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What Business Leaders Can Learn From Online Dating

This article is more than 9 years old.

“All he did was talk about his past girlfriends,” she said. “It was probably one of the worst dates I’ve ever been on.”

These are comments we overheard by a woman talking to her friend at a recent HR conference we attended. We simply couldn’t resist leaning further into her conversation when this spirited, well-dressed and very vocal woman spoke her next sentence: “It was like he was giving me his resume of failed relationships.”

Those were interesting word choices. We wondered, “Is this the kind of thing that companies are requesting from job candidates—a list of failed relationships and uncomfortable separations?”

According to an article in Business Insider, the very first resume on record was written by Leonardo da Vinci in 1482. Its purpose, back then, was more of a written introduction—a chance to say hello to someone you don’t know—than a document used to outline and communicate skills, knowledge, and career history like it is today.

Through time, the resume evolved and eventually it became standardized—where certain expectations, rules, and guidelines dictate whether your document is sufficient. No longer just a letter of introduction, today’s resume acts as a filter (both in good ways and bad ways) for organizations to quickly process candidates.

It is interesting to consider how the current resume structure affects the kinds of questions we ask in a job interview. The questions naturally orient themselves around the work experience on the resume.

Comparing today’s resume with a first date, why do we focus so much of our attention on where a person has been rather than where they want to go and what they want to become part of?

Match.com claims to have launched the first online dating website in 1995. Its purpose was much like it is today—to match compatible people in a hope that they could create a long-lasting relationship. Over the next several years, other online dating sites such as eHarmony, Zoosk, Mate1 and Tinder jumped into the market and attempted to play cupid.

Are the questions being asked on online dating sites more effective than the questions asked by a hiring manager? Are the types of conversations in online dating communities more effectively focused on predicting successful relationships?

As important as it is to see what kinds of questions are being asked, it’s also fascinating to see what the dating sites don’t ask. We don’t see the same fixation on previous experience as we do in corporate settings. Some of the questions asked by online dating sites to determine compatibility that we found most intriguing (not in the exact wording, but a conceptual generalization of what we found) were questions like:

1. How do you like to spend a Friday night or weekend day?

Although online dating services that use algorithms to determine ‘fit’ would typically list multiple choice answers to questions that try to assess how a person spends their free time with or without a partner, we found these questions intriguing because they reveal a person’s truest interests. In fact, these types of questions (often breezed over in a job interview) may actually be some of the most revealing. Choosing to spend your free time exploring a hobby, a passion, or an interest reveals a lot about job fit. People who are truly passionate about something do it, think about, and act on it, whether they get paid for it or not. “How do you spend your free time” is a big question.

2. What are you attracted to the most?

Again, although this question is worded in many different ways across numerous online dating sites, many of the sites use multiple choice answers so that they can run the results through an algorithm. But, think about how this question would relate to a cultural fit of an employee. Are you more attracted to cultures who focus on performance and growth? Or a workplace that appreciates humor and creativity? Are you simply attracted to organizational or financial stability? Or, are you more attracted to companies who are all over the media, or companies who shine because the environment is so cool?

3. Other questions we found intriguing include:

  • How are you contributing to the world/community/greater cause? Questions like these reveal a greater sense of what people really care about.
  • What’s your biggest goal in life right now? Although questions like these can often be answered with somewhat generic answers (a better job title, a better living situation, more vacation time or acquiring certain possessions like boats, cars, etc.) they reveal what people want as the result of their effort.
  • What’s your favorite thing about yourself? Apart from physical attributes, understanding what talents or skills people value about themselves typically reveals areas of strength that they wish they could use more in every day life.
  • Who has been the biggest influence in your life? More important than the ‘who’ of this question is the ‘why.’ Listen carefully to the details of why a person impacted a person’s life for the better. And, also ask what people learned from negative people in their life—what did they not want to be like?
  • What is your greatest achievement? Again, with questions like these, it’s not always the ‘what’ that can teach you the most about a person but the ‘why’. Pay attention to how a person explains the hurdles they faced, or how someone believed in them, or how they were given autonomy to own the outcome.

The resume might be outdated—and ready to learn from the new age of internet profiles and matching. Today, experience, interests, and achievements might be more accurately exposed on tools like LinkedIn, or even Facebook…yet, resumes remain a standardized expectation within the corporate world. Online dating might actually be better at making matches than the recruitment industry —as even in a still repressed economy The Center for Creative Leadership suggested that nearly 40% of executives hired at the senior level are pushed out, fail, or quit within the first 90 days. And, a joint survey conducted by Yahoo! Finance and PARADE magazine of 26,000 Americans found that almost 60 percent would choose a different career.

Hey, we’re optimists too. We hope the well-dressed woman from the conference finds a perfect match the next time she dates. And, no matter what, we hope that everyone can find a match in the workplace—with people who inspire great ideas, great collaboration, and great work.

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