Compassionate skepticism: the most important skill of my career
My growth and progression as a communications and marketing professional can be most directly tied to one skill: my ability to be a compassionate skeptic. But a generation of leaders are held back from unlocking its power. What is this skill, why has it helped me so much, and why are so many blocked from its power?
First, at its most basic level, skepticism is the art of not being easily convinced. It’s the practice of asking thoughtful questions to get to a better answer. Some qualities of great skeptics could include:
Deep, apply-able subject matter expertise
A clear idea of the rightness or quality required to achieve goals
The willpower to resist “good enough” outcomes and instead dig further to find “great”
But we’ve likely all encountered the downsides of such skepticism in others. The skeptic who questions things endlessly. The skeptic who believes they “know it all” and resists learning. The skeptic who questions, to seem counter-culture or non-conformist (aka, the edgelord). The clinical, sterile skeptic who treats feedback as an intellectual exercise only. These styles of skepticism lack heart, empathy and shared responsibility.
What does it look like to blend heart, empathy and shared responsibility to the skeptic skills? These skeptics would:
Take a shared responsibility for the outcomes of the problem. They think carefully before asking their questions about whether the inquiry could add value to the outcome. They either refine, or discard, questions that would waste the recipient’s time or not add value.
Take a shared responsibility for the outcomes of the recipient. They learn, understand, acknowledge and connect with the process and place that led the recipient to their current point. When they question, they focus on unpacking the problem, rather than disarming the recipient. They aim to instill camaraderie, curiosity and confidence in the recipient, as to improve their outcomes for next time.
Always have a learning mindset. They don’t question to prove their strength, standing or authority. They understand that even the top experts don’t know everything, and new information and perspectives can enrich everyone. They’re open to the idea of learning something by looking at the problem through the perspective of the recipient. And they share with their team when they’ve learned something that evolved an older point of view.
Surround the problem, and themselves, with diverse perspectives. They acknowledge they may have biases, even if they can’t identify them clearly. They combat this by bringing diverse sets of skills and backgrounds to solve problems, and listening carefully and non-defensively when perspectives differ from their own.
Keeps focus on issues, and not people. Not all debates are handled with the kind of care and consideration we’d like. They monitor for when conversation focus turns from information, to people, and resets course accordingly.
Creates an open-hearted platform for progress and decisions. “Losing” a debate can be hard and painful. It hurts when decisions don’t go the way of someone who spent hours preparing for a different outcome. But eventually, decisions must be made. These skeptics set clear, understandable, accessible terms for decisions to be made, and will move forward when it’s time. Making a choice will disappoint some - there’s no way around that. But decisions can be made with respect, and acknowledgment, for those who researched the roads not taken.
This mindset forms a practice I call compassionate skepticism. It’s skepticism with heart.
I have found that the best leaders - especially in the artistic professions, like PR, marketing and advertising - practice compassionate skepticism. There is no singular right answer, but some answers are better than others. Getting to these answers takes lots of work and refinement, which take a ton of time, brainpower, creative risk-taking, and emotional energy.
I find that leaders who lead like compassionate skeptics run teams that develop the coolest ideas, have the most success, happy teams who bring the most of themselves, the highest retention rates, and the best people that stick together from company to company.
What holds back leaders from developing compassionate skepticism? It’s simple. Compassionate skepticism requires vulnerability, which runs counter to deeply-held, unconsciously passed beliefs about great leadership.
Compassionate skepticism runs counter to the toxic mythos of the creatively-gifted-but-tortured-genius, which I call “The Steve Jobs Myth”. This myth says that, as a creative leader, your vision is The One True Answer, and you must convince others of that answer at high cost. Teams are supposed to work in awe of their leaders’ creative genius, which somehow convinces them to endure the leader’s abrasiveness and dispassionate outlook. One day, these leaders think, when the world acknowledges their vision was “right,” all will be forgiven, and magically, their teams will thank them for the experience.
This mythos has proven highly destructive to a generation of young leaders, especially in technology, who read Walter Isaacson's biography of Jobs (or saw the Michael Fassbender movie) and came away with the lesson that it's correct to grind every person in your professional and personal life into dust to make your vision come to life.
For anyone who’s read the biography and followed Jobs’ career, such viewpoints ignore the broader argument that Jobs was a deeply flawed, singular genius…who nonetheless showed (imperfect) examples of compassion in his personal and professional life. Such viewpoints also ignore the countless, countless, countless studies that show the best leaders exhibit compassion and empathy.
In reality, this toxic mythos guards a deeper, pervasive, unconsciously passed belief that leaders can’t be vulnerable; that compassion is great for workplaces, but not for leaders; that compassion acts against swiftness and precision; and that compassion, especially for male leaders, is a symbol of weakness.
Vulnerability, which is necessary for true compassion, requires self-examination; requires you to admit when you’re wrong, or don’t know; requires you to think before you deliver feedback; requires you to challenge your experiences and perspectives.
As I have written in the past, the “lone tough guy” style of manliness - which tells men that it’s okay to not understand your emotions - is actually a cheapened, sugar-high, neutered form of power that generations of men were taught, purposefully or implicitly, is the right way to be a man in charge. But it’s not. In exchange for their unexamined, community-less, unempathetic life, studies show that these men are lonelier, burn out faster, less physically and mentally fit, and aren’t as good at their jobs.
True sovereignty requires blending personal and professional power. True creative leadership requires blending skepticism and compassion. Fewer skills have served me more over the course of my career than compassionate skepticism.
It's hard; it takes work; but study after study after study shows that the best leaders, the best organizations and the best creations come from this blend. It's never too late to learn, nor too early to start. Like every skill - and just like refining your creative expertise - you'll only get better with practice.