Dec 9, 2022 15 min read

The Case for Naive Leaders over Clever, Sophisticated Ones

Graphic: How naiveté evolves over time in effective leadership

Being naive has a default negative connotation —ignorant, uninformed, incredulous, or even incompetent. One class of people who exclusively avoid being seen as naive are leaders and managers.

Naiveté is considered a liability. But is it really? We've been oversold on the merits of sophistication and cleverness, meanwhile missing out on the benefits of a considered approach to naiveness.

I examine naiveté in its positive but often counterintuitive dimensions — as something to be cultivated rather than eliminated, for effective leadership.

The downside of cleverness

Competition is often seen as a zero sum game that makes us over-index for cleverness accompanied by a lack of trust. The solution is not to blindly trust everyone, but to avoid overcorrection towards cynicism and mistrust.

James March highlighted the problems of cleverness as a default strategy:

Many popular applications of decision theory and game theory to problems of leadership emphasize the cleverness of strategic maneuver and practiced deception in bargaining. In these treatments, the secret to success is found in misleading, outwitting, and outthinking opponents. 

‌‌‌‌Modern investigations in a game theoretic tradition have raised questions about such strategies, however. The issues are threefold:‌‌‌‌

1. Strategic cleverness often presumes that you are dealing with people who have substantially less intelligence than you do, a presumption that rarely is accurate.‌‌‌‌

2. Strategic cleverness undermines trust. As a result it precludes, or at least makes difficult, the long-term understandings and alliances that are necessary for long-term success in repeated games.‌‌‌‌

3. Strategic cleverness emphasizes the personal joys of being more clever than anyone else, thus challenges the personal self-worth of others and makes them willing to sacrifice their own interests in order to deny you victory. 


- James March, Thierry Weil in On Leadership

While strategic cleverness might afford us a competitive advantage in the short-term it might not be the best strategy in the long run at least when done exclusively. At the highest levels, where cleverness is on a level playing field, naiveté might hold a slight advantage.

An excess of cynicism appears to lead us to over-think the actions of others and make negative attributions about their motivations without sufficient cause. In the process, we may miss opportunities that greater trust might capture.

‌‌‌‌…your stubborn cynicism may lead you to suboptimal outcomes in interactions requiring trust.
 Our myopic focus on ourselves and our failures to consider others and the situation itself can also lead us to both naive and cynical errors. 


- Tsay, Shu and Bazerman [4]

‌The paradox of sophistication

It might be cliched but consider why we don’t trust car salesmen or politicians. They are too slick to be trusted. Politicians are clearly masters of language, manipulation, and of course clever. But nevertheless those are the very reasons that create mistrust.

In trying to be sophisticated we instead end up doing the opposite — being naive. TS Eliot captures this paradox in The Rock:

Where is the Life we have lost in living? ‌‌

Where is the Wisdom we have lost in knowledge? 
Where is the Knowledge we have lost in information?

In contrast, being considerately naive is a form of ultimate sophistication only a self-assured leader can pull off.

Being sophisticated per se is not necessarily the issue. It becomes one when it turns into rigid routines that close us off, and impedes being responsive to our direct experience. Sophistication can create an external veneer that creates mistrust and distance. For leaders, that’s the exact opposite of what they want.

Leaders can become clever and sophisticated to the point where they are completely out of touch with their own humanity let alone that of others. Naïveté can be the heat that softens this dynamic enough to make them more adaptive.

Our knowledge has made us cynical, our cleverness hard and unkind. We think too much and feel too little. More than machinery we need humanity; more than cleverness we need kindness and gentleness. Without these qualities, life will be violent and all will be lost.


— Charles Chaplin (speech from Jewish barber in The Great Dictator)

Charisma and confidence are often mentioned in the context of having “leadership presence”. But people can sense false competence and hokey confidence, and won’t buy it. On the other hand, cultivating naiveness is strategic and thus sophisticated in practice.          ‌

The evolution of our naïveté

If sophistication and cleverness are not the answer what should we do instead? It’s helpful to think of naiveté on an evolving spectrum.

Competence requires us to lose the initial naïveté that comes with ignorance of a given field. But it need not stop there or worse turn into cynicism and disengagement.

Often when we think of naïveté it is of the kind that stems out of ignorance. The naïveté that I am referring to is less of the ignorant kind and more of a deliberate one.

It stems from deep knowledge and awareness that you don’t in fact know everything. And the only way to keep learning and evolving is to have an open mind — aka being naive about a given topic or situation.

John Dewey called this cultivated naiveté :

We cannot permanently divest ourselves of the intellectual habits we take on and wear when we assimilate the culture of our own time and place. ‌‌‌‌But intelligent furthering, ...demands that we take some of them off, that we inspect them critically to see what they are made of and what wearing them does to us. 


We cannot achieve recovery of primitive naiveté. But there is attainable a cultivated naiveté of eye, ear and thought, one that can be acquired only through the discipline of severe thought. 


- John Dewey in Experience and Nature

As Dewey hints at, achieving this stage is anything but natural or easy. Abraham Maslow and others have written about people at the highest levels of self-actualization exhibiting a childlike curiosity and approach to everything. Maslow called this childlike fascination and the willingness to appear naive as Second Naïveté:

It was in this childlike sense that my subjects were creative…they had either retained or regained at least these two main aspects of childlikeness, namely, they were non-rubricizing or “open to experience” and they were easily spontaneous and expressive. ‌‌‌‌If children are naive, then my subjects had attained a “second naivete,” as Santayana called it.

Their innocence of perception and expressiveness was combined with sophisticated minds.
‌‌‌‌‌‌… we are dealing with a fundamental characteristic, inherent in human nature, a potentiality given to all or most human beings at birth, which most often is lost or buried or inhibited as the person gets enculturated.‌‌‌‌‌‌‌‌‌‌

— Abraham Maslow in Toward a Psychology of Being

Others have mentioned second naïveté as the ability to revisit a domain of expertise in a completely new light and engaging with it anew to uncover new ideas. The banal becomes the sublime over time.

With each engagement the expert finds new nuances and distinctions they hadn’t seen before. In contrast, the layperson goes numb and becomes disengaged. While others become jaded by familiarity over time, the masters find ways to engage with renewed rigor and vitality.

Thus naiveté can be seen as evolving from : Crude Naiveté to Calculated Sophistication to Cultivated Naiveté. In zen, this is the journey from beginner, to the expert know-it-all, to ultimately being the master and fool simultaneously.

Graphic: How naivete evolves over time in effective leadership
Study, learn, but guard the original naivete. It has to be within you, as desire for drink is within the drunkard or love is within the lover.

‌‌‌‌‌‌‌— Henri Matisse

‌             ‌

The upside of naïveté

Culture trains us against being naive and thus we are very alert to it. We end up over-indexing for sophistication and cleverness, while under-indexing for naiveness. Let’s look at some of the positive but often counterintuitive aspects of an active, cultivated stance towards naiveté.

1. As a requirement for genius

When learning something new, it requires us to give up existing notions and surrender to the practice. In a sense, it’s a naive belief in what we are learning, and that we can actually learn. Without that naive belief, we won’t be spurred into action.

Our natural habit is to think associatively about what is salient to us in the immediate situation or what is immediately available from memory. It takes willpower and training to escape from the ”dominance of the given” and to actually think about events and relationships that are not salient and explicit in our experience.


— Reid Hastie, Robyn Dawes in Rational Choice in an Uncertain World

Naïveté is one way to escape this “dominance of the given” and the reason why it’s a key element of genius and creativity.

Leadership at its essence is a creative act that requires stepping into an unknown and unknowable future. It’s also about constant learning, unlearning and relearning to stay ahead of the curve. And the only way to continuously learn and create is to have what the zen masters call the beginner’s mind.

As soon as we reflect, deliberate, and conceptualize, the original unconsciousness is lost and a thought interferes. … The arrow is off the string but does not fly straight to the target, nor does the target stand where it is. Calculation, which is miscalculation, sets in….Man is a thinking reed but his great works are done when he is not calculating and thinking. 

‌‌‌‌“Childlikeness” has to be restored…


— D.T. Suzuki in Zen in the Art of Archery

Naiveté is about being able to see things anew or seeing the actual picture by not falling to preconceived notion or jaded mental models. As a leader this is hard to do. After all, we got to where we are today because of what we already know.

But to see things differently, to see new things, or adapt to new emerging realities, requires a different kind of innocence and naiveness that's different from the primitive naïveté of ignorance. It’s a cultivated version that recognizes the limitations of what we already know and how it restricts from learning something new.

Geniuses are willing to look foolish more than you and I are. Conventional wisdom got us “here” but to get “there” will require a completely different level of thinking and approaches.

How many times have you failed to try something new out of fear of being thought silly? How often have you censored your spontaneity out of fear of being thought childish?
‌‌‌‌‌‌I began to see more than a casual relationship between learning and the willingness to be foolish, between the master and the fool. By fool, to be clear, I don’t mean a stupid, unthinking person, but one with the spirit of the medieval fool,… signifying the fertile void from which all creation springs, the state of emptiness that allows new things to come into being.‌‌‌‌‌‌

What we frown at as foolish in our friends, or ourselves, we're likely to smile at as merely eccentric in a world-renowned genius, never stopping to think that the freedom to be foolish might well be one of the keys to the genius's success.

‌‌‌‌—  George Leonard in Mastery

2. As a requirement for innovation

Companies tout innovation as a buzzword but typical systems are designed to discourage it. Conventional wisdom is abundant in business thinking perpetuated as best practices, efficiency, predictability, and so on. But in complex domains without clear answers or pre-proven solutions, these approaches become an impediment to innovation.

Jim Collins, bestselling author of Good to Great and Built to Last highlights this notion:

Daniel Boorstin in his landmark work, The Discoverers (a detailed history of human discovery and invention), observed that many significant contributions came about because people were naive. In describing Ben Franklin’s electricity discoveries, for example, Boorstin explained:‌‌‌‌‌‌

"In fact his (Franklin’s) achievement illustrated the triumph of naivete over learning . . . . His amateur and non-academic frame of mind was his greatest advantage; like many another discovering American, he saw more because he knew much less about what he was supposed to see.‌‌ ‌‌‌"‌

The same thing happens in business. When people become fat with conventional wisdom, they’re dangerous. A lot of being innovative in business is being willing to give something a try because you don’t know it flies in the face of conventional wisdom. ‌‌‌‌As Debi Colman, Apple VP of information systems and technology, puts it: “The single biggest roadblock to creativity and innovation I’ve encountered in business is conventional wisdom.” 


- Jim Collins in Beyond Entrepreneurship

Conventional thinking while promising efficiency and results limits breakthrough performance rather than enabling it.

Paradoxically, the more we act in terms of anticipated outcomes according to what James March called a “consequentialist theology”, the more likely we are to produce conformity and mediocrity in performance. The more we crave public acceptance, recognition, and material achievement, the less we are able to produce great works that withstand the test of time. This is the paradox of performance.


— Robert Chia, Robin Holt in Wisdom as Learned Ignorance

3. As a requirement for extraordinary performance

There are no guarantees when we set out to do something. It requires a certain form of naivete to believe that our efforts will in fact lead to something.

Being worldly and wise might be about understanding what works and what doesn’t, what makes for a good return on effort and what doesn’t. But extraordinary performance requires more than the usual calculations of input and output. It requires a borderline obsession with putting in the work without necessarily knowing the outcome in advance.

The best real world example of this is entrepreneurship, which requires a level of “foolishness” that ignores conventional wisdom. It’s a form of naïveté that goes beyond the calculated rationalism of decisions and returns on investment.

The greatest successes…have come from products for which there was no initially proven demand. This uncompromising attitude echoes Ruskin’s insistence on “selfishly” seeking perfection regardless of popular public opinion. 

…underpinning all of this is the importance of ignorance of orthodoxy and the unlearning necessarily associated with it.‌‌‌‌


— Robert Chia, Robin Holt in Wisdom as Learned Ignorance

Audacity, courage, and obsession can be seen as varying levels of naiveness. The naivete is in enjoying the journey itself more than the destination.

4. As a requirement for operating in complexity

Sophistication and competence often come coupled with ingrained thinking and behaviors developed over a lifetime. These can be hard to “unfreeze” and often impede good decision making. Developing naiveté actively can help buck this trend.

Leadership is about stepping into the unknown and helping others navigate complex environments riddled with ambiguity. From this perspective, a certain degree of naiveness is almost a requirement to be effective.

Perfect knowledge can cause indecision and inaction. Consider the following exchange:

Calvin: The more you know, the harder it is to take a decisive action. Once you become informed, you start seeing complexities and shades of gray. You realize that nothing is as clear and simple as it first appears. Ultimately, knowledge is paralyzing. Being a man of action, I can't afford to take that risk.


Hobbes: You're ignorant, but at least you act on it.‌‌‌‌


— Calvin and Hobbes, Bill Watterson

Knowing less aka being naive can make it easier to take action in complex environments with incomplete information, contradicting inputs, or that of information overload.

Karl Weick recognized this role of naïveté when operating in complexity in his classic paper on the effectiveness and robustness of small wins:

First, being naive simply means that we reject received wisdom that something is a problem….We are always naive relative to some definition of the situation.‌‌‌‌‌‌‌‌

Second, being naive probably does have a grain of denial embedded in it. But denial can lower arousal to more optimal levels, so that more complex actions can be developed and more detailed analyses can be made.‌‌‌‌‌‌‌‌

Third, to be naive is to start with fewer preconceptions. People with naive preconceptions will see a different set of features and are less likely to become fixated on specific features.‌‌‌‌‌‌‌‌

Fourth, naive beliefs favor optimism. Many of the central action mechanisms for small wins…gain their energy from the initial belief that people can make a difference. That belief is not naive when the world is tied together loosely. Firm actions couple events. And firm actions are more likely to occur when belief is strongly positive than when it is hesitant, doubtful, or cynical.‌‌‌‌

— Karl Weick in Small Wins

5. As being politically savvy

At the highest levels, politics and egos start playing a larger role in success and failure.

There are occasions when the highest wisdom consists in appearing not to know—you must not be ignorant but capable of playing it. It is not much good being wise among fools and sane among lunatics. He who poses as a fool is not a fool. The best way to be well received by all is to clothe yourself in the skin of the dumbest of brutes. 


— Baltasar Gracián

Robert Greene, in his underground bestseller The 48 Laws of Power, gives a strategic albeit dark use case for playing naive. He highlights how in highly competitive environments, naïveté can be used as a weapon of deception.

His 21st law of power states : play a sucker to catch a sucker—seem dumber than your mark.

No one likes feeling stupider than the next person. The trick, then, is to make your victims feel smart—and not just smart, but smarter than you are. Once convinced of this, they will never suspect that you may have ulterior motives.
To reveal the true nature of your intelligence rarely pays; you should get in the habit of downplaying it at all times. If people inadvertently learn the truth—that you are actually much smarter than you look—they will admire you more for being discreet than for making your brilliance show.

Greene highlights how this approach is more critical at higher rungs on the career ladder versus earlier when technical chops might get you ahead.

At the start of your climb to the top, of course, you cannot play too stupid: You may want to let your bosses know, in a subtle way, that you are smarter than the competition around you. As you climb the ladder, however, you should to some degree try to dampen your brilliance.

6. As a bridge to credibility and trust

Owning mistakes upfront might sound naive. But it has the opposite effect of increasing rather than decreasing trust. Acknowledging shortcomings builds trust faster than trying to put up a facade of confidence and competence.

Being candid is often considered naive. Managers hesitate to state things as they really are and sugarcoat things.

The manager hopes “they got the point”, but the person never hears what they really need to hear. This sugarcoating stems from the “social competence”we all learn. But in the context of helping, it’s essentially incompetence. Thus, social competence in effect increases incompetence.

Truth doesn’t mean being blunt and inconsiderate. When in a respectful, empathetic manner and it can be one of the fastest ways to build credibility.

7. An antidote to leadership derailment

Leadership derailment and managerial incompetence are fairly well understood phenomena and there are four common failure modes:

  • lack of interpersonal skills
  • inability to get work done
  • inability to build a team
  • failure to transition into a new role after promotion

Naïveté is an effective antidote against these.

8. An antidote against expertise traps

What got us here will not get us there. Strengths becomes weaknesses because they prevent us from seeing problems anew or to miss them completely.

What we already know becomes our go-to routine until it starts becoming a crutch. It’s an old tool that is not applicable anymore but we continue to use it because of familiarity, plain habits, and the fear of appearing incompetent when learning something new. Staying naive prevents this hubris from stopping our evolution.

9. An antidote to cynism

Organizational life can be frustrating. Sophistication and knowhow can easily transform into cynicism over time. We know all the ways something won’t work.‌‌ It often masquerades as expertise but also means being closed to possibility.

Cultivating naïveté is one way to counter this tendency towards cynicism especially amongst experienced managers.

Cynicism applies not just to ideas but people as well. Hanlon’s razor states: never attribute to malice that which is adequately explained by carelessness or stupidity. Essentially, give people a second chance. We are much more likely to be more forgiving with a naive stance than with a cynical one .

‌             ‌

Leaders as coaches and masters of context

Leadership effectiveness often hinges on how effectively leaders are able to navigate and maintain context rather than delving directly in content and trying to control everything.

It’s fashionable these days to tout the notion of a “coaching style” of leadership or that great leaders are great coaches. But this is still pretty rare. Because as with anything effective, it’s simple but not easy. One place to start is to get more comfortable with asking simple questions that might appear naive or even dumb.

To be a teacher does not mean simply to affirm that such a thing is so, or to deliver a lecture,… No, to be a teacher in the right sense is to be a learner. ‌‌‌‌Instruction begins when you, the teacher, learn from the learner, put yourself in his place so that you may understand what he understands and in the way he understands it.‌‌‌‌

The disciple is the opportunity for the master to understand himself, as the master is the opportunity for the disciple to understand himself.  


— Soren Kierkegaard, Philosophical Fragments

A naive approach keeps us open and free from the limiting constraints of previous knowledge. It’s the naive question that often challenges the status quo and opens up options. Being too hung up on sophistication actively prevents us from asking seemingly dumb but potentially breakthrough questions.

Steve Jobs is someone who exemplified this “naive” stance. He was famous for walking into meetings and asking dumb questions but that questioned the norms and surfaced underlying assumptions. Invariably, a seemingly lame line of questioning would often lead to exploring new avenues and options previously unconsidered leading the company in a new direction.

Clearly under-indexing on naiveté is a mistake. In the short run cleverness and sophistication might work better, but, as Naval Ravikant put it, when “playing long term games with long term people” it pays to develop skills on the other end of the spectrum in a cultivated form of naïveté.

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Another counter intuitive aspect of effective leadership is negative capability. Leadership is usually thought of as a positive capability and improvement is couched in additive terms— this skill or that competence. Subtraction can be equally effective but its subtler and hard to do. I examine the application of negative capability to leadership in Why Developing Negative Capability is Critical to Effective Leadership.

Sources and References

  1. 48 Laws of Power by Robert Greene.
  2. Ambiguity And Accounting: The Elusive Link Between Information And Decision Making by James March.
  3. On Leadership by James March, Thiery Weil.
  4. Naivete  and Cynicism in Negotiations and Other Competitive Contexts by Chia-Hung Tsay,Lisa She,  and Max Bazerman.
  5. Wisdom as Learned Ignorance by Robert Chia, Robin Holt.
  6. Rational Choice in an Uncertain World by Reid Hastie, Robyn Dawes.
  7. Experience and Nature by John Dewey.
  8. Towards a Psychology of Being by Abraham Maslow.
  9. Zen in the Art of Archery by D.T. Suzuki.
  10. Mastery by George Leonard.
  11. Beyond Entrepreneurship by Jim Collins.
  12. Small Wins by Karl Weick.
  13. Philosophical Fragments by Soren Kierkegaard.
Sheril Mathews
I am an executive/leadership coach. Before LS, I worked for 20 years in corporate America in various technical & leadership roles. Have feedback? You can reach me at
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