Six “Wicked Questions” Every Leader Must Ask

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Competence, Character & Leadership …
We are not the first to suggest leadership needs to be defined in a more robust and all-encompassing manner. In fact, we believe the definition of what constitutes great leadership is not static, but rather needs to evolve with the times and the particular challenges posed by a specific moment or era. In this sense, leadership is something that can only be judged by the relevance of the person (or persons) to the particular stage on which they perform and the unique context within which they have been asked to lead.

All leadership is, so it has been said, situational!

In my book “Straight Talk on Leadership” (Wiley and Sons, 2013), I introduced the eight transformational leadership competencies I believe are required for the times in which we live. The good folks at Western University in London (Crossan, Gandz and Seijts) offered up their ten “Dimensions of Leadership Character” and the two together give us a very good model with which to evaluate the nature of leadership today.

This powerful combination of character traits and leadership competencies offers a roadmap to those who wish to examine not only their own fitness, but the fitness of the leaders below them. No worthy leader should shy away from holding themself, and others to the very highest of standards and asking the tough, “Wicked Questions” needed to accurately assess how competent they are.

Power of Wicked Questions …
We have always been fascinated by the magical art of asking “Wicked Questions”, those questions that do not have an obvious answer. In fact, we would go so far as to suggest great leaders know how to craft wicked questions, and it is their ability to do so that marks them as truly unique individuals.
At their very essence, wicked questions are questions of exploration or discovery.
Wicked questions are used to expose the assumptions which shape our actions and choices. They are questions that articulate the embedded, and often contradictory assumptions, we hold about an issue, a problem or a context. Unlike everyday questions, wicked questions do not have an obvious answer, and their value lies in their capacity to open up options, expand the scope of inquiry and surface the fundamental issues that need to be addressed, rather than the symptoms which often mask or distort the truth.
On the following pages we offer up the questions we believe leaders must ask themselves, and then act upon, no matter what the ugly truth reveals. To play on the famous quote by British Prime Minister Winston Churchill (a situational leader if ever there was one), the ability to answer these questions is “Not the end. It is not even the beginning of the end. But it is, perhaps, the end of the beginning.”

Are We Really Clear Headed? …
We can all be blinded by distraction and deafened by noise, but the true test of a leader is their ability to rise above all of that and, in the words of Rudyard Kipling, “Keep your head when all about you are losing theirs and blaming it on you”. When a leader allows their cognitive abilities to become impaired, for whatever reason, they lose the crucial ability to accurately orient themselves, and their organization, in both time and space. As a result, their judgment can be seriously flawed and, even worse, they may not even realize it until it is too late.
Leaders must possess the strength of character, and depth of competency, to avoid this trap. They must force themselves into asking the wicked questions to seek the truth and ensure the validity of their thinking. They cannot rest until they have punctured every half-truth or bias that may have crept into their thinking over time.

Leaders must be wide awake and hyper alert. They must possess a combination of:

Contextual Intelligence (CQ) – sensing subtle shifts and predicting their implication
Ambiguity Intelligence (AQ) – living comfortably with uncertainty and not knowing

Transcendence – appreciative, inspired, purposeful and future oriented
Humility – modest, reflective, continuous learner, respectful and grateful

Are We Using The Right Lens? …
Our perspective on an issue, or on a challenge, or on people is what ultimately shapes the conclusions we reach and, therefore, the actions we take (or don’t take). If we get the initial frame wrong, then we will very likely make the wrong assumptions, and they will fog up the lens through which we look at the situation. We will end up drawing the wrong conclusions based on a faulty premise – or an outright distortion of reality.
Our mental models are powerful, often invisible, prisons that can trap us into a belief system that is both inaccurate and dangerous. When leaders allow themselves, or their organizations, to twist and distort the reality of any given situation, they become complicit in a chain of events that will almost always lead to failure. Leaders must be at their best when things are foggy or vague, and they must have the balance just right between what is fair and just, and what is required to alter old, tired mindsets in order to unlock the potential found in a new way of thinking.

Leaders must be vigilant, calm and rational. They must possess a combination of:

Strategic Intelligence (SQ) – deep insight , clear foresight and peripheral vision

Justice – fair, equitable, proportionate, even handed and socially responsible
Temperance – patient, calm , composed, self-controlled and prudent

Have We Been Totally Honest? …
It’s very easy to tell little white lies, we all do it from time to time. Some are simply innocent lies, with no malice or ill intent, and some are lies of convenience, designed to get us out of an uncomfortable or tight spot. No matter how we cut it, honesty is a practice rooted deeply in our character, and it is either a covenant we keep with ourselves, or something we allow to roam at will, depending on the situation.
We consider candour to be the ultimate lubricant for a high performing organization because it assumes the shortest distance between any two points is a straight line, and beating around the bush is nothing more than waste and inefficiency. The trouble is, most people have a limit to their candour. In critical situations, they allow themselves to hold back from telling the truth for fear of recrimination or some form of backlash.

In our view – the worst truth is still better than the best lie!

Leaders must be humble and authentic. They must possess a combination of:

Emotional Intelligence (EQ) – ability to know yourself and connect with others

Integrity – authentic, candid, transparent, principled and consistent
Learning – open, aware, informed studious and inquisitive

Has Our Culture Evolved With The Times? …
Some people believe an organization’s culture should remain static, preserved in a pickle jar and never allowed to change over time. They believe their culture is somehow a guarantee of continued success, or an anchor in a storm, or some other colourful metaphor that suggests the past is a harbinger of the future. While there may have been a time when this was more true than false, the fact of the matter is – times have changed.
Cultures need to evolve with the times, and the continued relevance of your organization may very well be determined by whether or not your culture has allowed new oxygen to creep into the lifeblood of what it believes and how it acts. At its core, culture is the way things get done, it’s what people believe and how they choose to work together. It is not determined by the organizational chart, or hierarchies of control and authority, but rather by what people think and do on their own, when no one is watching.

Leaders must have an eye for talent. They must possess the combination of:

Talent Intelligence (TQ) – capacity to spot, develop and release latent talent
Collaborative Intelligence (COQ) – connect with and work comfortably with others

Humanity – considerate, empathetic, compassionate, magnanimous and forgiving
Accountability – takes ownership, accepts consequences, conscientious, responsible

Have We Banished Complacency? …
The well-known author and business guru Jim Collins once said “The enemy of great, is good”. He was right – but he may not have gone far enough because complacency still remains the silent killer of organizational effectiveness. Perhaps it is sheer laziness, or maybe it is fatigue, but leaders everywhere are guilty (at some level) of allowing their organizations to drift into a repetitive pattern of subdued mediocrity.

Harsh words, perhaps, but with more than a little truth!

As complex social structures, organizations cannot be managed solely, or even effectively, through a dense set of policies and procedures. The human element will always come into play and, like water, it will find its own natural level, regardless of how it may be contained by a set of structures. Leaders must be the energy source that fights back against the dark forces of complacency, and they must do so by continually agitating, stretching, challenging and provoking.

Leaders must disrupt and disturb. They must possess a combination of:

Decision Making Intelligence (DMQ) – ability to frame problems and resolve issues

Courage – brave, determined, tenacious, resilient and confident
Resourcefulness – able, imaginative, adroit, able to deal well with difficult situations

Are We Breaking New Ground? …
Yesterday is the land of nostalgia, while tomorrow is the land of opportunity. Since we will be living in the future, whether we like it or not, a leader who is not thinking fast forward is leading their organization backwards in time. While breaking new ground is hard work, full of risk and peril and with no guarantee of success, it remains the only way to move ahead and, in the process, remain relevant.
Over the broad sweep of economic and social history, progress has been marked by the brave pioneers who were driven to the future by the allure of its promise, not the comfort of its certainty. Progress is a necessary part of evolution, and adapting to new conditions is what ultimately allows us to prosper and grow, both personally and organizationally. Leaders, above all others, must be the ones to challenge convention and stir the pot of discovery to ensure their organizations move forward. They must discard the shackles of convention and embark on a journey into the unknown.

Leaders must be brave and curious. They must possess a combination of:

Innovative Intelligence (INQ) – ability to inspire, imagine and invent new solutions

Driven – passionate, vigorous, results oriented, takes initiative, strives for excellence
Determined – resolute, purposeful, unwavering, undaunted and tenacious

Steps to Take :: Actions to Consider
It is our strong conviction that the times in which we live change the very nature of the leadership we need. In a world as fast-paced, demanding and ever changing as the one we find ourselves in today, we believe leaders need to be more open than ever before to new mindsets and new possibilities. To quote the author Marshall Goldsmith “What got us here, won’t get us there”.
As such, leaders have to master the stubborn paradox that has always been part of leadership, the ability to embrace new ways of thinking while being guided by a set of character traits and virtues that provide balance in the midst of chaos and confusion.
Here are some things to help get you started.

Abandon Perfection as the Goal
In a world that is fundamentally imperfect, populated by less than perfect people, the very pursuit of perfection may be a cruel form of flawed logic. In fact, one can argue that arriving at a state of perfection is what actually inhibits you from getting better, doing more, or inventing something different. Give imperfection its rightful place.

Focus on Asking Better Questions
We all like answers, but the thing that actually moves us forward is questions, questions that challenge what we believe and what we have come to accept. The ability to ask “Wicked Questions”, the kind that disrupt, and stretch us beyond our own boundaries, are the gold dust of success.

Keep Things in Constant Flux
The role of the most senior leaders of any organization is not to keep things in check and under control, it is exactly the opposite. Great leaders thrive in the midst of chaos, and even create it as a means to push their organizations forward. They realize that keeping things in motion, and allowing ideas to collide (sometimes violently), is the best way to remain agile and opportunistic.

Tinker and Experiment Continually
Curiosity may have killed the cat, but it is what all great leaders, in today’s environment, must have in spades if they wish to guide their organizations forward toward sustainable success. Complacency, in all its forms, must not be allowed to put its evil hands around the neck of the organization and choke the ability of people to innovate on a daily basis. Innovation is a free spirit and a restless soul, it cannot become institutionalized.

Honour Your Rebels
In times like this, your best friend may very well be the crazy person you always feared in the past. The person who seemed just slightly off kilter, the creative deviant, the slightly twisted thinker who might have always been the one to challenge you. Today, you might want to keep that person close to you, and give them the immunity of the court jester to say what they think and to think outside of the box.