After 11 years at MINDEF, I found myself itching for a new challenge. It was time to explore the private sector and see if I could scratch that curiosity itch. To give you some perspective on how long I’d been in my previous role—if you’d had a child when I started, they’d be a year away from taking the PSLE now.
But job hunting wasn’t as easy as I thought. It wasn’t that I lacked skills—I’d been offered a full-time position during an internship at an advertising firm in London just four years ago. What I didn’t realize was that, just like dating after a long-term relationship, the game had changed. I wasn’t familiar with the new “rules.” In the same way you’d struggle to navigate a new dating scene after being happily married for a decade, I found myself out of step with the job market. For me, the turning point was realizing that AI filters were automatically rejecting resumes without the “right” keywords. I had been applying for months with zero success—it was a rude awakening.
A former colleague told me, “Interviewing and landing a job is a skill in itself.” It didn’t hit me until I started applying for jobs. So here I am, sharing what I learned, paying forward the advice I’ve gathered along the way.
Tip 1: Network Smartly—Leverage Your “Peripheral Friends”
The quickest way to bypass AI filters? Get a referral. Of all the interviews I secured, only one wasn’t through a personal connection. In fact, LinkedIn research shows that 80% of successful job seekers get their referrals from distant acquaintances, not close friends.
At a networking event, I casually asked around if anyone knew of companies looking for political analysts while grabbing dessert. A week later, I had an interview with HR at a shipping company. Another time, I reached out to a former military colleague who now works at Meta, after hearing him on the podcast Purple Light discussing how SAF personnel transition into civilian careers. He recommended me for two positions at Meta.
Asking for favors can feel awkward—I’ve been there. But it’s not begging; it’s a win-win. People love to help. I experienced this firsthand on my last day at MINDEF when I met a potential recruit interested in joining my team. Even though I was leaving, I still took the time to help guide him. It gave me a deep sense of fulfillment.
Tip 2: Reframe Your Answers Around the Interviewer’s Pain Points
Early on, I thought, “If only they’d ask better questions, I’d impress them.” Then I realized—it wasn’t the questions that needed improving, it was my answers. Inspired by New Sales, Simplified by Mike Weinberg, I started crafting what he calls a “power statement”: short on what I do, long on how I solve the company’s problems. This became the framework for my interviews.
For instance, in an interview with a shipping company, I framed my response like this:
“I know your expansion into Vietnam hit a snag due to political instability—the PM you worked with was ousted. As a geopolitical analyst, I could have helped foresee this and advised on strategies to mitigate disruption. In 2021, I helped policymakers handle similar risks by [insert specific contribution].”
When I interviewed at Mastercard to build an all-threats intelligence center, I emphasized my unique skills:
“You’re building a team from scratch, and I thrive in that environment. In my previous roles, I spearheaded new initiatives across multiple domains, from counterterrorism to cyber threats. [Insert specific contribution]”
Tip 3: Tell Stories that Stick
Initially, I tried to cram my entire career into each interview, which led me to speak too fast and miss impactful moments. But Yuval Noah Harari, in Sapiens, reminds us that humans are wired for stories—the simpler, the better. So, I started crafting concise, punchy stories and practiced them aloud at least ten times before each interview.
For example, when asked about soft skills, I shared this personal anecdote:
“One of my most valuable soft skills is knowing when to put ego aside. I once wanted to get my dad into stock trading—not for financial gain, but to keep his mind sharp and ward off dementia. He wasn’t interested, so I pretended I needed his advice. His instinct to protect kicked in, and he dove into the market to help me. This taught me the power of stepping back, which has been invaluable in building effective teams.”
Tip 4: Turn Awkward Silences Into Opportunities
Zoom interviews can be full of awkward silences, especially at the start. Instead of offering a bland “How are you?” response, I’d turn the moment into an opportunity to stand out. Inspired by How to Talk to Anyone by Leil Lowndes, I’d say:
“I’m great! Just finished a night class on English-Chinese translation, and my brain’s still buzzing.”
This invites conversation and shows that I’m a lifelong learner.
If a technical issue happened mid-interview, I might say:
“I must have been so boring that my internet fell asleep!”
Tip 5: Build Rapport—Find Common Ground
Before each interview, I’d research my interviewers on LinkedIn. Finding common ground can work wonders. During an internal interview for an overseas posting, I said:
“I’ve been here for 11 years, and I remember you running around the office in heels while heavily pregnant. Now your child is taking the PSLE—that’s how long I’ve been here!”
And when highlighting similarities, I’d say:
- “Like you, I started competitive sports as an adult. Competing with those who’ve been doing it longer takes grit. That same grit shows up in my work.”
Tip 6: Adopt the Right Mindset
Mindsets matter. I’ve seen it firsthand with my cousins, who all became entrepreneurs. Meanwhile, my sister and I stayed employees. The key difference? Mindset. Their dad was an entrepreneur, so they grew up believing that was the natural path.
The same applies to job hunting. Here are some mindset shifts that helped me:
Deliver with passion—be enthusiastic about the role because you know you’ll excel and make a difference.
Be confident—believe the job was written for you.
Enter the interview as if you’ve already got the job.
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