Finding your Fit — Why Landing your Next Career Should be a Bit More like Dating

by Rodrigo Sosa

Finding the perfect job is much more like finding a good romantic partner than most people realize. You can put your best face forward during the dating — or interview — phase, but if you aren’t honest about who you are and what you are looking for, you might end up wasting your time. While we all attempt to hide our flaws early on, trying to look like the ideal candidate, we often don’t focus enough on figuring out what about our personalities makes us a good fit for a person or job.

Early on in the dating process, we look for clues as to what preferences, interests and traits we might have in common with a partner. But in job search, both candidates and companies try to present the most polished version of themselves, so it becomes more of a sales pitch then a compatibility test. Often, how we go about appearing attractive to employers depends on the context or channel of communication (Lily Zhang, a career development specialist, writes about this here) Ultimately, what we should strive for in our career progression is a complimentary match between the characteristics and attributes of ourselves and our employers.

Let’s face it, you will likely spend as much time, if not more, at your job than with your family, friends, or partners. So understanding how to assess your fit for a company or job matters a lot more than you think. Do you like working alone or in teams? Learning best practice or innovating? Do you want to climb the corporate hierarchy of a top-brand firm or roll your sleeves up with a scrappy start-up? Would you thrive in a role where you are presenting ideas or solving technical problems?

Just as you may want your partner to share your love of animals or passion for volunteering, it is just as important for your preferences, priorities and values to match those of the organizations you are seeking to join. Culture fit is a measure of how strongly matched your values are to the potential company’s values. Robyn Melhuish, a communications manager at, has a good article on communicating that you are a good culture fit. Just like in relationships, be careful not to overdo it.

Person-to-organization fit depends on broad attributes of both the employee and company, and is different from culture fit. This kind of fit depends on attributes (i.e. enduring qualities) of both parties. See below for a representative list of work-related attributes. Just as you may want a partner who is not shy, that high-powered sales job may want someone who is persuasive. Or what if a company valued your ability to generate new ideas, or your hustle to finish tasks quickly?

Measure your workplace attributes here before your next job search

So, how can you identify your dominant traits, and what companies might be a good fit for you?

No, it’s not Myers-Briggs (that won’t help you much on the job front). Many choose to go to career counselors or assessment centers to take validated tests that measure their traits, but this can be expensive and time-consuming. SquarePeg is a new startup which will assess you for your top workplace attributes, and send you a free JobFit report with your results. It will tell you which attributes are strongest and weakest, how you compare to others, what to watch out for, and what roles and environments might be best suited for you. It also goes one step further, matching you with top companies based on your fit with them, and connecting you directly to your top choices.

No, it’s not OKCupid for jobs, but the idea is that we need to take the guesswork out of job search to find environments and roles where we are more likely to thrive — before we apply! Just as we take the time to assess a partner before we commit, we should take some of the guesswork out of job search. This means figuring out what fit means for you, and then finding a career match based on compatibility.