The Art of the Ask

In his book, Outliers: The Story of Success, Malcolm Gladwell introduces the concept of the 10,000-Hour Rule. In a world that seems to have a plethora of instant expertise, it is quite a refreshing bar he establishes in one earning their way to the level of an expert. It reminds me of my friend Maryann sharing related wisdom from her grandfather:

Nothing great happens quickly.

In so many ways, experts aren’t the ones boasting instant answers as if every problem has a solution … but rather they are the ones asking really difficult questions being fueled by deep and diverse experiences that can only come from the investment of a lot of hours. No doubt, when someone has invested 10,000 hours into anything, there is the opportunity to run into a lot of questions – both externally and internally. It may be fair to say that one can’t live on the surface of anything over the course of 10,000 hours.? At some point, often unintended, the bottom falls out and one goes plummeting into a depth that only beckons them to fall ever deeper into their experience.

The ego seems to love an answer – especially when it’s our own! On the other hand, the heart and soul long for an adventure that never reveals itself in a moment’s notice. It is an adventure that calls us to trust the experience, moment-to-moment, over a very long period. While Malcolm’s 10,000-Hour Rule isn’t a new concept (consider the old saying: It took him 20 years to become an overnight success!) it certainly quantifies the investment in a stark and bold fashion.

Yet, with a market obsessed with speed while propelled by many addicted to competition, it makes for a lethal combination of serving up short term answers with little or no concern for long-term consequences – often unintended. Quick answers have a way of closing heavy doors.

Questions have a way of re-opening them.

In my years while working in the World Headquarters of Arthur Andersen, I had a 9-block walk from our offices at 69 W. Washington to Union Station. I became quite efficient at navigating the crowds, the lights, and the cross streets to limit my time from office to boarding the train. This efficiency allowed little time to notice anything along the way other than the time left before I would miss my train.

Yet, during that same season of life, I developed a practice to, once a week, leave the office a few minutes early intentionally slowing down my stride to pay particular attention to those I saw along the way. As my eyes glanced from person-to-person – from a professional moving at my typical efficient pace, to a parent patiently pushing a stroller, to an artist delightfully sharing their gift on a random street corner, to a homeless person quietly sitting with a tin can and a sign – I repetitively wondered what I would discover if I could simply sit with that person for an entire afternoon listening to their life story while only asking them questions.

It mentally forced me to start with a blank sheet of paper.

And it never failed in allowing me to arrive to my seat on the train feeling a deeper sense of humility and a richer sense of curiosity – characteristics I intentionally wanted to deepen in my own life journey. Meaningful questions have a way of nurturing both.

It was during this same period of time, amongst our Firmwide Recruiting Team, that we were embarking on a sophisticated and significantly different form of conducting interviews. The methodology demanded your curiosity while neutralizing your assumptions. It required you to actively listen, focus and probe with simple questions.? The outcome of the interview literally depended on the art of asking. The methodology wasn’t about just any question – it was about the right question at the right time asked in the right way. And rarely did it fail to deliver delightful surprises along the way.

As I look back on the most meaningful conversations I have experienced in my own life, the narrative always involved a lot of questions back-and-forth.? Not any question – but the right question at the right time asked in the right way. And yes, almost always, the questions were hard, authentic, and vulnerable.

Spiritual teacher and psychologist, James Finley. says that in a counseling session there often comes the right moment when he asks a question that he knows the counselee can’t immediately answer. Searching for an answer in an elongated silence, the counselee can only turn inward for a response that is not easily accessible – perhaps only leading them to a deeper question.

It strikes me that in a world searching for answers, and plenty of spontaneous “experts” looking to serve-up teflon solutions, we might be best served in asking a lot more questions – really hard, difficult, uncomfortable and inconvenient questions. The quality of the results will, of course, depend on the art of the ask.

As Malcolm Gladwell so clearly expressed: one dimension of expertise is measured by the number of quality hours invested. Maybe another dimension might very well be measured by the number of meaningful questions asked.? Perhaps a combination of the two would take us to a whole new level of wisdom and understanding – of the complex issues of our day and of each other. Maybe it could evolve into a masterpiece worth hanging in some future museum showcasing the history of our times. Surely, it's worth asking about!

As always, I would love for you to share your thoughts … or maybe more importantly, a question that has recently moved you, invited you or challenged you!? Please share below.