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She shares insights from her career on purpose and trust in leadership, supporting women at work, navigating AI and global uncertainty, and raising confident, resilient young people.
Leadership must be anchored in purpose and trust – this was one of the many learnings that resonated with us from a session with Halimah Yacob, Singapore’s first female President.
The ex-head of state was speaking in a fireside chat with DBS CEO Tan Su Shan on 1 April, at DBS' International Women’s Day (IWD) 2026 event attended by Human Resources Online.
The session brought together employees across the bank, including union leaders and young professionals, for a discussion on leadership, gender equality, and the future of work.
Purpose as a guiding force
Opening the conversation, Madam Halimah reflected on her journey from the labour movement to becoming Singapore’s first female President, highlighting the importance of having a clear sense of purpose.
She said individuals need a purpose and a meaning in life to guide decisions and sustain them through challenges.
"We cannot just navigate through life aimlessly."
Earning trust through action
Responding to a question on leadership lessons from her time in the labour movement, Madam Halimah said there is no shortcut to leadership.
She shared that early in her career at the National Trades Union Congress, she had to earn the trust of experienced union leaders who were initially sceptical of her despite her qualifications.
Over time, she built credibility by engaging consistently and demonstrating that she could support and guide them. This approach proved critical during periods of economic difficulty, when she had to work closely with unions to explain policy changes and help workers understand long-term benefits.
She stressed that trust is built through actions and track record, not titles.
Leading in a complex environment
On the challenges facing leaders today, Madam Halimah pointed to growing polarisation, declining trust in institutions, and a post-truth environment where facts are increasingly contested.
She said leaders need to focus on strengthening the middle ground and bringing people together, rather than allowing extremes to dominate. This requires clear communication and the ability to explain not just decisions, but the reasoning behind them.
To this point, Tan noted that organisations often focus on the ‘what’, ‘how’ and ‘who’, but need to do more to communicate the ‘why’ to employees.
Supporting women to step forward
The fireside chat also addressed mentorship and the development of women leaders.
Madam Halimah said many of the challenges women face remain, particularly around balancing responsibilities and managing time.
She noted that women often hesitate to take on leadership roles unless they feel fully ready, which can hold them back. In contrast, men are generally more willing to step into roles even if they are not fully prepared.
Women, she said, tend to underestimate their abilities and believe they need to be 150% prepared before stepping into leadership roles.
"Give yourself the opportunity to do it and to prove yourself, because then you pave the way for other women."
Her advice here was for women to have confidence in their abilities and not underestimate their potential – adding that leadership should be anchored in values and principles, regardless of gender.
AI and the risk of bias
As the discussion turned to technology, Madam Halimah highlighted concerns about artificial intelligence (AI) reinforcing existing biases.
She explained that AI systems are trained on data that may reflect societal prejudices, which can affect decisions in areas such as hiring and pay.
Adding to this, Tan noted that AI systems can mirror and amplify user perspectives if left unchecked: “AI is a stochastic parrot.”
"You need humans both in the loop and on top of the loop to make sure that it's safe and it's neutral."
Balancing leadership and family
On managing work and family responsibilities, Madam Halimah acknowledged that the challenge remains significant, often requiring individuals to juggle multiple roles.
She pointed to the importance of shared responsibilities at home and noted that workplace policies have improved over time. However, she said, individuals must still make choices that work best for their own circumstances.
Encouraging the next generation
Closing the session, Madam Halimah spoke about how parents and leaders can better support young girls growing up in an uncertain future. She said it is important to encourage children to speak up, think independently, and not be constrained by stereotypes, noting that an environment where girls feel safe to express their views and challenge ideas helps build resilience from a young age.
She also cautioned against reinforcing traditional gender expectations, highlighting that subtle biases in everyday interactions can influence how girls perceive their own potential.
Beyond gender, she stressed the importance of a play-based childhood over one centred on mobile devices, pointing to research linking higher screen exposure with rising levels of anxiety and depression among younger generations.
Importantly, she highlighted, children should also be given space to navigate challenges on their own, rather than having problems solved for them, as this allows them to develop confidence and learn through experience.
Images / DBS
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