Superbosses

What makes a leader unforgettable? Superbosses show us that visionary, fearless, and authentic leadership can inspire employees to achieve excellence and transform entire industries.

1: The Three Faces of Superbosses

There are three types of superbosses, each with unique leadership qualities – iconoclasts, inglorious bastards, and nurturers. Their differing styles show varying paths to excellence.

Iconoclasts lead with unwavering focus on their vision and unintentionally inspire others as they relentlessly pursue their goals. Their dedication often spills over to those they work with, igniting creativity. For example, jazz legend Miles Davis constantly collaborated with young musicians, though his aim was personal growth, not mentorship. His influence naturally shaped others' careers.

Inglorious bastards push teams hard to get results. These bosses might use tough measures or pressure to reach their goals. Larry Ellison, founder of Oracle, exemplified this. Known for his demanding standards and management through ridicule, his tactics, though harsh, led to remarkable corporate achievements.

On the opposite side are nurturers who deeply care about their team’s growth. They see their employees as mentees and guide them to success. Restaurateur Norman Brinker, for instance, fostered multiple future leaders in the restaurant industry. Eighteen of his employees later became heads of major restaurant chains.

Examples

• Miles Davis inspired younger musicians by pursuing his artistic innovation.
• Larry Ellison’s tough style built a high-performing team at Oracle.
• Norman Brinker developed leaders who impacted the restaurant business.

2: The Core Traits of Superbosses

Superbosses excel because they possess vision, competitiveness, and a fearless outlook. These traits are not learned but are part of their core being.

Vision allows superbosses to see possibility where others see obstacles. Ralph Lauren exemplified this ability through his meticulous designs of the lifestyle associated with his brand. He would visualize entire worlds and strategically bring them to life.

Fearlessness defines how superbosses challenge themselves and others. Whether racing sailboats like Larry Ellison or taking extraordinary risks like Norman Brinker, they live boldly both professionally and personally.

Lastly, their competitiveness drives success. Michael Milken, known for his work with junk bonds, even approached daily chores as challenges to improve on. This mindset made competition an intrinsic part of his leadership and life.

Examples

• Ralph Lauren’s vision shaped the global identity of his fashion brand.
• Larry Ellison’s fearless sailboat racing mirrors his corporate daring.
• Michael Milken’s competitive approach extended into all aspects of life.

3: Integrity and Authenticity Fuel Charisma

A superboss’s charisma is deeply rooted in their integrity and authenticity, which energizes and attracts others to them.

Integrity comes from unwavering commitment to their vision. Conductor Jorma Panula focused solely on the quality of the music, rejecting ego or praise, making him a standout in his field.

Authenticity allows these leaders to be relatable and genuine. Tommy Frist, founder of HCA, openly shared personal parts of his life, like writing letters to his children during business trips. This approach endeared him to his team.

When leaders embody these traits, they leave lasting impressions and energize those around them. Employees remember their integrity and authenticity long after parting ways.

Examples

• Jorma Panula kept his music-focused integrity intact amidst industry pressures.
• Tommy Frist shared his love for his family openly, earning staff admiration.
• Teams feel energized by bosses staying true to their vision and values.

4: Superbosses Seek Employees Who “Get It”

Superbosses excel at recruiting by identifying candidates with intelligence, creativity, and flexibility that align with their team vision.

Intelligence is a cornerstone quality, as it drives collaboration and success. Ralph Lauren sought “fashion intelligence” in every hire, prioritizing style awareness in all job roles. He even promoted a model to a design leadership role based on her understanding of his brand.

Creativity allows employees to offer fresh ideas and new perspectives. Larry Ellison welcomed innovative contributions, while Norman Brinker eagerly learned from employee ideas during hiring interviews.

Flexibility, for superbosses, means adaptability to challenges and roles. Roger Corman moved actors into production roles to evaluate their versatility, ensuring they could thrive in multiple situations.

Examples

• Ralph Lauren promoted a model who deeply understood his brand’s identity.
• Norman Brinker listened for unique ideas during job interviews.
• Roger Corman shifted new hires into varying roles to test adaptability.

5: Pushing the Limits for Excellence

Being a superboss means pushing employees beyond their comfort zones to help them uncover untapped potential.

Superbosses maintain high expectations, continuously raising the bar for team achievements. Ralph Lauren did this with young designers, constantly challenging them to reach unimagined levels of creativity and skill.

Confidence is a tool superbosses use to motivate others. Bill Walsh, coach of the San Francisco 49ers, transferred his unshakeable belief to his players, inspiring them to overcome doubts and perform.

Teams perform at their highest capacity not just from pressure, but from the belief that they can achieve greatness—a belief instilled by their leaders.

Examples

• Ralph Lauren motivated designers to exceed their usual creative limits.
• Bill Walsh harnessed confidence to uplift his players’ mindset.
• Superbosses use raised expectations to drive both personal and collective successes.

6: Bonding and Competition in Teams

Superbosses foster emotionally connected teams while introducing competitive elements to enhance productivity.

Vertical bonds connect leaders to employees, creating trust and alignment. Horizontal bonds build camaraderie among team members. Lorne Michaels achieved this on Saturday Night Live by fostering a family atmosphere.

To boost performance, superbosses introduce friendly competition. Lorne Michaels hired more staff than necessary, spurring individuals to refine their skills for a chance in the spotlight.

By blending emotional connections with competition, superbosses build high-performing, tightly knit teams.

Examples

• Lorne Michaels cultivated a “family bond” among SNL cast members.
• Friendly competition among staff raised SNL's performance quality.
• Former employees of superbosses maintain long-lasting relationships.

7: Superbosses Shape Talent and Let It Shine

Superbosses help employees grow and encourage them to succeed elsewhere, trusting that their achievements will reflect well on their own legacy.

Employees who thrive under superbosses often go on to become industry leaders. Roger Corman adopted this belief in Hollywood, encouraging team members to create elsewhere but maintain ties to his network.

By mentoring employees and giving them freedom, superbosses expand their professional influence and attract strong talent to work for them.

Examples

• Roger Corman urged former workers to achieve success beyond his company.
• Superbosses encourage professional independence to build their legacy.
• Teams are always willing to reconnect with their former leaders.

8: The Secret Sauce: Three Questions

The superboss quotient reveals your leadership level, starting with three vital questions: Do you have a clear vision, foster team connections, and invest in employee growth?

A vision inspires both the leader and the team. Strong team bonds create loyalty and trust, while encouraging development leads to higher workplace satisfaction.

Using this quotient as a guide helps leaders identify where change or improvement is needed to become a better boss.

Examples

• Clear visions enable leaders to remain motivated and inspire teams.
• Effective team bonds foster loyalty within organizations.
• Investing in employees helps leaders ultimately drive company success.

9: Try a Superboss Day Experiment

Adopting different superboss styles can help you discover which methods work best for your leadership development.

Take a day to act as an iconoclast, nurturer, or inglorious bastard in your management style. Over time, reflect on its effectiveness and adapt the strategies learned for long-term use.

Such experiments can help you align with and fine-tune your leadership methods.

Examples

• Testing nurturer traits can help foster mentorship.
• Attempting competitiveness can reveal team resilience and growth.
• Leveraging vision-driven approaches can foster innovation.

Takeaways

1. Embrace your vision and make it a clear, motivating force behind your leadership.
2. Push your team to new heights by setting higher expectations while giving them confidence.
3. Build strong bonds with your team while fostering healthy competition to inspire collaboration and performance.