The 7 Counterintuitive Habits of Highly Effective Leaders

What traits come to mind when you think of great leaders?

You’re probably thinking: visionary, charismatic, assertive, or smart.

While all those traits are nice to have, the habits that set the most effective leaders apart from the rest — the ones that truly matter — are often the most counterintuitive, surprising, yet incredibly inspiring.

Steve Jobs, the co-founder of Apple, famously said:

“Here’s to the crazy ones, the misfits, the rebels, the troublemakers, the round pegs in the square holes… the ones who see things differently.”

These leaders are a cut above the rest. They are different, in a good way. Their habits are unconventional, and these habits take them from being good leaders to great leaders.

Allow me to indulge you for the next few minutes, as we discuss the 7 Counterintuitive Habits of Highly Effective Leaders.

Habit #1. Embrace Failure

Just look around you.

Observe the people walking briskly down the streets, those who are frantically speeding away in their cars, or those who are (im)patiently lining up at the local Starbucks. Everyone seems to be chasing one thing, and one thing alone.

Success.

Over the last 100 years, with the rise of capitalist economies, success has become synonymous with high status and well-being, while failure has earned a negative reputation that people want to stay away from. In my article Trapped in the Rat Race: 3 Factors That Keep Us Stuck, and How to Escape, I discussed how fear of failure is a major contributor to people getting stuck in this rat race.

Don’t get me wrong. Success is not a bad thing. In fact, the most effective leaders chase success too. The difference, however, is that they see failure as a stepping stone to success.

They understand that failure is an inevitable part of the journey to growth and success.

Consider Steve Jobs: he was well-known for his willingness to take risks and learn from failure. He faced setbacks early in his career, and even got ousted from his own company.

But those setbacks didn’t set him back.

They only propelled him further forward, with a renewed resolve, energy, and several new lessons under his belt. He ultimately persevered and revolutionized multiple industries with innovative products — including the Mac, the iPod, and the iPhone.

Elon Musk, the CEO of SpaceX and Tesla, and now the owner of Twitter (X), famously said:

“Failure is an option here. If things are not failing, you are not innovating enough.” — Elon Musk

The hallmark of a highly effective leader is that they encourage risk-taking, and experimentation, and create a culture where failure is celebrated as a valuable learning experience.

Habit #2. Be Authentic

Have you watched the TV series The Office?

While the series is meant to be a fictional (and should I say, hilarious) comedy representation of everyday management and office work, it does highlight some key elements of the traditional association of managers at work. Michael Scott, the manager, “puts on a show” of a tough manager who knows how to get work done. Michael has his vulnerabilities and weaknesses, but he tries really hard to hide them from his team.

Traditionally, leaders were associated with traits like strength, assertiveness, and dominance, who would use command-and-control approaches to get stuff done.

However, (and thankfully!) the archetype of a leader has evolved.

Highly effective leaders today are those who embrace vulnerability and authenticity. They are comfortable with their true selves, including their strengths, weaknesses, and insecurities. They recognize the importance of connecting with people on a human level, rather than hiding behind a fake mask (or a podium for that matter).

In my article The Dumbest Mistake Leaders Make in Communication, I discuss how authentic communication plays a vital role in building trust and mutual respect in an organization.

Howard Schultz, the former CEO of Starbucks, transformed the company into a global brand by staying true to his vision and values. Schultz’s authenticity resonated with both employees and customers, fostering a culture of trust and loyalty within the organization.

“Authentic leadership is revealed in the alignment of what you think, what you say, and what you do.” — Michael Holland

Highly effective leaders are unapologetically themselves. They lead with authenticity, openly sharing their values, beliefs, and vulnerabilities.

Habit #3. Ignore Selectively

We live in an information-saturated world today.

There is an overwhelming amount of data, countless distractions, and competing priorities vying for our attention.

It is not humanly possible for us to catch every ball thrown at us.

Leaders who fail to discern what truly matters from the massive onslaught of information can get overwhelmed, and end up burning out themselves and their teams, while still not delivering the results.

Effective leaders understand how to distinguish the signal from the noise, and the importance of selective ignorance.

They weight the urgent vs the important, and commit their time to tasks that will yield the highest and most meaningful results. They keep their teams focused, and actively remove distractions and cut out things that are not strategically important.

“Deciding what not to do is as important as deciding what to do.” — Steve Jobs

In my article Making the Hours Count: The Misconception Behind Smart Work, I discuss the importance of efficiency and how leaders need to make the hours count by adopting ruthless prioritization.

Indra Nooyi, during her tenure as CEO of PepsiCo, implemented a strategy called Performance with Purpose, which involved prioritizing healthier products, sustainability initiatives, and investing in emerging markets. This intentional strategic focus helped PepsiCo emerge strong during her tenure as CEO.

Highly effective leaders are masters at selective ignorance, which helps them to drive productivity and efficiency in their organizations.

Habit #4. Embrace Imperfection

Imagine what would happen if a team spent 6 months building a “perfect product” that nobody wanted.

There was a time when perfection was seen as a symbol of power and legitimacy, reinforcing the leader’s position at the top of the hierarchy.

And leaders themselves started expecting nothing less of their teams.

However, the world is a different place today.

In my article about The Value Triangle, I discuss how changing user expectations and technological advances are pushing leaders to become more agile and drive value generation as against output generation.

Leaders need to adopt a mindset of continuous delivery and experimentation, and be willing to take calculated risks.

Sheryl Sandberg, former COO of Meta (Facebook), advocates for embracing imperfection in her book Option B: Facing Adversity, Building Resilience, and Finding Joy. In the book, Sandberg emphasizes the importance of finding strength in vulnerability, both in personal and professional contexts.

“Embracing our imperfection puts the emphasis back where it should be: continual improvement.” — Ryder Carroll

Highly effective leaders embrace imperfection, and they are obsessed with innovation through rapid experimentation and adaptation.

Habit #5. Be Transparent

In my article about The Power of Clarity, I discussed how the corporate world today is filled with corporate jargon and ambiguous words.

It is widely believed that using wishy-washy, abstract terms and corporate jargon can make you sound smart, intelligent, and “senior”.

The reality is that many leaders do this to mask (or sugarcoat) a difficult message, or to avoid taking accountability for what they are saying.

Highly effective leaders, on the other hand, prioritize open and honest communication, even when it is uncomfortable or inconvenient.

Kim Scott, a former executive at Google and Apple, wrote a book on Radical Candor, where she emphasizes the importance of caring personally while challenging directly.

As another example, Ray Dalio, the founder of Bridgewater Associates, advocates for radical transparency within his company where employees are encouraged to speak openly about their opinions and concerns. He discusses this at length in his best-selling book Principles.

Jeff Bezos, the founder and former CEO of Amazon.com, is known for his “door desk” meetings, where he sits at a makeshift desk made from a wooden door to encourage accessibility and transparency.

By practicing transparency, leaders foster a culture of continuous improvement, where feedback is viewed as a gift rather than a threat.

Highly effective leaders believe in transparency as a cornerstone of trust and accountability.

Habit #6. Cultivate Empathy

In a fast-paced world, leaders are inundated with competitive threats and opportunities.

These forces can make them obsessed with achievement and results.

They end up promoting a hustle culture, and ignoring their own and their team’s physical, mental, and emotional well-being.

However, effective leaders recognize that well-being is not a luxury, but a necessity for sustained success and resilience.

They recognize that they need to take care of themselves first, before they can take care of their teams.

Thus, self-care goes hand-in-hand with empathy.

Arianna Huffington, the co-founder of The Huffington Post, famously collapsed from exhaustion in 2007. This incident made her realize the importance of sleep and mindfulness, and she later became a strong promoter of well-being in the workplace.

Doug Conant, the former CEO of Campbell Soup Company, is renowned for his commitment to gratitude. He wrote over 30,000 handwritten thank-you notes to his employees during his tenure.

In my article Good to Great: The Most Overlooked but Critical Skill of a Leader, I discuss the critical relationship between People and Results, and why great leaders focus on developing their people first before expecting results.

“Leadership is about empathy. It is about having the ability to relate to and connect with people for the purpose of inspiring and empowering their lives.” — Oprah Winfrey

Highly effective leaders foster a culture of empathy and gratitude with their organizations, while not neglecting their own well-being.

Habit #7. Embrace Change

Only 1 out of 10 things around you today will remain the same in 5 years.

That’s the speed at which the world is changing.

Leaders who do not embrace change are bound to fall behind, as they risk becoming obsolete and losing relevance.

A striking example (and a popular MBA case study) of the consequences of failing to embrace change is Kodak. Despite being a pioneer in digital photography research, Kodak failed to capitalize on its innovations due to a reluctance to shift away from its film-based business model. While Kodak’s digital camera technology could have positioned it as a leader in the digital age, the leadership’s hesitation to embrace change ultimately led to its downfall.

Leaders who embrace change allow themselves to stay agile and innovative, and position their organizations for long-term success.

In my article about the 5 Timeless Chess Principles You Can Apply as a Strategic Leader, I discuss the importance of adapting your strategy as a principle for chess masters, just like it is for great leaders.

Reed Hastings, co-founder of Netflix, led the company's transformation from a DVD rental service to a streaming platform. Hastings has consistently emphasized the importance of embracing change and adapting to the changing landscape, and Netflix has continued to evolve and stay relevant as a company.

“Change is hard at first, messy in the middle, and gorgeous in the end.” — Robin Sharma

Highly effective leaders embrace change, and continue to evolve their organizations to stay relevant and competitive.

In Summary: The 7 Habits

When we think about the most effective leaders, we often think of traits such as visionary, charismatic, and assertive.

However, the reality is that the most effective leaders share some unique traits that are not as obvious, and may even come across as unconventional or surprising to many.

The 7 Unconventional Habits of Highly Effective Leaders, Illustration Credit: Gaurav Jain

In this article, we discussed the 7 counterintuitive habits of highly effective leaders:

Embrace Failure. Highly effective leaders celebrate failure as a valuable learning experience. They see failure as a necessary stepping stone to success.
Be Authentic. Highly effective leaders are unapologetically themselves. They lead with authenticity, openly sharing their values, beliefs, and vulnerabilities.
Ignore Selectively. Highly effective leaders are masters at selective ignorance, which helps them to drive productivity and efficiency in their organizations.
Embrace Imperfection. Highly effective leaders embrace imperfection, and they are obsessed with innovation through rapid experimentation and adaptation.
Be Transparent. Highly effective leaders believe in transparency as a cornerstone of trust and accountability.
Cultivate Empathy. Highly effective leaders foster a culture of empathy and gratitude with their organizations, while not neglecting their own well-being.
Embrace Change. Highly effective leaders embrace change, and continue to evolve their organizations to stay relevant and competitive.

These leaders are different. Their habits are counterintuitive, surprising, yet inspiring.

And that’s precisely what makes them highly effective.

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