Lead Like You're Retired (Part 3: Ask Great Questions)

In my last post, I described some things I learned about the wonders of curiosity – like how it can get Venetian gondoliers to work together. However, I think curiosity is more of a state of being than an action. Asking great questions is how we activate curiosity – even if we’re just asking ourselves those questions.

In preparation for this post, I wanted to start with a great quote, and I learned that you can be busy for a very long time when you Google ‘quotes about asking questions’. Here’s a few:

“The man who asks a question is a fool for a minute, the man who does not ask is a fool for life”. - Confucious

“To ask the right question is already half the solution of a problem”. - Carl Jung

“The power to question is the basis of all human progress”. - Indira Gandhi

I guess I’m late to the party on the whole questioning thing! It seems like every wise person in history has talked about how important it is to ask great questions.

If that’s the case, why don’t more people do it? Why does it feel like a lost art?

Maybe we start by going back to Edgar Schein, who defined humble inquiry as asking questions to which we do not already know the answer.

Therein lies problem number one: We don’t really want to ask about something we don’t know the answer to. In fact, we often just want to talk about ourselves and skip the questions entirely. Eventually, when politeness requires us to ask a question, we don’t aim high. Maybe because when we’re listening, we’re really just thinking about what we want to say next.

We expect conversations to reach some conclusion which is by telling and not by asking. To ask is to reveal ignorance and weakness. And most of us desperately don’t want to reveal ignorance or weakness. Instead, we often frame our questions to impress you with our own knowledge, or shine up our own self-image, or as a not-so-subtle way of telling you what to do. Healthy self-esteem is in short supply. I prefer that you talk about your ignorance so I can impress you with my knowledge. And there lies the grave of Curiosity – we wish we knew him better.

Paraphrasing Mr. Schein, we are especially prone to telling when we have been promoted to a position of power. The art of asking becomes more difficult as status increases. Our culture emphasizes that leaders must be wise, set direction, and articulate values, all of which predisposes them to tell rather than ask. Yet leaders need humble inquiry most because complex interdependent tasks will require building trusting relationships and asking great questions. 

James Ryan recognizes this in his powerful book Wait, What?

“Many of us spend too much time worrying about having the right answers.” It’s common in our professional lives and pervades our personal lives, where we don’t want to seem clueless to those who might be depending on us. New parents, like new employees, “tend to get nervous if they come across a question they can’t answer, which happens frequently when you are new at anything”1.

I love this connection to parenthood. Like most leaders, as parents we tend to tell instead of question. And in so doing, we drive our audience away rather than gathering important information or building deeper relationships. We scratch our selfish itch of imparting wisdom, but we don’t get what we need: a fuller picture of the issue before we start solving the problem. Or better yet, guiding our child to resolve the issue himself.

As a defense to pretending to know all the answers, Mr. Ryan employed the classic defensive response: “That’s a good question. What do you think?” This should be very familiar to most parents and clever leaders. But this often doesn’t get us very far and we’re not really asking our own question.

Figuring out how to ask great questions is critical – not just to curiosity, but as the opening quotations suggest, it’s important to life itself. “Questions are like keys. The right question, asked at the right time, will open a door to something you haven’t yet realized, or something you haven’t even considered”2. Which may open avenues into life’s magnificence.

Even if we can get past our own shaky self-esteem and desire to talk about ourselves, “posing good questions is harder than it might seem…because it requires you to see past the easy answers and focus instead on the difficult, the tricky, the mysterious, the awkward, and sometimes the painful”3.

Mr. Ryan suggests these five essential questions:

1.     Wait, what?

2.     I wonder…?

3.     Couldn’t we at least…?

4.     How can I help?

5.     What truly matters?

I started using “I wonder” in retirement, before I read this book. “I wonder” helps me deal with the desire to tell. It can package a suggestion in a way that is unassuming and curious. It often leads to important information that I would not have heard if I just launched into a solution. When my urge to tell threatens to take over the conversation, I shift to “I wonder”.

Couple that with some version of “wait, what?” and you’re on the road to curiosity. I haven’t used “wait, what?” – but I like the flexibility and the personality of it. Instead, I’ve used “Tell me more” – which, while not a question, does practice curiosity by probing for more information instead of reverting back to telling you what you should do based on my very limited knowledge.

Any fan of the television show New Amsterdam is familiar with “How can I help?” – which approaches service from a softer and more genuine start. I’m not assuming I can help you (i.e. I’m better than you), I’m asking how I can be of service – genuinely. Ego takes a step back into the shadows and allows me to focus completely on the needs of the person in front of me.

“How can I help” also provides a measure of protection. Some people take help too far – okay, you want to do my job, go right ahead, and I can sit back without responsibility while you take the entire load. Not a good place to be, especially if you’re the kind of person that will do that in the name of being “good”. We’re not being good, just like we’re not being nice by withholding critical feedback or failing to make difficult decisions. “How can I help?” puts responsibility back where it should be.

“Couldn’t we at least?” is essential for bridging differences. It seeks to find a spot of common ground where we can start moving forward together - even if we just openly recognize a pesky dynamic tension that we need to balance in most difficult problems. This is another must for leaders; when are we ever involved in a situation without disagreement or competing values?

“What truly matters?” may be the most powerful problem-solving question of all time because it helps us ensure we identify the unifying, purposeful reason we are talking in the first place. A retirement that revolves around what truly matters is one that I will look back on with satisfaction when my time runs out.

Mike O’Krent is the founder & CEO of ConvoMasters & LifeStories Alive. Between 1996 and 2000 he interviewed Holocaust survivors for Steven Spielberg’s Survivors of the Shoah Visual History Foundation. I’ve learned a lot about asking great questions from his weekly emails.

In a recent posting, Mike quoted Joseph Campbell: “the cave you fear to enter holds the treasure you seek”. He then posed a question: What is the cave you fear to enter and what treasure might you find there? This is a great question, which Mr. Ryan defines well:

“Good friends ask great questions as do good parents. They pose questions that, just in the asking, show how much they know and care about you. They ask questions that make you pause, make you think, provoke honesty, invite a deeper connection. They ask questions that don’t so much demand an answer as prove irresistible. Posing irresistible questions is an art worth cultivating”4.

In another posting, Mike O’Krent quoted Jon Berghoff as saying that “we move in the direction of the questions we ask”. Mike built on that by saying:

“The nature of the questions we pose to ourselves and others play a crucial role in shaping our thoughts, actions, and ultimately our lives…questions can lead us to explore new ideas, seek solutions to problems, and gain a deeper understanding of ourselves and the world around us. In this sense, the quality and nature of our questions determine the course of our intellectual, emotional, and personal development.”

He gives an example of how, when we ask ourselves negative questions like “What’s wrong with me?”, we limit ourselves. Instead, if we frame the question positively, like “What did I learn?”, we’re on a path to personal development (and away from unnecessarily torturing ourselves).

The questions we ask ourselves might just be the most important questions we ask.

After considering what I’ve learned about curiosity, and the importance of the great questions that activate it, I’ve come to more deeply appreciate a life that features these two things prominently. Without curiosity, life is like walking down a tunnel with a flashlight. Yes, I’m always moving forward, but I sure do miss a lot of life’s magnificence.

I’ve been doing some mentoring with a wonderful company called Ceresa (www.ceresa.com). In preparing mentees for this work, they ask each person to consider what they want out of this one precious life. This is “what truly matters?” on another level. It fits Mr. Ryan’s description of a great question. And it’s a good one to ask at all stages of our lives, especially as the years we have left in this one precious life start to dwindle.

I assigned myself some homework to tackle before my next post. First, I want to practice one of Mr. Ryan’s essential questions for a month and take notes along the way about what I learned that I wouldn’t have learned if I hadn’t practiced asking good questions. Maybe I’ll even find some moments of magnificence that I would have missed. During my annual yearend reflection, I plan to spend quality time contemplating what truly matters right now and ask myself what I want to do in 2024 to get the most out of this one precious life.

What great questions will you ask yourself to kick off 2024?

1 James E. Ryan, Wait, What? And Life’s Other Essential Questions, (NY, NY, HarperCollins, 2017), 10-11

2 James E. Ryan, Wait, What? And Life’s Other Essential Questions, (NY, NY, HarperCollins, 2017), 20

3 James E. Ryan, Wait, What? And Life’s Other Essential Questions, (NY, NY, HarperCollins, 2017), 14

4 James E. Ryan, Wait, What? And Life’s Other Essential Questions, (NY, NY, HarperCollins, 2017), 15