If you want to start your season off on the right foot next year, conducting strategic planning is fundamental practice you need to master.
“I think for those who are not sure about investing the time, you really have to ask yourself, ‘Where do you want to be in 10 years?’” says Justin White, owner of K&D Landscaping, Inc., based in Watsonville, California. “In 10 years, if you want to grow your company by 3x, 5x, 10x, 20x, there’s really no other way to get there unless you’re going to invest the time in strategic planning.
Bryan Christiansen, CEO of Mariani Premier Group, based in Lake Bluff, Illinois, adds that strategic planning is a continuous process.
“Throughout the year, we review our results on a monthly basis and adjust our current year plans accordingly to ensure we hit our budget goals,” Christiansen says. “We then embed our ongoing learnings to be applied to next year’s plan.”
Structuring Strategic Planning Meetings
How often you meet to discuss strategic planning will vary. K&D Landscaping has 90-day planning sessions, but at the very least, you should hold a strategic planning session near the end of the year.
For Mariani Premier Group, their planning process starts in earnest in September. The leadership team will meet to debrief on their progress against goals and outline preliminary objectives for next year.
“We hold an annual top leadership summit typically in September as well as weekly Executive Leadership Team meetings,” Christiansen says. “We also hold monthly financial and operational reviews with the family companies and periodic visits or regional meetings to focus on operational progress and best practice sharing.”
Once they’ve firmed up their goals, they will outline their financial and operating plans by December, allowing them to hit the ground running in January.
Ashly Paladino, COO of Sun Valley Landscaping, based in Omaha, Nebraska, says as EOS users, they have a structured annual planning process in the 4th quarter that includes reviewing and updating their vision traction organizer as well as their 10-year, 3-year and one-year goals. She says this meeting is held off-site and not in their city.
“This gives us a chance to focus on planning by getting out of the day-to-day grind,” Paladino says. “We can reconnect and focus on the bigger picture.”
Similarly, Andrew McCurry, owner of Father Nature Landscapes, based in Birmingham, Alabama, holds an off-site corporate meeting at the end of the year with their department heads, key decision makers, designers and project managers.
“For over 15 years, we have rented a large off-site house on a lake and have made this a multi-day event and have really tried to make this an event that the team looks forward to attending,” McCurry says.
The Father Nature team will discuss what worked, what didn’t and how to prevent issues in the future. They also conduct some forecasting and breakout sessions to discuss department-related challenges.
Barry Schneider, president of Surrounds Landscaping, based in Sterling, Virginia, says that at the end of the year, they gather their managers for an annual two-day meeting off-site to review their core values, customer satisfaction, and establish goals for the coming year.
“(We’re) often at a local hotel so we are away from the office but can be home with family at the end of the day so our managers are not sacrificing family time,” Schneider says.
White says they start with a two-day leadership planning retreat in January where they review how they performed against their goals, overall operational efficiency and their technology stack. Then they will have day-long departmental planning sessions off-site where they fine-tune their departmental goals for the upcoming year.
“All of that rolls into a final management team retreat, everybody that’s on the leadership team meeting, everyone that’s in the departmental planning sessions, rolls into a 30-person planning session where we go through and everyone presents their strategic plan to each other,” White says. “We remove the silos through that process and really emphasize team collaboration.”
Gathering Buy-In from Leadership and Employees
It doesn’t matter what initiatives or goals you set in these strategic meetings if you are unsuccessful in generating buy-in at the leadership level and the rest of your team. One method to ensure buy-in is to involve them in the planning process.
“I advise to involve as many of the leadership team as possible to get buy in and allow them to have a voice in part of the planning and execution of this corporate event,” McCurry says.
Christiansen agrees they’ve seen the best results by empowering their local company leaders and their leadership teams to own their goals and results.
Another way to generate buy-in is to select goals related to employee feedback.
“If you’re not listening to your regionals, and what they’re hearing from their team members, their district managers or branch managers, you’re doing yourself an injustice because they know their ear to the ground,” says Joe Chiellini, VP of Florida for Yardnique and founder of ASI Landscape Management, based in Tampa, Florida. “They know what’s going on in the field, so we literally listen to them. Our COO Jeff will do one-on-ones with the regionals, and that’s an opportunity for them to get some feedback on what’s going on.”
Paladino says they will conduct Crew Leader Forum meetings where the CEO and she discuss and gather feedback from their frontline teams.
“It’s also an opportunity for us to reiterate some of the goals we are focused on and give the crew leads more face time with top leadership,” Paladino says.
Schneider notes it’s best to get commitment from the managers as they are the ones whose job it is to coach the frontline teams on why the company chose certain strategies.
“We also reinforce our goals during presentations at our quarterly state of the company meeting where the entire team gets together,” Schneider says.
Communicating Next Year’s Goals
How you go about communicating your new goals to the team also makes a huge difference in how they are received by your staff.
Larger companies spread across the country like Mariani and Yardnqiue opt for a multi-channel approach, including meetings and newsletters. Mariani holds monthly meetings with their founders and company presidents as they rely on them to help disseminate information.
“We have also built a company-wide intranet and an internal newsletter called ‘The Premier Post’ where we share our goals, initiatives and progress,” Christiansen says.
Others like White, Paladino and McCurry all use their company kick-off days to share their direction for the new year. For McCurry, it’s their Vision Day.
“It is the day that we set aside on the first day back to the new year with our entire team to discuss wins, losses, vision & focus,” McCurry says. “This is after we provide a catered breakfast at our headquarters.”
Sun Valley hosts their first Scaling Up meeting in January or early February where they inform leadership, management, sales, and key office personnel.
“For the rest of the company, we do an annual company-wide Spring Extravaganza Meeting in April, which is where this information flows the rest of our team,” Paladino says. “Divisional meetings are also focusing in on the specific goals that affect their business lines.”
Similarly, at K&D’s ‘Raise the Bar’ spring kickoff event, they do a series of activities, games and competitions, as well as share their goals for the new year.
“We ensure that everybody knows exactly what the plan is going forward,” White says. “On top of that, we do a monthly internal newsletter where we share very detailed information about our strategic plan, about our initiatives, about our goals.”
White adds that in all of their meetings, they review the goals on a regular basis.
“It’s not just communicating them once, it’s communicating them every week, every month, for the entire year,” White says. “Otherwise, they’re just going to die on the vine.”
Key Takeaways
- Strategic planning is a time investment that can set your company up for long-term success.
- Off-site retreats create focus and alignment. Holding multi-day, off-site planning meetings with your leadership team allows them to step away from daily distractions and work on long-term vision.
- Engaging managers, regional leaders, and frontline staff in the planning process helps ensure alignment and ownership of goals.
- From kickoff events and company-wide meetings to company newsletters, goals should be reinforced repeatedly throughout the year.

