09/30/2014 01:38 pm ET Updated Nov 30, 2014

Socrates Over Milk and Cookies: Asking the Best Questions

As September winds down, my firsthand experiences this past month made me, once again, acutely aware of one of the briefest yet most familiar conversations echoing between kitchens and foyers:

How was your day, honey?

Its "cookie-cutter" content easily applies to a broad range of situations but rings especially true at the end of those precious first days of school (or a new job) when we wait "anxiously" for an answer as if a single word (e.g. alright, good) could convey the complete truth and legitimize the silence that follows.

Regardless of the context, when we ask or answer the "How was your day?" question, the words, as scripted above, roll off tongues almost effortlessly, yet robotically. This level of inquiry, in essence, requires little -- in its design, its articulation or its response.

How would Socrates -- the "Father" of questions -- grade our efforts?

The season of traditional learning may begin each Fall with a new wave of students going "Greek" in the form of studying the great philosophers of life or, in some cases, "rushing" toward a new philosophy on living. Yet, I suspect that Socrates would not be happy.

We learn very little because, more often than not, we ask very little.

Questions -- Socrates believed -- were the foundation of learning. When you effectively ask, you create conditions for:

• Clarifying your own or someone else's thinking
• Testing your own or someone else's assumptions
• Leveraging your own or someone else's alternative ideas

Yet, the content of your questions is not the only challenge. The voice behind them matters as well. Bold inquiry and, as such, deep learning requires you, in the roles of "master" (teacher, parent or boss), student, or "self," to be:

• Curious
• Open
• Patient
• Invested

Socrates' suggested script only turns tragic when we stand in the way of learning -- someone else's or our own. Failing to ask provocative questions means failing others in their growth or failing to grow ourselves.

"How was your day?"is not a "fine" question and we should not assume "self" or "other" satisfaction with the predictable answer. Whether looking into the eyes of a fourth grader, your spouse as newly minted manager, or into the mirror, the response, "okay," is not okay. Questions that loom large and their answers that loom long set the course for our real education.

Indeed, October will likely begin as September ended. We will greet our children or partners at the door with smiles and treats in the form of Oreos or dry Chardonnay respectively, asking about their days. We may similarly take stock of our own days and conclude simply and with ease that all is well. Both the inter-and intra-personal sugar and spice and everything nice exchange is never as compelling as the conversation that invites someone past the metaphoric doormat conversation into the more "hearty" dinner table one.

So, in the school spirit of deeper inquiry, ask yourself if the questions that you ask -- of others or yourself -- would disappoint Socrates. If your answer is "yes," ask yourself why and then how you can change the conversation.