Wicked: adjective, wick·ed \ ˈwi-kəd \
1 : morally very bad
2 : fierce, vicious; disposed to or marked by mischief
3 : disgustingly unpleasant; causing or likely to cause harm, distress, or trouble
4 : going beyond reasonable or predictable limits; of exceptional quality or degree
Why don’t fish have eyebrows?
When we were little, we would often pester the adults around us with the simple, repeated one-word question: why? Over time, our thirst for knowledge and understanding grew and we learned how to craft more specific and more difficult questions: Why do I have two eyes if I only see one thing? Why are there wars? Why don’t fish have eyebrows? Why do we have thoughts in our head that no one else can hear? Why is that person homeless? Why are you fighting?
Judge a man by his questions rather than by his answers.
But at some point, asking question after question after question became annoying. And as we grew older, society continued training us out of our precocious ways—annoyed parents told us to leave them alone, teachers taught us to regurgitate facts, the business world prioritized short-term solutions over big-picture ideas inspired by critical thought. For most of us, the inquisitive, exploratory nature that defined our early years never returned. It had been thoroughly extinguished by all those along the way who either didn’t have the answers or didn’t care about them.
Few of us ask “wicked” questions in the way we did as children—questions that are unpleasant, unpredictable, or unreasonable. Perhaps simply because we don’t want to be seen as unpleasant, unpredictable, or unreasonable people. But whatever the reason, too many of our interactions now bring closure rather than exploration, boredom rather engagement, and assumptions rather than inquiry.
Why wicked?
Good questions are often powerful and inspiring. But really important questions can also be scary or difficult to ask (and even scarier and more difficult to answer). Our truly wicked questions can feel unpleasant and unreasonable while also feeling exceptional and important; they embody a tension between good and bad, scary and inspiring.
The fear of not knowing
Let’s be honest. We’ve all pretended, at one time or another, that we watched that Netflix show our friends are laughing about, or sat glued to the political debate, or read that Oprah’s Book Club book. We might be “saving face” with our friends, but this compulsion to lie or deny also reflects our cultural anxieties about not knowing.
Quizzes, examinations, and aptitude tests all reinforce the value of correct answers. The business world is built upon hierarchies, consensus, and “towing the line.” We’re rarely asked to explore the unknown or to reflect. We have debates rather than dialogue and we talk more than we listen. In most places we look, answers have more value and are prioritized over questions. That’s a big part of why not knowing feels so uncomfortable and why truly wicked questions seem especially scary.
In the business world, many of us avoid asking questions about the way things are done because we worry it will make us seem either incompetent or insubordinate (or both). We stick to the agenda, we follow the plan, and we rely on assumptions and snap judgements more often than we may realize. The reward systems in our organizations don’t help. They often reinforce the value placed on answers and decisions and solutions and deliverables. Leaders believe that they are being paid for fixing problems, getting things done, keeping everything moving and putting out fires.
Sure, when we point the finger at our designer for blowing the scope of our project we may ask what went wrong. We shake our heads when budgets keep bleeding over and ask who is responsible. But those are accusations masquerading as questions. They seek admissions of guilt, not answers or insight or understanding.
This is not just a business-related phenomenon. In our personal lives, there is a similar tendency to move along on auto-pilot, zooming between errands and home and work without ever stepping back to question our career choices, attitudes, personal priorities, or beliefs—everything that makes up the way we choose to live our lives. It’s easier and safer to just keep our heads down and do what we’re told. Society is full of life-hacks and quick-fixes and “experts” explaining how to do (or not do) our jobs, how much coffee is healthy (or unhealthy), and which deadlines are more important (than others). With all those conflicting answers swirling around, we rarely have the time or space to investigate or reflect on what makes more sense or why we believe what we do.
Modern western society places far more value on answers than it does on questions. This article isn’t going to change that. But it might help you learn how to approach big problems and important conversations in a new way.
If I had an hour to solve a problem and my life depended on it, I would use the first 55 minutes to formulate the right question because as soon as I have identified the right question I can solve the problem in less than five minutes.
Asking with intention
If answers lead us toward closure, questions open us up to exploration, inquiry, and understanding. Asking the right question at the right time can be transformative. But how do we know what the right question is?
There are some defining characteristics that most “wicked” questions share. Wicked questions:
The usefulness of the knowledge we acquire and the effectiveness of the actions we take depend on the quality of the questions we ask.
- Generate curiosity and energy
- Stimulate conversation
- Demand reflection
- Surface underlying assumptions
- Invite creativity and new possibilities
- Channel attention
- Reach toward a deeper meaning
- Evoke more questions
- Stay with you for a long time
Learning how (and when) to ask important and “wicked” questions is one of the things we practice in the Louder Than Ten PM Apprenticeship program. Inspired by the Art of Hosting, Dialogue, and The Art of Powerful Questions, we focus on three dimensions (Structure, Scope, and Assumptions) and one rule—the rule of intention.
1. Structure
The words we choose when asking questions—the structure we give them—inform the potential of those questions. Some questions close down, ending the inquiry with a single word answer (e.g., Is this what you wanted? Should we postpone the launch date?) while other questions open up, inspiring further and greater inquiry (e.g., What are the implications of postponing the launch date? Why do we consider this thing good and this other thing bad?).
When it comes to the structure of our questions, there is a hierarchy of wickedness: some are more wicked—more powerful—than others.
↑ Less wicked | Which? Should? (Yes/No questions) |
Who? When? Where? | |
↓ More wicked | What? Why? How? |
Wicked questions create space for inquiry; they generate energy, invite curiosity, and challenge assumptions. They also lead to more and different questions. Consider the following line of questioning (a common one involved in employee reviews or stakeholder management) as it moves up the table from a closed question to increasingly open questions. The line of questioning doesn’t necessarily change, but the structure of the question does.
↑ Less wicked | Are you satisfied with our working relationship? |
When have you been most satisfied with our working relationship? | |
What is it about our working relationship that you find most satisfying? | |
↓ More wicked | Why might it be that our working relationship is less satisfying than it used to be? |
Depending on the answers you are looking for, “when” or “which” questions can be just as useful as “why” questions. One structure isn’t better than any other—rather, they are all useful in different contexts. What’s most important is finding a structure that best serves the intention behind your line of inquiry.
2. Scope
The next dimension is related to the scope of our questions. Scope has to do with how much of the world around us is informed by our questions. Are we addressing a big problem or a small problem? Are we solving a big part of the problem or a small part?
↑ Less wicked | How can we best manage the working relationships within our project team? |
How can we best manage the working relationships within our company? | |
How can we best manage the working relationships within our supply chain? | |
How can we best manage the working relationships within our market share? | |
↓ More wicked | How can we best manage the working relationships within our capitalist and global economy? |
Generally speaking, bigger scope leads to more interesting, thought-provoking, and wicked questions. However, too big of a scope can ignore the specifics of the problem or issue we’re facing and may also be beyond our capacity for action.
Be aware of the scope of your questions—their boundaries or sphere of influence—and learn how to shift the scope by recognizing smaller and larger frames of reference when asking important questions. Try to approach questions using a scope that is relevant and actionable for your specific situation. We may be able to affect change within our product team but not within our entire supply chain.
3. Assumptions
The third and final (and trickiest) dimension of questions has to do with the assumptions those questions embody. It can be hard to see the assumptions underlying our questions—and it is especially hard to do so while we are asking them—but learning to understand this dimension often has the most profound impact.
Because of the nature of our language, almost all of the questions we pose have multiple assumptions built right into them—either explicitly or implicitly (or both). Take, for example, the questions about “working relationships” used above. Each of those questions has multiple assumptions already built into it. They assume that the working relationship is the only aspect of that relationship of importance—or that the “working relationship” can be separated from other ways of conceptualizing a relationship between co-workers. They assume that working relationships should and/or can be managed at any point in time and they carry each person’s assumption of what “managed” means in that specific context. (For more reading about assumptions and limiting beliefs, check out this other excellent Coax article.)
In order to craft truly “wicked” questions, we have to become aware of our assumptions and learn how to use them appropriately and intentionally. Compare the questions below.
↑ Less wicked | What went wrong? Who is responsible? Where did things fall apart? |
↓ More wicked | What can we learn from this? What possibilities are now available to us? |
Think back about a recent issue or dilemma or difficult conversation. What kinds of questions did people ask? What assumptions did those questions carry? What kind of different, more wicked questions could people have asked in the same situation?
The first set of questions assume error and blame and systemic failure. They assume something and/or someone was wrong and can or must be fixed (or punished). It will be hard to answer these questions without feeling defensive or worried.
The second set of questions assume opportunity and knowledge. There may not actually be knowledge to glean but the assumption encourages reflection rather than finger-pointing. Answering these questions may be more difficult, but trying to do so will stimulate learning, dialogue, and collaboration among those involved rather than fear or blame or judgement.
The rule of intention
The rule of intention is quite simple: Don’t ask a question unless you are willing to listen to the answers—all the answers—that may arise.
In many fields and sectors, the ability to craft “wicked” questions is a mark of a successful leader; it can take companies and teams in bold new directions and open up new possibilities. However, questions can also be used in harmful, negative, or unproductive ways. This rule challenges us to recognize the intent behind the questions people ask (including you). Pay attention to the kinds of questions that don’t want an answer (and the situations in which people ask those questions).
Some questions can easily provoke a defensive response. “Why” questions can be used to justify answers or pass judgement rather than provoke inquiry and understanding (e.g., Why did you do it that way? Why don’t you ever run these things by me?). These kinds of questions don’t want an answer—they are judgements in the form of questions.
Over time, you’ll notice that some people ask questions just for the sake of it. Often, these people don’t actually want an answer—they want to waste time, direct attention, or project wisdom where there isn’t any. The rule of intention is about asking questions with a willingness to listen, observe, and pay attention to all of the reactions and results of our inquiries.
From asking to action
Example: AirBnB
AirBnB’s early days and exponential growth were actually fueled by a series of wicked questions that the two founders, Joe Gebbia and Brian Chesky, posed to themselves. Their story has been documented and explained at multiple conferences and in various journals and articles.
In the fall of 2007, the two roommates had one important question in their minds. It wasn’t particularly wicked—or even that unique. That question was: “How were we going to pay the rent?” They didn’t have a lot of money, they didn’t have jobs, but they did have a decent apartment in a city that regularly saw massive influxes of people coming to town for conferences—people who were desperate for a place to stay once the hotels all booked up.
Having had similar experiences themselves, they asked: Why can’t we find a place for these people to crash for a night or two? That led to: Why not our place? They could have stopped there and posted an ad on Craigslist and solved the problem of finding these people a place to crash. But instead, they continued inquiring, asking a series of increasingly wicked questions.
What if we provide more than just a mattress to sleep on? What if provide space for multiple people? What if we create our own website for this? What if you could pay online? What if we could create this same experience in every major city? What if we take this idea on the road, and test it in another city? What if we make a business out of this? Why should we settle for what currently exists? Why should we believe the people who tell us this can’t be done?
Initially, investors balked at the idea of funding a couch-sharing start-up. But the questions that led to the creation of Airbnb challenged a basic, long-standing assumption—that reputable hotels were needed to provide accommodation for out-of-town visitors. To be fair, it helped that they had first-hand experience of both sides of the problem they were investigating: Having extra space that people could use (in San Francisco) and needing to use other people’s extra space (when travelling to conferences themselves). Now, their questions might be: How does our sharing model ultimately impact the cost of living in a city and what is our responsibility to address this issue as a global platform that is profiting from it?
But seeing a problem and questioning why the problem exists is one thing. Inquiring into whether there might be a better alternative–and to keep doing so (even after the experts have told you that you won’t be able to change the situation) is another thing entirely.
Example: Prosthetic Foot
“If they can put a man on the moon, why can’t they make a decent foot?” That was the question 21-year-old Van Phillips began asking after he lost his left foot in a boating accident. At the hospital, he was given a pink foot attached to an aluminum tube and was told to “toughen up” and to “get used to his new best friend.”
Phillips eventually accepted his fate—that he was an amputee. But he refused to accept that he had to wear the lousy prosthetic given to him at the hospital. He began asking the question above. And instead of seeking answers, he just kept asking more questions.
If they can put a man on the moon, why can’t they make a decent foot? Why are we trying to replicate human bones with prosthetics? How can we create the energy required to propel a leg without a power source? What would a different kind of prosthetic look like? What can I learn from the world around me that will improve this process? Will this prototype hold up better than the last one? And if so, why?
At the time, most prosthetics were designed in terms of cosmetics. They were prosthetic feet that tried to resemble human feet. Phillips looked elsewhere—the animal kingdom, swimming pools, ancient Chinese battlefields—for inspiration and built hundreds of prototypes. Each one that broke was a site of further inquiry; each failure was a learning opportunity. Eventually, he created a C-shaped foot without a heel that could flex and bend under the weight of a body and changed the whole field of prosthetics.
Phillips solved his problem very early on but he kept inquiring and exploring. A wicked question started his journey: Why should I settle for this lousy foot? And another wicked question kept urging him on through hundreds of iterations: How can I make the next one better?
Stay with the questions
We expect kids to explore and inquire because asking questions is a fundamental way of making sense of the world around us. And we can tolerate kids who ask question after question after question, but only as long as we have the answers. As soon as the topics veer off into the absurd or the vague or the reflective, the inquisitive child becomes irritating. Having to respond to questions for which we don’t have an answer is uncomfortable. Having to ask those questions can be even harder.
It’s not that I’m so smart. But I stay with the questions much longer.
But the truth is that being willing and able to take a step back and ask big, important questions is good for us. It helps us solve problems instead of simply working around them. It helps us understand our needs and feelings and beliefs and biases so we can live happier lives and work better with others. It enables us to become more engaged in our work and more aware of everything going on around us.
What haven’t I thought of that could make this different or better or easier? Why am I feeling this way? What can we learn from this? Why do meetings with the VP always stress me out? How can we improve our relationship with this client? Why does last-minute QA always land on my desk? Why is that person homeless? Why are you fighting? Why do we have thoughts in our head that no one else can hear?
I don’t know. But I’ve learned that it’s not about having the right answers. It’s about asking the right questions.
