The Fearless Leader: Myth and Legend.

Let's stop glorifying toxic traits in corporate America.

These past few months have seen me learning a lot about new technologies (AI anyone? Even released my first mini album “AInastasia”) but also reading more than I anticipated (finally going through the pile of books on my bedside).

Whatever is the story, it seems to get me into 1 of 2 states. Either strong approval claiming “Finally, someone said it!” (Or like Jean-Louis Gassée’s book “Grateful Geek”, just “Finally!”) or putting myself in a strong antagonistic position. While neither may be good for my blood pressure, at least, it shows I am still highly passionate on topics around technology and leadership.

One of the articles I (strongly) agreed with was  “Anticipating Change: Transforming Fear into Empowerment in an Ever-Changing World “ by Daniel Burrus and published on LinkedIN on Jul 19, 2023.

Some excellent points are made, showing that fear is not really fear but an emotion which can be transformed into a positive trait. It very similar to the book “The anxious achiever” by Morra Aarons-Mele. Anxiety, stress, and fear can almost be paralleled or merged in the context of leadership.

The more I was thinking about this and my personal experience as a leader, always wanting to be authentic, vulnerable, and empathetic, the more I started to wonder if anyone ever tagged me as a fearless leader? Because I don’t want to. Ever.

You see from my experience having faced real life-or-death situations, I know 200% that no one has ever been fearless or if they were, you will find them in an mental institution.

The same applies for Silicon Valley or the Tech World leaders. The “Boys Club” (and the childish behaviors of some of its members; i.e., the recent interaction of Elon Musk vis-à-vis of Mark Zuckerberg who wisely choose not to escalate, just search MUSK VS ZUCK) has always tried to paint itself as the epitome of success, roughness and fearlessness (well for most).

But Corporate America is NOT a battlefield. Let’s stop using the term “fearless leader” like a CEO is a military officer leading troops into battle. Guess what. Officers do fear. Soldiers do fear. But there is a way to control these fears, to include them as part of the training, to focus on the mission instead of the emotions. There are no fearless officers. When you are task to command and protect the life of your soldiers, you always fear one or more may not come home. Courage is when you do not let these fears take over. You can be temporarily desensitized to fear but emotions and feelings always come back and sometimes hit your harder than wanted.

Let’s dig on some of the several self-described (or media heavily sponsored post) “fearless” leaders in the field of technology who have or may have made significant contributions and/or left a lasting impact. The leadership of these individuals is unmatchable but, full disclaimer, this is a list which was generated both by AI and an aggregation of articles via Google Search. Fearless is therefore debatable as it was decided by algorythms.

1. Steve Jobs: Co-founder of Apple Inc., Steve Jobs was known for his bold and visionary leadership style. He was not afraid to take risks and push the boundaries of technology, as evidenced by products like the Macintosh, iPhone, and iPad. Jobs' ability to create revolutionary products and reshape entire industries made him a fearless leader in the technology world. While Jobs’ reputation has been one of being a jerk at times, firing people in the elevator ride, his leadership was not fearless, it was made of fear. This is different but it worked. He did not fear the competition or what others may be thinking but I am sure he was not fearless. His later years illustrated his “humanity” with all its fears.

2. Elon Musk: The CEO of Tesla, SpaceX, Neuralink, and several other companies, Elon Musk is known for his audacious goals and relentless pursuit of innovation. He has revolutionized the electric vehicle industry, pushed the boundaries of space exploration, and is working on developing high-speed transportation systems, among many other ambitious projects. Well, there is a difference between childish and fearless. Kids have fears and anguish, and they acknowledge them. Musk has been going on a weird rampant series of incoherent tweets demonstrating he was like a child full of anguish yet not able to deal with them. So maybe Musk is part of the loonies or maybe he has the maturity of a petulant child but I am sure he has fears or should we call them insecurities.

3. Sheryl Sandberg: As the Chief Operating Officer (COO) of Facebook, Sheryl Sandberg has been an influential figure in the technology industry. She has been a strong advocate for women in technology and has played a significant role in shaping Facebook's growth and monetization strategies. This is probably the one where I would agree with AI/Google on her role and impact as fearless. Sandberg with her Washington DC experience and gravitas helped Facebook grow and she made some of the tough decisions. Being a female executive in a tech company is extremely hard and despite some controversies, Sandberg has given other women a voice and platform to be true leader, without fearing being gender discriminated against. And yet, she was the sacrificial lamb when Mark Zuckerberg had to make changes. So close enough to fearless.

4. Jeff Bezos: The founder and former CEO of Amazon, Jeff Bezos, transformed the way people shop and built one of the world's most valuable companies. Bezos embraced a long-term vision, disrupting traditional retail models and expanding Amazon's reach into various industries, including cloud computing (Amazon Web Services) and entertainment (Amazon Studios). There, Bezos has a similar reputation as Jobs. Sometimes abrasive, his drive to succeed cannot be ignored. If being driven is being fearless, then a lot of people are fearless. See earlier point, everyone has fears except psychopaths. Bezos talent was his understanding of finance and anticipating market changes not being fearless.

5. Sundar Pichai: As the CEO of Google and its parent company, Alphabet Inc., Sundar Pichai has steered Google's growth and diversification. Pichai has led the company through major developments, such as the transition to mobile-centric strategies and advancements in artificial intelligence. He has also emphasized the importance of responsible and ethical technology innovation. On this one, I cannot really say as I have not observed his actions under a microscope. I just know that during a couple of crisis (the AI team and the layoffs of senior staffs) he has displayed a dissociation of the events showing he was probably fearing more than being fearless. He has been having a hard time convincing his own executive team and never made the hard decisions during these crisis.

These are just a few examples of so called “fearless” leaders in technology, and there are many others who are happily claiming that similar trait.

While “fearless” leaders can bring many positive qualities to an organization, there can also be negative sides or challenges associated with their leadership style. So in that case, I would say a synonymous of “fearless” would be more “unchecked”, “unbalanced” or “uncontrollable” leaders.

Here are a few potential drawbacks:

1. Risk-taking without proper evaluation: Fearless leaders are often willing to take risks and pursue bold ideas. However, without proper evaluation and consideration of potential consequences, these risks can lead to poor decision-making and negative outcomes. Fearless leaders may overlook important details or fail to adequately assess the potential risks and downsides of their actions.

2. Lack of caution and recklessness: Fearless leaders may exhibit a tendency to act quickly and decisively, sometimes without sufficient deliberation. This can lead to impulsive decision-making and a disregard for potential pitfalls. The lack of caution and recklessness can result in costly mistakes or unintended consequences.

3. Resistance to feedback or dissenting opinions: Fearless leaders may have strong convictions and confidence in their own ideas, which can make them resistant to feedback or dissenting opinions. This can create a culture where open dialogue and constructive criticism are discouraged, hindering collaboration and stifling innovation.

4. Overwhelming pressure on employees: Fearless leaders often set ambitious goals and push their teams to achieve extraordinary results. While this can inspire and motivate employees, it can also create an atmosphere of intense pressure and unrealistic expectations. The relentless pursuit of success without considering the well-being and work-life balance of employees can lead to burnout and high turnover rates.

5. Lack of empathy and disregard for ethical considerations: Fearless leaders focused solely on achieving their goals may overlook the human impact of their decisions. This can result in a lack of empathy towards employees, customers, and stakeholders. Additionally, fearless leaders might be more prone to disregard ethical considerations or cut corners to achieve their objectives, which can lead to reputational damage and legal issues.

Now, let’s play a game. Can you match the “fearless” leaders mentioned earlier with the list of negative traits? No cheating. Please put your best guess in the comments below.

It's important to note that the negative aspects mentioned above are not inherent to all “fearless” leaders, but rather potential pitfalls that can arise if their leadership style is not balanced with critical thinking, humility, and an openness to feedback. And based on the book “The anxious achiever”, a fair amount of anxiety but not to a toxic level.

But how do you balance these behaviors? Excellent question and thank you for asking it.

Yes, a “fearless” leader can be balanced and controlled with a great executive team surrounding that person, and in fact, a strong executive team can help mitigate some of the potential negative aspects of fearless leadership.

Here's how a balanced executive team can work in conjunction with a fearless leader:

1. Complementary skills and expertise: A great executive team consists of individuals with diverse skill sets and expertise. They can bring different perspectives, knowledge, and experiences to the table, which can help provide a balanced view of situations. This can counterbalance the potential impulsive decision-making of a fearless leader, as the team can collectively assess risks, evaluate options, and provide valuable insights.

2. Constructive challenge and feedback: A strong executive team fosters a culture of open dialogue, constructive challenge, and feedback. Team members can provide alternative viewpoints, question assumptions, and raise potential concerns. This helps ensure that the fearless leader considers a broader range of perspectives and factors in their decision-making process, reducing the likelihood of overlooking critical details.

3. Checks and balances: An effective executive team establishes mechanisms for checks and balances to avoid the negative consequences of reckless risk-taking. This can include review processes, decision-making frameworks, and accountability mechanisms that help assess and validate the feasibility, potential impact, and risks associated with the leader's decisions. The team can collectively ensure that decisions are based on thorough evaluation and analysis.

4. Emotional intelligence and empathy: A great executive team can bring emotional intelligence and empathy to the organization. They can help balance the fearless leader's drive for results with a focus on employee well-being, morale, and work-life balance. The team can advocate for a healthy and supportive work environment, ensuring that employees are not overwhelmed by the relentless pursuit of ambitious goals.

5. Ethical guidance and considerations: The executive team can actively engage in discussions around ethical considerations and provide guidance to the fearless leader. By considering the broader implications of decisions and weighing ethical concerns, the team can help ensure that the organization maintains a strong ethical compass and upholds its values.

When a “fearless” leader is supported by a capable and balanced executive team, it creates a dynamic where the strengths of both the leader and the team members can be leveraged, leading to more effective decision-making, improved collaboration, and better overall outcomes for the organization.

But in order to achieve this great executive leadership team who can be called “decisive” vs fearless, it is important for the top leader to accept the help and acknowledge shortcomings and understand that behaviors displayed create the culture of the company. Fearless may mean never doubting a self. Yet, everyone in their normal mind will experience doubts and impostor syndrome. So, if a leader doesn’t experience doubt, is this normal behavior? Absolutely not. This is a sign that the company C-Suite has issues. The team is unable to drive decisively in the right direction, they may have lost sight of the long-term gains or even worst, the top executive being fearless has turned the culture of the company into one of fear and toxicity.  

In conclusion, let’s drop the use of “fearless” please. It doesn’t make any sense. Let’s reward well-informed, well-supported, rational and decisive leaders and not the impulsive, ill-informed (i.e., valuating their opinion as the only important one), knee jerk self-grandiosity and ego boosting psychopaths.

Thanks goodness, most captains of industry are in the first category. Even the ones who had been classified prematurely and early in their career as “fearless” with the negative connotation attached to it have been able to reform their leadership style to a more authentic and truthful style. This is the important difference, they are decisive leaders and not fearless. Or should I dare to say, the future is meditative leadership.