Leadership, Culture and Coaching | Oprah Moments
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Oprah Moments

Oprah Moments

Twice a year I moonlight as a tour leader for small groups of 10-15 international travellers.  Its a dream job, really.  For a few weeks in the Spring and then again in the Fall, I get to travel to some of the world’s most incredible places.  Places like Tuscany, the Greek Isles, Machu Picchu, Andalusia and Patagonia.  And on top of it all, I get paid.

The biggest perk of the job, though, is the people I get to meet.  People whom I would ordinarily never have the chance of coming in contact with. People like Barbara, the civil servant from Eugene, Oregon who, besides being a walking encyclopedia, also helped orchestrate an impromptu meet and greet with the President of Chile.  Or Ron, the librarian from Southern California, whose quiet demeanour eroded whenever he came across a karaoke machine in Japan.  Or Mike, the aerospace engineer from Atlanta, whose geeky charm had locals swooning over him in every city we’d go to on both of the trips I’ve lead him on. 

Leading groups of 10-15 travellers to exotic places around the world is actually very similar to the leadership work I do when not abroad.  In trainings and facilitations, just as in group travel, there is a experiential arc.  People start out nervous and at times awkward, then gradually begin to feel comfortable in their new settings.  If I do my job right, the experiential arc peaks with a moment of self discovery — a moment when people realize something powerful about themselves in a way they never had before.  Its incredible, really, how leadership development and travel can do that.

My role throughout these experimental arcs is, at the core, to make people feel safe, comfortable and most importantly, valued. Seen for who they are and simply appreciated.  I call these Oprah moments.

Oprah recounts that in more than 37,000 one-on-one interviewers she has given in over 4500 shows, once the cameras stop rolling and the interview has ended, every guest — be it a head of state, artist, murderer or Beyoncé — leans over and asks her the same question in their own way.

“How did I do?”

Oprah says its humanity’s common denominator.

“Everybody just wants to know that you heard me, you saw me, and that what I said mattered, ” she stated in an Independent interview.

Part of my personal purpose in life is to give people Oprah moments — small but important nods of validation that speak to everyone’s intrinsic worth.  I look for moments to do this everyday in my life, sometime succeeding, others not so much (especially when iI lose my lose with call-centre customer service agents).

On a recent trip to the Amalfi Coast, I had a passenger who put my Oprah moment mantra to the test.

Naturally shy and with English as her third language, Mindy didn’t join the rest of the group in any scheduled activities, rarely ate meals with the rest of us, sat on the bus with a backpack in the seat next to her so that the seat next to her couldn’t be taken, and rarely responded with more than one word answers. No matter my efforts, Mindy simply did not want to participate with the group.

As a tour leader and specialist in leadership development, I have learned a few things about introverts.  Reservedness should not be confused with disinterest.  Quietness should not be mistaken as disdain.  That said, I have also learned that gentle nudges can help introverts come outside of their protective shells, oftentimes opening them up to experiences and insights they would have missed otherwise.  Navigating those two polarities is a delicate act, particularly for an extrovert like me.

So, everyday at breakfast I would politely share with Mindy the day’s plans, and invite her to come along.  And most every time, she would decline.  I would make sure to send her a text to let her know where we would be having lunch.  More often than not, the text would go unanswered. And at night, I would always make a reservation for 15 half knowing that we would likely be one less. And most every time, we were.

Intellectually, I knew not to take this personally.  This was not about me or the group. Mindy wanted to be alone and it was my job to honour it.  Emotionally, I had to remind myself of that every day. Several times a day, actually. 

“This is not about you, Casey. This is not about you,” I told myself.

After nearly two weeks of Mindy’s refusals, I still was reminding myself.  Even when she missed the last group dinner (which I took particularly hard).

As we were saying our final good byes and exchanging phone numbers and emails, Mindy appeared at the restaurant.  Quietly, she pulled me aside and gave me the largest tip I’ve ever received on a tour.  Then, she thanked me. 

“These past two weeks were the first time in my life that I was allowed to just be me.  No pressure.  No expectations,” she said.  “I have never felt more respected.”

And with that, I knew that my reminders paid off.  I had given Mindy her Oprah moment — something far more important than a group dinner or scheduled activity.

Who needs an Oprah moment in your life?

Casey Miller

Casey A. Miller, President of 6 ½ Consulting, is on a mission: to help create environments where people value one another. In his consultancy, this means teaching business owners and executives how to build workplaces that inspire. In return, their organizations see positive returns on their time, teams, and profits.

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