How to Choose a Tree Service Company: 8 Questions to Ask Before You Hire

By: Shelby McCullough| Published: October 11, 2026

TL;DR: Florida doesn’t license tree service companies the way it licenses electricians or plumbers, so the burden is on homeowners to vet credentials, insurance, and equipment before hiring. This guide covers the 8 questions to ask any tree company serving Orlando, Sweetwater, Union Park, Pine Castle, or Conway, from verifying ISA arborist certification to understanding local tree permit rules.

Central Florida’s sandy soil, heavy summer storms, and hurricane exposure put real stress on trees. That makes hiring the right tree service company just as important as the work itself. A bad cut, an uninsured crew, or an unpermitted removal can cost you more than money.

Unlike roofers or electricians, tree service companies in Florida aren’t required to hold a statewide contractor license. The Florida Department of Agriculture and Consumer Services doesn’t regulate or license contractors or companies providing tree services, so consumers need to check credentials themselves before hiring. That means the vetting job falls on you. Here are the 8 questions to ask before any crew touches a tree on your property in Orlando, Sweetwater, Union Park, Pine Castle, Conway, or anywhere else in Central Florida.

1. Are your arborists ISA-Certified, and can I verify it?

Anyone can call themselves a “tree expert.” An ISA Certified Arborist has actually proven it. An ISA Certified Arborist is a tree care professional who has passed a rigorous 200-question examination covering tree biology, planting, pruning, diagnosis, and safety, and candidates need at least three years of full-time arboriculture experience to qualify. The certification isn’t a one-time badge, either — it’s maintained through continuing education units, at least 30 over each three-year cycle.

Don’t just take a business card at face value. Go to the International Society of Arboriculture’s consumer site, treesaregood.org, and use the credential verification or find-an-arborist search, entering the name or number to confirm the listing shows an active ISA Certified Arborist credential. A company with multiple certified arborists on staff — not just one name on the website — is a strong signal of depth and consistency.

2. Is the company properly insured, and will they prove it?

Since Florida doesn’t license tree companies, insurance is your main financial protection if something goes wrong. Some counties or municipalities may require an occupational license, the company should be bonded, and you should ask for a copy of their insurance policy. Ask for a Certificate of Insurance sent directly from the insurer — not a photo of a document — and confirm the company name matches. This should cover general liability and workers’ compensation, since tree removal is one of the more hazardous trades around your home.

3. Will the certified arborist actually be on-site, not just on the letterhead?

A company can employ a certified arborist yet send an uncertified crew to do the climbing and cutting. Ask directly who will assess your tree and who will supervise the crew doing the work. If the job involves a large canopy tree near a structure, a complex removal, or a property line dispute, you want the certified arborist present, not just consulted by phone.

4. Do they carry the right equipment for the job — including a crane, if needed?

Not every removal is a straightforward drop-and-haul. Large oaks, sabal palms wedged between structures, or trees leaning over a roof or power line often require specialized rigging. If a company’s only tool is a chainsaw and a chipper, they may not be equipped for tightly placed or oversized trees. Ask whether they offer crane-assisted removal for situations where a conventional approach risks damage to your house, fence, or neighboring property.

5. Do they know local permit rules for Orange and Seminole County?

Orlando and Orange County both regulate the removal of certain trees, and the rules differ by jurisdiction. Removal of trees from private property requires a permit if the tree is larger than four inches in diameter at chest height, with a permit fee of $25 per acre for residential removals and $50 per acre for commercial removals. In the city itself, trees with a trunk diameter of 6 inches or more measured at 4.5 feet above ground are considered protected and require a permit, which the city may grant if the tree is dead, diseased, poses a safety risk, or interferes with construction. A reputable local company working in Sweetwater, Union Park, Pine Castle, or Conway should know which jurisdiction your property falls under and pull the correct permit — you shouldn’t have to figure that out yourself.

6. Can they explain whether you need removal or just trimming?

A trustworthy company won’t default to “remove it” when pruning would solve the problem — and vice versa. Ask them to walk you through their reasoning: is the tree structurally compromised, diseased, or simply overgrown and crowding a structure? If you’re not sure which category your situation falls into, this guide to tree removal vs. trimming breaks down the warning signs for each.

7. How do they price the job, and is the estimate free and in writing?

Reputable companies offer free, no-obligation estimates and put the scope of work in writing — not a verbal number scrawled on a business card. Request a written estimate itemizing removal, stump grinding, debris haul-off, and any permit fees separately. If you’re budgeting ahead of time, this Orlando tree removal price guide gives a sense of typical cost ranges so you can spot a lowball bid or an inflated one. Also ask about payment timing: a consumer protection best practice is to only pay after the job is completed, and to get estimates from several companies before choosing one.

8. Do they handle storm damage and emergency calls?

Central Florida’s hurricane season runs June through November, and a single storm can leave a split canopy or a tree down across a driveway overnight. Ask upfront how the company handles emergency calls: Do they prioritize storm cleanup? Can they respond within hours, not days, during a widespread event? A company with deep local roots in Longwood and the surrounding counties will have crews who already know which neighborhoods flood, which streets lose power first, and how to stage equipment before a storm hits — rather than scrambling after the fact.

Bonus: ask about species-specific knowledge

Central Florida’s canopy is dominated by live oaks, laurel oaks, and sabal palms, each with different pruning needs and failure patterns. If your property has palms, ask how often they recommend trimming — over-pruning palms is a common mistake that weakens the tree. For specifics, see this guide on how often to trim palm trees in Florida.

The bottom line

Because tree services in Florida are not regulated by a single state board with a unified license, and what exists instead is a patchwork of business registration, local permits, and voluntary certifications, the questions above are your real due-diligence checklist. A company that answers all eight without hesitation — and backs it up with verifiable credentials, insurance paperwork, and local permit knowledge — is one worth trusting with a 60-foot oak next to your roof.

McCullough Tree Service has served Orlando, Sweetwater, Union Park, Pine Castle, Conway, and the rest of Central Florida for over 30 years, with 3 ISA-Certified Arborists on staff, full insurance, and free estimates. Building relationships one tree at a time isn’t just a tagline — it’s how we’ve stayed family-owned for three decades.

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Shelby McCullough

About The Author: Shelby McCullough

With over two decades of experience in the tree industry, Shelby McCullough is a highly skilled certified arborist and the proprietor of McCullough Tree Service. His unparalleled expertise and profound understanding of trees set him apart in his field.