Training Your Successor: Another Fleet Manager's Advice on Succession Planning
Pass the Baton: Planning the Perfect Handoff
Why one industry veteran says a succession plan should be a part of every fleet manager’s toolkit.

A successful fleet management operation is done with succession planning in mind.
Photo: Canva/Government Fleet
In the case of track and field relays, a team is only as good as its baton handoffs. The runners on a team can be perfect at pacing themselves, but one poor handoff from one runner to the next can put a major dent in the team’s run. Similarly, a change in leadership in fleet operations can ruin the flow of operations if not done well.
A successful fleet management operation is done with succession planning in mind. And it doesn’t always mean planning for retirement or a job change, one longtime fleet manager tells Government Fleet.
“It is ensuring that there are no breaks, if you will,” says Darryl Syler, CPFP, fleet services division chief for the city of Alexandria, Virginia. “It means if someone's out, there’s someone there to be able to cover for that person.”
One Above, One Below
Before working for local government fleets, Syler served in the U.S. Army as a Motor Sergeant in Germany, South Korea, Kuwait, Kansas, and Georgia. One approach he took with him from his 24 years in the military: one above, one below.
It means ensuring that if something happens to the person above or below Syler in the line of succession, he can step in and fill in as needed. The same applies to the next person below that person, and so forth. It all boils down to ensuring there are no hiccups in the daily operation of the fleet division. This approach also allows for easier upward mobility for employees who are interested.
Succession Planning in 2023

Darryl Syler
Syler believes succession planning today has different challenges than it did in the past. One of those challenges is finding qualified managers. Nobody is immune to the labor shortage in this industry, and the shortage of skilled workers is impacting those at the top. Fleet managers are often people who have years of experience in the industry. But a shortage of new people entering the industry can have a negative effect on the pool of people qualified to fill management roles.
Working in this industry also doesn’t seem to be as appealing to younger generations, Syler thinks. That can be attributed to the push for young people to attend college. However, there does seem to be an increase in those interested in learning skilled trades. A 2020 Big Rentz survey revealed one-third of Americans view trade school as a more favorable option than college. This is good news for the public fleet industry.
Syler’s advice: when you do find a staff member who is interested in upward mobility, mentor them. Prepare them to someday step into a management role.
A Committed Staff Makes All the Difference
A successful succession planning approach requires having team members who are committed to the business and interested in growth. It all starts with good leadership and a good approach to managing your team. You must follow the Golden Rule, Syler says. Treat your team the way you would want to be treated.
A fleet manager needs to be able to understand — and be open to — new ways of thinking.
“I love listening to other people,” Syler says. “One thing I've had to learn in this industry is you have to open your ears and listen. Listen to what your staff saying, listen to what your peers are saying, and listen to what your bosses are saying. You have to adapt to [what’s happening in your department] to move forward.”
Syler also recommends surrounding yourself with people who have industry wisdom. Attending the Government Fleet Expo & Conference is one way to do this.
“One thing I have tried to do these last 12 to 15 years is surround myself with people smarter than me, and good people. Not only does it make me successful and the organization successful, but it also makes them successful. We're all able to put our heads together and collaborate,” he says.
Syler says he has witnessed people fail when they were put in leadership positions. He also says he’s seen people excel. The difference in outcome was determined by whether a solid succession plan was in place within the organization.
Finding the Right Fit
Syler cautions against fleet management teams or the departments above them hiring someone to fill an open position simply for the sake of having a body to hold the title.
“That's doing that person and injustice, as well as the organization. They struggle because they don’t know what to help [the new manager] with, and they don't know what to guide them.”
Fleet is also an industry that oftentimes takes a backseat because governmental leadership doesn’t always understand the importance of having working vehicles when they are needed the most, Syler says. This can lead them to rush the hiring process and hire the wrong person for the job. Syler urges governments to do a thorough search to find the right fit, whether internally or externally.
Fitting Succession Planning into Your Schedule
One challenge Syler believes fleet managers may face when it comes to having a succession plan in place is their workload. Finding the time to train those in leadership positions to step up can be difficult.
Syler says he was fortunate in this regard because he was able to divvy up the work. In June 2022, Syler hired a dedicated acquisition manager to take some of the responsibilities off his plate. Now, he’s working on expanding his administrative team.
“We need to get an organization built to where we can support the city's fleet to be able to be successful. Being able to color outside the lines a little bit helps,” he says.
The pandemic has forced many fleet organizations to adjust their operations and focus on other things, like vehicle shortages. But foregoing a strong succession plan can lead your organization to fail.
“It should be a part of your toolkit, if you will, as fleet manager. Because there's going to come a time when you get of age and you say, ‘okay, I'm done,’” Syler explains. “So, when I do decide to retire, I can walk away leaving the next man or woman in charge, and leave it better than what I found it because that’s the way I was always brought up.”
The approach to succession planning should be the same when planning for both unexpected absences or retirement, Syler explains. The only difference is that a management change could happen sooner in one scenario versus another, depending on the organization.
Another perspective Syler gained during his time in the military is always being prepared for the unexpected.
“If we don't put an emphasis on our fleet and take the time to train the operators and the leaders over the operators…we're not going to be successful.”
Bottom line: don’t overlook the benefits of having a succession plan in place. It could mean the difference in a winning fleet management operation and a losing one.
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