The insurance checklist

Who this is for

• Landowners hiring machinery onto their property for the first time
• Anyone whose work is near a structure, a boundary, or a buried service
• People who have been sent a certificate and do not know what to look at

The short answer

Four things are worth confirming: general liability that covers the activity being performed, workers’ compensation if anyone other than the owner is on site, cover for the equipment and any vehicles operating on your land, and current dates spanning your work window.

Read the certificate rather than accepting a description of it. The three fields that matter most are the named insured, the policy period, and the description of operations.

Exclusions are where the surprises live. Policies covering landscaping sometimes exclude tree work; policies covering excavation sometimes exclude underground damage. The activity you are buying has to be inside the cover.

Where the value at risk is meaningful, confirm the policy with the agent named on the certificate rather than relying on the document alone.

What changes the answer

• Whether work happens near structures, vehicles, or a boundary
• Whether buried services cross the working area
• Whether the contractor has employees or works alone
• Whether a lender, insurer, or authority requires evidence
• The replacement value of what could realistically be damaged

What each type of cover is for

These protect against different events, and having one does not imply having another.

How to read a certificate in two minutes

You are looking for four things, in this order, and none of them require insurance expertise.

• Named insured: does it match the legal name of the business you are contracting with, not a trading name that differs?
• Policy period: does the window include your work dates, including any likely overrun?
• Description of operations: does it describe the activity you are buying, or something adjacent to it?
• Limits: are they proportionate to what could realistically be damaged on your property?
• Certificate holder: ideally you, which means it was issued for this job rather than recycled.

The exclusions worth asking about directly

A policy can be genuine, current, and still not cover the thing that goes wrong.

Tree work is frequently excluded or separately rated on general liability policies written for landscaping, because felling near structures is a higher-severity activity. If your job involves stems near a building, ask specifically.

Underground damage is often carved out of policies that otherwise cover excavation, which matters because striking a buried service is among the more expensive things that happens on clearing sites. Ask whether damage to underground facilities is covered and what conditions apply — usually a documented locate request.

Damage to the property being worked on is sometimes treated differently from damage to adjacent property. Since the whole job happens on your land, this distinction is not academic.

What to do when the contractor is a sole operator

A large share of clearing work is done by owner-operators, and the checklist adapts rather than disappearing.

Workers’ compensation may genuinely not apply where there are no employees, and some states allow owners to exempt themselves. That is legitimate, and it means an injury to that person is not covered by a policy — which is a risk you should be aware you are accepting.

General liability still matters and should still exist. Equipment cover is their business rather than yours, though a contractor whose machine is uninsured may simply stop mid-project if it fails, which is your problem in a different form.

What to do with the certificate once you have it

Obtaining the document is half the exercise. The other half is keeping it usable.

Save a copy with the date you received it, alongside the written scope. If something is damaged months later, the two documents together establish who was working, under what agreement, with what cover in force — and reconstructing that from memory and a text thread is unpleasant.

Note the policy expiry date against your work window. Jobs slip, and a policy that covered the original dates may not cover the rescheduled ones. A one-line diary note is enough.

If the contractor is working across a boundary, near a shared drive, or in any situation where a third party could be affected, keep the certificate accessible rather than filed. That is the situation in which somebody will ask for it quickly.

What drives the cost

Common mistakes

• Accepting a verbal assurance that everything is covered
• Not checking that the policy period spans the work
• Assuming general liability includes tree work near buildings
• Assuming excavation cover includes striking a buried service
• Not asking who is covered when a subcontractor turns up instead

Questions to ask a contractor

• Can you have a certificate issued naming me as the holder?
• Does the general liability cover tree work near a structure?
• Is damage to underground facilities covered, and on what conditions?
• Will any part of this be subcontracted, and who covers that crew?

What to do next

1. Request a certificate from every bidder before comparing prices
2. Check the named insured, the dates, and the described operations
3. Ask directly about tree work and underground exclusions if they apply to you
4. Confirm with the issuing agent where the value at risk justifies it

Questions people actually ask