The Right Way to Answer “What’s Your Greatest Weakness?”
Thomas Jefferson once said that “honesty is the first chapter in the book of wisdom”. Though truth-telling abounds in grade school platitudes, it seems scarcer the older we get. But this decline in honesty — let’s call it dishonesty — isn’t necessarily innate. Dishonesty can be taught. In my experience, I’ve noticed that, of all culprits, college career centers are exceptional traffickers of such miseducation. In the process, they’re hurting their brightest students’ chances of making it in the world of startups by convincing them to give dishonest answers to tough interview questions.
Full disclosure: I work at a startup, and it’s my job to quickly build a team of the right people. Throughout my earlier career in larger companies, honesty and being self-critical have always been obvious qualities to look for in candidates, but it wasn’t until I joined Medallia that I realized their special significance for startups. Brandon Ballinger’s now famous blog post about his experience with Y Combinator’s Paul Graham shows why. To cut a long story short, Graham told Ballinger (to his face) that his startup idea sucked — a tough-love approach Ballinger now extols. Why? Well, in a startup, it’s much more comfortable to be a “team player” than “the bad guy,” as Ballinger describes it. The real hard work in a startup, however, is being able to openly admit that the current strategy is just not working — no matter how uncomfortable it is, or how much has been invested in getting to that point.
In other words: one of the biggest dangers for a young company is that a roomful of smart people who aren’t being honest could easily be steering their rocket ship into the ground.
And yet college career centers continue to operate in a 20th century world in which top talent was funneled into careers in mature, staid organizations and industries. These are cultures where people are much more likely to divulge their net worth than a weakness. While a mature organization might have once been able to get by with a “don’t stick your neck out” culture, that attitude is simply lethal to startups.
Nonetheless, the importance of this simple truth seems to still be elusive for the Office of Career Services at many of the nation’s top colleges and universities. Besides guidance on basic items like resumes, cover letters, how to dress, and how to eat, many of these schools are providing either noadvice or bad advice on how to adequately answer important questions. Take a very common question that I always like to ask, for example:
What is your greatest weakness?
Even if you’ve only had just one professional interview in your life, then you’ve probably still been asked some version of this question. Do you remember how you answered? Did you say that you work too hard? That you have perfectionist tendencies? Or that you’re too passionate? Be honest.
The truth of that matter is that a quick search of career center websites indicates that students are being encouraged to apply this type of spin to their answers. Even for those that advocating for honesty, there’s often still the contradiction that one’s answers must always be positive. The result of which? Answers that focus on lesser skills (but still skills) rather than actual problems or challenges. One school goes as far as to call it an “angelic weakness.” And if you’re pressed to give a real answer about a flaw, nearly every career center in the universe has apparently decided that “public speaking” is an appropriate response.
Others are more direct at giving the advice that everyone seems familiar with — to make weaknesses into strengths (and vice versa). Northwestern tells grad students, “Turn a negative into a positive.” Boston College advises students to “Turn your weakness into a positive (for example) ‘Because I tend to procrastinate, I have learned to work well under pressure in order to always get work done on time.’”
This is terrible advice. Responses like these tell me little about how a candidate faces challenges and immediately implies a lack of sincerity. It doesn’t demonstrate to me how they think — beyond their ability to creatively avoid being honest or self-critical. It indicates to me that they’re not willing to stand up and say what’s not working — the opposite of what a startup needs. That’s why my recent interviews with college graduates have all started to follow the same pattern. I start with two sentences: “Forget what your career center has taught you about interviews. I want to have a real conversation with real answers, and I promise to do the same.” The candidates take a minute to evaluate whether I’m somehow tricking them. If they lean into their discomfort and take me at my word, the level of conversation improves dramatically — we have a great time getting to know one another in an authentic way. I’m not really looking to find out whether their organizational skills could use improvement, or that they struggle with presenting to large groups or even leading large teams. I’m trying to find out whether they have self-awareness; whether they are able to be critical; and most importantly, whether they’re able to tell the truth — when it’s difficult.
For those candidates who don’t buy in, however, I spend the majority of the interview trying to pry off their layers of canned responses. I leave the interview wondering: Who are you? And what’s worse — I’ll never know. Because they’ll never get the job.
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