Epiphany – The Power of Questions in Leadership

By Drew Dudley

Updated Over a Week Ago

Minute Read

I’m sure everyone has epiphany moments of realization as a leader when you realize something both obvious and important has been sitting directly in front of you.

I had one of those moments, and I’m glad that I did.

Leadership Notes

To explain this particular “epiphany,” I have to return to a train trip across Canada that I’ve referenced in previous articles. Initially intended to be a month-long escape from everyone and everything, it was turned into something entirely different by an unexpected encounter in the first few hours of the voyage.

I used the trip as an opportunity to talk to strangers about their lives. More specifically, I talked o them about the most important things they had learned through their experiences. It was one of the most enlightening months of my life, and many of the lessons that I learned and stories I was told are a part of a book I’m writing entitled Accidental Teachers.

Home for the holidays a few weeks ago, I took an afternoon to sit next to my parents’ fireplace and read over my most recent draft. At one point, I thought to myself, “I am so lucky to have stumbled into situations where these people could share these amazing insights.”

Then I reread this particular story from that trip. It took place the day after I’d spent an enlightening afternoon with a former CEO in the train’s lounge car:

As I entered the lounge car the next afternoon, I smiled at Patty (who worked the bar) and ordered a beer before settling into what had become my usual seat.

A few moments later, Patty approached with my drink and asked, “Drew, do you mind if I answer a question you didn’t ask me?”

Confused, I asked, “What do you mean?”

She smiled and, with a little bit of embarrassment, said, “Well, it’s hard not to overhear conversations in here, and I hope you don’t mind, but I got really interested in what you and Albert were chatting about yesterday, so I kind of listened in.”

“I don’t mind at all,” I laughed. “In fact, I feel lucky that I myself got to listen in!”

“Well,” she said, “At one point, you asked him what he thought was the most important thing he had learned in his life. I don’t know why, but I couldn’t get that question out of my mind, and I’ve been thinking about my own answer ever since.  I know I’m just a bartender, but I was wondering if I could tell you what I came up with?”

“Of course,” I said, “I’d absolutely love to hear it!”

Patty did a quick glance at the other patrons before placing my beer on the table and sitting down next to me.

“Well, first, let me ask you this: why are you on this trip?”

“What do you mean?” I asked.

“There are a lot of much faster, less expensive ways to get around than the train, so why are you on this trip?”

“Oh,” I replied. “I’m heading all the way across Canada.  It’s something I’ve always wanted to do.”

Patty smiled.

“I’ve been doing this job for 23 years, and I’ve discovered you can learn so much about someone by how they answer the question: ‘why are you on this trip?’  The richest people tell me exactly where they’re going.  The most interesting people tell me where they’ve been.  The happiest?  They just tell me what direction they’re pointed.”

“So the most important thing I’ve learned?  It’s that the key to getting the most out of life is understanding each one of three crucial things: where exactly you want to get to, what direction you need to go to get there, and what steps you need to hit along the way. “

“You know what’s funny?”  She commented as she stood up and headed back towards the bar. “I’ve always known that, but until I heard you ask, ‘What’s the most important thing you’ve learned, I never realized I knew it.”

Reading that final comment was when I was struck with my “you’re an idiot” moment.

The reason that particular trip had so many lessons included in the book was that I had gone looking for them. I wasn’t “lucky to have stumbled into” those situations; I had consciously created them. However, once I returned to work – a place where my role wasn’t as an “accidental teacher” but rather as a formal one– I inexplicably stopped doing so.

I had returned to a life where I saw my role as someone who answers more questions than he asks.  After all, that’s what I was paid for! Thinking back to my experience with Patty, however, I realize that some of the most powerful lessons in my life—both those I’ve learned and those I’ve taught—came as a result of asking questions.

Sometimes we become so convinced that we do something “all the time” that we actually stop doing it.

Like so many things in life and leadership, the problem isn’t that we lack the capacity to do something but rather that some things are so easy to do that we simply assume we’ll do them without effort or attention. Asking others to share their insight is too often one of those things.

Epiphany Resolutions

Epiphany: Leadership Resolutions

Don’t get me wrong; our jobs often require us to ask others how to solve problems or deal with specific situations. The insights I’m talking about surround broader questions that focus less on solving particular problems than they do on enhancing life and leadership in general.

The fact is, people may possess tremendous lessons but have rarely been asked to share their “meta-advice” (for lack of a better term).  Have you ever been convinced you know the answer to something until someone actually asks you the question?

I know most of my articles and new material for my presentations are born when people ask me questions that stump me, and I feel compelled to formulate an answer with which I’m happy. I almost always come out of that process feeling as though I’ve gained new insights and grown as a leader and a person.

What is leadership if not trying to create situations where others can do the same?

And so I’ve set out to do just that. My leadership resolution is to try to return to the attitude I had on that train: creating opportunities for people to share their best life lessons, on the premise that in the process of doing so, I’ll be asking them to clarify their own thoughts, beliefs, values, and most importantly, their own wisdom. That can be a powerful and empowering process.

I’ve chosen to do it with something I call the “Edge of the Bed” Question:

If you were sitting on the edge of the bed of your son or daughter the night before they left home for good, what advice would you give them? What are the most important lessons life has taught you so far? Ultimately, what perspectives, actions, or ideas have played the biggest role in your happiness?

I’ve posed the question to dozens of people, from my father to millionaire CEOs to my first-grade teacher, and will be sharing their answers at mylollipopmoment.com. In the few weeks I’ve been asking the “edge of the bed question,” my contributors have not only provided extraordinary advice, but sent it along with notes on how much they enjoyed the process, how sharing the question and their answer started powerful conversations with their friends and loved ones, and how emotional and revealing they found the process of creating their answers.

All of them have thanked me for the opportunity.

Sharing Leadership Skills

It has been a powerful chance to both further my own knowledge and act as a catalyst for others to acknowledge and share their wisdom.

I encourage you to think of your own “Edge of the Bed” advice and ask others you care about to do so as well. I’ve found it to be a remarkable opportunity for mutual growth and understanding.

Have You Had a Leadership Epiphany?

If you have ideas about leadership epiphanies that might be helpful to readers, share them in the comments section below. Thanks!

Would you like to contribute a post?

Drew Dudley
Drew Dudley
Drew is the Founder and Chief Catalyst of Nuance Leadership, Inc., and the former Coordinator of one of Canada’s largest leadership development programs at the University of Toronto.
  • R.D. Choudhary says:

    I was touched by this article, and particularly the answer given by the bartender reveals the outcome of her inner engineering with mindfulness on the purpose of life and living. Her thought is the essence of perhaps all religion. It also reflects her attentiveness and mindfulness so tragically absent in modern civilisation. All rich and famous attend retreats and seminars to develop the power of mindfulness which she has been able to do in a routine and ordinary course of duty as a bartender attending to all types of travellers. Her observation exemplifies the power of being attentive and in presence. I was also struck with my ” You are an idiot” moment, but everything then immediately vanished in heartfelt blessings to the bartender. You are perfectly right in your statement that without asking questions inner clarity of thought and purpose is not revealed, but at the sametime it ia absolutely necessary to be perfectly calm,observant without judgement to enter into that beautiful zone of insight and understanding which comes by asking questions and listening to answers under total attentiveness. Once again thank you for your awareness which you are destined to spread through your writings. All glory and success to you in your mission.

  • David McCuistion says:


    Those personal “idiot moments” are really embarrassing sometimes, aren’t you glad they are personal and not open for others to see? I know I am.

    However, I think they are great and quite often lead to new insights beyond the moment.

    Another thing that I read is about the Bartender, who is obviously much smarter than her “just a bartender” comment. She is obviously a “seeker” and an astute one at that.

    Great article. Thanks for sharing.

  • David McCuistion says:

    Oh, by the way, I am sharing the article with my Leadership Seekers Group to whom I provide various leadership tips and articles.

    Thanks again.

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