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How to Hire a Tree Service Company: 10 Questions to Ask First

A tree comes down in minutes, but the mistakes that cost homeowners money are made days earlier, at the moment they hire a tree service company without checking who’s actually showing up. The ten questions below take about an hour to ask and answer, and they cover credentials, the estimate, and how the job is paid for.

Most of them work whether the job is a trim, a removal or a stump. Ask them of every company on your list, including us.

Credentials to check before you hire a tree service company

Start with proof of who the company is and what it’s allowed to do. These four questions are quick to answer, and a company that dodges any of them has told you what you need to know.

1. Is a certified arborist on staff?

Ask whether someone at the company holds International Society of Arboriculture (ISA) certification. The city of Maplewood, Minnesota, notes in its guidance on hiring a tree contractor that ISA certification requires education or training and passing an arborist exam, and that a city license alone doesn’t guarantee expertise.

Having a certified arborist on the job matters because the first question is often whether the tree needs work at all. That distinction matters for judgment calls such as whether a tree can be saved or how much of a canopy to take. Monkeyman’s has an ISA Master Arborist among its credentials, and our arborist services include written evaluations when you need a second opinion on a tree.

2. Are you licensed, and what’s the license number?

Get the number and look it up yourself. The Oregon Construction Contractors Board runs a public License Search, and its homepage puts the reason bluntly: “Anyone can pretend to be a contractor. Check licenses.”

We’re licensed in Oregon under CCB #206934, and you’re welcome to check it. Whoever you choose should hand over a number without hesitation.

3. Can I see proof of insurance?

Ask for certificates showing personal and property damage liability and workers’ compensation. The Better Business Bureau’s tip sheet on hiring a tree service lists exactly those two, and Maplewood adds that a professional company will give you the insurer’s name and policy number so you can confirm the coverage is current.

Good tree service insurance is cheap to verify and expensive to be without. A phone call to the insurer takes five minutes. An accident with a dropped limb on a roof takes months to sort out.

4. Do subcontractors carry their own insurance?

Companies sometimes bring in extra hands for big removals. The BBB suggests asking whether those subcontractors carry their own coverage and whether the workers use personal protective equipment.

You’re looking for a plain answer. A crew in helmets and chaps with its own insurance is the baseline for work that happens above your house.

Getting a written estimate before you hire a tree service company

Credentials tell you who to consider. The estimate tells you what you’d actually be buying, and a verbal number over the phone isn’t one.

Walk the property with each company that bids, and point at the trees yourself. When you hire a tree service company on a handshake, the argument about which limbs were included usually starts after the invoice arrives.

5. What exactly does the written estimate cover?

Insist on a written estimate, not a number over the phone. Maplewood’s guidance says a good estimate spells out the work, the start and end timeframe, a total price including taxes and discounts, and the procedure and charge if additional work turns up.

The BBB adds that you should compare estimates on both price and what each one includes. Two bids that differ by a few hundred dollars often differ in exactly the items below.

  • Which trees or limbs are being cut, and how much of each
  • Whether cleanup and hauling are in the price
  • Whether stump grinding is in or out
  • What happens, and what it costs, if the scope changes

6. Is cleanup and stump work included?

This is the line item that most often turns a cheap bid into an expensive one. Both the BBB and Maplewood say to confirm whether stump and wood cleanup are included and what they cost.

If a removal bid leaves the stump, price it against one that doesn’t. Our stump grinding and tree removal work can be quoted as a single job or separately, so you can compare like with like.

7. Who handles permits?

Some removals need a permit, and the rules depend on the city, the size of the tree and sometimes where it stands. The BBB tells homeowners to confirm who will get any required permits before work starts.

Don’t assume the answer. If the crew expects you to file, you should know before the date is booked, not on the morning the truck arrives.

8. When will the work start and finish?

Dates belong in the contract. Both sources above list start and completion dates among the things to pin down in writing.

A company that can’t commit to a window is either overbooked or improvising. Urgent damage is a different case, and our emergency tree service exists for the nights when a limb is already on the roof.

Checking the company’s record and how you’ll pay

Hire a tree service company with a written estimate: arborist talking with a homeowner

Photo by Vanessa Garcia on Pexels

The last two questions cover what other customers say and how money moves. Both are about not being the first person to find a problem.

It helps to treat these as a filter rather than a score. If you plan to hire a tree service company for a big removal near the house, a missing answer on insurance or the contract should end the conversation, however friendly the estimator was.

9. Can I talk to recent customers?

Ask for references and call them. Maplewood recommends asking the business for references and checking them, and the useful questions are simple. Did the crew show up when promised, and what did the yard look like afterward?

Reviews are worth reading too. Monkeyman’s has been named Best of Portland four times, but a reference you phone yourself tells you about the specific kind of job you’re planning, whether that’s a pruning job or a large removal.

10. How and when do I pay?

Don’t hand over a large deposit. The BBB’s warning is direct: “Never make a large payment or deposit upfront.” It suggests spreading payments across stages of the work and paying by check or credit card, because a card offers some recourse if the job isn’t completed as the contract says.

And don’t let work begin without a signed written contract. It should name the dates, the exact costs, the specific work, how your property will be protected and how cleanup is handled.

Keep a copy of everything you collect: the license number, the insurance certificate, the signed estimate and the contract. If something goes wrong with a limb, a fence or a payment, that folder is what lets you settle it quickly. For work in Portland itself, our Portland tree service page lists what we cover, and the same ten questions apply to us as to anyone else you call.

Frequently asked questions

How many estimates should I get before I hire?

The BBB recommends at least three written estimates. Compare what each includes, not just the total at the bottom.

Does my homeowner’s policy cover a worker hurt on my property?

It may not, according to the BBB. That’s why the company itself should carry liability coverage and workers’ compensation.

Is a contractor license enough on its own?

A license shows a company is registered to work, which is why checking it matters. It doesn’t tell you how much the crew knows about trees, so ask about ISA certification as well. If you’re in the Portland area and want those answers from us, contact us and ask for the credentials above.

Sources

Cover photo by Rodolfo Gaion on Pexels