For one senior banking executive, the Master of Technology in Digital Leadership at NUS-ISS pushed him to rethink strategy, adopt systems thinking and broaden his influence in leading organisational change.
Caption: (From left) Thaddaeus Lee with teammates Alden Neo and Charmaine Cheung, whose 11-month capstone project produced an AI learning analytics prototype to help early childhood teachers observe and document student learning and enhance teaching proficiency, earning them the 2025 Best Project Award.
In 2020, Thaddaeus Lee’s career could not have looked any rosier. A seasoned executive with over two decades of experience in financial services, he had just returned from a management stint in Japan to lead an innovation centre at Sumitomo Mitsui Banking Corporation in Singapore.
But as he watched the early stirrings of the artificial intelligence (AI) revolution and the acceleration of change in multiple industries, he began to question his readiness for the future.
“I was doing well, but I was at a crossroads,” says the now head of strategy for Asia-Pacific at the bank. “I knew there was a bigger world out there. As the person leading the innovation centre and taking the team to the next stage, I asked myself, if what I knew about strategy was good enough and whether I should push myself beyond my personal boundaries. I then decided to rewire myself and see where it would take me.”
For Lee, that meant going back to school. He already had a Master of Business Administration from the National University of Singapore (NUS) under his belt, but was intrigued by the Master of Technology in Digital Leadership (MDL) course offered by NUS-ISS.
MDL is a two-year graduate programme that focuses on how the role of the digital leader has become increasingly complex as technology permeates through organisations and drives new business models. The part-time course is designed for senior executives who wish to strengthen their leadership capabilities and transform their businesses to gain a competitive edge.
Lee found that MDL was structured very differently from the MBA he took 17 years ago at NUS.
“In business school, we talked about financial models, human leadership and capacity building,” he says. “For MDL, it focuses more on future technology and how to take an organisation from its current state to a future state. And that actually created a lot of deep questioning within me.”
Becoming a novice again
In the MDL course, Lee dove into unfamiliar topics such as building digital architectures and managing the complexity of digitalisation.
“I used to view architecture purely as IT (information technology), but now I ask: What are the strategic levers, and how are parts like enterprise architecture and data architecture coming together?” he says. “I began to understand how these platforms, ecosystems and operating models can be structured for agility and aligned with business values.”
He then asked himself how leaders like him could help employees operate in the uncertain and ambiguous environment of today.
“We have to create common sets of data and communicate with the right digital platforms to get the message across, reduce tension and remove silos,” he says.
At work, he now evaluates significant digital infrastructure investments with deeper understanding. “If I don’t understand them well enough, I won’t be able to evaluate them,” he says.
The course also reshaped his relationship with data and decision-making.
“After being in the industry for this long, you tend to be the go-to person for solving problems,” he says. “MDL made me review my habits, change my tendency to give quick answers and relearn how to deconstruct the problem with academic rigour, anchored in data and research.”
Learning from practitioners and peers
The MDL programme has a unique blend of academic rigour and industry expertise through its faculty.
“MDL brings together instructors and industry practitioners who actively operate at the front line of digital transformation,” Lee says. “Their insights are grounded in lived experiences across sectors, which shaped our learning to be agile, relevant and immediately actionable.”
Lee fondly remembers NUS-ISS graduate programme director Dr Leong Mun Kew, a strong advocate for practitioners with over 25 years of experience in research and development, and IT leadership. Dr Leong holds a PhD from Stanford and has held roles at A*Star and National Library Board in Singapore.
“Dr Leong would push me out of my comfort zone, constantly challenging me to consider both sides of innovation – of empowerment and disruption – and my willingness to take calculated risks,” Lee says. “He often emphasised that technology is not just about tools, but also about transforming how organisations think and act.”
He says the peer learning experience proved equally valuable.
His course mates were high achievers from diverse backgrounds, creating rich collaborative opportunities. They were so passionate about the coursework, they would visit each other’s offices to discuss MDL topics and projects.
Turning insights into action
After graduating from MDL this year, Lee has developed a “prompt, lead and repeat” approach to leadership, modelling it after how Generative AI works.
“Leaders must master the art of prompting people and not just instructing,” he says. “At work, I now pause to ask better questions, not just give instructions.”
He uses this “prompting method” to encourage understanding among his teams and to help them think forward. And instead of designing rigid three-year strategic plans, he is implementing “agile feedback loops” as “the plans can go out the window anytime because of the rapid changes in AI innovation”.
Lee advises anyone considering a graduate programme to approach it with an open mind and a willingness to embrace the unknown.
“It is okay not to have all the answers,” he says. “What matters is your readiness to ask questions, make mistakes and learn from them.”
“Don’t pursue a Master’s just for the paper qualification or to fit a job. Do it for how it may shift your mindset, sharpen the way you lead and help you to grow.”
For more information on the Master of Technology in Digital Leadership, visit here.
The article first appeared in The Business Times here.