All photos courtesy of Cherrylake

When Jim Lieffort asked his employees to rank their experience at Cherrylake on a scale of 1-10, he didn’t expect anyone to answer with a “1.” But that’s exactly what one disgruntled employee did — he even told Lieffort that he would’ve responded with a “0” if that was an option.

Cherrylake, an Orlando-based company with tree farm, landscape construction and landscape maintenance divisions, had long followed the Net Promoter Score system. Any client who says they’re 8-10 likely to recommend Cherrylake to a friend is tagged as a “promoter.” Anybody with a 6 or below is a “detractor.” Many companies use NPS to determine the satisfaction levels of their clients.

But Lieffort, the director of landscape maintenance, wanted to take a data-driven look at the satisfaction levels of his employees, too. He asked them, “How likely are you to recommend Cherrylake as a place to work?” So when one employee rated the company so low, Lieffort’s initial response was incredulous.

“I’m like, ‘A one?’ A one is unacceptable for me,” he says. “(If) this guy is totally disengaged in our work, then we have a big problem.”

As it turns out, sitting down with the employee to outline a clear path to a promotion was the key. The employee had been burned by previous jobs that overpromised a career and underdelivered. Lieffort and his leadership team assured the employee of his skills — he had plenty to offer some of the younger guys on staff who could learn a thing or two from a seasoned pro. The employee now runs an enhancement crew.

“Now this guy would probably give us a 15,” Lieffort says.

This focus on building a leadership culture has long been the backbone at Cherrylake, a company that Lieffort says is rapidly growing. The company's maintenance division earned roughly $3.2 million in 2020 and currently employs 75 people, which Lieffort attributes to a strong core executive team.

“It starts with the whole management team that has a tremendous level of trust and open, honest communication,” he says. “I think it really starts with our executive group.”

Role models

There are at least two Google group chats the maintenance division frequently uses at Cherrylake: one where they offer critiques of everybody’s work out in the field and another where they constantly share leadership and inspirational videos.

In the educational group chat, they’ll share videos that explain the company’s core values or principles they apply like the Lean business model. The thought process is that exposing the employees to some of these ideas early could help them develop entrepreneurial mindsets. With that comes an added level of responsibility to the company — Lieffort says people get promoted quickly when they show their job isn’t just earning a paycheck. If the company belonged to them, and the equipment, and the customers, how would they approach their job differently?

Lieffort says he sits in on as many hirings as he can, including entry-level labor positions, because he wants to find employees who embody that thought process. He’ll outline the company’s promote-from-within strategy and emphasize that he wants them engaged with Cherrylake’s vision. They’re not going to go out and advertise for open leadership positions until they’ve already looked at promoting from within first.

He wants everyone to hone in on leadership skills as they work their way up the team’s career ladder. Even if they leave Cherrylake later, Lieffort takes pride in sculpting them into better human beings first. “The core philosophy for me is, we need to provide these (employees) with good role models, good leadership and not just to be good workers,” Lieffort says. “We don’t ever talk about good workers. We want to make you better men or better women.”

Cherrylake asks employees to train their replacements.

Time to rise

Lieffort admits that at times, they’ve promoted people who just weren’t ready. Lieffort says they’ll simply slide the employee back into their previous position and let them continue to refine their skillset.

“For the most part, the guys who feel they’re ready are ready,” Lieffort says.

That’s in large part because all Cherrylake employees are asked to focus on training their replacements. Lieffort says his employees aren’t afraid to do that because there’s so frequently upward mobility at the company. The catch is often that promoting from within creates a problem — who’s going to do the soon-to-be vacant job?

“I’ve been in leadership a long time, and I tell guys, when you come to someone like myself and you say, ‘I want this job,’ what is my problem?” Lieffort says. “My problem is, who’s going to do your job? So that’s where ‘always propose a solution’ comes in.”

This solutions-based mindset trickles down to regular work conflicts, too. Lieffort prefers employees have an idea in mind to remedy workplace problems before they even set foot in his office. Sure, Lieffort has final say over how a problem is handled, but often times, the fix is already known.

“If you come (with a problem), the first thing I’m going to ask you is, ‘What do you think we should do?’” he says. “It’s about empowerment, mentoring caring.

So, when it comes down to replacing the talent that’s missing when an employee gets promoted, Lieffort says much of the responsibility comes down to how the employee who wants a promotion trained their replacements. They should have a good idea of who will take the position once they get promoted, and there should have been training already done so the transition is relatively seamless.

Lieffort, of course, also advises the training of employees. By and large, he wants the training to be a bit more organic, coming from the employees rather than the executive team. That doesn’t mean he doesn’t have some ideas on where the next team leaders will come from along the way, though.

“We basically go through a constant evaluation,” he says. “We’re looking at our entire roster and saying, ‘Okay, who’s the next man up?’”

Cherrylake created three remote deployment locations to cut down on commutes.

Building some trust

Traffic can be tricky to navigate as Orlando is such a natural tourist attraction (Disney World drivers have to go somewhere!).

So, they established three remote deployment locations so employees no longer had to drive in to headquarters first before hitting their assignments out in the field. This benefits the employees because they’re able to leave home later and get home sooner, but it also benefits the company so they’re not paying out so much transportation time.

“We’re paying a guy to drive 30 minutes in Orlando traffic,” Lieffort says. “That could be spent on the job.”

Of course, that comes with a good deal of trust in his employees since he isn’t personally seeing them off to their jobsites. But the trust isn’t unwarranted: So far, Lieffort hasn’t had any issues with employees not showing up to their assigned spots.

Their entrepreneurial mindsets have coincided with a much smaller need to micromanage.

Besides, if there were issues with slacking or failing to do work, Lieffort believes he’d find out.

“You can get away with a lot for a while,” he admits, “but eventually, with open and honest communication…it’ll come out.”