Boland said she's the most conservative in terms of launching projects, but generally, the three make decisions by consensus. That's more important than ever in this era of margin pressure and industry disruption. Investment decisions involving brick and mortar, in particular, are increasingly risky. Boland noted the fate of Barnes & Noble — rapidly expanding until it was eclipsed by Amazon's online model.
Smith is optimistic about the market for now: People are still going to buy cars for the foreseeable future. And he trusts his daughters to make the right decisions.
"I found that 90 percent of the time that I disagree with my daughters, they're right and I'm wrong," Smith said. "All I had to do was to get out of the way."
Cobb, from Presidio Group, said communication — or lack thereof — is where a succession usually breaks down. Parents often fail to talk through future roles with their children.
"They're usually told what's going to happen, if they are told at all ahead of time," he said.
"There could be a surprise and a disagreement from the beginning, and potentially lead to some next-generation dysfunction."
Succession planning is often postponed until the last minute, partly because successful entrepreneurs are often focused almost exclusively on building their enterprises, not pulling back from them. Nonetheless, Cobb offered a ray of hope. "There are many success stories of multigeneration families who've grown the business over time."
One reason succession has become more difficult is because the auto retailing business is getting harder.
Roberts, with Rawls Group, said it's tougher to make a profit and dealers have to be more on their game than ever. Still, it remains attractive despite the headwinds.
While it's early for the Smiths to talk about a fifth generation, there are candidates.
Andrews has two young children who won't be ready for the showroom floor for some years, but Boland has three boys who aren't that far off. The oldest is 16.
"Once he has his driver's license, he'll be coming to work, like next summer," Boland said.
But whether he makes a career of it will depend on what's the right fit for him — and for the business.
"My hope is he'll go to college, kind of experience things and decide. Because I kind of feel like my parents did this for me," Boland said. "They didn't make me stay local; they didn't make me feel like I had to do this. So I think it's important for the kids to forge their own path and decide what they want."