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Bobby Herrera Helps Leaders Climb with Generosity

Bobby Herrera Helps Leaders Climb with Generosity

Populus Group Founder Bobby Herrera shares the foundations of his leadership and how he continues to serve others

Photo by Devon Michelle
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Throughout his video interview with Hispanic Executive, Bobby Herrera steps away from his screen a few times and returns with mementos from all over his home office. His father’s Bracero identification and draft cards are framed together in the entryway. Herrera was able to live his father’s dream of military service, eventuating a sergeant rank in the US Army.

Photo by Devon Michelle

These mementos serve as a foundation for the founder and president’s leadership journey: a successful stint in the Army, a quick succession of promotions in the corporate world (at one employer, he was promoted four times in less than four years), and the successful 2002 founding of employer services business Populus Group.

Herrera’s mementos showcase his ability to understand the importance of crucial moments of his life and use them as fuel to serve others. One of those moments is the Bus Story.

Lessons on the Bus

He holds up to the camera a photo of himself and a man named Harry Teague. Teague is the genesis of the Bus Story, a moment so moving that it made its way into Herrera’s 2019 book The Gift of Struggle: Life-Changing Lessons About Leading. It’s a story his fellow “climbers” (teammates) at Populus Group have heard countless times. And he says they’ll hear it again.

When Herrera was seventeen, he and his younger brother Ed were on a trip home from a basketball game. They had grown accustomed to staying on the bus while the rest of the team got off to eat dinner. Herrera has twelve siblings and his immigrant parents worked hard for their family, but money was always tight.

That’s where Teague, the father of one of Herrera’s teammates, enters.

“Mr. Teague came on the bus and walked back to us and said something that I’ll remember forever,” Herrera recalls. “He said, ‘It would make me happy if you would allow me to buy you boys dinner, so that you can join the rest of the team. Nobody else has to know. All you have to do to thank me is to do the same thing for another great kid just like you.’”

Herrera was able to reach back out to Teague to recount the story and tell him how much it meant to him. The photo of him with Teague in his office remains a tribute to a man who was able to help Herrera see just how impactful one person can be.

Photo by Devon Michelle

Spark and Service

The Army provided Herrera the chance to pay his gift forward. While polishing his boots by flashlight just before midnight a few weeks into basic training, Herrera remembers listening to the groans and complaints of his fellow enlisted troops, knowing that their 4:30 a.m. alarm was coming sooner than later.

“It hit me all at once,” he recalls. “I had been waking up at five in the morning since I was in the third grade to work almost ten hours in the fields. I know blatant racism, and I know extreme modesty. Nothing that they can say or do to me here isn’t something I haven’t already experienced.”

That was the spark. Herrera motivated his own platoon by highlighting their own backgrounds, urging them forward with the knowledge that their own life experience could power them through their training. This approach would be the foundation of his leadership philosophy and book.

The CEO remains close to veteran issues any way he can at Populus Group. “Veterans are an important part of our communities and workforce,” the company website reads. “We’re passionate about supporting veterans in and out of the office and we’re committed to giving back to veterans organizations throughout the year.”

Generosity as Culture

Nearly twenty years in, Herrera feels like the best times at Populus Group are still ahead of the organization.

“I still feel like we’re kind of the big eleventh grader in high school,” Herrera says, laughing. “In the early years, I think we flunked at least a few times. Now, the dream here is to make lives better for kids and veterans. I want to do Good, with a capital G, for the people that are a part of my community.”

At Populus Group, culture isn’t just a work in progress. It seems more like an orchestra in the middle of a challenging symphony. Every note may not be perfect, but the intent and skill on display is quite clear.

“Every climber here knows what this job is about,” Herrera says quietly but confidently. “We give more than we take. We speak from the heart. And we go off the beaten path. I want to do a lot of good in helping our climbers reach their summits, so their story is very important to mine.”

He recounts a woman approaching him after a storytelling presentation to some two hundred CEOs and asking him what he considers to be the most important attribute for a leader to have. It’s a difficult question, but Herrera answered with a caveat. “We had to agree that there wasn’t just one, but with that in mind, I think it’s easy,” Herrera recounts. “It’s generosity.”

Herrera’s insistence on generosity as a personal tenet is also easy to prove. Just ask any of his kids, aged thirteen, eleven, and nine.

When anyone comes to Herrera for advice, he asks them what their daily prayer is. “Do you have something that reminds you every day, that acts as your compass for why you’re doing what you do?” Herrera asks.

Any of his “three little coconuts,” as Herrera calls them, can rattle off a prayer from St. Ignatius Loyola:

Lord Jesus, teach me to be generous;
teach me to serve you as you deserve,
to give and not to count the cost,
to fight and not to heed the wounds,
to toil and not to seek for rest,
to labor and not to seek reward,
except that of knowing that I do your will.

This prayer helps Herrera remember to pass on the generosity of people like Harry Teague, who helped a young man reframe his beliefs about people and find himself through service. The grounding words for hard days remind Herrera that, ultimately, he has one goal: to give more than he takes.

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