On Leading With Greatness
On Leading With Greatness
Revolutionary Bossing: Unleashing the Pioneers
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Revolutionary Bossing: Unleashing the Pioneers

Get Ready for Some Inspiration!
Confident businessman looking up surrounded by cartoon space images including a rocket orbiting his head

Okay, I admit that I spend way too much time grousing about bad bossing. I mean there have to be a few good bosses to look up to, right? Well, I have done the research and can assure you that there are some outstanding innovators to admire. Let’s check out a few of these trailblazers—explorers, if you will—boldly bossing where no boss has bossed before.

Attentive Bossing: Learning from the People

Most bosses are clueless about what their people really think, feel, or even do let alone what evil lurks in their minds and souls. Meet Eduardo Hernandez, owner of a California taqueria chain. His genius plan to take on this common dilemma was to disguise a friend as a Catholic priest to hear his employees’ confessions. The faux cleric then tried to ascertain their loyalty to Hernandez and whether they were stealing from the restaurant. Sadly, as with so many great pioneers, Hernandez had to pay a price for his audacious trailblazing. In this case $140,000 to the Department of Labor.

Decisive Bossing: Making the Tough Calls

Restaurants are truly laboratories for groundbreaking bossing strategies. Just take legendary Boston restauranteur Barbara Lynch. After her head chef and a line cook died suddenly, she gathered her grieving team to get them back on track. Despite her willingness to candidly air all her personal grievances during this meeting, her new head chef dared to question her compassion. Boldly decisive and impetuously self-protective, she fired him on the spot. When he responded with some choice words, she promptly offered to push his head through a window. Talk about take-charge, take-no-guff, take-no-prisoners leadership! I bet no one will be so quick to carp the next time she has too many drinks and sexually harasses them!

Motivational Bossing: Igniting Inspiration

And it's not just the restaurant industry that breeds innovative motivators. James Clarke, CEO of Clearlink related a touching story to his employees to inspire them to shed “blood, sweat, and tears” for him. Here is his epic story of sacrifice and heartbreak in its entirety: a company manager sold the family dog so that he could work longer hours. Heartwarming, right? Clarke then raised the stakes by challenging his overworked employees to “outwork” him although he neglected to indicate if their remuneration would then be commensurate with his.

Similarly, Andi Owen, the CEO of MillerKnoll furniture, wanted to alleviate employee concerns about bonuses amidst slumping sales. Instead she grew angry at them and demanded that her workers stop grousing and “leave pity city.” Nothing fires people up like being publicly called whiny by a millionaire CEO. That is some top-level bossing!

Talking Bossing: Communicating Clearly

Mass layoffs are often unavoidable, but—as invigorating as they can be—there is a right way to handle them and a wrong way. Vishal Garg of Better.com chose the wrong way when he fired 900 people via Zoom. After all, he could have accomplished the same result with much less fuss by taking to email or even Twitter. Being an inventive boss, though, he corrected his error by writing anonymous posts on social media. Using the handle “uneducated,” he explained that many of the fired employees were not working their full hours and were therefore “stealing from you and stealing from our customers who pay the bills that pay our bills. Get educated.” In one genius stroke, Garg managed to communicate his logic, establish his superiority, and define the sort the culture he wanted for his company!

Resolute Bossing: Sticking It Out

When things get tough, many bosses are tempted to abandon ship, but not the intrepid Steph Korey of Away, the trendy luggage company. When allegations of Korey’s online bullying surfaced, Korey initially stepped down as CEO, an error she quickly rectified. When the company hired a new CEO, Corey announced her triumphant return as his “co-CEO.” That is the dogged determination of a true boss! Alas, as with many groundbreakers, Korey eventually succumbed to pressure and stepped down again after posting more toxic messages on social media. The lesson here is that old habits can be challenging even for a pro like Korey!

Peerless Bossing: Setting Expectations and Delivering Feedback

Being a well-established and celebrated boss does not mean you can’t unleash your creativity, even in Hollywood. Mega-producer Scott Rudin communicates his expectations and feedback with inimitable clarity. According to reports, the resulting dedication of Rudin’s employees is such that they sleep in the office just to meet his exacting demands. Meanwhile Rudin’s impressive list of hit productions and top awards testifies to his effectiveness as a boss. Sadly, after four decades of unrivaled success, the politeness police have finally caught up to him, forcing him to “step back” from his many projects. We may now only dream of the glorious films that will never be made because Rudin can no longer forge them on the broken backs and souls of so many of his nameless workers.

Superlative Bossing: Being the World's Greatest

It’s no surprise that the world’s richest man, Elon Musk, is also its greatest boss. As an entrepreneur renowned for his cutting-edge business acumen, it's only natural that he possess a cutting-edge management style. In the face of accusations of impulsiveness and cruelty from employees and the media, Musk has explained that his nastiness is nothing more than “clear and frank” feedback. And who are you going to trust, a bunch of disgruntled workers or the man whose Twitter account is a monument to his impeccable candor? Thanks to Musk’s skills, his various enterprises have largely remained immune to pesky distractions such as labor unions, Covid restrictions, feminist squawking, and even black people. Narrow-minded critics may gripe about Musk’s idiosyncratic choices, such as artificially inseminating one of his employees, but they fail to grasp his macro managerial genius; for him the workplace has become a literal family where he models the behavior needed to overcome what he sees as the twin global crises of human underbirth and population collapse.

Despite a few small setbacks in his various endeavors, be it Tesla, SpaceEx, or even the indomitable Twitter, Musk’s undeniable business brilliance manifests the very best a boss can bring to achieving success.

Shiny Bossing: Living in A Golden Age

What a wondrous time to be alive! To walk the same Earth with so many genius bosses! Let us celebrate their dazzling brilliance as they inspire us to develop innovative and prosperous workplaces. And when you ponder the Great Resignation and other examples of turmoil across the workforce, don’t dare point a finger at these super-bosses. After all, what’s the point? It’s not in their nature to accept blame.


Who do you admire as a boss? How often do you emulate behavior like that described here?

Good bosses learn from leaders and the study of leadership to succeed, and I can help.

If you want to learn more about how to become a great leader in this world of bad bosses, visit GuidanceForGreatness.com.

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On Leading With Greatness
On Leading With Greatness
Each Thursday I share new ideas for leaders and aspiring leaders on mission clarity, self-awareness, and human skills — a slightly irreverent kit of Tools+Paradigms for leaders and aspiring leaders like you. Visit GuidanceForGreatness.com