Strong Springs Start with Winter Training: Best Practices from Wilson360 Office Hours

Winter shifts the pace of work, but it also gives teams the space to grow. For landscaping companies, it’s one of the most valuable seasons to sharpen skills, reinforce expectations, and build momentum for spring.

During a recent Wilson360 Office Hours Session, landscape leaders from across the country shared what’s working in their winter training programs, what hasn’t, and how to better prepare teams for the upcoming season. The conversation was full of practical, field-tested ideas — here are the highlights.

Begin by Identifying What Really Needs Training

Many companies default to the same “spring rodeo” every year. Mower safety. Pruning basics. Trailer backing. etc. But the group emphasized the importance of looking back before training forward.

Ask:

• Where did quality slip last year?
• What safety issues repeated?
• Where did margins suffer?
• What did account managers spend time fixing?

Winter is the perfect time to address those gaps rather than just repeating routine topics.

Short, Consistent Training Beats Occasional Long Sessions

One of the strongest themes in the discussion: Frequency matters more than duration. Short, predictable sessions help teams retain skills and build confidence.

What’s working well:

• Weekly 15-minute Monday huddles
• Daily quick refreshers before tasks
• Short seasonal “refresh weeks” before major service transitions

Teams engage better with shorter, focused, and predictable content. And leaders reinforced that a simple mindset shift helps: call it a huddle, not a meeting.

Use Your Winter Training to Strengthen Culture

A training program works best when it’s part of the company’s culture, not a seasonal event. Several leaders shared approaches that increase  buy-in: 

• Train-the-trainer models, where team members demonstrate the skill back to the trainer
• New crew leader mentorship pairings with seasoned veterans
• Peer-led demonstrations using highly skilled long-term employees
• Lunch-and-learn style gatherings supported by local equipment dealers

Winter downtime is also a great chance to reinforce expectations around consistency, safety, and efficiency.

Make Training Engaging: Gamify It

Energy matters. When training feels fun, teams participate more and remember more.

One company shared a creative approach: a fully gamified winter rodeo.

• Branches were split into teams with local sports identities
• Events focused on core skills like pruning, planting accuracy, equipment operation, and trailer backing
• Champions were selected at random to ensure everyone was  prepared

The result? High engagement, great energy, and far better retention. Sometimes the difference between training that sticks and training that drags on is as simple as fun.

Leverage Video…and Don’t Overthink It

Short clips of your own crews performing your standards are often the most effective training tools. 

Leaders emphasized:

• Videos don’t need to be perfect
• Feature actual team members
• Shoot quickly with phones and save clips for future refreshers
• Should be saved and improved over time
• Add subtitles or use simple tools like Loom or Scribe for clarity

Authenticity matters more than production value. The goal is accessibility, not perfection.

Soft Skills Matter Just as Much

Technical skills keep the work moving. Soft skills keep customers coming back.

Leaders highlighted the value of winter training focused on:

• How to speak with customers
• How to handle complaints
• How to “read the room”
• How to communicate respectfully 
• How crew leaders should offer constructive feedback

Many field employees feel less confident with customer interactions. Winter is the ideal time to role-play those conversations and build confidence.

Don’t Forget: Bilingual Training Improves Retention

Training lands best when everyone fully understands it.

• Entirely in Spanish when needed
• In separate sessions for English and Spanish speakers
• Without constantly stopping to translate

It requires more planning, but the results show up in performance, confidence, and retention.

Final Thought: Training Isn’t a Cost — It’s an investment!

Every leader in the conversation agreed on one thing: Winter training drives performance; you can’t afford not to train.

Companies that invest in their people now see it reflected in:

• Quality
• Customer satisfaction
• Safety
• Equipment life
• Margin erosion

Winter training is not downtime; it’s preparation time. Your spring performance will show who used it well.

Stronger crews start with structured training. Visit www.wilson-360.com for coaching, tools, and support that help landscaping teams hit spring with confidence and consistency.

About the author: Brian Brueggemann, with a BS in Landscape Horticulture from SIU-Carbondale, formerly directed landscape operations at Focal Pointe Outdoor Solutions. Now an Operations Consultant at Wilson360, he excels in enhancing productivity and service quality within the green industry. Connect with Brian at [email protected].