Why the Best Leaders have Little Fear of Failure or Being Disliked

In public, leadership is often described in flattering language: vision, confidence, influence, inspiration. In reality, it is just as often an exercise in discomfort. To lead well is to make decisions before certainty arrives, to take responsibility when outcomes are unclear, to absorb criticism without collapsing into defensiveness, to speak truth to power and to disappoint people who would have preferred an easier answer. This is why some of the most effective leaders in business are not those who are most universally liked, nor those with the neatest record of uninterrupted success. They are the ones who have learned to tolerate two things that derail lesser leaders: failure and disapproval.

That does not mean great leaders seek failure, or treat other people’s concerns with contempt. Quite the opposite. The strongest leaders are often deeply conscientious. They care intensely about standards, people, outcomes, and trust. But they understand something essential: if you are trying to build, change, reform, or protect anything meaningful, you will occasionally get it wrong, and you will inevitably upset someone. The question is not whether leadership can be made safe from these experiences. It cannot. The question is whether a leader can remain principled, clear-minded, and effective when things are not going to plan.

This is more than a matter of temperament. It is supported by management research, organisational psychology, and the real histories of high-profile companies and executives. Harvard Business Review has long emphasised the role of candour, learning, and adaptive decision-making in leadership. The Economist has repeatedly focused on the realities of leading under uncertainty, where risk cannot be eliminated and difficult trade-offs are unavoidable. Psychologists from Carol Dweck to Albert Bandura to Brené Brown have shown, from different angles, that resilience, self-efficacy, and growth depend on how people interpret setbacks and social judgment. And popular interest in “The Courage to Be Disliked” by Fumitake Koga and Ichiro Kihimi speaks to a growing recognition that freedom, responsibility, and approval can have a relationship built on tension.

The best leaders do not fear failure or being disliked because they understand that both are often side effects of doing the job properly. Their task is not to preserve an image of flawless competence or universal approval. Their task is to move the organisation toward reality, learning, and long-term value. In practice, that means choosing truth over comfort, experimentation over paralysis, standards over popularity, and mission over ego.

Leadership Is Not the Same as Popularity

Many leadership failures begin with a simple confusion: mistaking being well-liked for being effective. These are not the same thing. A popular leader may be charming, agreeable, reassuring, and generous with praise. An effective leader may sometimes be those things too. But effectiveness demands more. It demands judgment, clarity, accountability, and a willingness to make decisions that not everyone will welcome.

A leader who wants to be liked by everyone is vulnerable to avoidance. They postpone difficult conversations. They soften feedback until it becomes useless. They leave poor performance unaddressed because confrontation feels unpleasant. They drift toward consensus even when consensus is wrong. They preserve short-term harmony at the expense of long-term trust.

This is one of the enduring lessons of serious management thinking: people do not ultimately trust leaders because they are pleasant; they trust them because they are fair, competent, and clear. Teams can tolerate an unpopular decision more easily than they can tolerate hidden standards, evasiveness, or silent dysfunction. In fact, a leader’s refusal to address what everyone else can already see is often more damaging than the hard decision itself.

That is why one of the central insights associated with “The Courage to Be Disliked” feels so relevant to leadership. As the book puts it, “It’s that you are disliked by someone. It is proof that you are exercising your freedom and living in freedom, and a sign that you are living in accordance with your own principles.” Taken literally, that line can be misused; not every disliked person is principled. But in the context of leadership, it captures something true. If you are setting direction, allocating scarce resources, saying no to some priorities in order to protect others, and holding people accountable, some degree of disapproval is inevitable.

Leadership is not a popularity contest. It is a responsibility.

Why Fear of Failure Shrinks Leadership

Fear of failure damages leadership in a different way. It makes people smaller. Leaders who are ruled by the fear of getting things wrong become cautious in the least productive sense. They avoid risk not because they have carefully judged it to be unwise, but because they cannot bear the psychological cost of visible error. They choose defensible decisions over bold ones. They protect themselves rather than the mission.

The result is not excellence but stagnation.

This is especially dangerous in environments shaped by uncertainty, innovation, or change. In such settings, waiting until every decision feels safe means waiting too long. New products, new strategies, new business models, and cultural transformations all involve incomplete information. If leaders demand certainty before acting, they eliminate the conditions that enable learning.

Amy Edmondson’s work is especially useful here. The Harvard Business School professor has distinguished between blameworthy failure and what she calls intelligent failure. An intelligent failure occurs in new territory, where the outcome cannot be fully known in advance, where the effort is thoughtful, and where the learning can improve future performance. This idea is crucial because it rescues leadership from a simplistic binary. Not all failure is good. But not all failure is bad either. Some failures are tuition.

The strongest leaders understand this. They do not glorify mistakes, but they do not turn every setback into shame. They ask: What did we assume? What did we learn? What should we change? That orientation matters not just strategically, but culturally. Teams quickly notice whether their leader treats error as information or as humiliation. In the first culture, people speak up early, surface risks, and experiment responsibly. In the second, they hide problems, protect themselves, and allow small mistakes to become big problems.

So the issue is not whether great leaders fail. Of course they do. The issue is whether failure becomes a source of fear or a source of intelligence.

What Psychology Says About Setbacks and Approval

The psychological foundations of this idea are strong. Carol Dweck’s work on mindset has shown that people who believe abilities can be developed are more resilient in the face of setbacks than those who see ability as fixed. One of her most memorable formulations is: “Becoming is better than being.” That sentence captures the essence of why fear of failure can be so destructive. If every mistake is interpreted as a verdict on identity, then failure becomes unbearable. But if mistakes are part of growth, then leaders can remain open, adaptive, and persistent.

Albert Bandura’s theory of self-efficacy adds another layer. Self-efficacy is not blind confidence. It is the belief that one can act effectively and respond to challenges. Leaders with high self-efficacy are not immune to doubt, but they are less likely to freeze under uncertainty because they trust their capacity to cope, learn, and recalibrate. This matters enormously in leadership, where certainty is often unavailable.

There is also an important motivational dimension. Self-determination theory, developed by Edward Deci and Richard Ryan, argues that human beings function best when their motivation is rooted in autonomy, competence, and relatedness. Leaders who depend too heavily on external approval become psychologically fragile because their internal state is governed by reactions they cannot control. Leaders with a stronger sense of autonomy can hear criticism without becoming controlled by it.

Brené Brown has brought these ideas into mainstream leadership language through her work on vulnerability and shame. Her widely cited line captures the emotional reality of leadership with unusual precision: “Vulnerability is not winning or losing; it’s having the courage to show up when you can’t control the outcome.” That is leadership in a nut shell. To lead is to show up in conditions where success is not guaranteed and applause is not assured. A leader who cannot endure that vulnerability will either avoid responsibility or perform certainty while privately shrinking from it.

These psychological perspectives converge on the same conclusion: resilient leadership depends less on eliminating setbacks and criticism than on changing one’s relationship to them.

The Business Case for Not Needing to Be Liked

In business, the costs of approval-seeking can be enormous. Companies do not usually fail because nobody in leadership cared. They fail because leaders avoided reality. They delayed hard choices, protected underperforming structures, failed to challenge assumptions, or allowed political comfort to outweigh strategic necessity.

This is why so much executive thinking, especially in forums like Harvard Business Review, returns to the value of candour. Honest feedback, clear accountability, and transparent trade-offs are not signs of harshness. They are the architecture of trust. A leader who says what needs to be said, even when it is unwelcome, gives the organisation a chance to adapt. A leader who smooths everything over in order to be liked leaves the organisation blind.

Kim Scott’s framework of “radical candour” expresses this elegantly: care personally, challenge directly. The first part matters because leadership without care becomes brutality. The second part matters because care without challenge becomes indulgence. Teams do not grow from being comforted into mediocrity. They grow from being respected enough to hear the truth.

This is one reason weak leaders are sometimes liked at first and resented later. Their agreeableness feels pleasant in the short term. Only over time does the cost become visible: low standards, unclear expectations, tolerated dysfunction, and a culture in which nobody is quite sure where they stand.

The strongest leaders know that temporary discomfort can be a form of service. The hard conversation, done well, are often kinder than the avoided one.

Famous Business Leaders Who Understood the Trade-Off

Steve Jobs is one of the clearest examples of a leader who was not governed by the need to be liked. He was demanding, often abrasive, and impossible to mistake for a consensus-seeker. Not every aspect of his style deserves imitation; many do not and there was definitely something of the megalomaniac about him at times. But his example remains useful because it reveals how much leadership at the highest level involves the willingness to disappoint people in the service of clarity and excellence.

Jobs once said, “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas.” There is a leadership philosophy inside that sentence. Focus is not merely preference; it is disciplined exclusion. And exclusion always creates friction. If you cannot bear disappointing people, you cannot focus.

He also said, “I’m convinced that about half of what separates successful entrepreneurs from the non-successful ones is pure perseverance.” Perseverance is impossible if failure is interpreted as humiliation. Jobs was publicly fired from Apple, the company he co-founded. That experience would have permanently diminished many leaders. Instead, it became part of the larger arc of his development.

Jeff Bezos has institutionalised a similar attitude toward failure, though with a different style. His oft-cited observation, “If you know it’s going to work, it’s not an experiment” is more than a clever remark. It is a philosophy of organisational learning. Innovation requires a tolerance for initiatives whose outcomes are uncertain. If every decision must focus on minimising reputational damage, experimentation dies.

Satya Nadella offers a striking contrast to both Jobs and Bezos. His leadership at Microsoft is widely associated with empathy, humility, and cultural renewal. But it would be a mistake to read that as softness. Nadella’s emphasis on a “learn-it-all” rather than “know-it-all” culture required confronting deeply embedded habits. It meant challenging defensiveness, status behaviour, and certainty-as-identity. Culture change at that scale is impossible without a willingness to endure skepticism and resistance.

Indra Nooyi likewise showed that strategic leadership requires comfort with disapproval. Shifts in portfolio, health strategy, performance systems, or capital allocation do not produce unanimous enthusiasm. Yet large institutions cannot be transformed by leaders who require universal reassurance before acting.

In very different ways, these leaders point to the same truth: serious leadership demands the capacity to remain steady when not everyone agrees, approves, or applauds.

The Courage to Be Disliked… and to Fail

The appeal of “The Courage to Be Disliked” lies partly in its challenge to one of modern life’s deepest anxieties: the need to be validated. For leaders, that need can be especially dangerous because status makes approval both more available and more addictive. Praise, influence, and visibility can create an illusion of authority while weakening the capacity for independent judgment.

One of the book’s most useful ideas is that freedom and approval are often in tension. To act from principle is sometimes to invite resistance. Another relevant line is: “A healthy feeling of inferiority is not something that comes from comparing oneself to others; it comes from one’s comparison with one’s ideal self.” That is a better standard for leadership. The crucial question is not, “Do they all like me?” It is, “Am I acting as the role requires? Am I meeting the standard I claim to serve?”

The book also stresses the possibility of change in the present. “No matter what has occurred in your life up to this point, it should have no bearing at all on how you live from now on.” For leaders, that is an important reminder that failure need not become identity. A failed strategy, a bad hire, a public mistake, even a dismissal: none of these has to become destiny. The best leaders metabolise failure rather than worship or deny it.

This Adlerian lens is powerful because it reframes disapproval. Being disliked is no longer automatic evidence of wrongdoing; it can simply be the cost of autonomy, standards, and truthfulness. Again, that does not excuse arrogance or insensitivity. A wise leader remains open to feedback and deeply curious about dissent. But after listening and thinking, they still must choose. Leadership requires ownership, not endless emotional negotiation.

Why Teams Need Leaders Who Can Bear Discomfort

There is also a systemic reason this matters. Teams need leaders who can tolerate discomfort because groups are often bad at metabolising tension on their own. Organisations drift naturally toward avoidance. People delay awkward conversations, preserve failing projects because too much pride is invested in them, and soften language until hard realities disappear behind euphemism.

A leader who cannot bear disapproval makes this worse. If every sign of tension is treated as danger, it becomes emotionally expensive to tell the truth within their organisation. Decisions get postponed. Standards become inconsistent. Informal resentment grows underground while formal communication becomes bland and useless.

By contrast, a leader who can bear temporary dislike becomes a stabilising force. They can say:
This initiative is ending.
This behaviour is unacceptable.
This strategy is no longer working.
This role must change.
This feedback is difficult, but necessary.

In the short term, such leadership may feel less comfortable. In the long term, it is usually far more trustworthy. Teams do not need leaders who make every moment pleasant. They need leaders who can help the organisation face reality without panic or denial.

The Freedom at the Centre of Leadership

The best leaders do not fear failure or being disliked because they understand what leadership asks of a human being. It asks for action without certainty, candour without cruelty, conviction without rigidity, and resilience without self-deception. It asks people to expose their judgment to risk, to hear criticism without becoming captive to it, and to keep acting in service of a mission larger than their own image.

Fear of failure makes leaders defensive, cautious, and performative. Fear of being disliked makes them vague, conflict-averse, and manipulable. Neither fear can be fully eliminated. But both can be put in their proper place.

The leader who is free from domination by these fears becomes more useful to others. They can experiment without recklessness, listen without surrendering judgment, care without indulging dysfunction, and decide without needing to be adored. They become capable of the rarest and most valuable kind of steadiness: not the steadiness of certainty, but the steadiness of responsibility.

This is why the deepest lessons from psychology, business, and philosophy converge. Growth requires setbacks. Learning requires candour. Freedom requires accepting that not everyone will approve. Trust requires standards. And leadership, at its core, requires the courage to be seen trying, failing, adjusting, and leading anyway.

That is not the glamorous version of leadership. But it is the real one. And in the end, it is what makes great leadership possible.