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.

How to Fix a Bad Question

I recently worked with a group of managers employed by a Fortune 100 insurance provider. We spent the day on the topic of getting unstuck by learning to ask better questions. One manager in the session so dramatically transformed the question that had him stuck, it has become one of my favorite examples of the power of overhauling a poorly constructed question.

The insurance company mainly sells its products through local agents. The agents are most comfortable selling automobile insurance, but the company would like the agents to cross-sell its other insurance products (e.g. homeowners insurance, life insurance, etc.). “Cross-selling” is when a company offers an existing customer a different, but related product. When Amazon informs you that people who purchased the toothbrush you just ordered also purchased dental floss, Amazon is cross-selling.

The manager in our session that day walked in feeling stuck. He had been tasked with increasing the sales of products other than automobile insurance in California. He started the day with the question, “How do we get our agents to cross-sell our insurance products?”

Before we step through the process of “fixing” the question, let’s remind ourselves of the four criteria by which we determine whether one question is better than another. We refer to the four criteria as the Unstuck Minds Imperatives:

  • Avoid solving the wrong problem
  • Reduce the risk of missing something important
  • Make it easier for people to take concerted action, and
  • Increase the novelty of our options

Like any professional remodeling project, we have to start by understanding the existing state of disrepair. The form of the question, “How do we get our agents to cross-sell our insurance products?” is the most common form of the question I hear from organizational leaders. Essentially, the question reads as a complaint about other people who need to adopt a different behavior in order for the leader to meet an objective. Other than the topic, the question sounds a lot like a parent lamenting, “How do I get my teenage daughter to keep her bathroom clean?”

One way to begin fixing the question is to uncover needs and interests. The idea of framing a question around an insight about what people need is a tenet of Human-Centered Design. You could say that one way to fix a question is to make sure the question doesn’t presuppose fixing other people. A poorly constructed question will emerge from a strategy to alter the behavior of others in pursuit of your own needs. A better question will emerge from a strategy designed to explore shared interests

You can tell that you have identified a need or an interest if the people at the heart of your question change their attitude toward helping you answer it. I’m unlikely to get much enthusiasm from my daughter if I start a conversation with, “Let’s talk about how I can get you to keep your bathroom clean?” On the other hand, she might be happy to participate in a conversation about how to reduce the amount of nagging going on at home. You can tell immediately that the second question is an improvement because both parent and daughter would willingly take time to answer it. Similarly, the insurance company will have limited success putting on a training program called, “How to cross-sell.”

The manager considered what the company’s insurance agents care about. “The best agents” he told me, “want to be seen as community leaders.”

After more conversation and a few revisions, we came up with a different question, “How might we help our agents become their neighborhoods’ trusted, go-to resource for protecting against the costs of injury, damage, or loss?”

When it comes to the Unstuck Minds Imperatives, the remodeled question about insurance agents is clearly better. More importantly, if agents truly want to be seen as community leaders, they would be motivated to learn about becoming a “trusted go-to resource.” The question also opens the door for innovations that may have nothing to do with cross-selling insurance products.

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?



What would you accept as evidence that you’re wrong?

Virtual instructor led training will never replace in-person classroom training.

When I facilitate a discussion about the challenges of leading organizational change, I often use a personal example. I mention that Interaction Associates, the training and consulting firm where I work, has been developing modules of instruction that can be delivered through web conferencing platforms. Our clients want virtual training and we are responding.

To emphasize the challenges of organizational change, I bluntly describe my aversion to participating in webinars, which is exceeded only by my aversion to leading webinars. I then ask participants to imagine that they are my bosses and that they would rather help me adapt than replace me.

By the way, if you are one of my clients and I’m scheduled to lead a virtual learning session for you, don’t worry… keep reading. The point of this blog post is to share what I’ve learned about making it easier for people to be wrong so that they can avoid getting stuck. Spoiler alert: I have turned the corner on my resistance by better understanding its source.

We have learned from the work of Kahneman and Tversky that when people consider options and outcomes, “Losses loom larger than gains.” From William Bridges work on “Managing Transitions” we understand that people experiencing change will first consider what they are losing before they can accept a new beginning. Ron Heifetz warns us not to ignore the adaptive aspects of change (aspects that require us to transform our repertoires) by only focusing on the technical aspects of a change (aspects that we have the expertise to deal with). The more a change threatens something a person considers core to their identity, the greater the resistance.

For those of us with a more analytical bent, our resistance often masquerades as well-reasoned conclusions. We experience the fear associated with the threat of loss, but we’re more comfortable with rationale than raw emotion and by the way, so are our organizations. We build theories to justify our opinions, and then we interpret the inevitable missteps that accompany any large-scale change as evidence that we were right all along.

In 1959, the philosopher Karl Popper introduced the concept of “falsifiability” as a way to distinguish a legitimate scientific claim from a pseudo-scientific claim. For Popper, an empirical scientific system is one that can be refuted by evidence. Borrowing the concept of falsifiability can be useful when people raise reasonable sounding objections to hide their fear of loss.

Ask someone who argues in support of the status quo two questions:

  1. What should we accept as evidence that we’re wrong about making this change?
  2. What would you accept as evidence that you’re wrong about preserving the status quo?

If we want to have a conversation about the emotional impact of change, then it’s best not to argue about whose theory of emerging trends is more accurate. Simply give people the time and space to express and empathize with each other’s reaction. If we want to have a conversation about the most reasonable course of action given our hypotheses, we should be prepared to look for falsifying evidence, not just confirmatory evidence. If I can’t imagine discovering evidence that I’m wrong about one of my theories, then it’s not a theory; it’s something I take on faith.

If you’re a leader or manager and you’re dealing with a pain-in-the-ass employee like me, consider allowing your employee to pontificate, and then acknowledge that they may have a point. If the employee has a reputation as an alarmist, they’re unlikely to sway others. If the employee is respected and trusted, he or she will come around or opt out because that’s what people with integrity do.

Sometimes being stuck is like recognizing that we’ve stepped into quicksand and we struggle unproductively to free ourselves. Sometimes being stuck is like standing still while the ground beneath us turns to quicksand. At first we feel comfortable and settled. We scoff at the frenetic activity around us. We’re content to stay put. What we need is a better question to wake us up to the sinking feeling that we may be left behind.

When it’s your turn to present, start with a question

“That staff meeting was the best part of my day,” said no one ever.

People in organizations endure staff meetings and status update meetings everyday. Of all the dreaded rituals of organizational life, update meetings seem to be the most impervious to change. Staff meetings, task-force meetings, and information sharing meetings according to one study of meetings in America, make up 88% of all meetings. Over 33% of the time spent in meetings is considered, “unproductive” by participants.

We’re not suffering from a lack of effective meeting practices. The founder of the consulting firm where I work, Interaction Associates literally wrote the book on how to make meetings work in 1976.

We’ve known for years how to fix bad meetings, yet we don’t.

I have a theory that partially explains why we allow ourselves to be tortured by bad update meetings and I have a simple suggestion, in the form of a question, for making them better.

Team leaders and functional leaders who generally convene the update meetings are getting their needs met at the expense of all the other participants. If you lead a group and need to know what is happening so that you can anticipate problems, allocate resources or reassure others that you are in control, the most efficient way to get your needs met is to convene the group. The problem is that while the leader gets his or her needs met, everyone else at the meeting gets bored.

If everyone attending a meeting could get their needs met, not just the leader, meetings would be better. When it’s your turn to present at an update meeting, start by asking the group, “what are you listening for?” You don’t pitch in baseball without first checking to see what the catcher wants. Similarly, presenters should never pitch ideas without knowing what their audiences want. Don’t guess, ask.

Suppose you are responsible for working with a technology vendor on a project involving a software change that will impact accounting procedures. You have been allotted fifteen minutes on the agenda to update the team. Before giving your update, you say, “Before I begin, what information do you need from me?” Here are some possible responses:

  • Leader: I need to know if we’re on track with milestones and whether or not you anticipate any budget overruns.
  • Team member A: I need to know when to schedule training classes for the accounting department.
  • Team member B: I don’t need to know anything about this part of the project. If you need support, I’d like to know how I can help.
  • Team member C: I’m curious about your impressions of the vendor. I need a team of developers for a different project

Knowing what people are listening for allows you to tailor your update to the needs of the team. If the meeting is face-to-face, write down what people are listening for on a flip chart or whiteboard and respond to the items one by one. If the meeting is virtual, use the meeting platform’s shared screen to capture the list. Of course you may have important information to share that others won’t know to ask about. You can always add something to list. Most update meetings have nine or fewer participants. If you have a larger group, you may need to have people submit their information needs ahead of the meeting.

Once the idea of presenters responding to what people want to know becomes routine, you won’t even have to ask the question. When transitioning from one topic to the next, participants in the meeting will let the presenter know what they need. The group will understand the expectation that they share responsibility with the presenter for ensuring that only useful information gets exchanged. As a side benefit, people won’t be able to multi-task because they have a role to play even when it’s not their turn to present.

If you want to drive greater accountability, not just greater engagement, you can pair the question, “what are you listening for?” with the question, “what will you do?” at the conclusion of the topic. Before you present, you will know what information people need. After you present everyone will know the action steps people will take with the information you have provided.

Recalculating: When is responding to change better than following a plan?

At some level I understand that the artificial intelligence behind the voice of my navigation app is not judging me when I make a wrong turn. Still, I can’t help sensing a tinge of disappointment behind the announcement that my route is being “recalculated.” Why not just provide the re-routed directions? Better yet, let’s program the navigation system to compliment me for making a bold move: “Interesting choice. Now, continue straight for 1000 feet and make a U-turn.”

Speaking of programming, some of you may recognize the reference in the subtitle of this blog to the Agile Software Development Manifesto. The manifesto was written and signed in 2001 when a group of software developers met in Snowbird, Utah. The document codified values and principles representing a methodological shift in how software developers meet client requirements. Caroline Mimbs Nyce provides an engaging history of the agile software development movement in her 2017 article for The Atlantic, “The Winter Getaway that Turned the Software World Upside Down.”

The manifesto includes four value preferences. The fourth value preference reads, “…We have come to value responding to change over following a plan.” The manifesto does not oppose “following a plan.” The idea is that adopting a preference for “responding to change” will provide a more efficient, more targeted solution to the customer or end-user.

Recently, organizational leaders have taken note of the “Agile” philosophy. The idea of self-managed teams working cross-functionally and collaborating with customers seems like an approach the entire organization should embrace. Agile software development emerged as a response to “Waterfall” software development. The waterfall model is linear and sequential. The waterfall model favors analysis, documentation and design over end-user testing and iterating. The organizational equivalent of waterfall software development is “command and control” management.

Given the current volatility and uncertainty of our business environment, should organizations transition away from a “waterfall” leadership style to an “agile” leadership style?

I recently had the pleasure of partnering on a leadership development program with Bjorn Bihhardt, Owner and CEO of Abilitie. Bjorn introduced me to the Cynefin framework* for making sense of the contexts within which leaders solve problems and make decisions. David J. Snowden, the founder and chief scientific officer of Cognitive Edge developed the framework with input from a number of his colleagues. In November of 2007, Snowden and Mary E. Boone, President of Boone Associates co-wrote a Harvard Business Review (HBR) article about the framework.

The Cynefin Framework

CynefinThe right-hand side of the framework describes contexts that are either “simple” or “complicated.” In both cases, cause-and-effect relationships exist. In simple contexts, cause and effect are apparent to everyone. In complicated contexts, there may be more than one right answer and it requires expertise to analyze the situation and determine an appropriate response. A simple business problem is collecting a late payment from a customer. A complicated business problem is improving the company’s cash flow.

The left-hand side of the framework describes contexts that are either “complex” or “chaotic.” In a complex context, no amount of expert analysis will result in a single solution or right answer. In their HBR article, Snowden and Boone write that a complicated context differs from a complex context in the same way a Ferrari differs from the Brazilian rainforest. The car is complicated, but static. An expert can take it apart and put it back together. The rainforest, on the other hand is in a constant state of unpredictable flux. Instead of conducting expert analysis, decision makers in a complex context must investigate, sense and then respond.

In a chaotic context, there is only turbulence and ambiguity (e.g. conditions in the midst of the events of September 11, 2001). Attempting to make sense of conditions before responding does not help. In a chaotic context, one must simply act and learn from how the environment reacts to what you do. The fifth element of the framework is represented by the open space at the intersection of the other four contexts. Snowden calls the fifth context, “disorder.” Disorder applies when one cannot discern which of the other four contexts pertain.

I mention the Cynefin framework because it seems to me that following a plan works when contexts are either simple or complicated. In both cases, expertise can determine a workable solution, routines and authority can ensure people implement the solution. When things become complex, responding to change with agility will be more useful. When things become chaotic, just do something.

The question then is not whether today’s leaders should adopt a waterfall style or an agile style. The question becomes, how do we know which context we should apply when framing our situation? In other words, when should we follow the plan our navigation software put us on and when should we turn off the app and respond to the changes we are sensing?

* Cynefin (ku-nev-in) is Welsh for habitat. It carries the connotation of factors that influence us in ways we can’t understand.



Consultants on Balconies Getting Comfy

Netflix recently released Season 10 of Jerry Seinfeld’s Comedians in Cars Getting Coffee. If you haven’t seen the show, its title is its premise. The episodes run for about 15 minutes. At the beginning of each episode, Jerry picks up his guest in an exotic car meant to capture the spirit of the featured comedian. Jerry and his guest drive around, grab a cup of coffee, sometimes eat a meal, sometimes run an errand all the while chatting about whatever interests Jerry. Often, what interests Jerry most is philosophizing about stand-up comedy.

In the first episode of the current season, Jerry’s guest is Zach Galifianakis. After picking up Zach in a Volkswagen Thing (fun, inventive, unique, irreverent… like Galifianakis, get the idea?), the comedians end up getting their requisite coffee in a donut shop. Zach becomes nostalgic about his pre-fame days when he could spend uninterrupted time observing people in nondescript places. He explains that after the success of the Hangover movies, he feels that he lost the ability to simply hangout in ordinary places and observe. He recalls wistfully, “I got to sit and watch people… and that’s where I got everything.”

After watching Jerry and his guests discuss how comics get inspired, one gets the impression that stand-up comics split their attention as they go about their lives. The comic blends in with the rest of us Earthlings attending to the activities of daily living while simultaneously watching life from some detached, alien perspective.

For example, as Jerry and Zach are driving past a couple of elderly gentlemen greeting each other on the street, Jerry observes, “There’s two old friends. See that hug? Those guys have known each other a long time. They’ve eaten the exact same food. That’s why they’re the exact same weight.”

Facilitators and organizational development consultants also exploit the power of the detached perspective. For leaders, a detached perspective is more difficult, but no less important. Ron Heifetz and Marty Linsky in their 2002 book, Leadership on the Line compare leading to dancing, ask leaders to imagine the difference between the experience of being on a dance floor and being on a balcony overlooking the dance floor:

Achieving a balcony perspective means taking yourself out of the dance, in your mind, even if only for a moment. The only way you can gain both a clearer view of reality and some perspective on the bigger picture is by distancing yourself from the fray. (p. 53)

Consultants often provide leaders with a balcony perspective because the consultant is less attached to the specific ideas and opinions surrounding a challenging organizational situation. A consultant acting as a meeting facilitator on behalf of a leader can focus on the process of the meeting and the way participants interact to ensure the meeting leader gets full advantage of convening stakeholders with diverse points-of-view.

Of course, just as leaders can get stuck on the dance floor and miss the big picture, consultants can get stuck on the balcony. Too much time on the balcony and helpful insights can become unproductive criticisms. Consultants who get comfortable on the balcony risk becoming like the “cold and timid souls” in Theodore Roosevelt’s famous speech who, “…know neither victory nor defeat.”

When Dennis Rebelo and I were students at Saybrook University working on our doctorates we developed a reputation as captious bystanders during our program’s residential conferences. At some point we started referring to ourselves as Statler and Waldorf, the cranky, wisecracking hecklers that would sit in the balcony during The Muppet Show and amuse themselves with insulting comments about whatever was happening on stage. We were never sure which of us was Statler and which was Waldorf, but we embraced the nicknames and the personas.

To be fair, Dennis gets antsy if he spends too much time on the balcony. He is a busy guy with a string of accomplishments. Check out his latest project called StoryPathing™ designed in part, to help people during transitions develop their identity through the power of narrative. I, on the other hand, get very comfortable on the balcony. Sometimes, when I facilitate meetings, the dynamics playing out in front of me can distract me from intervening and redirecting the discussion.

The view from the balcony can help a team get unstuck.

If you don’t have access to a consultant or facilitator… or a stand-up comic, you can still benefit from a detached perspective. In every group and during every meeting someone at some point in a process or discussion is paying more attention to how things are going (balcony) than to the work at hand (dance floor). Moreover, the person most likely to have a useful opinion about how things are going may be the one who seems disengaged or even anxious about participating.

If you have created an environment in which people feel safe expressing their thoughts and feelings, you can simply pause the meeting or process and ask people for feedback. If not, follow the example of Jerry Seinfeld and take a coffee break. Simply stop the action for five or ten minutes and talk to someone whose opinion you respect and who has not had much to say. When attempting to learn from someone who has been on the balcony, don’t ask, “What should we do?” Instead, ask, “What are you seeing?”