Retention and the AI Squeeze: Singapore Legal Experts Discuss Fundamental Industry Challenges

This article was first published on 28 April 2026 in Law.com. SLW obtained permission to reproduce the article to give the legal community a broader view of legal reports for various news syndicates.

Singapore's legal profession faces fundamental challenges in addressing lawyer attrition and rapid advances in artificial intelligence, which will require reassessment of the way the industry works, according to panellists at a Singapore Supreme Court event.

The discussion titled “Charting the Path Forward”, which marked the launch of the 2026 Hackathon for a Better World, focused on how the country's profession could remain sustainable given associate dissatisfaction and the increasing deployment of AI.

Paul Neo, assistant chief executive at the Singapore Academy of Law (SAL), moderated the talk and explained that “one in three newly admitted lawyers are looking or planning to leave the profession within three years.”

Retention beyond rules and hours

Panellists agreed that retention cannot be solved with cosmetic fixes or simple working-hour restrictions.

Raeza Ibrahim, a partner at Singapore firm TSMP Law Corporation, cautioned against relying on rule-making to address burnout and attrition.

“It’s not about implementing rules,” he said. “If I still have my young people, my middle people, and my senior people thinking about all their work after 7.00 PM and at 1:00 AM… nothing will be achieved. We would have just made a rule.”

Instead, he pointed to deeper drivers of dissatisfaction: “bad processes,” “bad bosses,” and what he described as performative approaches to metrics that fail to tackle root causes.

For Ibrahim, any serious attempt at retention must confront how work is allocated, supervised and evaluated, rather than merely imposing formal limits that do not change expectations.

At the organisational level, autonomy emerged as another key factor.

Sadhana Rai, chief representation officer at Pro Bono SG, recounted how early opportunities to manage her own cases were pivotal to her development and decision to stay in practice. Allowing younger lawyers to exercise judgement and take ownership, she suggested, not only builds capability but also gives meaning to long hours.

But she stressed that this autonomy must be balanced with safeguards in a high-stakes profession, where mistakes carry significant consequences for clients. The challenge, she implied, is designing workplaces that are both developmental and protective.

Retention is also shaped by clients. Chee Kin Lam, group head of legal and compliance at Singapore’s flagship bank DBS, argued that sustainability depends not only on courts and law firms but also on the behaviour of clients. “The conversation is not just courts and lawyers… It is also with the clients,” he said. “Clients can have unrealistic expectations… and that is something that we do need to design for.”

Lam emphasised that a sustainable profession cannot abandon high performance. “There is no success if we don’t commit to high performance,” he said. The question is how to uphold exacting standards while recognising different life stages and personal circumstances, and while pushing back against unreasonable demands that make retention harder, he added.

AI as accelerator and pressure point

Against this backdrop, artificial intelligence (AI) loomed as both a tool and a stressor.

Ken Hwee Tan, chief transformation and innovation officer of SG Courts, urged practitioners to experiment with emerging technologies to improve their own working lives.

“You have the ability to try things out, understand what is possible with the technology… to make your work easier, to make your work better, less repetitive, less painful,” he said.

Yet he warned that widespread AI adoption will almost certainly raise the bar for lawyers.

“The quality that is going to be asked of lawyers is going to be so much higher, and you’re going to have to do things so much faster,” Tan said, pointing to tools capable of detailed analysis of legal submissions.

For a profession already grappling with burnout, this acceleration cuts both ways. AI may relieve some drudgery, but it may also intensify expectations around speed and perfection. The panel suggested that, unless workflows, support systems and client norms evolve in tandem, AI could exacerbate attrition rather than alleviate it.

Ibrahim highlighted another unresolved tension: AI and billing. While alternative fee models are often proposed as a response to technology-driven efficiency, the mechanics of implementation remain unclear.

“I don’t know how to merge that with the taxation process… because right now there is no real metric,” he said, noting that time-based billing is deeply embedded in existing systems.

Lam, meanwhile, urged the profession not to get lost in narrow debates over billing alone. With global investment in AI at scale, he said, the legal sector must think in terms of overall system design.

“There is a temptation to go into the user layer,” he noted, calling instead for a broader view of how institutions, regulators, clients and lawyers should collectively respond.

Despite AI’s growing capabilities, the panellists were clear that human judgement remains central to sustainable legal practice.

Rai described her approach as ensuring technology remains a tool, not a substitute for professional responsibility. “I will use AI, but I ensure that there’s still a human being at the helm, in the loop, and on the loop… to ensure that the AI serves the user,” she said.

That framing of AI supporting people, rather than people serving AI-driven expectations, underpinned much of the discussion. Retention, the panel suggested, will depend on whether Singapore’s legal ecosystem can align incentives, processes and technology so that careers remain both demanding and viable.

Co-organised by SAL, DBS Bank and the Singapore Courts, the 2026 Hackathon for a Better World, which began on 27 April, is discussing these themes, focusing on AI integration, internationalisation and the long-term sustainability of legal practice.

Used with permission of Law.com International. Copyright © 2026. All rights reserved.

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