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Can I Ask You a Question?


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The greatest compliment that was ever paid me was when someone asked me what I thought and attended to my answer.

– Henry David Thoreau

Are we asking each other the right questions? Or are we just being polite?

Are we asking each other questions that are meaningful? Or just transactional?

Are we asking each other questions that matter? And are we really listening to the response?

We seem to be moving too quickly and without intention or curiosity. When and where can we pause to connect and reflect?

What if we move further away from ‘How are you?’ and closer to ‘What is the best thing that happened to you today?’ Or if we are at a social gathering instead of ‘What do you do?’ to “What is happening in your life right now that you would like to share?’ Imagine how you would feel if someone asked you a question with sincere interest and then actively listened to your response.

The idea here is for us to cultivate deeper connections through authentic engagement, and sincere curiosity. At our core, don’t we all just want to be seen, heard, and understood?

Two things to consider here are, what questions can we ask that push past the obvious and open the door to topics where we can find common ground or learn something new. And what is the quality of our listening?

I love what David Brooks says: “Be a loud listener. When another person is talking, you want to be listening so actively you’re burning calories.”

I recently rediscovered ‘The Proust Questionnaire’; a set of questions designed to reveal people’s personality, values, and preferences. It originated from a parlor game popularized by Marcel Proust, the French writer and essayist, who believed that one’s answers to these questions could provide insights into their character. These questions are frequently used even today for interviews.

Some examples:

What is your idea of perfect happiness?

What is your greatest fear?

Which living person do you most admire?

What is your greatest extravagance?

What is your current state of mind?

What do you consider the most overrated virtue?

What do you most dislike about your appearance?

What is your motto?

I think it is understood these are not typical or casual questions, but they do give us the opportunity to go deeper in understanding the essence of the person we are connecting with.

So come up with some questions that feel right for you and create an opportunity to really engage at a new level of curiosity and connection.

My question for you:

“What is the best concert you have ever attended?”

I really want to know.

Carolyn Lebanowski
Carolyn Lebanowski
Carolyn began her professional career in retail and grew to become an experienced and respected senior-level executive with expertise in strategic development, organizational communication, and executive coaching. After nearly three decades of career growth in corporate organizational development, Carolyn was ready for a career change—and a life change. This led to a new role and the most challenging, enriching, and rewarding work of her life, as a Strategic Business Leader for nonprofit spiritual institutions. As Executive Director and Chief Opportunity Officer for 2 large organizations, it gave her the opportunity to fuse the professional and the personal, aligning her business acumen with her spiritual identity and passion for the development of human potential—in her colleagues, in her community, and in herself. Carolyn is a writer who seeks above all to share from the heart. Her impulse to write began 20 years ago with letters to her children and grew into journaling that was unedited and life-affirming. Today she writes with a focus on raw, authentic, and lived experience, to explore, express, and make sense of the pain and joy, and struggles and triumphs, of life. In all her endeavors, she champions connection, integrity, and radical positivity. Today, Carolyn is a published author and a Columnist/Featured Contributor at BIZCATALYST 360° and is living in Cascais, Portugal.

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