Fleet safety directors spend years building compliance programs that nobody ever asks them to defend out loud, and when someone finally does, it is a plaintiff's attorney with a court reporter in the room. Trucksafe Consulting is selling the 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, and this year's program adds a half-day Live Deposition Simulation and Rule 30(b)(6) Preparation Seminar on Sept. 18.
Trucking deposition preparation usually begins after a lawsuit is filed, which is also the point at which the record stops being fixable. Attendees will watch a realistic deposition of a fleet safety director in a serious highway-accident case. Plaintiff and defense attorneys will demonstrate the questioning strategies, document issues and credibility challenges they use in live cases.
A panel discussion afterward will examine how testimony and company records affect liability exposure and settlement value. "Today, a compliance failure rarely stays confined to an enforcement proceeding," said Brandon Wiseman, president and founder of Trucksafe Consulting. "After a serious accident, attorneys will scrutinize years of driver files, maintenance records, safety data, policies, emails and management decisions." The exposure is retroactive, and it reaches documents nobody wrote expecting an audience.
Corporate representatives walk into those depositions ready to talk about the compliance program, and then the damage comes from the shape of the questioning. "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," Wiseman said in an interview with FreightWaves. "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." 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.
"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," Wiseman said. Settlement value is where documentation quality stops being an abstraction and becomes a number. Research the American Transportation Research Institute released 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, the ones that do the real damage, grew at an average of 5.7% a year across the six years of cases studied. Wiseman founded Trucksafe five years ago alongside Childress Law, the transportation firm where he practices, and the gap he saw was informational.
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