Fleet Leaders Unplugged: Why Some Fleets Soar, and Others Self-Destruct

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In the business world, you may not always be able to choose your teammates, but you can cultivate a powerful strategy emphasizing the ‘why.’


In today’s competitive business landscape, why do some fleets thrive while others stumble? What distinguishes those who ascend to new heights from those who crash and burn?

The answer isn’t solely in vehicles, vendors, or technology but in the strategies, mindsets, and decisions that drive success.

From innovative practices to proactive leadership, the differences are profound. In this piece, we’ll explore the key factors that can propel fleets to greatness or lead them to self-destruction. Buckle up — your fleet’s future could depend on it! 

Why the Right Talent Drives Fleet Success 

Consider the U.S. Navy SEALs, renowned as one of the highest-performing teams in the world. Their selection process is among the most rigorous and demanding, boasting an attrition rate of 70%-80%.

Instructors emphasize that you can’t predict who will succeed. SEAL training is designed to weed out the self-centered, self-serving, and mentally weak. Surprisingly, what remains isn’t necessarily the strongest, fastest, or smartest.

What remains are the individuals, talented in all regards, with a mentality of using that talent inside a system designed for the team’s betterment. What remains is the right talent.   

The best fleets — characterized by efficiency, low total cost of ownership (TCO), and effective service to their businesses — aren’t defined by the number of vehicles, the incentives they receive, contractual rebates, economies of scale, or the vendors used.

They are led by experienced fleet managers, supported by executives who empower their teams, aided by procurement specialists who understand both value and price, and the right ecosystem of providers and consultants to make them effective in achieving their goals.

The best fleets have the right talent to manage their program with a strategy designed for the company’s betterment.   

In the business world, you may not always be able to choose your teammates, but you can cultivate a powerful strategy emphasizing the ‘why.’ When implemented effectively, this strategy fosters buy-in and alignment across the board, proving as reliable as a well-administered anesthetic — just give it time, and it will yield results. 

Narrow Minds Are the Nemesis of Innovation 

Take a page from the tech industry, particularly the legacy of Steve Jobs at Apple. I had the good fortune to be a part of the customer relationship with Apple at an explosive period for the company.

The iPhone was the hot thing, the first-generation iPad was just being released, and there were rumors that Apple would get into the TV and watch games. Stock prices were at an all-time high, and a buzz was felt every minute spent at 1 Infinite Loop (Apple’s former corporate headquarters).

What was apparent from working with so many people at Apple is a set of fundamental principles pervasive in the organization filtered down from Steve himself: sell a vision, set high standards, invest in people, and listen to others, particularly the information and insights from people at lower levels.  

“It doesn’t make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do,” Jobs famously said.

This philosophy of accepting new ideas is a cornerstone of innovation. It reflects the belief that great leaders trust and empower, avoid a fixed mindset, and place high value on new ideas as a part of their innovation system. In the case of Apple, we all see the results of that approach! 

We often find ourselves in an insular bubble in the fleet industry. Aside from the shift toward alternative fuels, little has changed. This tight-knit community, proud of its accumulated knowledge and relationships, can become resistant to external ideas and parallels in other industries.

However, those who view fleets without a fixed mindset are those who dare to challenge the status quo, are often the ones driving meaningful innovation, and consistently emerge as the most efficient, collaborative, and profitable in the industry.

How they do this is not complicated. It’s a mentality that anybody can adopt. 

Smart People Sometimes Make Popular Decisions 

One case stands out as we reflect on numerous competitive bids throughout our careers. A corporation (who anyone would love to have as a customer) was out to bid, ran an exceptionally professional and unbiased procurement process, and down-selected to two top providers, of which we were included.

We had full support for selection, and the RFP team told us they would recommend our firm to the final executive board decision-makers as a formality. We were confident. Even the company’s fleet team proactively prepared to engage with us as a provider before the ‘final’ decision.  

So, imagine, to our surprise, when the committee awarded the business to our competitor.

We were left scratching our heads and came to find out in the following months that the CEO of this organization was a childhood friend of an executive of our competitor, which was a key factor in the final decision. Nobody else on the selection committee stood up for the fleet team’s recommendation!

They followed the popular decision. Less than a year later, with the partnership not working out, the company was out to bid again for the same services, incurring disruption and further cost of change. 

The reality is that fleet decisions are critical — seemingly small choices can have significant implications for operating costs. Fleet experts are tasked with analyzing vast amounts of data, conducting thorough research, and synthesizing this information into concise recommendations that inform multimillion-dollar budgets.

With surprising frequency, emotions and personal prejudices override logic and fact. Fleets that soar treat fortitude as a virtue. They don’t criticize people for being strong in their views or positions. They model the behavior they expect and don’t let the popular decision get in the way of the right decision.  

Building Fleets That Soar 

The stark truth is that fleet success relies on more than vehicles, vendors, contracts, or technology; it’s about the people, mindset, strategies, and systems driving them.

The most effective fleets invest in the right talent, embrace innovative thinking, and foster a culture prioritizing informed decision-making over fleeting popularity. Much like elite teams in other industries, they thrive by embracing diverse perspectives and encouraging collaboration

So, as you reflect on these insights, ask yourself: Is your fleet positioned to soar, or is it at risk of self-destruction? The choice is yours, and the time to act is now. 

About the Authors: 

Brad Jacobs, a fleet industry executive with 20+ years of experience, specializes in commercial fleets, rentals, and product development. Recognized with awards like the Business Intelligence Award for Sustainability, Jacobs has driven transformative change, enhancing efficiency and sustainability across hundreds of organizations.

Diana Holland, founder of CAVIS, brings 27+ years of experience in fleet, logistics, and supply chain optimization. An award-winning leader, her accolades include the 2022 Women in Supply Chain Award and the AFLA’s 2020 President’s Award, reflecting her innovative approach to driving growth and industry impact.

This article was authored and edited according to Automotive Fleet’s editorial standards and style. Opinions expressed may not reflect that of Automotive Fleet.



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Alexandra Williams
Alexandra Williams
Alexandra Williams is a writer and editor. Angeles. She writes about politics, art, and culture for LinkDaddy News.

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