Trucking fleets that wait until a lawsuit is filed to prepare safety directors for depositions have already missed the point at which the record stops being fixable, and Trucksafe Consulting is selling a rehearsal. The DOT compliance consultancy will hold its fifth annual Fleet Compliance Bootcamp Sept. 16-17, 2026, at the Crowne Plaza Indianapolis-Downtown-Union Station, adding a half-day Live Deposition Simulation and Rule 30(b)(6) Preparation Seminar on Sept. 18, according to FreightWaves.
Live Deposition Simulation Takes the Stand
Attendees will watch a realistic deposition of a fleet safety director in a serious highway-accident case, with plaintiff and defense attorneys demonstrating the questioning strategies, document issues and credibility challenges they use in live cases, FreightWaves reported. A panel discussion afterward will examine how testimony and company records affect liability exposure and settlement value.
The half-day exercise seats a plaintiff's attorney, a defense attorney and a safety director around an invented fact pattern and lets the questioning run, according to FreightWaves. Trucksafe president and founder Brandon Wiseman explained the rationale: "We thought it would be interesting to spend a half day of just kind of simulating those with a plaintiff’s attorney, a defense attorney, sitting there, a safety director, kind of going through a fact pattern for a made-up case and seeing where those traps are and how best to navigate them."
Why Deposition Preparation Is a Liability Issue
The exposure is retroactive, and it reaches documents nobody wrote expecting an audience, according to the article. "Today, a compliance failure rarely stays confined to an enforcement proceeding," Wiseman said. "After a serious accident, attorneys will scrutinize years of driver files, maintenance records, safety data, policies, emails and management decisions."
The traps are not intuitive, Wiseman told FreightWaves:
"The manner in which the plaintiff’s attorneys are asking the questions, the things that they’re really digging into, a lot of that isn’t all that intuitive. And so if you’re not prepared for that, if you don’t take the time to understand their games that they play and the things that they try and hang you on, then you can really find yourself in a bad place in those types of depositions."
Settlement Data Shows Documentation's Dollar Impact
Settlement value is where documentation quality stops being an abstraction and becomes a number. Research released by the American Transportation Research Institute in December 2025 found that settlements came in below verdicts once awards reached $5 million or more; below $1 million, verdicts came in under settlements. The largest half of awards grew at an average of 5.7% a year across the six years of cases studied, per the ATRI research cited by FreightWaves.
| Award level | Outcome |
|---|---|
| $5 million or more | Settlements below verdicts |
| Below $1 million | Verdicts below settlements |
| Largest half of awards | Average annual growth 5.7% |
Bootcamp Curriculum Targets Compliance Gaps
Wiseman founded Trucksafe five years ago alongside Childress Law, the transportation firm where he practices, according to FreightWaves. The gap he saw was informational: fleet safety professionals, risk advisors and insurance people had almost nothing to work from on DOT regulations, or on the risk that thin compliance creates.
The bootcamp came out of that, a 2½-day format that covers two full days of training across:
- Driver qualification
- Hours-of-service management
- Drug and alcohol testing
- Fleet maintenance
- Driver-facing policies
- CSA scores
- DOT enforcement and audit preparedness
- Insurance and litigation exposure
That list has barely moved in five years, but what changed is what the plaintiff's bar can do with it, the article noted. For fleet safety directors, risk advisors and insurance professionals, deposition preparation cannot wait until the lawsuit arrives, because by then the record is already locked in.
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