Heavy Duty Trucking Logo
MenuMENU
SearchSEARCH

How to Develop the Next Generation of Fleet Leaders

Four trucking industry leaders give tips on how to overcome the challenges they've faced in developing the next generation of leaders.

April 23, 2021
How to Develop the Next Generation of Fleet Leaders

If fleets are not investing time into training the next generation of leaders, they face the challenge of lossing a wealth of tribal knowledge at their operation.

Photo: Gettyimages.com/kali9

3 min to read


While multi-generational workforces present some obstacles to employers, operations could arguably be more productive and experience less employee turnover than those without generational diversity, said TravelCenters of America Vice President of Truck Service Homer Hogg during a virtual session on leadership development at the ATA Technology & Maintenance Council’s spring meeting.

Ad Loading...

During the session, four panelists from the trucking industry spoke on the challenges they've faced in developing the next generation of leaders in their operations.

The rapid pace of technology development in this ever-changing industry means companies need to constantly learn, adapt and adjust to their environment more than ever. That also means having to rethink what leadership may look like in the future, said Tim Foley, director of performance and learning at Navistar.

Ad Loading...

On top of that, the challenge of the “changing of the guard,” as Evan Erdmann, fleet service manager at Clarke Power Services, put it, can often mean the loss of a wealth of tribal knowledge if you’re not investing the time it takes to train the new generation.

“How do you get all this tribal knowledge from somebody that has been around this industry, or this company, for 20-30-40-plus years?” Erdmann explained. “That breadth of experience, tribal knowledge that is gained … how do you pass that on to the new, up-and-coming leaders? The folks you’ve identified that you do want to groom into those leadership roles?"

 The panelists shared these tips for preparing new leaders, all centered around the sentiment of embracing change.

1. Identify Employees with Leadership Ambition

First and foremost, leaders need to identify the people in their operation would want to advance into leadership roles. And it all starts with a conversation, Erdmann said.

“It’s really having those personal one-on-one conversation with folks within your organization, and figuring out what their goals and aspirations are. I think that’s critical,” Erdmann said. “ I found that I think some people be a great leader, and you talk to them, and it’s not what they want to do.” It's important to know their personal aspirations and goals.

Ad Loading...

2. Give Employees a Chance to Try

But once you do identify them, begin training right away, recommended Anthony Marshall, vice president of transportation fleet maintenance and engineering for UPS.

“The sooner we get people into certain roles, and give them exposure, that allows you to help develop those folks,” he said.

Using a baseball analogy, Marshall explained that sometimes the people on the bench need to get a swing at the bat to get a feel for how things could be. Giving those folks that “swing” not only helps the company as far as future talent acquisitions, but it also helps ensure you have the right people in the right position, he said.

Erdmann echoed the sentiment, saying it’s all about putting people in different roles and situations in order for them to gain valuable experience and learn as much as possible from their mentors.

3. Create Space for Failure

With the industry constantly changing and growing more complex, there’s not a compass or roadmap to leadership development. More than ever, leaders need to be more comfortable with experimenting, testing new ways of doing things and make space for failure and growth, explained Foley.

Ad Loading...

“We’re looking to help people learn how to tolerate ambiguity, because most of what we’re facing is brand new,” Foley said.

Leaders who are curious, resilient and optimistic will be able to stand the test of time as the “usual way of doing things” inches out of the conversation.

To create an environment that makes space for failure, and allows leaders to develop their skills of resilience, organizations should focus on their values from the top down, said J.B. Swanson, director of continuous improvement at Empire Truck Sales and Stribling Equipment.

“You need an environment where you can fail, and where you can learn, and where you can develop,” he said.

Subscribe to Our Newsletter

More Fleet Management

TEN disaster prep.
Fleet ManagementMay 1, 2026

How Fleets Can Avoid Equipment Blind Spots in Disaster Response

When the unexpected happens, how you react to, and deal with operational blind spots is critical. Here’s how to keep you recovery on track, when nothing is normal.

Read More →
Illustration of cybersecurity images with "The Cyber Stop" text
Fleet Managementby Ben WilkensApril 30, 2026

AI Security Risks for Trucking Fleets: What to Know About Deepfakes and Agentic AI

As fleets adopt artificial intelligence for routing, maintenance, and load matching, new security risks are emerging. Learn where the vulnerabilities are and how to put the right controls in place.

Read More →
Mobile tablet showing Motus screen against highway background with Motus logo

FMCSA’s Motus System Is Coming. What Fleets Need to Know Now

The long-awaited registration system promises a single portal — and tighter fraud controls.

Read More →
Ad Loading...
CargoNet 2026 Qi report.
Fleet Managementby News/Media ReleaseApril 24, 2026

Cargo Theft Incidents Fall in Q1, but Organized Crime and Impersonation Drive New Risks

CargoNet reports fewer supply chain crime events to start 2026. But losses hold steady as organized crime shifts tactics toward impersonation schemes and high-value goods.

Read More →
Graphic with light bulbs, HDT Truck Fleet Innovators logo, and the word Nominations
Fleet ManagementApril 24, 2026

Nominations Open for HDT Truck Fleet Innovators 2026

Heavy Duty Trucking is searching for forward-looking leaders at trucking fleets as nominations for HDT’s Truck Fleet Innovators 2026. Deadline is May 15.

Read More →
Illustration with trojan horse and lock with inside of cargo container in background
Fleet Managementby News/Media ReleaseApril 23, 2026

New Trojan Driver Cargo Theft Scam Bypasses Carrier Vetting Systems

Cargo theft rings plant operatives as drivers inside legitimate, fully vetted carriers, then execute coordinated thefts that look like a traditional straight theft from the outside.

Read More →
Ad Loading...
ATA Truck Tonnage Index March 2026.
Fleet Managementby News/Media ReleaseApril 22, 2026

March Truck Tonnage Posts Strongest Annual Gain Since 2022

A modest sequential increase capped the strongest quarterly performance in years, signaling continued freight momentum in early 2026.

Read More →
Toll road.
Fleet Managementby Jack RobertsApril 22, 2026

Ohio Turnpike Targets $5.2 Million in Unpaid Tolls from Trucking Firms

More than 300 carriers across 26 states have been sent to collections as the Ohio Turnpike cracks down on toll evasion and delinquent payments.

Read More →
Illustration with ATRI logo and square blocks spelling out "research"
Fleet Managementby Deborah LockridgeApril 20, 2026

'Beyond Compliance,' Regulations, Driver Coaching on ATRI’s 2026 Research List

The American Transportation Research Institute will examine driver coaching, regulatory impacts — including the "Beyond Compliance" concept —and weather disruptions that shape trucking operations.

Read More →
Ad Loading...
Brian Antonellis, senior vice president, fleet operations, Fleet Advantage.
Fleet Managementby Jack RobertsApril 17, 2026

Fleet Advantage's Brian Antonellis on the Growing Need to Replace Old Trucks

Fleet Advantage's Brian Antonellis says it's time for fleets to get back to the fundamentals of good maintenance practices. And that includes replacing older, inefficient equipment.

Read More →