5 Things I Learned About Dating From Job Interviews (And Vice Versa)

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Carrie Bradshaw once famously said, “In New York, you’re always looking for a job, a boyfriend, or an apartment.” Well, just add “better” in there and we are all set.

Not too long ago, fresh out of grad school, I had found myself job-less, boyfriend-less, and apartment-less. A literal Triple Threat, if you may. I began my journey to actual adulthood by tackling the job issue, while using dating to distract myself from obsessing over unanswered job applications. Perhaps this isn’t so shocking, but there was actually significant parallel between the two, whether it be the gruesome uncertainty of the process, the reality of limited opportunities, or the paralyzing disappointments that had become a norm.

Eventually, everything turned out okay. I found an amazing job, which, one year later, has afforded me the opportunity to hire my own intern. While I’d always pined for this day when I’d finally be in the Seat of Greater Power, I was shocked to find that over the phone interview with the candidate, I was just as nervous as the person being interviewed. I stumbled over my sentences, sounded naïve and unsure, and asked horrible questions that failed to let me optimally evaluate each candidate.

By my third interview, I was starting to appreciate having sat at both sides of the table. I thought about the parallel process of dating, and perhaps even trying to find an apartment to share with a future roommate, and I came to a simple epiphany: being successful in any of these things required the fundamental skill of being able to sell well. In these specific cases, you’re not selling a product or a service, but rather, just your good old self.

So I’m going to share with you some tips that I’d personally observed to work. They can be applied to just about anything that involves making a positive impression on a one-on-one basis. It’s not meant to be some manipulative list you can check off to “trick” people into giving you what you want. It’s really about genuinely finding that perfect fit for you, one that is also sustainable.

1. Have a very specific list about exactly what you want.


And along with that, what you don’t want but can possibly tolerate, and what you absolutely cannot stand. When I was interviewing candidates, I was hesitant to stick to the job requirements I’d drafted in fear of being irrationally judgmental — what if I miss out on the best candidate because they didn’t check off one item on a stupid list? But without a hard list, your judgments become soft. By not producing such a list (whether mentally or on paper), I was cheating myself by making do with those who were not best fit for the position. Easy? Yes. Comfortable? Yes. Sustainable in the long run? No. Be real about what you want, and don’t feel guilty about it. After all, once you know what you want, you’re half way to the finish line.

2. Don’t share everything about yourself in the beginning.


Everyone loves to talk about themselves. We’re all human — it’s a built-in weakness. The key is to reveal information in a targeted manner. Think about if you were to create an online dating profile — you’re not going to write out a 100-page autobiography that includes things like what you had for breakfast. If you have, you’re either an ineffective communicator, or just really, really self-absorbed. People’s attention spans are extremely limited, and while you’re talking, they’re probably thinking about themselves. So only say things that make your audience relate to you, so they think, “Oh my god, she gets it! I like her.” This is why, during a job interview, you highlight those past experiences that demonstrate similar day-to-day work as the one you’re interviewing for. This is also why, during a date, you try to talk about things you have in common.

3. Listen. Don’t pretend to listen.

One of the most undervalued skills in management that I’ve come to appreciate is good listening. Employers hardly ever emphasize this on a job ad, and while everyone wants to share his or her life with a “conflict resolver”, what does that really entail? Good listening skills. This doesn’t mean you stop having an opinion and become mute. Quite the opposite: it means you are genuinely interested in the conversation, and can follow up with smart questions that further stimulate the other person’s interest. The goal is to make this person feel valued, like their time spent on you is not wasted. Fundamentally, I think this really comes down to open-mindedness and being able to step — however temporarily — out of your thought bubble brimming with your own life problems. I mean, hey, we all got issues, but there are better situations to brew over them. Like, over alcohol.

4. Don’t try to hide your imperfections.

If you read comic books, you’d know that heroes are rarely exemplified through perfection, but rather through natural imperfections that they overcome with perseverance. Perfection is nice on the outset, but if you really think about it, it makes a person un-relatable, even intimidating. “What is one of your weaknesses?” I once asked a candidate. “Uh, I’m a bit shy sometimes around people,” he replied. Inadequate answer, but I’ll take it. “What is another one of your weaknesses?” “Um….nothing. That’s it, haha.” Needless to say, he didn’t get the job. Don’t try to pretend you have no faults, because people can easily see through that. Be honest about yourself, but even more importantly, proactively share the million ways you’re trying to improve and be better. This shows drive, confidence, and self-leadership — hallmarks of personal and professional success.

5. Passionately stand for something.

Once I asked a senior partner at my firm for networking tips. I was about to be thrown into a sea of senior executives who were also potential clients, and I had to figure out a way to seem older than I was (25) and wiser than I was (um), to start building relationships with them. “What should I talk about? Our thought leadership?” I asked. She then asked me a whole bunch of unrelated questions, mostly about myself — my education, why this job, why this company, why this industry. And as I spoke, I realized I was speaking with far more conviction than I ever could about my firm’s “thought leadership”. When you speak passionately about something (anything), people listen. This, of course, requires that you have a strong sense of self and know what you stand for, but once you do, your presence will captivate, and you will naturally win friends and influence people.

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