Organisations are constantly pursuing change and innovation, yet often fail to recognise that independent, strong-minded employees are frequently the key to success. Instead, the system tends to preserve itself, observes Simone van Neerven.
Too headstrong
Charles Wintour was editor-in-chief of the Evening Standard for many years and one of Britain’s most influential newspaper editors in the 1960s and 1970s. He regularly invited his daughter Anna to brainstorm ideas on how newspapers could be more appealing to younger readers. These conversations taught her to think critically and develop her own opinions from an early age.
Anna attended the prestigious North London Collegiate School, but she was far from a model student. She rebelled against the school’s strict dress code by wearing her skirt shorter than permitted and having her hair cut into a strikingly sleek bob. The hairstyle would later become her trademark, but at the time, it was considered a bold fashion statement that reflected her independent, strong-willed personality.
At sixteen, Wintour left school and chose to start working rather than pursue higher education. Her first major break came after she moved to New York, where she landed a job as a junior fashion editor at Harper’s Bazaar. But the opportunity proved short-lived. Just nine months later, she was fired after her editors concluded she was too headstrong and her ideas were too radical.
Missed opportunity
In 1988, Wintour became editor-in-chief of American Vogue, and she had lost none of her rebellious spirit. She immediately made her mark by featuring a model in jeans on one of her first Vogue covers, photographed on the streets of New York—a striking contrast to the elegant, meticulously staged covers that had long defined the magazine. The change was so radical that the printers reportedly called the Vogue editorial office to ask whether the cover had been sent by mistake.
Wintour went on to become one of the most powerful and influential figures in the fashion industry. Her success was built on the very qualities that had once been seen as liabilities: her individuality, unconventional taste, and willingness to challenge established norms. Ironically, these were the same traits that had cost her her job years earlier.
Staying on the beaten path
Wintour was not fired because she lacked talent, but because she didn’t fit the mould. Her supervisors viewed her unconventional behaviour as a problem and had been unable to see it as an opportunity. They judged her on her ability to adapt, not on her potential to bring innovation.
This is precisely the problem. Organisations constantly talk about the need for change and innovation, yet often fail to recognise that the independent, outspoken, and sometimes headstrong employees are the very people who drive it. A lot of time and energy is spent on trying to bring these ‘difficult’ employees into line, whereas managers should be asking themselves how they can create a context in which their talent can flourish.
Why? Because the system reinforces itself. If nonconformists are not pushed out, they often choose to leave on their own. Those who remain are the people who adapt most easily to the prevailing culture, and, once they become managers, they tend to reward the same behaviour in others. The result is an organisation that values conformity over originality, even as it claims to prize innovation.
Unmanageable
Creative people rarely fit well into systems built around predictability, efficiency, and control. As a result, they are often seen as difficult to manage. They challenge conventional thinking, bypass established hierarchies, and propose ideas that initially appear messy, risky, or even absurd. This inevitably clashes with organisations that are designed to minimise mistakes rather than explore new possibilities.
Managers should not see employees who challenge the status quo and create friction as a problem to be solved, but as a sign that innovation may be taking shape. These so-called “unmanageable” people are rarely trying to undermine the organisation. More often, they are trying to make it better.
Embrace creative talent
The fewer creative people an organisation has, the more sluggish innovation becomes. And the more innovation slows, the more organisations rely on processes and frameworks to “manage” it. But innovation can only be managed to a certain extent. More often than not, it begins with someone who dares to think differently, challenges convention, and colours outside the lines.
Organisations do themselves a disservice by failing to embrace these free thinkers. In doing so, they miss the opportunity to innovate and adapt from within, with greater commitment from employees and without the enormous costs of external consultants.
And what about the creative individuals themselves? They rarely stay discouraged for long. More often, they emerge stronger. Anna Wintour is a case in point. She has never viewed her dismissal from Harper’s Bazaar with resentment, but rather as a valuable moment of reflection that forced her to reassess her direction. As she famously put it: “Everyone should be sacked at least once.”
This article was originally published in Dutch on CHRO.nl – the platform for HR executives.
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