Their focus is now on higher-level, bigger-picture tasks and decisions.


Those of us who believe in the power of the humanities have a once-in-a-century opportunity to go to market with confidence that the real superpower of the future will emanate from fields like history. By 2030, we’ll be able to do our financial modeling or computer programming with AI as our copilot. But when we’re sitting in a meeting room in 10 years, it’s those humanistic skills that will be most important in discerning a breakthrough comment, idea, or leader.


The interesting thing to me is that this has already long been true in what I call Greater Silicon Valley. The co-founder and first CEO of AOL was a politics major. Two of Airbnb’s founders were design majors. The founder of Slack was a philosophy major. I think this trend will only accelerate and become more visible and mainstream.


In the technology world, we talk about this notion of a stack, which refers to the layers of technologies that sit behind the apps we use. There's the front-end stack, the back-end stack, the API [application programming interface] that helps you connect the app into other technologies, and so on. One thing I think about a lot, inspired by the pioneering work of Scott Hartley, is what a "full-stack human" will look like in the coming decades. In the same way that full-stack technology is a prerequisite for a fully-functioning consumer or enterprise technology solution, a full-stack human is one way to think about the superpower of the future.


Another way to put it: A year ago, we were talking about crypto and blockchain; today we’re talking about generative AI; in five years, there might be another train coming to the station. Scott and I often talk about the liberal arts and humanities as the “infrastructure layer” of the full-stack human of the future, equipping us with the elasticity of mind and spirit to navigate this pace of change—and to lead and thrive through these waves of transformative technologies. That's what I'm trying to do here at Virginia Tech with the Institute for Leadership in Technology: building what you might call a “Full-Stack Human” institute.


Saybrook: What do you think an executive education course focused on those historical and humanistic perspectives should include?


Jaitly: There's one strand of thinking that suggests it ought to focus on the humanities in and of themselves. Meaning we need not bridge a course on history, for instance, with our current world or its relevance to a “Monday morning meeting” in the tech sector. Just cultivating that muscle is what’s important. Another view suggests we should tie themes in the classroom directly to the problems that business leaders face today. So, here at the Institute, we’re in the midst of this dance at the moment, and we look forward to sharing what we learn.


For now, we’re spending this first semester trying to cultivate introspection in our Fellows, with courses on the understanding and practice of human leadership over many centuries and on the religious and cultural history of the West and East. In the spring, we’ll turn to imagination, offering a seminar on creative writing, where our Fellows will reflect on the power of storytelling in business and hone their own functional skills in that regard. And then, finally, we’ll have a course on the humanities and the role they have played in the digital world.


What we know definitively is that there’s demand for this kind of coursework. According to The Economist, the three most popular courses at Stanford Business School are all focused on soft, “fuzzy” skills. I think emerging business leaders are already telling us that it's these kinds of courses they believe are most essential to their future leadership.


For leaders of all stripes, in the private or public sectors, I’ve found that history helps develop both retrospective and prospective vision by cultivating a habit of leading with big questions. Almost every startup or every big idea had its genesis in a big question, which then led to a high-altitude vision. Those are skills that you develop through thinking historically—asking big questions, then developing a big vision followed by big execution—because otherwise you're just drowning in facts. History helps you sort through, understand, and shape those facts towards some larger purpose.

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