Why is a Raven Like a Writing Desk?

A couple of weeks ago, I spent time with a group of leaders in Singapore working on how to form better questions as part of a workshop on leading with agility. I returned home through Tokyo, which meant that I arrived in Dallas two hours earlier on the same day than when I departed Japan. You would think that after years of international travel, I would no longer be entertained by the idea of arriving earlier than I departed. “What happened to those two hours?” I thought when I landed in Dallas. Of course the question can’t be answered because it rests on a fundamental misunderstanding. However, asking myself the question got me thinking about nonsense, which in turn got me thinking about Lewis Carroll.

In Chapter Seven of Lewis Carroll’s Alice in Wonderland, after some back and forth about whether there is room at the table for Alice to join the Mad Hatter’s tea party, the Hatter poses the question, “Why is a raven like a writing desk?” The precocious Alice is eager to work out the riddle, but gets caught up in the chaotic tea party conversation. Later, when the Hatter asks Alice about the riddle, she admits that she has not worked it out and asks the Hatter for the answer. He tells her that he does not have the slightest idea*.

Some nonsense questions amuse us in the same way we might be amused by the charming innocence of a child’s question. Decades before Bill Cosby shocked and disappointed a whole generation, my friends and I spent hours memorizing his routines. I can still picture the cover of his album, “Why is there Air?” Cosby’s question is elegant, simple and nonsensical. Asking, “Why is there Air?” and “What happened to the two hours I lost during my twelve hour flight?” indicate that the person asking the question is either confused or trying to be funny.

Like Lewis Carroll, I’m a fan of wordplay, puns and riddles. I pay close attention to how people express themselves looking for interesting or clever ways to interpret a turn of phrase. It turns out, not everyone delights in my attempts at wit. What I imagine to be an endearing habit quickly becomes obnoxious if I’m not careful.

The Unstuck Minds Method is based on the idea that you can tell a lot about how people think by paying attention to the questions they ask. The key to helping people explore the thinking behind their choice of question is not to place too much emphasis on their choice of words. Consultants should not engage with a philosophical or lawyerly mindset. Philosophers worship clarity. Lawyers weaponize clarity. Consultants and coaches should focus on constructing meaning, not deconstructing meaning.

Don’t focus on what the question means, focus on what the person means by asking it.

As an example, when a client frames a consulting request as, “How do we get people to be more accountable?” I need to let go of my reflex to dismiss the question as nonsense and instead, help my client clarify the unexpressed need. I might take an appreciative approach and say, “Tell me a story about someone acting with accountability to help me picture what you want more people to do.” Or, I might offer options to get the conversation moving, “When you say ‘accountable,’ is it more about keeping commitments or not blaming others or maybe it’s simply about complying with directives?”

I don’t ask questions to hear answers. I ask questions to summon insights. Answers are dead ends. Insights open doors. Sometimes people look forward to opening doors and sometimes opening a door can be scary. If the mind is stuck, then summoning an insight will be consequential. Not everyone is eager to chase a white rabbit down a hole without a companion.


*After the publication of Alice in Wonderland, Lewis Carroll was pestered to provide a response to the Mad Hatter’s riddle. Here’s a blog post describing Carroll’s response.

A Thought Experiment for Getting Reacquainted

Last week I was in Southern California. I had volunteered to drive my daughter’s car from our home in Dallas to Los Angeles so she would have it for commuting to and from school. She is getting a physical therapy degree and had been on a clinical rotation in Dallas for the summer. She didn’t have time between the end of the rotation and start of school to drive back. Since I had client work in Los Angeles, I agreed to drive west with the car and fly home after my work. The client work got rescheduled to October, but I already had my flight and the time blocked, so I turned my parental good deed into a road trip and rewarded myself with a day off in Santa Monica.

A week before my road trip, Rochelle, a friend that I hadn’t seen in over 30 years sent me a message through Facebook. After a few e-mail exchanges, I discovered that she lived near the hotel in Santa Monica where I’d be staying and we made plans to meet for breakfast before my flight back to Dallas.

I had several days and about 1,400 miles to try and remember when I last saw Rochelle and to think about what I most wanted to know about her life since then. Apart from class reunions, we rarely get a chance to skip ahead on a relationship to see what you still recognize about one another. It’s like finding yourself in front of a current episode of a TV series you stopped watching after season one. What will be surprising and what will be familiar? “You don’t go backpacking anymore?” she might wonder aloud. “You still eat too fast I see.”

Amidst all this over-thinking, I came to an insight. I know it counts as an insight because it revealed something that both surprised me and became obvious the moment I recognized what I had previously failed to notice. I’ll share the insight with you, but first the experiment.

Step 1: Think about someone from your past that knew you well. Someone from a different era of your life. Perhaps someone from a time when you imagined your life turning out differently than it has.

Step 2: Imagine that you only get to ask them one question. The purpose of the question is to re-establish the rapport you once shared. You are not trying to get caught up on the activities and events you’ve missed; that’s what Facebook is for. You want a question that when answered honestly will disclose how your friend feels about their current situation and perhaps about the future. A provocative question that your friend will want to answer truthfully and completely and in so doing may come to realize something that they have not been paying attention to.

Don’t go to step 3 until you have a question in mind


Step 3: Now, imagine your friend posing that question to you.

Here’s the question I imagined that I would ask Rochelle, “What are the most satisfying aspects of your life these days and what needs remain unfulfilled?” I didn’t actually pose this question; I’m not a complete social nitwit. I wanted to reminisce, not conduct research or therapy. Most of our conversation was about our kids and our spouses, and most of the questions started with, “Do you remember…?”

In a moment of clarity that came to me somewhere between Albuquerque and Flagstaff, I realized that I was projecting my inner critic onto the Rochelle I anticipated meeting. When you imagine seeing someone you haven’t been in contact with for over 30 years, you are also imagining the earlier version of that person encountering the current version of you. The question I had crafted was designed for me, not for her. My 60-year-old self wanted to get reacquainted with my 25-year-old self. My 60-year-old self wanted to be reassured and refocused.

What was it like when I asked you to imagine posing to yourself the question you designed for a long lost friend?