How to Evaluate Your Insurance Coverage with a Seasonal Insurance Review

No One Sees the Storm Coming, Until It's Too Late

Jake had been running his landscaping company for over a decade. He wasn’t new to the game. Every spring, his phone lit up with new projects, retaining walls, sod installs, irrigation setups, high-end backyard renovations. The big jobs. His crews were sharp, his gear was loaded, and the schedule was full.

But what he didn’t expect that March was the freak windstorm. Two trailers, a skid steer, and several grand in damaged tools, all gone in a single afternoon. When he called his insurance agent, he assumed he’d be covered. He wasn’t.

That’s the kind of mistake no business owner wants to make. And it’s exactly why a seasonal insurance review should be part of your spring, summer, and fall routines, right up there with oil changes and blade sharpening.

As the seasons shift, so does your risk. More crews, more gear, different jobs. What made sense on paper in January might leave you wide open by July. And if something goes sideways, hailstorm, theft, an accident with a borrowed truck, you don’t want to find out after the fact that you were underinsured or misclassified.

This post breaks down what to check and why it matters, especially for landscaping companies like yours who handle more than just mow-and-go work. Think of it as a quick gut check before the next job starts. You’ve already got enough on your plate, your insurance shouldn’t be another guessing game.

Why a Seasonal Insurance Review Isn’t Just About Weather

Most landscaping business owners think about coverage when a storm rolls in or equipment gets stolen, but that’s just the tip of the iceberg. A seasonal insurance review goes deeper than the weather report. It’s about how your business changes with the season, and whether your insurance is keeping up with you.

Think about it: in the winter, maybe you’re trimming trees, clearing snow, or doing design consults. Come spring, the trucks are back on the road, crews are running full throttle, and equipment is out at multiple job sites. Your operation looks completely different, and so do your risks.

Here’s where most policies fall short:

• Staffing shifts: You bring on seasonal help or ramp up subcontractors, but your policy may not automatically reflect that increase in headcount or liability.
• Equipment movement: You’re rotating gear in and out, moving trailers between sites, maybe even renting heavy equipment short-term. Each change creates new exposure if it’s not already in your policy.
• Job complexity: Spring and summer often bring the big-ticket jobs, retaining walls, drainage work, hardscaping. These require different liability considerations than mowing or maintenance.
  
  

The problem is, insurance policies aren’t dynamic. They don’t flex with your schedule unless you tell them to. And if you haven’t reviewed things since you renewed last year, you might be gambling with outdated limits or exclusions that don’t match what you’re doing now.

That’s why a seasonal insurance review isn’t just smart, it’s necessary. It gives you a moment to step back and say, “What’s changed?” before a claim ever forces you to ask that question the hard way.

Equipment and Vehicle Coverage, What Gets Missed Most

Ask any landscaping company where the money is, and they'll point to the gear. Trucks, trailers, loaders, trenchers, saws, it all adds up fast. You already know that. But what often gets missed is how quickly that coverage can fall behind when the season ramps up.

You buy a new enclosed trailer in March. Rent a skid steer in May. Move your dump trailer to a satellite crew in June. Did all of that get reported to your insurance company? If the answer is “probably,” that’s not good enough.

A seasonal insurance review forces you to hit pause and check:

• Is every vehicle titled to the business listed on the policy?
• Are your new attachments and implements covered?
• Are rentals protected or excluded?
• If a trailer gets stolen off-site, will you be made whole, or stuck eating the loss?
  
  

A lot of business owners assume “covered is covered.” But policies often split coverage between what's owned, what's rented, and what's permanently attached. And if it’s not specifically listed, it might not be included at all. Even something as basic as transporting gear between job sites can trigger gaps, especially if employees are using their personal trucks or you’re working across county or state lines.

Another thing worth checking during your seasonal insurance review: Are your current limits still realistic? You might’ve started the year with $75,000 worth of equipment, but now you’re running closer to $125,000. If your limits didn’t keep up, you could be facing a serious shortfall if something goes wrong.

The bottom line? If your equipment moves, your coverage should move with it. A short review at the start of each season helps you stay ahead of surprises, and protects the gear your entire operation depends on.

Liability Moves with the Workload

Liability isn’t static, and neither is your work. As the seasons change, so does the type of job you're doing. Spring might be dominated by hardscaping and irrigation installs. Summer could bring bigger commercial projects or slope grading. And by fall, you’re doing drainage work or last-minute sod before the frost hits.

Here’s the thing: different jobs carry different liability profiles. Just because you’ve got general liability coverage doesn’t mean you’re covered for every kind of work you take on.

A seasonal insurance review helps you catch mismatches before they become expensive. Ask yourself:

• Has the scope of your work expanded? If you’ve started taking on grading or excavation, but your policy still reflects "basic landscaping," that’s a red flag.
• Are you working in new environments? Jobs near public sidewalks, high-traffic areas, or multi-family residences can trigger more liability exposure than residential backyards.
• Are your subcontractors pulling their weight? If you're relying on subs for concrete, irrigation, or design work, their coverage (or lack of it) could end up being your problem if something goes sideways.
  
  

Many landscaping business owners assume their liability policy will “flex” with the workload. It won’t. Your carrier needs to know what kind of work you're doing and where you're doing it. If that hasn't been updated since last renewal, there’s a decent chance you're out of step.

During your seasonal insurance review, it’s smart to look at your liability limits too. What felt like plenty of coverage last year might not be enough for the size of jobs you’re booking now. And if your clients are starting to ask for COIs with higher minimums, that’s a clear signal you’ve outgrown your old policy.

Don’t wait for a lawsuit or denied claim to find out your coverage didn’t keep up with your calendar. One short check-in could keep your business from absorbing a hit it wasn’t built to take.

Subcontractors, Temps, and the Fine Print That Bites Back

When the workload spikes, you do what any smart landscaping company does, you scale. You bring in a few extra hands. Maybe call up a crew you’ve used before. Hire your cousin’s kid for the summer. It’s all part of keeping jobs on track and cash flow moving. But here’s the problem: not everyone who works with you is actually protected by you.

This is where things get murky fast, and where a seasonal insurance review can save you from a major headache.

A few key questions to ask yourself:

• Are your subcontractors really independent? If a claim happens and the insurer determines that your subcontractor is actually functioning more like an employee, it could trigger a coverage dispute, or worse, a denied claim.
• Do you have up-to-date COIs from every subcontractor? And are you actually reading them? You’d be surprised how many have expired, exclude certain types of work, or are missing key endorsements like additional insured status.
• What about seasonal or part-time workers? If they’re not formally added to your policy or you're paying them under the table, you could be exposed on both the liability and workers’ comp fronts.
  
  

Insurance policies tend to treat subcontractors and temp workers very differently than full-time employees. And if you haven’t reviewed the fine print recently, it’s easy to assume everyone on the job site is covered, when in reality, some of them aren’t even on your policy's radar.

That’s why a seasonal insurance review is the perfect time to audit your team setup. Who’s doing the work, how are they classified, and what documentation do you have to back that up if a claim ever comes into play?

It’s not just about protecting your business, it’s about avoiding the kind of paperwork mess that eats up hours you don’t have.

The 30-Minute Habit That Could Save Your Season

You already stay ahead of the weather, the job board, and your crew’s workload, your insurance should be no different. A seasonal insurance review doesn’t need to be complicated or time-consuming. It’s a simple habit that gives you peace of mind before you ramp up for the next busy stretch.

Instead of guessing what’s covered or hoping you’re protected, take thirty minutes to talk it through with someone who knows this world. Landscaping isn’t one-size-fits-all, and your policy shouldn’t be either.

If you want no-BS guidance from someone who actually gets how your business runs, we’re here to help. Start with a quick conversation about your Landscaping Contractor Insurance options and get back to what you do best, running jobs, keeping crews moving, and building a business that lasts.