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How Entitlement Compromises Leaders’ Generosity

In the United States, the idea of becoming a self-made success has taken on mythical proportions. From Ralph Waldo Emerson’s classic “Self-Reliance” essay to the adage “pick yourself up by your bootstraps,” Americans have salivated over the idea of combining independence with success.


As a country full of pioneers, self-made success has gained particular importance here. With self-determination and hard work as virtues, businesspeople propelled themselves forward, believing that they and they alone were responsible for their success. But is that really true?

Fast Company recently questioned the “self-made” myth after Kylie Jenner was crowned by Forbes as the world’s youngest self-made billionaire. The majority of Jenner’s net worth came from her cosmetics company, but Fast Company said it would be disingenuous to say she built her successful business herself: “Has Jenner built her company ‘unaided’? Of course not. She has benefitted enormously from the financial aid afforded to her by her family name, as well as the intense scrutiny it has yielded.”

And therein lies the crux: While many successful leaders have fueled their accomplishments through their own skills, strategies, and ideas, they’ve also had to rely on their networks and relationships to achieve their goals. Overlooking that help not only hinders their self-awareness, but it also compromises their ability to be generous.

Entitlement Is a Silent Killer

James Lenhoff, CFP and president of financial planning firm Wealthquest, wrote about this phenomenon in his book, “Living a Rich Life.” In discussing generosity circuit breakers — things that short-circuit our ability to extend generosity toward others — Lenhoff explained that leaders need to remain aware that their story has many influences on it beyond their control.

“The grateful, or fortunate, leader looks at his status and position and can’t believe it — he asks his employees, ‘Can you believe we get to do this together?’” Lenhoff said. “The entitled, or self-made, leader thinks, ‘I paid my dues. I did it all; I climbed the ladder.’ He expects his employees to do completely unreasonable things because he did.”

But that mindset misses a very important component: The leader (grateful or not) didn’t achieve his success on his own, and his employees won’t, either. By pushing them to buy into a self-made fallacy, he focuses on their production and output and overlooks the need to help his employees grow. By downplaying growth and development, leaders can push their teammates into playing a zero-sum game: I earned my stuff; now you have to earn yours.

What Fuels an Entitled Mindset?

How do purportedly confident leaders end up falling into this mindset? Are they threatened by scarcity or pure competition? Are they simply self-centered? Lenhoff says it’s all these things. “It’s a power grab, a fight for significance,” he says. “In business, titles and status carry cache — there can only be so many VPs, and that feeds into it. But the biggest problem starts with how we tell our stories. There are people who tell their story in a way where they’re not the star; their focus is on relationships, experiences, and connections to others. That frames their position in the story.”

For others, however, they view their story as if they’re the main character, and the people they encounter on a daily basis are bit players. That changes the way they interact with others, directing attention and recognition toward themselves rather than spilling it onto others.

David Sturt, the executive vice president at HR consulting firm O.C. Tanner Co., wrote about a survey his company completed in Harvard Business Review. Among the 512 U.S. employees who say their company has strong recognition practices, 87% feel a strong relationship with their direct manager,” Sturt explains. “That number dips to 51% among those who reported a lack of such practices at their companies.”

The significance of recognition couldn’t be understated by Sturt’s team. He said, “The same study found that a new leader can foster an immediate boost in employee job satisfaction — by 31 percentage points — just by recognizing those who have never received any appreciation from their superiors.”

That means that leaders who insist upon having every answer and putting the spotlight squarely on themselves are not only holding unrealistic expectations, but they’re also hindering their ability to build strong relationships and long-term job satisfaction with their employees. By not expressing their appreciation and showing gratitude, they’re also jeopardizing higher productivity and lower turnover.

Reinjecting Gratitude

Lenhoff says the key is for leaders to realize the story isn’t really about them — and to start telling stories about others. By calling out exceptional performance and acknowledging shared work that led to achievements, leaders give employees their due. Beyond that, however, leaders will hear themselves describe how they didn’t achieve it all by themselves.

Another important step for leaders is to check their motives. Are they taking action — whether it’s lauding a co-worker or delegating important work — in order to make themselves look good or to engage with people they care about? Shifting the focus to relationships or purpose negates the shallow motivation that’s fueled by titles or status.

By focusing on relationships, leaders will also be able to create opportunities for others. This entails promoting other people to opportunities that would truly help them and giving them recommendations or access to do something impactful or important. Entrepreneurs fall into the trap of believing they’re the only ones who can do something, which means they get the glory and adulation.  The truth is that lots of other people in the organization could do it (and some can even do it better). Engaging others’ skills results in higher-quality output and has a benefit for entrepreneurs as well: It alleviates the stress of achieving everything on their own terms, which will eventually crush them if they don’t accept help.

The self-made myth can make successful entrepreneurs feel good — but they’re the only ones. By acknowledging the help they’ve received from those around them, leaders can remain self-aware of the factors that led to their success and pour gratitude for that success on others. Applauding oneself for being self-made doesn’t result in more success, but telling positive stories about others certainly can.

Author : Holly Hutton

Born in the Big Easy and raised in the Sunshine State, Holly has spent the last five years brunching in the Big Apple and bantering with Big Ben. As a wandering writer, techy-in-training, and avid alliterator, Holly has written everything from educational policy and political news briefs to web content and travel blogs. She is thrilled to be a part of the KS team and working with a community of smart, savvy, entrepreneurs on all things startup!

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