As trucking leaders age, many aren’t prepared to retire or sell, even when they can see it’s time to pass the reins to the next generation.

My magic moment came when we renovated our head office. It was my job to buy the office furniture. Instead of shopping online I spent weeks touring every showroom in town with no luck finding modern-looking desks large enough to store all our paper files.

I was expressing my frustration to our team of millennials when a young stagger piped up to set the record straight: “We don’t need desks with storage. You’re the only one in the company who prints anything. We store everything on the G drive in the cloud.”

My response: “What’s a G drive?”

It was a clear sign that I was slowing our young energetic team down. We needed to transition the day-to-day leadership at Left Lane Associates. Here’s what I learned during the process:

The signs

After the furniture debacle there were other indications that it was time to step aside.

During our post-pandemic planning I was reluctant to agree to a hybrid work model. Why did we spend all this money on renovations if people were going to work from home half the time? Still don’t understand how anyone can be productive (and have fun) working from the kitchen table. Yet the company thrived. Apparently, you can be very productive.

Next was the phone system. What do you mean we don’t need a receptionist or a phone on every desk? I was politely told my cell phone was now my office phone, and that our business manager wanted to subcontract all of our administrative functions to a third party.

The coup de grace came when I was told that oh, by the way, we’re switching from Outlook to Google Chrome… Here’s another password to remember.

Reluctant to change

Old farts like me get set in their ways. What looks inefficient to the younger set (and probably is) works for me. Why change?

Case in point: the company has a high-end CRM to manage the sales funnel. My CRM is in my head. No chance a computer is telling me how to manage my customers every day.

And here’s the problem. When the entire company is working one way and you’re doing it your way, there’s a disconnect that many would consider bad leadership. It’s impossible to be an effective leader when you have a “do what I say, not what I do” mentality.

Sort of gone

For trucking owners who don’t want to run the business but still want to keep working there are options. My solution was to set up a board of directors that would allow me to stay involved as the owner while bringing in valuable outside expertise to help grow the company.

My new role relieves me of the day-to-day grind while letting me do the things I love: strategize, mentor, and make money. I do insist every board meeting be done in person. Zoom calls are nauseating.

The next leader

The million-dollar question is who takes over? We’re fortunate at Left Lane. We were only five years old when we started our transition and I had a bright young partner who is more capable of leading the company into the future than I am. Something about relating to people his age. 

The transition wasn’t forced. We worked together and took things slowly. To start, where possible, we shifted relationships at our suppliers from my old cronies to my partner’s professional network.

Next, I bowed out of our daily deal briefings and weekly strategy meetings. Eventually, I don’t think they noticed I was gone, which makes me feel pretty satisfied.

No doubt succession planning gets super complicated when you have a family business. It’s a whole different animal when it impacts the Christmas dinner table.

Speaking of family business, my son Patrick noticed I was getting restless without a job to go to every morning and conned me to into getting back into the freight-chasing business. Together we started Rite Route Supply Chain Solutions. Promised him our new family business will handle Succession a lot better than the Roy family. When the time comes!