Don Osterberg: Why Risk Leadership Is Essential in Risk Management

By Mary Gerard

In this week’s blog, we get to know Don Osterberg, who will be one of our featured speakers at Fleet Success Summit 2023. Don recently appeared on our podcast, “The Fleet Success Show.” He blew us away with his Risk Management insight, and for being just an overall good guy! In fact, years ago when our co-host Jeff Jenkins first started at Schneider National, a co-worker pointed out Don to him. She said, “See that guy right there, Don? He’s the best boss I’ve ever had.” Why? Because he put the person first when he managed. Don married culture and safety throughout his career – which you’ll get a glimpse of below and in the full episode of the podcast.

After a long career in the Army, Don Osterberg transitioned into transportation when he took a job as a Chief Operating Officer at a distribution center in Atlanta.

It was a bumpy start.

“On my very first day on the job we got a debrief from a (Department of Transportation) audit, and they didn’t get a conditional rating – they got an unsatisfactory rating,” Don said on “The Fleet Success Show” podcast. “It was my job to really crash the FMCSA regulations and learn everything there was in trucking regulations.”

He was new to the industry, but he immediately had to jump head-first into safety regulations and get the operation up to a passing grade.

“I should have walked right back out probably, but I accepted the challenge,” Don said. “And we did pass the reaudit, by the way.”

From there, Don’s career took on a new focus – safety.

In addition to taking a role as a Senior Vice President at Schneider National, Don served on numerous boards, including on the Board of Delegates for the National Safety Council, a member of the FMCSA’s Motor Carrier Safety Advisory Committee, chairman of the American Trucking Association’s Safety Policy Committee, vice chairman of the ATA Safety Taskforce, and numerous other boards.

His experiences have led him to become an expert in both Risk Management and leadership. He will speak on these topics at the Fleet Success Summit, March 21-22, in Las Vegas, where he will give a session on “Mitigating Risk Through Effective Leadership.”

“I am going to look at Risk Management through the lens of leadership. There are a lot of people that use the phrase Risk Management. I use the phrase Risk Leadership.”

Don feels that making necessary changes to improve safety requires leadership. He also makes a case for change. He feels that fleet operations need to adopt new tactics and strategies to better mitigate risk.

In his presentation, Don will also talk about the importance of culture. He’s learned that trying to improve safety and limit risk will be limited without the right culture in place.

Jeff, a former trucking executive, agreed with Don’s insights about culture on the podcast.

“You’ve got to have that culture vs your active values,” Jeff said. “A lot of people, until there is a catastrophic safety event, they preach safety and risk management, but they don’t actually live by those words.”

Don agreed. He said he’s been to numerous operations that have safety goals and priorities displayed around the company, but when it came down to it – they were just words.

“Make sure you’re walking your talk,” Don said.

After he retired, Don consulted a few fleet operations and performed assessments.

“I went to where the drivers were and I would talk to the drivers and give them scenarios,” Don said. “The drivers would tell me what the real culture of the organization is.”

Drivers would reveal to Don that even though the organization preached safety first, the drivers knew if they ever pulled off the road with a service-sensitive load because they were too tired to drive, they would be in trouble. Even though they told the drivers to be careful, at the end of the day, they didn’t prioritize safety.

“Safety has to be a core value,” Don said. “Priorities change within an organization – they are situational. Core values essentially don’t change.”

Part of this requires empowering drivers to be safe.

“We have to constantly remind drivers to be disciplined enough to do what they know is right,” Don said.

This can require standing up to their boss or other leadership, which can be extremely difficult. However, Don says that no matter your role, you must have the courage to do the right thing.

“We can’t let ourselves off the hook just because we’re not the decision maker.”

To hear Don’s full interview, listen to the “The Fleet Success Show.” If you want to see Don in person and hear his presentation on “Mitigating Risk Through Effective Leadership,” sign up today to join us at Fleet Success Summit 2023.