Applying for your dream job

May 21, 20207 min read

Photo by Drew Hays on Unsplash

Finding our dream job - one that fits our ikigai - is one of the few most important decisions we can make.

Most of our adult waking hours are spent at work. Nothing is more miserable than feeling trapped, under-appreciated, and alienated in jobs and companies that we don't like.

In my previous companies, I have read thousands of resumes and interviewed close to a hundred applicants.

Here are some perspectives and tips you might find helpful.

Table of Content:

  1. Referral
  2. CV / Resume
  3. Hunger / Indication of Interest
  4. Interview
  5. Asking Questions
  6. Junior vs Senior Roles
  7. Likeability Trumps Intelligence

0 - Referral

None of your resume and interview preparation matters if no one reads your resume.

These days, if you apply through a system, chances are your resume will be filtered out by the system or by screening H.R. before it gets to the eyes of the hiring manager.

If you are interested in a company, the most effective way of applying is to get referral. If you know someone in the company, ask them to put in your resume.

f you don't, find someone in the company through LinkedIn, even if it is a second-degree connection, e.g. someone who is an alumnus of your school. Get on a 15-minute call to learn more about the company. If it is a huge company, you need to be more selective and try to find someone in the right team for referral.

After college, a friend of mine applied to 200 companies. And out of the 20 companies that got her an interview, 18 of them come from referral.

1 - CV / Resume

I usually spent only a few seconds to skim through a CV before discarding it or bookmarking it for deeper scrutiny.

That means, within a few seconds, you need to be able to grab attention and tell your story clearly.


Tell a focused and coherent story. Remove everything else that doesn't support the narrative.

Humans have a tendency to categorise and box things into "labels" - make sure you give them the labels clearly and strongly.

If you are an engineer, you want your CV to convey:

  • experienced engineer
  • has built large-scale modern application
  • always learning new technologies

If you are in sales, you want these labels to come across immediately:

  • proven sales record
  • understand our industry

Less is More

Focus on the 2 most relevant and important experience. Don't clutter your CV with things just because it might look good.

If you have 5 years of working experience, don't include your 3-month internships during your university days.

If you are a designer or developer, pick your 2 best projects in your portfolio, instead of a list of 10 small projects.

Summary / Highlights section

Some people add a summary section at the top of CV. But most of these summaries are generic and a waste of attention and space.

You should only consider adding it to tie up your story if your background is non-standard.

And if you do, try not to write more than 2 sentences.


  • "to utilise my skill set and passion to help company achieve objective"
  • "goal-oriented, highly motivated, good leadership skill"

Do (maybe):

  • "Tech Lead with over 10 years of experience in fast-growing tech companies, seeking to help elevate the engineering team"
  • "Head of Sales with expertise in B2B SaaS, looking to help grow my next company 10x"



Don't do this

Don't list common interests such as traveling, photography, or cooking, unless you have a cooking youtube channel or a photography blog.

If you are a part-time DJ, or a national poker champion (heh), by all means include these.

Ignore adding interests if there's nothing outstanding or if it doesn't fit your story.

Also, you don't need to add "languages" unless it is relevant to the job. Your beginner level of Italian is not very interesting or impressive.

If you add Microsoft Office as your skills, god bless you.



Don't list 4 schools

I honestly don't care about this, unless you went to the top schools in your field.

List only your latest school, unless your high school is a strong signifier (e.g. Raffles / Hwa Chong in Singapore).

Also, don't care about your "relevant coursework", "co-curricular activities" or "community service" at school. Unless it is unique or relevant to your story.

Does knowing that you are "Vice President of XXX University Music Club" helps?

Instead, focus more on what self-initiatives and courses you have been taking, outside the normal schooling track, to learn and grow.

Skills Rating


Don't do this

Some candidates has a "skills" rating section.

Please don't do that.

Trust me, nothing good will come out of this.

Whoever invented this have done a disservice to mankind.

2 - Hunger / Indication of Interest (IOI)

If a candidate doesn't understand my company well, either through a cookie-cutter Cover Letter or failing basic question during interview, the candidate will be rejected immediately.

It shows a lack of hunger and interest in the role.

This seems like common sense, but a good 30% of candidates I've encountered failed even a simple "what do you know about my company" question.

A few things you can do to convey strong IOI and an insatiable hunger:

  1. if the company has a product, make sure you sign up and use the product. Share your analysis and thought process either in Cover Letter or during interview.

  2. do some work to show you're ready to hit the ground running. Some real-life examples I've seen:

    • came up with a marketing strategy and user acquisition plan when applying for a marketing role.
    • designed, built, and demo-ed an app to show his understanding of app development when applying for a technical project manager role. Needless to say, this guy went on to be an absolute rockstar in the company history.
    • wrote an email to startup CEO with a business plan - with market analysis, user pain points, competitive landscape, etc - for a role in said startup. I did this and got in.
  3. if you are making career/industry switch, make extra effort to explain the "why", elaborate your interest/passion in the new industry, and show how your different experience and perspective can be valuable.

It is true that for some, your stellar credential and CV speaks for itself.

But for most people, this is the best way to make yourself stand-out and show your character.

3 - Interview

I usually made up my mind within the first 5 minutes of interview.

The rest of the 30-40 minutes of interview is merely for the candidate to prove me wrong — but more often than not, my initial assessment stood.

My methodology might not be systematic or scientific, but I suspect most hiring bosses share the same intuitive approach.

SoftBank CEO Masayoshi Son famously invested in Jack Ma's Alibaba before they had any revenue, partly because "his eyes were very strong", i.e. Jack Ma's force of personality. The same approach might have led him to the fiasco of WeWork's Adam Neumann, but that is another story.

If a candidate made it to the final interview round, he/she usually has the requisite hard skills/knowledge for the role. Thus, the in-person interview is more to judge a candidate's soft skills and fit.

These are what go through my mind as the final hiring manager during an interview:

  • will I enjoy working with this person?
  • culture fit: can this person work well with people in the company?
  • attitude: is this person hungry and willing to learn?
  • how does this person deal with failures and mistakes, or react when things go rough?
  • is this person personable and likeable, someone human and relatable?
  • thinking: does this person listen well, and does his/her answers show coherent and mature thinking process?
  • passion: does his/her eyes lit up when talking about his/her proud achivement/project?

Having a good sense of humor helps too — more specifically, the social awareness and confidence to carry humor in a supposedly tense interview situation.

4 - Asking questions as a candidate

A good mental model to approach a job interview is to view it as a two-way process, both parties trying to get to know the other, much like a dating process.

And that means asking good and earnest questions to learn more about the company and the job.


  • ask questions for the sake of asking
  • ask questions to sound smart and coming across as smug

Some reasonable questions to ask:

  • "What will my KPI look like in the first quarter and the first year?"
  • "what does a star performer look like in this role?"
  • "How does the growth path of this role look like?"
  • "Who will I be working with and reporting to?"
  • "How is the design/sales/engineering culture like here?"
  • "Where is the next growth frontier for the company?" note: this is not an easy question to pull off. ask this only if you have talked strategies with the CEO/top executives; don't just abruptly ask this to HR.

Asking good questions achieves a few things:

Firstly, a job is a huge commitment. so you want to know what you're jumping into.

Secondly, it is a good indicator of interest from your part.

Also, people like talking about themselves, and companies are no different.

Lastly, it levels the power dynamics. When a company knows that you are not desperate, that you have standards, and that they are being evaluated, it subconsciously elevates your value in the company's eyes. Similar principles when it comes to dating — have standards and don't be desperate.

There is a famous saying: "people don't leave bad jobs, they leave bad bosses".

If possible, find out if your direct manager is interviewing you, and make sure you evaluate the manager too, since, well, you have standards and only want to work for someone who've a good fit.

5 - Junior vs Senior roles

There are common elements to evaluating both junior and senior roles — communicate well, motivated and driven, personable, dedicated, and having requisite skill set.

However, in more advanced roles, there are extra things to consider in the decision matrix:

  • network: when we hire this person, who is he/she bringing along (clients, employees, industry contacts etc). When we are marrying someone, we are also marrying the family.
  • track record & referral: is there a history of excellence, does the candidate's past co-workers and clients have good things to say about him/her?

6 - Likeability trumps intelligence

In almost every job application, there is a final gatekeeper - a human person making the call whether to hire/reject.

For 2 candidates with similar qualifications, if the gatekeeper likes you more, you will get in. The gatekeeper will be your internal champion, to promote your candidacy and push you through the door.

Unlike A.I., human beings have preferences, biases, and flaws. And almost universally, we have preference towards likeability.

What constitutes likeability?

If you have watched the AlphaGo documentary — I highly recommend it, it's released free on Youtube — the Chinese chess dude Fan Hui is an embodiment of likeability.

Someone with earnest passion.

Someone with vulnerability.

Someone we can identify with and root for as human.

He does not try too hard to please or be likeable. He's simply being himself and showing his character.

It is difficult to advise how to increase your likeability. But just know that if you let your personality shown, and if the company doesn't like what they see, that means the company is not a good fit for you anyway.

Thank you for reading

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