What To Look For in a Landscape Contractor: Questions Worth Asking Before You Hire
Transforming your backyard is a big step filled with excitement and possibility. But with so many options and questions about who to trust, it’s not uncommon to feel uneasy. This is a major investment and you want to ensure it’s done right. Asking the right questions and having a clear set of criteria upfront will go a long way in helping you feel confident in your contractor from the very beginning.
Choosing which landscape contractor to work with is an important decision. As with most home renovation projects, it’s not only the final product that determines your satisfaction—it’s the experience along the way. A contractor’s process, communication, and craftsmanship will shape your experience, and a poor one can sour even the most beautiful finished result.
The good news is that there are many excellent landscape contractors in the Greater Hamilton area—professional, skilled crews who will check all the boxes. The key is to know what you’re looking for and go into the research process with a clear list of non-negotiable criteria.
In this post, the team at Three Seasons shares key questions to ask and things to look for so you can hire confidently and feel good about your project right from the start.
QUESTIONS TO ASK BEFORE YOU HIRE
1. Process: What Kind of Experience Can We Expect?
Before committing to a contractor, it’s important to understand what kind of experience you can expect—from the first phone call to the final walkthrough. Ask specific questions about their process, timelines, and approach to planning and design. This will give you a good sense of how organized and professional they are—and how smooth your project will go.
Questions to ask:
What’s your typical project lead time?
How long will it take to receive an estimate? An initial design?
During construction, will your crew be here everyday or will they rotate between projects?
Do you work weekends, and what happens in the event of bad weather?
Will the project require permits? And do you handle that?
Are there any site challenges or local by-laws that could impact the project?
How do you ensure that the design we agree on can actually be built well?
2. Communication: Will We Be Kept Informed?
Even the best plan can fall apart without good communication. These questions help you understand how your contractor will keep you informed and supported throughout the process.
Questions to ask:
How often will you provide project updates?
If we have questions, how long should we expect to wait for a response?
Will we have a dedicated project manager or main point of contact?
What’s your process for communicating unexpected issues or changes?
How do you handle design or scope adjustments once construction begins?
3. Craftsmanship: Will the Work Stand the Test of Time?
A well-built landscape not only looks great on day one—it endures. Craftsmanship is about more than what you can see on the surface; it’s about attention to detail, care for your property, and pride in doing things the right way. Here are a few questions to dig into a contractor’s commitment to premium craftsmanship.
Questions to ask:
Do you use subcontractors?
What warranty do you offer on materials and workmanship?
How do you ensure long-term durability in your construction?
How do you handle cleanup and property protection during and after construction?
How do you approach small adjustments or details that come up on site?
THINGS TO WATCH FOR
In addition to asking good questions, there are several key things to observe as you research potential contractors. These details can give you valuable clues about how they’ll work and what kind of experience you’ll have.
1. Do They Have a Professional Image?
Whoever you hire will be working in your neighbourhood—and their professionalism will reflect on you. Things that seem simple—like clean, branded vehicles, polite and tidy crews, and equipment that’s well-maintained—can make a big difference in minimizing disruption and maintaining good relationships with your neighbours. Ensure the contractor you hire is professional and courteous so that the experience is positive for everyone around you.
2. Can They Provide Reviews & References of Similar Projects?
You also want to ensure you’re trusting your project to someone with the capability to meet your expectations. Reviews and references are invaluable—especially from projects similar to yours. This is particularly important on large-scope work, where experience and resources really matter. Make sure the contractor has a proven track record of delivering on time, on budget, and to a high standard. Don’t hesitate to ask for specific references or photos of comparable projects so you can start with confidence that they can deliver what they promise.
3. Do They Have an Established Presence & Reputation?
Be cautious of names you’ve never heard of. With so many reputable landscape contractors in our area, it’s best to start your search with those that you’ve seen or heard about before. At minimum, be mindful of brand new names particularly if they don’t have any reviews available.
Your goal isn’t just to avoid the wrong fit—it’s to find the right one. Seek out teams whose work and approach you genuinely admire, then use these questions to confirm they’re as professional as they seem.
How to Get Started
Not sure where to begin? These simple steps will help you feel confident as you start planning your landscape project:
Make your shortlist (3–5 contractors). Look for reputable local companies with strong reviews and portfolios that fit your style. Having a few to compare helps you get a clearer sense of scope, cost, and values-fit.
Book consultations. Meeting face-to-face (or virtually) gives you a feel for each contractor’s process and communication style—both key to a smooth experience.
Use the questions in this post as your guide. Bring them to your meetings! They’ll help you uncover important details early on and make it easier to identify the right fit for your project.
We’re Here to Help You Build With Confidence
Upgrading your outdoor space is a major investment, and you deserve to feel confident every step of the way. At Three Seasons, we’re committed to ensuring your experience is smooth, transparent, and enjoyable—and that your finished landscape is exceptional.
Looking for a landscaper you can count on? Let’s start with a conversation.