05/09/2014 06:02 EDT | Updated 07/10/2014 05:59 EDT

If You Want an Amazing Job You Have to Ask the Right Questions

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Our company's "ask technology" is always on. We pose questions to hundreds of thousands of randomized people across every country and territory of the world. Tens of millions of people have provided us answers.

But I am fascinated by questions vastly more than answers.

Socrates was a genius because he asked questions -- all the time. When I meet a company founder, he or she tends to ask bucket-loads of killer questions. Why is that? "Company men" and women in my experience tend not to ask any questions. Why? Great salespeople ask questions -- all the time.

What is a question?

A question is something to which you don't know the answer, and something to which you want to know the answer. "Will the weather turn for the worse?" is not a question that matters terribly much. I can Google it. Neither, generally, is "How are you?" (Unless you know them intimately, people in crappy jobs or stifling relationships will shrug and answer: "fine.")

My brilliant undergraduate professor at Queen's University, J.A.W. "Jock" Gunn, taught me that "How are you?" is what the celebrated political scientist William E. Connolly might have described as a 'suitcase' question, much like a suitcase word, such as 'liberal' or 'friend'. We've dumbed down the question so much, just as we have the words 'liberal' and 'friend', to the point that it means, well, nothing.

Imagine you are at a social gathering. "Did I tell you about my bachelor party at the Master's tournament in Augusta?" is a question from a young dolt that would turn Socrates to self-immolation. A good question should not enable the asker to reveal any vanity. Quite the opposite is the case. Asking amazing questions is often a great way to deflect imbecilic cocktail banter from another's chest-thumping about his or her fancy second home or renovations or flashy car.

Pretend I'm an interviewer and I ask you, "What was the most interesting thing that happened to you in the past 24 hours?" I really want to know the answer. By giving me an awesome answer -- something fascinating happens to every one of us every 24 hours -- you are telling me that you are self-aware, curious, empathic and communicative. You are teaching me something I didn't know and might never be able to Google. I'll take a great answer to that question over a 4.0 GPA any day.

The Stoics knew that the pursuit of reason comes through asking questions - all the time. Many confuse this with the Hollywood-glamorized law school pedagogy of the 'Socratic Method'. Have no doubt: when the person (the tenured academic) knows the answer to the question he or she is asking, it's not a question that Socrates would approve of. (I respect lawyers, just not the self-important ones... you might know one or two.)

Why do Entrepreneurs ask Questions?

Is there a positive co-linear relationship between founders who ask a lot of non self-important questions and their companies' success? Are people happier in their job if they can ask more questions? Entrepreneurs want to be surrounded by people who ask questions, not by those who are trained to be solution-solvers only.

I wonder whether this explains why people trained in narrow 'answer' professions -- say, law -- find it discomfiting to land in blurry entrepreneur-land or self-employment after a downsizing. I also think this is why people in 'answer' professions, despite how much they might earn financially, self-report high levels of unhappiness (e.g., specialist physicians and, a decade or so ago when it was easy comfy cash, lawyers).

Why are you reading this post? Why does any of this matter? If you've read this far, you know why.


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