Singapore Prison Service official Matthew Wee Yik Keong is transforming how the system rehabilitates inmates and ex-offenders — with the goal of creating a safer, more inclusive society.
Matthew Wee Yik Keong didn’t intend to spend his career inside Singapore’s prison system. He earned his bachelor’s degree in hospitality and tourism management, hoping to land a job with a hotel chain. However, hotels were not hiring at the height of the Asian Financial crisis in 1998 when he graduated. He was drawn to the prison service by its social mission and nature of being a helping profession. He wanted to help individuals and families affected by incarceration.
Matthew was no stranger to the hardship endured by families whose loved ones are incarcerated. Three of his uncles had fallen into a life of drugs, crime, incarceration, and homelessness. “They were hardcore repeat offenders,” Matthew shares. “I remember my mother visiting them in prison.” The lives of all three men ended tragically.
He volunteered with the Salvation Army early in his career, working with children of incarcerated parents, while pursuing graduate studies in social work to deepen his knowledge and skills. A chance encounter drastically changed him and how he viewed his job.
“I overheard a conversation between two boys, ages 8 and 10,” Matthew recalls. “The younger boy asked the older boy, ‘Do you know when your daddy will come home?’ The older boy replied, ‘When my daddy comes home, I’ll be an adult already.’” The younger boy said that he, too, would be old when he saw his parents again. “These words struck me to the core. The children were innocent. That was a defining moment for me.”
Matthew’s volunteer experience inspired him to do his best at work. It was no longer just a job, but a way to help others, especially children and families, achieve happiness and social mobility.
Embarking on a career of service
Matthew started out as a corrections officer more than 25 years ago. “I interacted with people from all walks of life,” he recalls. “Murderers, rapists, drug traffickers, very violent people. But inside the system, they seemed normal. I was curious how they ended up there. I wanted to have empathy, to understand their behavior and connect with them. Not to judge them.”
Matthew moved up through the ranks over the years, becoming a leader for hundreds of staff overseeing thousands of inmates. “You have to separate the person from the crime. I still struggle with that,” he notes. “Yet, that has helped me survive in the prison system for 25 years.”
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, a model program, placing thousands of ex-offenders in jobs.
Changing from the inside out
In August 2023, Matthew was asked to return to the 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. Lowering the long-term recidivism rate requires multiple stakeholders to work together — families, employers, volunteers, and social service agencies. I needed to reinvigorate my leadership capabilities and gain new insights to be more effective.”
Matthew attended the immersive, on-campus Stanford Executive Program (SEP) to gain the knowledge and skills he needed to move his organization’s strategic plan into the future. He enjoyed all of the content and was especially impacted by the grounding he gained from the mindfulness sessions.
“The SEP experience focuses on the whole-person development,” he says. “My takeaway is that to change lives, change organizations, and change the world, I have to change from inside out. I must unlearn my old habits. I must be a better person.”
Matthew made a presentation to his cohort during the program, as most had never met anyone working in corrections. “I realized my colleagues are successful business people, and they also want to do good,” he shares. “They want to help the less fortunate, the less privileged. I was very pleased that this presentation actually started a conversation on how businesses can do good.”
New beginnings for ex-offenders
Matthew has taken what he learned in SEP about organizational leadership — and himself — to coach a new generation of corrections officers. “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 and public sector, to get the whole of society on board.”
His goal is to reduce intergenerational recidivism, improving the lives of individuals and families, while creating a safer, more inclusive society. He hopes to share what he believes is a model rehabilitation program for ex-offenders on an international scale.
“We are seen as transforming the prison system in Singapore,” Matthew says. He points to the work of Yellow Ribbon Singapore, which partners with 6,265 employers. Some 2,300 inmates and 3,740 ex-offenders take part in work and training programs each year, with 93 percent of inmates referred to the program gaining employment prior to release.
Matthew thinks back to the boys he met while volunteering at the Salvation Army, and hopes to improve the lives of families like theirs. He believes in second chances, even for those who’ve made serious mistakes. An SEP session on the Stanford Forgiveness Project impacted him.
“Who would expect to attend an executive program, and learn about forgiveness?” he notes.
“The action needed to transform society takes place outside the prison walls, not inside.”
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