12 Questions to Ask a Wisconsin Tree Service Before You Sign

Tree work is one of the few home services where the gap between the best contractor and the worst one is measured in property damage, injuries, and dead trees. A bad tree service can cost you more in cleanup, claim disputes, and replacement than the price of the original job. A great one extends the life of the trees you already have. The price quote alone tells you almost nothing about which kind of company you’re hiring.

Before you sign anything, run through these 12 questions. The answers — and how the company answers — separate the qualified crews from the ones who showed up because someone could afford a chainsaw and a pickup truck.

1. Are you ISA Certified, and can I see the certification number?

The International Society of Arboriculture (ISA) certifies arborists who pass an exam covering tree biology, pruning standards, diagnosis, and safety. Certifications are tied to a numbered credential you can verify at treesaregood.org. A real company has at least one ISA Certified Arborist on staff and is happy to give you the number. A company that fumbles this question or claims certification without a number is not certified.

2. Do you carry general liability AND workers’ compensation insurance?

This is the one question that protects you the most. If a worker falls from your tree and the company doesn’t carry workers’ comp, the worker (or their family) can come after your homeowners policy. Ask for a Certificate of Insurance (COI) showing both general liability and workers’ compensation, naming you as the certificate holder. Don’t accept a verbal claim. Don’t accept a screenshot. A reputable company will email you the COI from their insurer within minutes — that’s how it’s supposed to work.

3. Is the company TCIA Accredited?

Tree Care Industry Association (TCIA) Accreditation is the industry’s top business credential. It requires a written safety program, audited financial responsibility, ongoing training, and ANSI A300 compliance. TCIA Accreditation is rare — there are fewer than a thousand accredited companies nationwide. Tree Wise Men LLC is TCIA Accredited; if your contractor isn’t, ask them why.

4. Will you follow ANSI A300 pruning standards?

ANSI A300 is the national standard for tree care operations. It governs where cuts are made (just outside the branch collar, not flush, not stubbed), how much canopy comes off in one session (never more than 25%), and the objective of every pruning type. Topping — cutting branches back to stubs — violates A300. If a contractor offers to “top” your tree, end the conversation. Topping destroys trees and creates a decade of expensive structural problems.

5. Who will actually be on my property?

Some companies sell jobs and then subcontract the work. The estimator you liked may not show up at all. Ask: are the crew members W-2 employees of the company? Are they trained internally? Will the ISA Certified Arborist be on site, or only quoting? You’re hiring people, not a brand.

6. Can you provide a written scope of work?

Verbal scopes are how disputes start. The written estimate should specify: which trees, what work (removal, pruning type, stump grinding depth), what gets hauled away vs. left on site, who handles permits, debris, cleanup, and damage to lawn or hardscape. If you’re comparing two estimates and they don’t look alike line-by-line, you’re probably not comparing the same job.

7. What’s your plan for protecting my property?

Lawns, sprinkler heads, hardscape, fences, and adjacent trees can all be damaged by careless tree work. Ask what plywood, mats, or ground protection they use under heavy equipment. Ask how they rig limbs to avoid impact damage. A pro has a real answer; a guess means the damage will come out of your driveway repair budget later.

8. Do you handle permits, or is that on me?

In Wisconsin, trees in the public right-of-way (terrace trees), historic-district properties, HOAs, and some shoreline parcels require permits or coordination. Ask whether the contractor handles permit research and submission. A local Wisconsin company should know which municipalities require what — Madison, Janesville, and Madison’s lakeside neighborhoods all have different rules.

9. What’s your oak wilt timing protocol?

If you have oaks, this is a non-negotiable test. The safe pruning window for oaks in Wisconsin is November through March. Pruning between April and October exposes wounds that attract sap beetles carrying oak wilt — a fatal fungal disease. A contractor who offers to prune your oak in June without flagging the risk is either uninformed or willing to kill your tree to book a job.

10. How do you handle storm-damaged trees and insurance claims?

If you’re calling after a storm, the right contractor will ask about your insurance situation, offer to photograph damage for your claim, provide an itemized invoice in claim-ready format, and meet your adjuster on site if needed. They will also tell you straight: which trees can be saved with cabling and bracing vs. which need to come down. A contractor pushing total removal without alternatives is selling, not advising.

11. Do you have references from properties like mine?

Anyone can show you a photo of a felled tree. Ask for references from similar properties — historic homes, lakefront, HOA, commercial — close enough that you could drive past. A company that has worked in your neighborhood for years can name streets, customers, and specific trees. A company that can’t is either new or churns through clients.

12. What happens if something goes wrong?

The honest answer is “our insurance covers it, here’s the COI again, and we’ll work directly with you and our carrier.” The dishonest answer is anything that involves you fighting with the contractor. Ask before there’s a problem. You’ll know in three seconds whether you’re hearing a real protocol or improvised reassurance.

The shortcut version

If you’re comparing two contractors quickly, the three highest-leverage questions are: Certificate of Insurance with workers’ comp, ISA certification number, and a written scope of work. Any contractor who can’t produce all three within a business day shouldn’t be working in your trees.

Tree Wise Men LLC has been TCIA Accredited and ISA Certified since 2010, with 4 Certified Arborists on staff and headquarters in Janesville plus a Madison office. We email a COI before every job, write detailed scopes of work in plain language, and never top trees. For a free on-site estimate anywhere in Southern Wisconsin, call (608) 751-4171 or visit https://www.treewisemenllc.com/contact-us.