Fleet operators tend to think of risk in terms of isolated events, such as a crash, a failed inspection, or a compliance lapse. But according to Bob O’Connell, Account Executive of Strategic Accounts at J.J. Keller & Associates, that way of thinking is itself the biggest blind spot in the industry.
“A lot of carriers, big and small, believe that their risk is based on isolated incidents,” O’Connell said in a recent appearance on FreightWaves’ What the Truck?!? with host Malcolm Harris. “That’s really not the case. You’re being judged on all of it, the consistency of your entire operation.”
The distinction matters because regulators and plaintiff attorneys alike are looking at patterns, not snapshots. A fleet that performs well on one audit but lacks the operational discipline to sustain that performance over time is exposed in ways its leadership may not fully appreciate until it’s too late.
O’Connell laid out a three-part framework for how fleets of any size can close their risk gaps and move from reactive to proactive postures: operate as though a merger or acquisition is imminent, build genuine regulatory expertise internally, and maintain litigation-ready records at all times.
Run your fleet like someone’s about to buy it
The first strategy O’Connell outlined may sound like it belongs in a boardroom rather than a dispatch office, but the logic is straightforward. A fleet that’s always ready for due diligence is a fleet that’s always ready for scrutiny from any direction, whether that’s an insurance carrier, a federal auditor, or a plaintiff’s legal team.
“A merger and acquisition forces discipline, not only on the financial side, but through the entire operational side,” O’Connell said. “If you’re taking a look at it from that viewpoint, what you’re going to see is that if you’re always ready for a merger and acquisition, you’re always going to be ready for somebody to come in and pull the covers back on your entire operation.”
That readiness, O’Connell argues, has compounding benefits. Fleets that maintain tight operational visibility are better positioned to push back on insurance rate increases, respond to audits with confidence, and demonstrate to outside parties that they’re running a disciplined shop.
“If you’re ready for somebody to be viewing your organization in a very detailed format, you’re ready for a lot of things,” he said. That includes showing your insurance provider how well you perform to get lower rates.
The same principle applies when litigation enters the picture. A fleet with a merger-ready posture already has its documentation organized, its compliance records accessible, and its operational narrative coherent.
Regulatory expertise can’t live in one person’s head
The second pillar of O’Connell’s framework centers on regulatory knowledge, and specifically on why fleets can’t afford to treat compliance as a static competency that lives with a single internal hire.
The Federal Motor Carrier Safety Regulations (FMCSRs) are constantly evolving. The pipeline of changes (from the congressional record to the federal register to state and municipal rulemaking) is broader than most fleet operators realize.
O’Connell says that outside compliance partners exist precisely because no single internal team can track the full scope of regulatory change in real time. “You would have to have a fleet of people to manage that,” he said. “Why not turn that over to a specialist that does nothing else every single day?”
But outside expertise alone isn’t sufficient. The real value comes from pairing external regulatory intelligence with internal operational knowledge.
“It’s not just the regulations,” O’Connell said. “It’s how those regulations affect your organization, because regulations aren’t really one size fits all. You have to be able to look at the regulatory expertise, make sure you understand those regulations, and make sure you’re being notified of when they’re changing and how they’re changing.”
Cookie-cutter compliance strategies fail because operations can be very diverse from one fleet to the next. The regulatory burden looks different depending on whether a carrier is running small-cap package delivery, waste haul operations, or long-haul linehaul, and each type requires its own operational interpretation of the same regulatory landscape.
“You have to have bench strength so that your inside person understands the operation,” O’Connell said. “All of your competitors have to comply with the same regulatory landscape.”
J.J. Keller’s Certified Transportation Regulatory Expert (CTRE) Program bridges the gap between regulatory knowledge and operational application so a fleet’s internal staff can fully understand the FMCSRs and comply with them more effectively.
If it’s not written down, it doesn’t exist
Litigation-ready record keeping may be the most immediately actionable of O’Connell’s strategies, and it’s where the consequences of failure are most visible.
Both regulators and plaintiff attorneys evaluate fleets holistically, not on the merits of a single event. When records are organized, accessible, and comprehensive, it fundamentally shifts the dynamic of any legal or regulatory engagement.
“What better way to demonstrate, not only to a regulatory official, but also a plaintiff attorney, that you have everything wrapped up pretty tight?” O’Connell asked. “It’s great to be able to demonstrate that your records are easily accessible and easily produced for any regulatory agency or a plaintiff attorney. That immediately changes the tone of the whole conversation.”
The inverse is equally true. When records are disorganized, incomplete, or difficult to produce under pressure, it invites deeper scrutiny and raises the risk of any enforcement action or lawsuit.
“If it’s not written down or you can’t produce it, it doesn’t exist,” O’Connell tells clients.
Spoliation, the obligation to preserve records once litigation is reasonably anticipated, is a practical example of why record-keeping discipline can’t be built after the fact.
“If you are going to get into litigation or you believe that you could be getting into litigation based upon an incident, you have a legal responsibility to start gathering all of those records and to not destroy any of those records,” O’Connell said.
Build the system before you need it
If there is any single change in thinking that would make the biggest difference for fleet leaders, O’Connell says, it’s a change in posture.
“The safest, most resilient fleets that I’ve come across in my thirty-seven year career don’t react to enforcement,” O’Connell said. “They build defensible systems right into their operations all the time so that when somebody comes knocking, whether that be an enforcement official, whether that be a plaintiff attorney, they’re ready to go.”
That readiness, he argues, is also a competitive advantage.
“You can’t control a lot of the things that are going on in your fleet on the road every single day, but you can control the systems that you have there.”
The time to build those systems is before they’re tested, not during a crisis.
“You don’t want on-the-job training when it comes to this kind of stuff,” he said. “Make sure that your systems are already up to speed and you’re ready to go before something happens.”
To learn more about J.J. Keller & Associates, click here.
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