I entered the workforce at a relatively young age, and what I observed almost immediately was the correlation between a happy work environment and a good leader. I spent my adolescence behind ice cream counters and restocking bakery aisles but no matter my task or role, whether I was going to have a good or bad day at work rested entirely on the leader.

During those early years, juggling both school and work, I encountered a colourful set of supervisors, managers, directors, and owners but not one was ever respected by us employees. They either ruled by fear or were completely disingenuous which filtered down and spread throughout the work environment.

I hoped, one day, when I did start my career, I’d meet my ideal leader. Someone who was not only fair but empathetic, mature, compassionate, understanding, decisive, and above all else, a non-conformist. A person who was able to separate themselves from the pack. A style that is underappreciated but a necessity in order to keep an objective stance on the bigger picture.

man holding sign up to a group of people sitting on a picnic table outside.

It’s Not About Making Friends

After university, I landed my first real job, and for ten years I would wither away in corporations that presented me with a string of managers who were more interested in making friends than hard decisions. Their convictions are easily swayed by any opposing opinion. I slowly lost respect for their word and even more so, the system that encouraged such rhetoric.

Their common Jekyll And Hyde persona became unbearable to watch. Their obvious desire to be liked by everyone made me coil at their lack of constitution. Their words conjured feelings of mistrust and their performance only jaded my hope of ever finding a great leader; a true leader. I felt like I was walking in a land mine; tip-toeing every step. A fear that slowly messed with my psyche.

Over the years, I saw countless missed opportunities to instill positive change at our office. There were numerous chances to shine a light on real issues, but they always moved to the sidelines.

The organization modeled a modern-day Salem, with regular witch hunts in place for those that sparked a more progressive conversation. A mob would wage, and alliances formed carrying their pitchforks and torch lights. And just like in the colonial Massachusetts town, we saw our own version of mass hysteria.

I often wondered if it was possible to stand up against the mob and fight for issues that questioned the office’s conventions. But time and again, I saw leaders slither and cower at the swarm of angry employees, and there, just like that, the moment to inspire real change vanished into the ether.

I do admit, it’s not an easy feat to stand alone in your convictions. So, I would ask myself, “Is it possible to garner respect as a leader while still moving against the grain?” I believe so, and I want to see more of it.

Balancing Convention While Fostering Change

Groupthink is a powerful tool; one that wields a tremendous amount of influence but is it doing more harm than good? Can cohesive collaboration exist while still questioning the status quo? Adam Grant, the notable psychologist and author, tackles the ideal model of groupthink in his book, Originals. It’s definitely worth the read.

Now it’s important to state that encouraging a positive workplace environment, one filled with collaboration and consensus is vital when nurturing a productive team. But a leader, in tune with the bigger picture, can also foster a safe space that encourages employees to question what’s been done before. They can cultivate an office free from bullying tactics and possible ostracization when an employee drives forward concepts that think outside the box.

This is how we push forward influential and innovative change. This is how leaders provoke unconventional thought and move new rhetoric in order to instill impactful differences. Leaders who take out the shovel and pass them to their employees to carve out a new path.

There are both positive and negative aspects to groupthink and it takes a leader who can think objectively to make the final call. One who isn’t apprehensive about offending frail and egocentric insecurities but stands behind their team.

Does such a leader even exist? Who is strong enough to stand against a group? Maybe they just don’t exist in the corporate world.

3 women wearing suits standing together

A Dying Breed

There was always one name that came to mind, who I felt held the qualities of a non-conformist, and unfortunately for me, I would never get to meet him.

I was first introduced to Major Richard “Dick” Winters when I watched the HBO series, Band of Brothers, which was based on a book by Stephen E. Ambrose which I also read. It follows the real events of a parachute infantry in World War II, called Easy Company which Winters commanded.

The Major was quiet, reflective, fair, compassionate, and strategic. But it was his innate introspection that made him an outsider and gave him an objective perspective on missions, the war, and his team.

During the war, Winters was fiercely respected by his men, but he never crossed the line into comradery. It is a dangerous territory to flirt with because the consequences can muddle your judgments. I believe this is true in any leadership role, not just the ones found in combat. And what made Winters a great leader: he was comfortable with, and almost preferred skirting the edges of a group.

Question the Convention

The outsider is often seen as the anti-social weirdo who avoids parties and carries an aloof air that is often misunderstood. But history has shown us a different narrative. One where the outsider made difficult and unpopular decisions to drive forward equality, and sought out revelatory change in science, religion, and technology that have shaped our world and steered our species to new heights.

Questioning may get you on the dean’s list, but it can also promote healthy conversation in hopes we can have a workplace with more diversity, equality, fewer burnouts, and brain drains.

4 people sitting on grass with wearing matching tshirts that read the word "team"

A Plea to All the Black Sheep

So, I’m calling on all you misfits and loners, the eccentrics that see the world differently and question the norm – not for cheap thrills and to stir up pandemonium, but for authentic growth.

To create systems that are genuine and creative. Where people’s curated personas fade, and we see our colleagues as the beautiful individuals they truly are. With their own opinions and life perspective that shape and colour everything they do.

We need leaders who see these differences as an asset, not a threat. We need leaders with kaleidoscope eyes, seeing the black, the white, and the shades of grey in between, but also the beautiful spectrum available in all of us.

Until next time, you Wildsoul – keep blooming!