Think like a boss: Lessons from women who lead with fire and grace

Hybrid fatigue, AI disruption and economic uncertainty are changing the rules – surviving isn’t enough. Professionals who learn to think and perform like leaders – acting decisively to find solutions, learning from setbacks and taking accountability – will be better poised to deal with the increasing demands and challenges of today’s workplace, no matter your role or position.

According to a 2025 McKinsey report, companies that consistently outperform in growth and profitability share five critical leadership mindsets: boldness, long-term thinking, customer obsession, rigorous execution, and talent development.

But while these traits sound lofty, they’re made real by those who embody them every day, whether they’re building a fintech platform, restructuring global teams, or navigating burnout.

We speak to four women in Singapore who are redefining what it means to lead – by taking ownership, nurturing others, and making bold moves with clarity and conviction.

Focus on your responsibilities

Cassandra Riene Tan, founder and CEO of The Well Group, is no stranger to reinvention. Having built ventures ranging from tech start-ups to wellness cafés, she says a boss mindset is less about bravado and more about personal accountability.

“Even before I was officially in charge, I’ve always treated budgets, clients and timelines like they were mine,” Cassandra recalls. “You don’t need the title to start thinking like a boss or leader. It begins with how you carry your responsibilities.”

That sense of ownership, she says, must be tempered with compassion – both for the people and the outcomes. One of the hardest lessons? Letting go of employees who don’t align with the evolving needs of the business.

“A nice person isn’t always the right person for that season,” she explains. “Being clear and kind protects the wider team’s health.”

Take ownership of outcomes

This echoes the approach of Fernn Lim, chief operating officer at Audax, a digital banking platform backed by Standard Chartered. She believes “boss” is an overrated word, but “ownership” is not.

“Whether you’re a junior analyst or a COO, you can think like a boss if you’re clear about what you’re accountable for, and willing to own the outcome,” says Fernn, who has helped scale multiple fintech ventures from zero to one, steering Audax’s expansion into multiple markets.

In an industry where stakes are high and information is often incomplete, Fernn relies on fast, informed decision-making: “You don’t always have the luxury to overthink. You make a business call and stick to it.”

But the work doesn’t end with decisiveness. Resilience is also important. “Success isn’t about winning every game. It’s having the stamina to stay in the game and win the next one,” she says.

Sustaining success with stamina

Sustaining that stamina, however, requires a fundamental shift in how we view performance – especially for high-achieving women who are used to equating output with worth.

Fernn, who once lived on four hours of sleep and eight cups of coffee a day, now maintains a regimented morning gym routine. “I used to wear exhaustion like a badge of honour, but I’ve learnt that health is performance,” she says.

Foo Siew Ting, former global chief brand and insights officer at HP Inc. and author of Building Brands with Soul, shares that same lesson. “You can’t pour from an empty cup,” she says. Her leadership rituals now include annual retreats, meditation, and rest, deliberately scheduled into her calendar.

Siew Ting calls herself a servant leader, and she sees self-care as central to the job. “To lead with soul, you need energy and empathy. That doesn’t come from burnout,” she says.

Nurture, mentor, lead by example

Across all four women, one theme is constant: They lead by developing others.

“I try to stretch a person’s potential by assigning roles that empower them,” says Siew Ting, who evaluates mentees not only by performance but also by values, moral compass, and willingness to grow. “Output matters, but so does motivation. It’s about what drives someone, and whether they can evolve.”

For Fernn, “curiosity, purpose, and a bias for action” matter more than credentials. “You can always teach skills. The people who ask why and take initiative are the ones you grow.”

Rocky Esguerra, who previously held senior HR leadership roles at P&G, Pfizer and Heineken before founding her own executive coaching practice, reminds us that mentorship is also about modelling behaviour. Having led major restructurings across Asia-Pacific, she never lost sight of the human cost.

“Throughout my career, I’ve had to lead major restructurings that impacted hundreds of employees,” she says. “The business needed agility and efficiency, but these were people with families and futures. Tough business calls can and should be made humanely. You may need to take away someone’s job, but never their sense of worth.”

Learn from our failures

Developing talent, however, also means preparing people for setbacks. Mentorship is not only about spotting potential but also about showing how to recover when things don’t go as planned.

All four women agree: Failure isn’t the opposite of success – it is part of it.

“Early in my career, I took rejection personally,” says Cassandra. “Now I see it as part of the process. If I’ve acted with integrity, I trust the timing, even if I don’t like the outcome.”

Rocky adds a tactical frame: “Failure is feedback. And if you’re never failing, maybe you’re aiming too low.”

She invokes the “Spotlight Effect” to illustrate how often we overestimate how much others are watching us. “Most people are too busy living their own lives to obsess over our failures. So don’t let one misstep define you,” she says.

Her advice to women feeling stuck? Reconnect with your values. “Sometimes we feel lost because we’ve been living someone else’s dream. Figure out what truly matters to you, and design your life around that.”

Master the boss mindset

• Leadership isn’t tied to titles: You don’t need to be a CEO or founder to think like a boss; it’s about mindset and action.
• Action matters more than ambition: McKinsey’s 2025 research shows that what separates high-growth leaders is not intent, but execution.
• Ownership is key: Treat projects, budgets and outcomes as if they were your own. Accountability builds influence.
• Momentum starts small: As Cassandra Riene Tan puts it, progress comes from taking the first step – whether it’s starting a website, attending an event, or applying for a role.
• Risk-taking drives growth: Leaders distinguish themselves by making bold, informed decisions instead of waiting for perfect certainty.
• Resilience sustains success: Failures and rejections are part of the journey; the best leaders bounce back quickly and use setbacks as feedback.
• Self-care fuels leadership: Energy, empathy and stamina – sustained by rest and routines – are non-negotiable for effective leadership.
• Talent development multiplies impact: Great leaders don’t just deliver results themselves. They nurture curiosity, initiative, and potential in others.