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4 Reasons Why Job Hunting Is Like Dating

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With Valentines Day right around the corner, love is truly in the air. However, there has been a recent trend of Singaporeans enjoying the dating phase a little too much and rarely reaching finish line of settling down. This increasing trend of dating without labels could be attributed to the abundance of choices from the several dating apps in the market.

In the working world however, this is the opposite. Job seekers are yearning to settle down and choices have gotten more and more limited due to COVID-19. However, there are quite a few uncanny resemblances between dating and job hunting. Here are the 4 similarities I have narrowed them down to, after speaking to senior recruiters in my professional network on what uncommon wisdom they can share with prospective job seekers.

1. Personal Profile

Much like your dating profile on dating apps, your personal profile be it on LinkedIn or Job Portals are highly crucial in determining whether you get a reply from the jobs you’re interested in or not. Whether you’re considering switching your line of work or looking for your next career challenge, we could all get better at positioning our personal brand in the market.

Lisa Campbell
APAC Director at Cogs Agency

“These computer systems can automatically dismiss amazing candidates because their CV does not specifically ‘word match’ the job description,” said Lisa Campbell, the APAC Director of Cogs Agency, a global specialist recruitment firm.

If computer systems are determining the odds, what can job seekers do?

2. Helpful “Stalking”

Elena Chow, Partner at ConnectOne advice job seekers to show a demonstrate a deep level of interest to their prospective employer. She shared the following example.

Elena Chow
Co-founder of ConnectOne

“It might be a small thing but it shows the level of involvement, diligence and attention to detail. All very important traits for a start-up company requiring one to be all hands on deck,” said Chow.

3. First Impression

Just like how you would spend hours picking and then re-picking your outfit for your first date, the same level of preparation is put into appearing smart and clean to your interviewers. Why? It’s all to create that stellar first impression so that they remember you positively and hopefully, you stand out from the sea of candidates they have been speaking to all day.

However, your appearance isn’t the only factor when it comes to forming first impressions. What many job seekers forget is how they come across during the job interview itself when they are answering questions and speaking to their interviewers for the first time. This moment can be highly impactful and can make or break your interview, making the interviewer either sit up a little more and lean in to listen or subtly strike off your name with their pen as they allow their mind to wander to where they should go for lunch as you ramble on.

Roger Grant, the Co-founder of PERSONNA, a leadership development company focused on the people side of transformation, kindly shared the repercussions of being loquacious for the wrong reasons during an interview as well as a relatable analogy to help us understand his point better.

Roger Grant
Co-founder of PERSONNA

“If you approach a girl in a nightclub and talk only about yourself, don’t be surprised that she thinks you’re a jerk and walks off never to be heard from again,” said Roger Grant, Co-Founder of Personna.

“Trying too hard to make a first impression could backfire but “not making an impactful introduction is an extremely common mistake.”


4. Conversation

Once a great first impression has been established, the journey does not end there. In order to successfully get your date to agree to go out with you on a second date, in this case, to hear back from your interviewer, you have to make sure your conversational skills are on-point. Chow encourage job seekers to be “persistent, without being irritating and to be humble about their gaps in their competence.” Now this can be harder than it looks and it’s really about maintaining that delicate balance between selling yourself and humility.

Abigail Lim, the Senior Talent Acquisition Partner at ExpressVPN, shared her views on this point as well on how she notices many job seekers these days being too rash on judging the companies they successfully manage to score an interview at.

Abigail Lim
Senior Talent Acquisition Partner at ExpressVPN

Abigail continues her sharing on her LinkedIn feed, saying, “Instead of why? Ask why not?—As long as the conversation is productive, you will walk away with a new name in your network, learned about a business that you are not familiar with and/or even functional knowledge that you have forgotten or not been in practice. It’ll be a bonus if you walk off excited with a new professional chapter in sight.”

“Instead of why, ask why not?”


Chow echoed the sentiment adding the following observation, “In Indonesia, Vietnam and Thailand, talent shortage is a real concern—with many talented individuals preferring to do their own thing than to be employed.”

Perhaps job seekers may also consider growing professionally with fast growing companies in developing economies and carve their own niche through their work. There’s always options out there, as limited as they can seem to be and it all comes down to opening our minds more, researching thoroughly and making the right connections.