Matthew Wee Yik Keong has worked in the Singapore corrections system his whole career. He tells of his three uncles who fell into a life of drugs and crime, all with sad endings. This experience inspired him early on to work to prevent recidivism and intergenerational crime. It takes a certain type of person — one with great strength and compassion — to help offenders turn their lives around.
“When I started work, I interacted with people from all walks of life,” says Matthew, who began his career in 1998 as a prison officer. “Murderers, rapists, drug traffickers, very violent people. But inside the system, they seemed normal. I was curious how they ended up there. I want to have empathy, to understand their behavior and connect with them. Not to judge them.”
He continues: “You have to separate the person from the crime. I still struggle with that. Yet, that has helped me survive in the prison system for 25 years.”
Matthew grew as a leader within the Singapore Prison Service, achieving the rank of Senior Assistant Commissioner, responsible for a cluster of 5 prisons housing over 5,000 inmates with 600 staff, before shifting into another public service agency. In 2018, he became CEO of Yellow Ribbon Singapore – a quasi-governmental agency that advocates for second chances and provides skills training and employment services to reintegrate formerly incarcerated individuals into society. Matthew transformed what was a struggling organization into one of the top public service high-engagement agencies, placing thousands of ex-offenders in jobs.
Then, in August 2023, Matthew was asked to return to Singapore Prison Service as deputy commissioner – a high-level leadership role with increased responsibilities.
“Every year, about 8,000 inmates are released,” he says. “The five-year recidivism rate remains high at over 40 percent. To be successful in lowering the long-term recidivism rate requires multiple stakeholders to work together – families, employers, volunteers, and social service agencies etc. I needed to reinvigorate my leadership capabilities and gain new insights to be more effective. I’ve been in prison – institutionalized – for 25 years. This is the context in which I came to Stanford.”
Driving Change in the Prison System
Matthew had colleagues in the civil defense force and immigration services who attended the immersive, on-campus Stanford Executive Program (SEP). “They were raving about how it changed their lives,” he says. “They told me, ‘When your time comes, just go to Stanford, it is the best!’”
Intrigued by the SEP curriculum and its one-of-a-kind approach to leadership development and personal growth, Matthew enrolled in the six-week program and traveled to campus. The courses and activities helped prepare him to develop the prison service’s long-term strategic plan and “drive change at the organizational, national, and international level.”
Most of his cohort members, many from finance, technology, and other sectors, hadn’t met someone working in corrections before. “Actually, I’m a capitalist,” he smiles. “I’m a venture capitalist, but my mission is to build human and social capital.”
Growing as a Leader “from the inside out”
The SEP curriculum offers real-world best practices that apply to government, business, and nonprofit operations. “We learned about leadership competencies, leadership behavior, and the leadership framework,” Matthew says. What surprised him, though, was the program’s focus on growing as a leader “from the inside out” with daily mindfulness and meditation sessions.
“SEP faculty brought us through a journey of introspection, of learning how to empathize and listen,” Matthew recalls. “That had a deep and profound impact on me. You can actually train your temperament, manage stress, and project calmness when there’s chaos. You can give clarity when everyone is confused. You can be like Yoda, a better master.”
Matthew spoke at his graduation ceremony, thanking participants for their support: “You were generous with your ideas and war stories, sacrificed your time and put in extra effort to help a fellow SEP-er, in good times and in the hour of need.” Many now stay in contact via WhatsApp groups. “We bonded, from day one,” he says. “I really valued their authenticity and openness.”
Building a Safer, More Inclusive Society
Matthew has taken what he learned about organizational leadership – and himself – to coach a new generation of corrections officers and prepare for what lies ahead. “We are looking at corrections in 2030 and beyond,” he says. “The next few years we are rolling out all the programs and initiatives, working across the private, people and public sector, to get the whole of society on board.”
Matthew’s goal is to create an exemplary corrections system that helps formerly incarcerated people restart their lives and builds a safer, more inclusive society. “Our role extends beyond the prison walls,” he says. “We have the ambition to be a social leveler. Now, we need the alignment from everyone to deliver the results.”
