Questions to Ask a Landscaper Before You Hire One

by Precision OutdoorsOct 23, 2026

The best questions to ask a landscaper cover six things: who does the work, what insurance and local licensing they hold, what the written estimate includes, how they handle drainage, how the schedule and payments work, and what they warranty. If a contractor answers all six clearly and puts the answers in writing, you can hire with confidence. If they dodge any of them, keep looking.

This guide is written for homeowners in Wentzville and St. Charles County. Missouri works differently from many states, so a few of these questions matter more here than they would elsewhere.

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TL;DR

Missouri has no statewide landscape contractor license, so you have to check credentials yourself: insurance, local registration and, for chemical treatments, a pesticide applicator license.
Wentzville requires contractors to hold a city-issued license, and patios, fences, driveways and taller retaining walls can need permits. Put in the contract who pulls them.
Get at least two or three itemized written estimates and compare the scope, not just the bottom line.
For drainage problems, hire the contractor who walks your yard and explains where the water goes, not the one with the lowest number.
Keep deposits small and tied to milestones, and get the warranty on paper.

Why the questions matter more in Missouri
Questions about the company
Questions about licenses and insurance
Questions about permits
Questions about the estimate and contract
Questions about your specific project
Questions about drainage
Questions about schedule and communication
Questions about warranty and aftercare
Our perspective: what we think matters most
Red flags to walk away from
Talk to Precision Outdoor Solutions
FAQ
Sources

Why the questions matter more in Missouri

Missouri has no statewide landscape contractor license and no state agency that issues a general landscaping credential, according to CheckLicensed. Anyone with a truck and a trailer can advertise as a landscaper.

That puts the checking on you. It is not hard, but it takes a few phone calls before you sign. The questions below are in the order we would ask them if we were hiring someone to work on our own yard.

Questions about the company

1. How long have you been in business, and who will actually do the work?

A long local track record is useful because you can check it. Ask for addresses of past jobs nearby and, if possible, drive by. Then ask whether their own crew does the work or a subcontractor does. Subcontracting is not automatically bad, but you should know who will be in your yard and who is accountable if something goes wrong.

2. Do you have a physical local presence?

Missouri State University Extension warns about high-pressure sales tactics, especially after severe weather. Its advice is to be patient, confirm the business is registered, and verify insurance directly with the insurer instead of trusting a printout. Crews that knock on doors and offer an immediate fix are the ones you are least likely to reach a year later.

3. Can I see photos of finished projects and speak to past customers?

Look for work similar to yours: a patio if you want a patio, grading if you have a wet yard. Photos should show completed jobs, ideally a year or more old, so you can see how they have held up. Two or three recent references are better than a page of anonymous reviews.

Questions about licenses and insurance

4. Are you registered and licensed in my city?

This is the question Missouri homeowners skip most often. In Wentzville, all contractors, general and sub, need a city-issued contractor license before working in the city, and it must be renewed every year by February 28. Ask to see the current one. Other St. Charles County cities, such as O’Fallon and St. Peters, have their own rules, so ask your city’s building department what applies where you live.

5. Can you send proof of liability and workers’ compensation insurance?

Do not take a verbal yes. Ask for a certificate of insurance and, better, ask them to have their insurer send it to you directly. CheckLicensed calls verifying liability and workers’ compensation coverage essential in Missouri, and suggests general liability coverage of at least $300,000. Without workers’ comp, an injured crew member on your property can become your problem.

6. Will you apply any chemicals, and are you licensed to?

If the job includes weed control, fertilizer treatments or any pesticide, the company needs a Missouri Department of Agriculture commercial pesticide applicator license in the Ornamental and Turf category, according to CheckLicensed. A general landscaper is not automatically qualified. If your project is only construction or planting, this one does not apply.

Questions about permits

7. Which parts of this job need a permit, and who is getting it?

The City of Wentzville’s building permit page lists fences, patio covers, driveways and retaining walls above a set height among the projects that need a permit. The height threshold for retaining walls has been listed differently on different versions of the city’s pages, so confirm the current number with the Building Division before your wall is designed. Permits also become invalid if work is suspended or abandoned for six months, which is a reason to ask about scheduling as well.

What you want to hear is a clear answer: yes, this needs a permit, and we handle it. Then make sure the contract says so. Many cities, Wentzville included, now take applications through an online portal, so a contractor who does this regularly will know the process.

7. Which parts of this job need a permit, and who is getting it? — overview diagram

Questions about the estimate and contract

8. Is your estimate itemized and in writing?

CheckLicensed recommends getting multiple written estimates that spell out the scope of work, materials (including brands and plant specifications), a timeline with start and completion dates, and a defined warranty on both materials and workmanship. That is a good checklist for any bid.

When you lay two estimates side by side, check these lines:

What to compare	What a good estimate shows	What should worry you
Scope	Dimensions, areas, what is removed and hauled away	“Install patio” with no size or details
Materials	Paver brand and style, base depth, plant species and sizes	“Materials as needed”
Site prep	Excavation, base, compaction, grading	Not mentioned
Permits	Who applies and who pays	Silent
Schedule	Start window and expected finish	“We’ll get to it”
Warranty	Written, for materials and labor	Verbal only
Cleanup	Debris and soil removal included	Left out

If one bid is far lower, find out which line is missing before you celebrate. Usually it is the base preparation or the drainage, the parts you cannot see once the job is done.

9. How much do you want up front, and how are payments scheduled?

This is where national advice and Missouri reality differ. California limits a home improvement deposit to 10% or $1,000, whichever is less, but that is California’s rule. In Missouri, a legal-help forum answer notes that no statute caps contractor deposits, so it is up to you to set a sensible limit. A small deposit to schedule the job and materials, then payments tied to finished stages, protects you. Be cautious with anyone who asks for most of the money before they start.

10. What happens if the plan changes?

Buried utilities, rock and bad soil show up on real jobs. Ask how change orders work. The answer should be that any added cost is written down and approved by you before the extra work begins.

Questions about your specific project

Patios and hardscape

Ask about the base: what material, how deep, and how it is compacted. Ask where water will go once the patio is down, because a patio that sheds water toward the house will cause problems. If you are weighing a patio contractor in particular, our guide on how to choose the right hardscape contractor goes deeper, and our piece on patio drainage design explains why slope and soil matter.

Patio base and slope direct water away

Fences

Ask how deep the posts will be set, whether the fence follows your property line survey, and how the contractor handles slopes. Our fencing advice on post depth lists what to ask for. Also confirm the permit, since fences appear on the city’s permit list.

Retaining walls and slopes

Ask how the wall will drain behind it and what happens at the base and top. Walls fail from water pressure more often than from weak materials. If your yard slopes, our article on erosion control on a slope shows why plants alone are not enough.

Lawn and landscape maintenance

Ask exactly what each visit includes, how often, and what is billed separately, such as mulch, pruning or leaf cleanup. Ask whether they handle chemical applications themselves (see question 6). Find out how they notify you when they will skip a week because of weather.

Questions about drainage

Drainage deserves its own section because it is the problem most likely to be solved badly. The mistake agricultural experts flag most is hiring on price alone instead of the proposed technical approach, according to CheckLicensed’s summary. Fixing the root cause, such as compacted soil, heavy clay or poor grading, costs less over time than treating symptoms repeatedly.

Here is what to ask:

Will you walk the property with me and point out where water comes from and where it collects?
Where does the water end up? Practitioners at Drainage Helper say a good contractor connects the source of water to a safe outlet without affecting neighbors or the foundation.
Why this solution, whether a French drain, a catch basin or regrading, instead of another one?
What are you assuming about my soil?

A contractor who proposes a product before walking the yard is selling, not diagnosing. Our post on signs you need a drainage solution will help you describe your problem before the first call.

Questions about schedule and communication

When can you start, and how long will the job take?
Who is my point of contact, and how will you update me?
What happens to the schedule in rain?

Project length varies a lot by scope. Our guide to landscaping project timelines shows the range from a few days to twelve weeks or more. A straight answer with a start window is a good sign.

Similar advice applies in other trades, and a list such as these questions to ask flooring contractors shows how the same habits of comparing written estimates and asking about warranties carry over to any home project.

Questions about warranty and aftercare

Ask what the warranty covers, for how long, and whether materials and labor are covered separately. Ask who you call if pavers settle or a plant dies, and how quickly they respond. Get it in the contract. A verbal promise is only as good as the person’s memory.

Our perspective: what we think matters most

After more than 25 years of working on outdoor spaces in Wentzville and St. Charles County, we see the same pattern. The projects that go well started with a contractor who walked the property, listened and explained the plan in plain terms. The ones that go badly started with a quote that was hard to say no to.

We build around durability, and that means drainage and the base come first. A beautiful patio or retaining wall that holds water against the house is not a good job. That is why we look at grading and water flow before talking about materials. It is also why our landscape design process starts with solving drainage.

We would rather you ask us every question on this list. Clear timelines, regular updates and a collaborative design process are how we work, and good questions make that easier for both of us.

— Precision Outdoor Solutions

Red flags to walk away from

Pressure to sign today or a discount that expires tonight.
No certificate of insurance, or one you cannot verify.
A request for a large deposit or cash only.
Vague estimates with no measurements or materials.
No city contractor license where one is required.
A solution proposed before anyone looked at your yard.
Door-to-door crews that show up right after a storm.

Talk to Precision Outdoor Solutions

If you are planning a patio, fence, retaining wall, drainage fix, concrete work or ongoing yard care, Precision Outdoor Solutions offers a site consultation and design planning for homes in Wentzville and across St. Charles County. You can see everything we do on our services page, or start with yard drainage solutions or landscape design. Bring this list. We are glad to answer every question on it.

FAQ

How many landscapers should I get estimates from?

Two or three is a practical number. That is enough to see which bid is an outlier and which is missing scope. Give each contractor the same description of the project so the bids are comparable.

Does a landscaper need a license in Missouri?

There is no statewide landscape contractor license, so the state does not issue one. Cities can require their own contractor license, and Wentzville does. A company applying pesticides or weed treatments also needs a Missouri Department of Agriculture applicator license.

How much deposit is reasonable?

Missouri has no statute capping deposits, so the amount is a matter of the contract. A small deposit to secure the schedule and materials, with further payments tied to completed stages, keeps your risk low. Be wary of any request for most of the cost before work starts.

Who is responsible for getting permits?

That depends on what your contract says, so make it say it. For fences, patios with covers, driveways and taller retaining walls in Wentzville, check with the city’s Building Division about what is required. A contractor who handles permits regularly will tell you right away.

What should a written estimate include?

It should list the scope with measurements, specific materials and brands, a start and finish timeline, a payment schedule and a written warranty. If a line is missing, ask for it to be added before you sign.