The Two Documents Every Homeowner Should Ask for Before Hiring a Contractor

After more than 30 years in the tree, landscaping, and construction industries, if there's one piece of advice I could give every homeowner, it's this:

Never hire a contractor until you've verified their insurance.

It amazes me how many homeowners spend weeks choosing colors, materials, comparing estimates, and planning their project, yet never spend five minutes verifying whether the company working on their property is properly insured.

That simple step may be one of the most important decisions you make during your entire project.

A Hard Truth Every Homeowner Needs to Hear

I'm going to say something that may sound blunt, but I believe every homeowner needs to hear it.

If you don't know enough to ask about liability insurance and workers' compensation insurance, then you don't know enough to make a fully informed hiring decision.

That's not meant as an insult.

The reality is that most homeowners have never been taught how to properly hire a contractor. They simply don't know what questions to ask.

That's exactly why Tree413 exists.

Our mission is to educate homeowners so they can make informed decisions, protect themselves, and hire qualified professionals with confidence.

The Two Types of Insurance You Should Ask About

Before anyone begins work on your property, ask about:

General Liability Insurance

This helps protect against covered property damage or other covered losses that may occur during the project.

Workers' Compensation Insurance

If the contractor has employees, workers' compensation insurance is an important protection for work-related injuries.

These are not unusual questions.

They're standard business practice.

Professional contractors hear these questions every day.

Never Accept Insurance Verification at Face Value

This is where many homeowners unknowingly make a mistake.

A contractor hands them a Certificate of Insurance or emails one directly from the contractor's own email address.

Most people assume that's enough.

I don't.

The best practice is to ask the contractor to have their insurance agent or insurance company send a current Certificate of Insurance directly to you.

Why?

Because you're verifying the information with the source.

Insurance policies can expire, be canceled, or change.

Receiving the certificate directly from the insurance company or insurance agent gives you greater confidence that you're looking at current information instead of simply relying on a document provided by someone else.

Never assume. Always verify.

This Is Standard Business Practice

Many homeowners hesitate because they think asking for proof of insurance is awkward.

It isn't.

Insurance agents send Certificates of Insurance every single day.

Professional contractors request them every single day.

This is routine throughout the construction industry.

A professional contractor should have no problem asking their insurance agent to send you a current Certificate of Insurance.

If someone becomes defensive or refuses to do so, that's a reason to slow down, ask more questions, and decide whether you're comfortable moving forward.

Don't Let Discomfort Cost You Thousands

Over the years, I've noticed something that has always surprised me.

Many homeowners don't ask about insurance because they feel uncomfortable.

They don't want to offend the contractor.

They don't want to seem distrustful.

They don't want to make the conversation awkward.

So they say nothing.

I find that incredible.

You're about to invite someone onto your property to operate chainsaws, cranes, excavators, skid steers, loaders, or other potentially dangerous equipment around your home and family.

Yet many homeowners hesitate to ask one simple question:

"Would you please have your insurance company send me a current Certificate of Insurance?"

That question shouldn't feel uncomfortable.

Not asking should feel uncomfortable.

Protecting your home and your financial future is far more important than avoiding a few seconds of awkwardness.

Professional contractors expect informed homeowners to ask professional questions.

Don't let fear or embarrassment stop you from protecting yourself.

The Questions You Ask Matter

Here's something many homeowners never think about.

The questions you ask tell a contractor a lot about you.

When you ask for proof of liability insurance, workers' compensation insurance, and verification directly from the insurance company, you're showing that you're an informed homeowner who takes hiring seriously.

Professional contractors are accustomed to these questions. They know they're part of doing business.

On the other hand, if you never ask about insurance, never verify anything, and simply accept whatever you're told, you're signaling that you may not know what to look for.

Unfortunately, that can make you more vulnerable to poor business practices from less reputable contractors.

Knowledge protects you.

The more informed you are, the better decisions you'll make—and the more likely you'll be treated like an informed customer.

One More Question Most Homeowners Never Think to Ask

Here's something many homeowners don't know.

In some situations, a business owner may legally choose to exempt themselves from workers' compensation coverage.

That means the company may be operating legally, but the owner may not personally be covered by workers' compensation while working on your property.

Most homeowners never think to ask about this.

You should.

Ask this simple question:

"Will the owner of the company be working on my property, and if so, is the owner covered under your workers' compensation policy?"

If the owner is not covered, take time to understand what that means before moving forward.

Personally, if the owner of a company is going to be performing work on my property and is not covered by workers' compensation insurance, I would not move forward until I fully understood the risks and was comfortable with the situation.

Every homeowner deserves to make that decision with complete information—not assumptions.

Accidents Don't Make Appointments

One of the biggest misconceptions homeowners have is:

"It probably won't happen to me."

The truth is, accidents happen every day.

Nobody plans to fall out of a tree.

Nobody expects a chainsaw injury.

Nobody plans for a skid steer to roll over, a ladder to slip, or someone to suffer a serious injury.

If we could predict accidents, they wouldn't be accidents.

That's exactly why insurance exists.

Most people working on residential properties aren't wealthy enough to absorb months of lost income, expensive medical bills, or other financial consequences after a serious injury.

If someone is seriously hurt and cannot work, the financial impact can be enormous.

When there isn't adequate insurance in place, questions about who is financially responsible can become stressful, expensive, and, in some cases, lead to legal claims.

Even if you ultimately aren't responsible, dealing with a claim or lawsuit can take time, money, and energy.

That's why these conversations should happen before work begins—not after an accident.

Insurance isn't about expecting something to go wrong.

It's about being prepared if something does.

Hope for the best. Plan for the unexpected.

Knowledge Is Your Best Protection

You don't have to know how to remove a tree.

You don't have to know how to build a retaining wall.

You don't have to know how to install a patio.

You don't have to know how to pave a driveway or install a fence.

But you should know how to protect yourself before hiring someone to do those things.

The few minutes you spend asking the right questions today could save you thousands of dollars—and countless headaches—later.

Final Thoughts

At Tree413, we believe informed homeowners make better hiring decisions.

Before hiring any contractor, make this request part of your routine:

"Before we begin, would you please have your insurance agent send me a current Certificate of Insurance showing your liability coverage and, if applicable, your workers' compensation coverage? Also, if the owner will be working on my property, is the owner covered under the workers' compensation policy?"

It only takes a few minutes.

It's standard business practice.

Professional contractors expect these questions.

Insurance companies handle these requests every day.

The best contractors won't be offended by your questions.

They'll respect you for asking them.

Tree413 Tip

Never assume. Always verify.

The questions you ask today could be the difference between hiring with confidence and learning a costly lesson after it's too late.