Take 5 With Sayan Chakraborty: The Art and Science of Innovation

Sayan Chakraborty, executive vice president of product and technology at Workday, is a voracious reader and enjoys both the creative and engineering aspects of woodworking. Read more on how Sayan’s personal interests influence his professional leadership.

Sayan Chakraborty, Workday’s executive vice president of product and technology, enjoys learning new things. That’s why he’s usually reading five or six books at a time on a wide array of topics.

His current reading interests include the major societal shifts that made the modern world possible, a study of geopolitics, and the development of aircraft carrier warfare in World War II. Beyond reading and his Workday duties, Sayan can be found in his woodworking shop, where his long-term project involves building a Japanese-style blanket chest for his daughter. And, if that’s not enough, he’s recently joined the National Artificial Intelligence Advisory Committee (NAIAC) to help advise President Biden and the White House on a broad range of AI issues.

A glimpse into some of Sayan’s “light reading” selections.

Sayan’s relentless curiosity not only fuels his reading interests, but also drives him to seek new ideas and ways of thinking and to bring those to bear on the challenges facing Workday and our customers—which is why he keeps abreast of cutting-edge technologies, and how they can possibly be used at Workday. We recently spoke with Sayan about his excitement for Workday’s future, what keeps him energized, and who inspires him every day and reminds him to never give up.

You joined Workday in 2015 as part of the GridCraft acquisition. Can you share a bit about your experience before that, and what’s kept you at Workday?

Before I helped found GridCraft, I worked in a variety of tech companies, including several startups, and I started my career on the technical team at NASA. One key takeaway from those experiences is the countless ways technology can transform and, ideally, improve our lives.

I have found that to be at the core of what we do at Workday too. But even more than that, I'm fascinated by the experiment that Aneel and Dave, the company’s co-founders, started with Workday—can you have a values-driven, ethical company and be financially successful, and have it be at the heart of why you are successful? I very much want that to be true, and I would much rather be part of that exciting experiment than simply watch it from the outside.

"It's our job to carry forward the mission Dave and Aneel started here and to fulfill both the words and the spirit of it."

Sayan Chakraborty Executive Vice President of Product and Technology Workday

Also, I get bored easily. But every time I’ve felt like I'm just getting a handle on my job at Workday, it has changed. That’s the dynamism of Workday and its tremendous growth. I started here with a team of six, and I have a few more than six people working for me now. I don’t have time to be bored given the pace of our growth and change.

How has the current state of the market influenced how you’re thinking about the direction of our products and technology?

The pandemic accelerated cloud adoption as companies have experienced the fragility of systems built on on-premise software. They’ve also witnessed the increased flexibility of their peers that have adopted cloud.

Employees have also become more vocal about issues related to equity and justice during the pandemic. From Workday’s product perspective, that translates to treating employees and customers well. Anytime a business decides to invest in their people, that plays directly to Workday’s strengths. 

You also have a fascination with space, among other things. How has your experience in the space program influenced your career?

I love everything to do with space, rockets, and airplanes; it’s been an interest of mine since I was a little kid. So it was exciting for me to work in the space program, and it taught me about goals, planning, and risk. 

When I look back at the Apollo program and President Kennedy’s call to put a man on the moon within a decade, I’m reminded that great accomplishments come when you set audacious goals and marry them with a pragmatic, practical, and incremental plan to achieve them. The very existence of Workday is, at its heart, an audacious goal, and I’m inspired by that goal and by helping the company achieve it. 

The space program also taught me about the pitfalls of overemphasizing risk aversion. During the Apollo program, at a time when everything to do with space was new, untried, and risky, we lost three astronauts. But later, when the reduction of risk became NASA’s central focus, 14 astronauts died. So emphasizing risk avoidance didn’t create the culture that leaders wanted.

Bureaucracies and companies can inherit that type of risk aversion and unwillingness to talk openly about problems that face them. I want to be a part of helping Workday not go down that same path, to have audacious goals, pragmatic plans, and take smart risks.  

In addition to being an aspiring astronaut, you’re also a woodworker. In what ways has that hobby made you a more effective technologist and/or leader?

They influence each other. Woodworking is fundamentally a craft, meaning that it is part creative and part engineering. Both of those matter immensely to the outcome.

For instance, I can build a chair. And somebody who's really good at woodworking can build a chair. Even though you can sit on both of them, and they are both made of wood, you can’t really compare them. That reveals the importance of creativity and experience, not just tools and materials.

After 30 years of managing software developers, I can definitively say that software development is a creative act like woodworking. You have to understand your material, whether it’s software or wood. Both materials are incredibly complex with a wide array of variables impacting the end result. You have to know your tools and the constraints of what is possible. Then you have to use your creativity to stretch the bounds of what is possible to get to the outcome.

Woodworking also satisfies my need for having a measurable result. That was easy to achieve back when I wrote software. I knew what I had checked into source code control each day and I had a record of progress or achievement. After getting into management, that felt like a gap in my life, so woodworking has helped me fill it.

Despite Sayan's many accomplishments, his Workdogs, Boomer (black) and Shasta (yellow), remain singularly unimpressed. Especially Boomer.

Which emerging technologies have caught your interest lately? And how do you see those impacting Workday and our customers?

Right now, I’m reading about attention mechanisms, transformers, and their applications in machine learning (ML), particularly as they allow for more parallelization. I think this is going to make people rethink how we approach problems, because it can speed up problem solving while making us better at it, and make currently intractable problems tractable. 

At the same time, we have to continue to look at the full range of possibilities and their implications. Does a technology, for example, help you address bias, or does the technology exacerbate and reinforce bias? We have our ML engineering team and lots of people working on these hard problems—but it’s still important for me to understand the technology and the implications of that technology well enough so that I can provide guidance on our investments in this space.

What are you most excited about for Workday’s future?

I always come back to the mission. It's our job to carry forward the mission that Dave and Aneel started here and to fulfill both the words and the spirit of it. How do you achieve that with 100 people, 500 people, or 15,000 people like we have today? How do we continue to bring our mission to life as we continue to grow and scale? 

The second part is that we still have tremendous opportunity in front of us at Workday. Not every company has been able to take advantage of their opportunities, even companies that were once really great. Many companies that were leaders in their field have disappeared, and we simply cannot take this opportunity for granted and expect to have long-term success. Every company thinks, “that's not going to happen to me,” but it does when people lose focus. With our continued focus on seizing the opportunities we have in front of us, we will continue to be leaders, and positively impact our customers and their employees—and I am excited to be part of that.

"I want to be a part of helping Workday have audacious goals, pragmatic plans, and take smart risks."

Who has been the biggest inspiration in your life? In what ways?

My biggest single inspiration is my son, who was diagnosed at a young age with a very rare and serious disability. He is one of my favorite people and I think the world of him, not just as my son but as his own human being. He gets up every day and has to deal with adversities and challenges that I, and frankly most people in the world, never have to deal with. The world, largely speaking, wasn’t built for someone like him. Basic day-to-day things that most people take for granted take him a tremendous amount of effort and time. But he does them with a smile on his face and doesn't complain very often. In the face of that, it's kind of hard for me not to feel like “come on Sayan…what do you have to complain about?” I aspire to be more like him every day.

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