How to Play the Career Dating Game

Finding a new job is like getting a new boyfriend/girlfriend.  You need to be confident, not desperate.  A cool indifference seems to work well, but careful toeing the line between attentiveness and neglect.


Keep in mind that you are always more marketable when you’re taken.  Never search for a new job or a new significant other until you have found an upgrade because truthfully, nobody wants someone who’s unemployed or forever single (red flags galore).

And as a general rule, the more attractive the job or person, the better your options will be in the future.  If someone sees you strolling down the street with a handsome guy or beautiful woman, they will be far more likely to stop and notice.  Similarly, if a recruiter or hiring manager notices a resume from a candidate working at a Fortune 100 company, they are more likely to review it.  Your past can and probably will dictate your future.

The following article will provide guidance on navigating the application, interview, and negotiation stages.  It will conclude with hazards to look out for along the way.  Happy hunting (or applying)!

  1. Applications

Job applications are a nightmare.  Before you’re even ready to approach that cute girl or guy at a bar, you need to prepare.  You would not wear a five-year-old faded shirt when single and ready to mingle, so do not treat your resume the same way.  Just as your appearance and personality are your key marketing tools when dating, your resume is your primary device to persuade employers to interview you.  Enhance the sex appeal.  Be organized.  Nobody likes a slob.

Your resume’s format is almost more important than its content.  If you present an aesthetically pleasing document (always in PDF format), where the rows and bullet points align, chances are it will be viewed favorably.  Of course, compelling content to support a well-organized resume will take it to the next level.

If you’re straight out of school, you have almost no choice but to lead with your education and anything interesting you did outside of the classroom.  And if you have nothing to say for the latter, consider volunteering a few times doing anything that interests you.  Or get a part-time job so you can at least show you have a work ethic.

If you are experienced, lead with it.  Gloss it up just before reaching the land of hyperbole.  As with dating, you need to sell yourself.  Nobody else will do it for you.  If you act like you were the only person who could have completed that project at work, or if there’s nobody more interested in [insert cute guy/girl’s interest], it’s not misleading.  It’s smart.  There is a big difference between puffery and lying.

And do not even consider extending your resume beyond one page.  Unless you have 20 years of experience or you’re a professor who has published over ten books and articles, nobody will be impressed.  In fact, they will question why you think you’re so special.  Most of that additional information is probably superfluous anyways.  Condense what you have and make it snappy, punchy, and eye-catching.

When it comes to cover letters, stop.  Never send anyone a cover letter unless it’s your dream job and the online application actually requires it.  They are a waste of time and countless HR and recruiting professionals have assured me that nobody reads them.  If your resume has not convinced someone to grant you a phone interview, even a cover letter drafted by Hemingway will not persuade them otherwise.  Imagine sending someone a drink at a bar with a long note attached.  If your drink gesture does not capture their attention, your prose does not stand a chance.

  1. Interviewing

Assume you’ve made it past the application stage and you’re finally seated next to that beautiful person you noticed across the room.  You’re talking!  This is the big moment you’ve been waiting for since submitting your application.  The key mindset to have is that you’re interviewing them as much as they interview you.  Investing substantial time in a job or relationship will impact your future significantly.  Although it is easy to fall in the trap of purely selling yourself because you want the position, force the other side to sell what they are offering too.  You will spend many of your waking hours at that company or with that person, and your time investment will follow you for the rest of your life, whether it’s on your resume or in casual conversation when asked about your past relationships.

Some key questions to ask include:

  • Is this a new position? If not, why did the previous person leave?  (applies equally to jobs and dating – if the person before you was fired, you’ll want to know why)
  • What is the make-up of the team I would be joining? (you should find out who you will be working with everyday, or who you’ll be forced to have brunch with on the weekends)
  • What is the typical day-to-day like in this job? (the more open ended the better – you’ll get a more human response)
  • Drop some knowledge: I recently read [insert recent news about company or person/interest they have]. How has this event/news impacted the way the company/person operates now? (this shows you’re already invested in learning more, and that you’re prepared)

Regardless of who you’re speaking with, it’s crucial to get them talking.  In general, the more they describe the position, the more you’ll learn, and the more the onus will be placed on them to sell it.

Other key points:

  • Always greet your interviewer with a firm handshake while standing. You should never shake someone’s hand while sitting down unless they are also sitting.  And if your handshake is weak, you’re probably a weak candidate too.
  • Maintain eye contact, but do not stare. This skill comes naturally with practice.  You want the other person to know you’re engaged, but you’ll come off as a creeper if you never blink or look away periodically.
  • Body language is crucial – face the person directly (if at a bar, turn your stool). Perhaps even lean in when making a point you want to emphasize, but keep a comfortable distance.  Nobody likes close talkers.
  • If they offer water, juice, coffee, etc., always accept it. Water is sufficient.  You look awkward if you attempt to brush off the offer.

The main takeaway through all of this is to remember that you’re having a conversation.  While you should always have a few questions (3-4 good ones) in your back pocket for the end of the interview when you’re inevitably asked, “So, do you have any questions for me?”, you should try to ask questions throughout.  Be human.  Even though it’s a formal interview or the first icebreaking conversation with the potential love of your life, simply pay attention and ask questions.  If there is a match, the rest will happen naturally.

  1. Follow-up / Negotiating Salary

After interviewing, wait until the next morning before sending a thank you e-mail.  If you do not have the direct contact information of your interviewer(s), contact whoever helped organize it with a draft e-mail, politely asking them to forward it.  The same is true for dating – if you really liked the person, send them a text the next morning or afternoon.  Not only does it get them thinking about you again, but if you’re able to emphasize a funny exchange or primary talking point, you only stand to benefit.  Do not be overly aggressive, however.  Two to three sentences is sufficient, and by waiting a while before sending your “thank you”, you will appear appreciative, not desperate.

So you convinced that beautiful person to go on a couple dates?  You were invited back for multiple rounds of interviews?  Now you’re asked the pivotal question: what’s your salary expectation?  Please note: if you work in New York City it’s now illegal for employers to ask for your current salary.

Before having this conversation, you should have a good idea of what you want.  What are you satisfied with based on your skills?  Have you done market research through Glassdoor or simply searching your job and average salary?  Are you happy if the person you’re about to date expects you to take them to dinner every Saturday night?  What will it take for you to endure that one annoying habit you cannot stand?  That is how much you should be paid.

Human Resources at most companies speaks in total compensation.  This means they will offer you a number that includes base salary and bonus or projected commission.  Depending on your industry, most of your salary may be determined by bonus or commission, and remember: regardless of industry, that amount is discretionary based on your numbers (PnL if in finance) and overall company performance.  If you expect a smaller bonus, make sure you negotiate a base salary you’re happy with at the end of the year.  Because bonuses are just that – uncertain.

For that reason, remember to aim high with your salary.  The person offering you the position is not quoting you a salary from their bank account.  Sure, they have a target range, and their job somewhat depends on hitting it, but everything is negotiable if you have the skills and experience (and/or looks) to back it up.  At the end of the day, it comes down to bargaining position, regardless of whether you’re negotiating for a new relationship or job.

  1. Hazards

Throughout this entire process, whether it’s applying for a new relationship or job, you will run into a number of hazards along the way.  Tread carefully with the following:

  • Recruiters: They are not your friends. They are not your agent.  And they are certainly not required to act in your best interest.  Remember that any company you apply to through them already has an agreement on file, paying the recruiter a commission only if they help the company hire someone.  That someone may not be you.  Understand the incentives before divulging too much information or placing too much trust in a recruiter, especially one who says they’re going to fight for you to get the job.
  • Best Friends: The recruiter corollary in the dating context are best friends. The best friend(s) of a prospective boyfriend or girlfriend is inherently biased.  There are some objective friends out there who will provide kernels of truth, but if you’re relying on what they say more than your gut, you have a problem.  Be with the person because you want to be there, not because their best friend painted a rosy picture about your future together.
  • External Influencers: As with “best friends”, in general, do not allow anyone to unduly influence your decision. Seek advice and consider different perspectives, but remember that your future belongs to you and nobody else.  Influencers will not have to endure that new job or new boyfriend/girlfriend on a daily basis.  You will.

Jobs and significant others go hand-in-hand.  They both involve a courtship process.  You have to play the game if you want to succeed in either.  Finding your perfect match is not always easy, but with persistence and resilience, a beautiful future awaits.

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