How to choose a landscaper on the North Shore — eight questions to ask

Hiring a landscaper sounds simple until you realize how many options there are. A quick search for lawn care in Glenview or landscape maintenance in Northbrook returns dozens of results, and from the outside they all look more or less the same: green trucks, mowers, a promise to make your yard look great.

The difference shows up later — in missed visits, surprise invoices, or the sinking feeling that the crew on your property today has never seen your yard before. The best way to avoid those problems is to ask the right questions before you sign anything.

Here are eight that matter most.

1 How long have you been in business?

Landscaping has a low barrier to entry. Anyone with a truck and a mower can hang a shingle, and many do — only to disappear after a season or two. Longevity is not a guarantee of quality, but it is a strong signal that a company knows how to hire, manage crews, handle the brutal swings of a Midwest climate, and keep clients happy year after year.

At Hillside, we have been serving the North Shore for over 25 years. That kind of tenure means we have seen every freeze-thaw cycle, every emerald ash borer wave, and every drainage quirk that comes with properties in Riverwoods and Lake Forest. Experience like that is hard to fake.

Ask any company you are considering how long they have been operating — and whether the current ownership is the same team that started it.

2 Are you licensed and insured in Illinois?

This is the single most important question on the list, and the one most homeowners skip. In Illinois, a legitimate landscape company should carry general liability insurance and workers' compensation coverage for every crew member on your property.

Why does it matter? If someone is injured on your property and the company has no workers' comp, that liability can fall on you as the homeowner. If a mower kicks a rock through your neighbor's window and there is no GL policy, you are looking at an out-of-pocket claim.

Do not just take their word for it. Ask to see a current certificate of insurance, and verify that your property's municipality is listed in the service area. Any reputable landscaper in Deerfield or Wilmette will hand this over without blinking.

3 Who actually shows up on day one?

This question catches a lot of companies off guard — and the answer tells you everything about how they operate. Some firms subcontract most of their work to whoever is available that week. Others rotate crews so frequently that no one on your property has any context about your preferences, your irrigation zones, or the perennial bed your spouse spent two years planting.

What you want to hear is that the company assigns a consistent crew to your property and that the same people will show up each visit. Crew consistency means fewer mistakes, less time spent re-explaining instructions, and a team that actually notices when something looks off — a brown patch in the turf, a leaning retaining wall, a sprinkler head that is not rotating.

Ask specifically: "Will I see the same crew every week, or does it change?" The answer should be clear and direct.

4 Can I see recent work in my area?

A portfolio of beautiful projects in another state does not tell you much about how a company handles North Shore conditions — the heavy clay soils in Northbrook, the deer pressure in Riverwoods, the salt exposure on properties near major roads in Glenview.

Ask to see completed work within a few miles of your home. Better yet, ask if you can drive by a current maintenance client's property to see what their weekly service actually looks like. A company that is proud of its work will welcome this. One that hesitates probably has a reason.

If you are in Lake Forest, Highland Park, or Deerfield, ask for references in those specific towns. Microclimates, lot sizes, and homeowner association requirements vary enough that local experience matters.

5 What is included in your maintenance plan?

This is where hidden costs live. A low monthly quote might cover mowing and blowing — and nothing else. Edging, bed maintenance, pruning, leaf removal, fertilization, and aeration could all be billed separately as add-ons. By midsummer, your "affordable" plan has quietly doubled in cost.

Before signing, ask for a written breakdown of everything the plan includes. Understand the difference between a basic mowing package and a full-service maintenance plan. Some things to clarify:

• Is spring and fall cleanup included, or quoted separately?
• How many fertilizer and weed-control applications are covered?
• Are shrub and ornamental pruning part of the plan, or a la carte?
• What happens when a storm brings down a limb — is cleanup covered?

A transparent company will walk you through all of this before you commit. If the proposal is vague, that is a red flag.

6 How do you handle communication?

You should not have to wonder whether your landscaper received your message. Yet poor communication is one of the top complaints homeowners have about service companies of every kind.

Ask these follow-ups: Who is my main point of contact? How quickly can I expect a response? Do you have a dedicated account manager, or do I call a general dispatch number? What happens if I need to reach someone on the day of service?

The best companies assign a single point of contact who knows your property, your preferences, and your history. That person should be reachable by phone or text during business hours and able to give you a real answer — not just take a message.

If a company cannot explain their communication process clearly during the sales conversation, imagine what it will be like once they already have your contract.

7 Do you offer design-build or just maintenance?

This question matters more than most people realize, especially if your property needs attention beyond weekly mowing. Maybe you want to add a patio next year, rethink the front foundation plantings, or install landscape lighting along your driveway in Highland Park.

A full-service landscape company can handle design, installation, and ongoing maintenance under one roof. That means a single team that understands your property from the soil up — and can grow with your vision over time. A mow-and-go outfit will need to hand you off to a separate contractor for anything beyond basic lawn care, which means more coordination, more cost, and less accountability.

Even if you only need maintenance right now, choosing a company with design-build capability gives you a built-in partner when you are ready for something bigger.

8 What do your reviews say?

Online reviews are not the whole picture, but they are a useful starting point. Search the company's name on Google and look at their Google Business Profile. Pay attention to patterns rather than individual reviews. Every company gets the occasional one-star rating. What matters is how they respond — and whether the overall trend shows consistent, reliable service.

Look for details in the reviews. "Great job" tells you nothing. "They showed up every Thursday at 8 a.m. for three straight years and my yard has never looked better" tells you everything. Also ask the company directly: What percentage of your clients come from referrals? A high referral rate is one of the strongest indicators of quality because it means real people are putting their reputation on the line to recommend the service.

If a company cannot point you to reviews, or if their online presence is thin, proceed with caution.

The bottom line

Choosing a landscaper is not just about price. It is about trust, consistency, and finding a team that treats your property with the same care you do. The eight questions above will surface the differences between companies that look identical on paper — and help you make a decision you will feel good about for years.

Take your time. Get at least two or three proposals. And do not be afraid to ask the uncomfortable questions. The right company will appreciate that you did.