Questions Every Owner Should Ask Before Hiring a General Contractor

Hiring the right general contractor can determine whether your project runs smoothly — or turns into a costly, stressful experience. Whether you’re managing a commercial property, overseeing a multifamily renovation, or improving your home, asking the right questions before signing a contract helps reduce risk, improve communication, and protect your investment.
At Landmark Associates, we’ve spent over 20 years working with property managers, facility teams, HOAs, and homeowners across Massachusetts, Rhode Island, and Southern New Hampshire. One thing we’ve learned is simple: successful projects start long before construction begins. They start with clarity, planning, and choosing the right partner.
Here are the most important questions every owner should ask before hiring a GC.
1. Are You Licensed and Insured?
This should always be the first question.
A reputable contractor should be able to provide proof of:
- State licensing
- General liability insurance
- Workers’ compensation coverage
According to FEMA and several construction industry experts, verifying credentials protects owners from liability, code issues, and unqualified work.
At Landmark Associates, we are fully licensed and insured and understand the importance of protecting both the property and the people inside it.
2. What Experience Do You Have With Projects Like Mine?
Not every contractor specializes in the same type of work.
A contractor who excels at residential kitchens may not be the right fit for occupied multifamily renovations, exterior envelope restoration, or commercial capital projects.
Ask for:
- Similar project examples
- Case studies
- Before-and-after photos
- References from comparable properties
Landmark Associates specializes in commercial renovations, repairs, exterior restoration, insurance reconstruction, and multi-trade projects throughout New England. Our team has extensive experience working in occupied buildings while minimizing disruption to tenants and operations.
3. Who Will Actually Manage My Project?
One of the biggest frustrations owners face is unclear communication once work begins.
Before hiring a contractor, ask:
- Who is my point of contact?
- Who supervises the field team?
- How often will I receive updates?
- How are issues documented and resolved?
Clear communication is one of the strongest indicators of a well-managed project. Industry experts consistently note that poor communication early in the process often leads to delays, disputes, and change order confusion later.
At Landmark, communication and transparency are central to our process. Our clients always know:
- What’s happening
- What the timeline is
- What the next steps are
- How the budget is tracking
That consistency helps eliminate surprises and reduce project stress.
4. How Do You Handle Permits, Inspections, and Code Compliance?
A professional GC should guide the entire construction process — not leave owners guessing.
Ask:
- Who pulls permits?
- How are inspections coordinated?
- How do you stay current with local codes and regulations?
Contractors who suggest skipping permits or avoiding inspections should raise immediate concerns. Experts identify this as a major red flag that can expose owners to legal and financial risk.
Landmark proactively manages permitting, compliance, scheduling, and coordination to help projects move efficiently while meeting local requirements.
5. What Does the Proposal Actually Include?
Not all estimates are created equal.
A quality proposal should clearly outline:
- Scope of work
- Materials
- Timeline expectations
- Allowances
- Exclusions
- Payment schedule
- Warranty information
Vague proposals often lead to disputes, hidden costs, and frustration later in the project. Construction experts recommend requesting detailed written documentation before any work begins.
At Landmark, we believe transparency builds trust. Our process focuses on providing clear, visual, and well-documented proposals so clients can make informed decisions with confidence.
6. How Do You Handle Unexpected Issues or Change Orders?
Every construction project has variables — especially in older buildings.
The important question is not whether challenges arise, but how the contractor responds when they do.
Ask:
- How are unforeseen conditions documented?
- How are change orders communicated?
- How quickly are solutions provided?
- How do you protect timelines and budgets?
Experienced contractors anticipate issues before they become emergencies.
For example, during the $14 million Old Reading School House condominium restoration in Reading, MA, Landmark Associates successfully coordinated multiple subcontractors and adjusted workflows in real time to accelerate the schedule and keep the project moving after severe fire damage.
That level of flexibility and communication is critical in complex renovation work.
7. Can You Provide References and Past Project Examples?
A contractor’s reputation matters.
Ask for:
- Recent references
- Completed project photos
- Testimonials
- Online reviews
- Examples of long-term client relationships
Strong contractors should be comfortable sharing their work history and demonstrating consistent results.
Landmark has built long-standing relationships with property managers, commercial owners, HOAs, and facility teams throughout New England by focusing on reliability, responsiveness, and quality craftsmanship.
8. What Happens After the Project Is Finished?
The relationship shouldn’t end when the final invoice is paid.
A dependable contractor should remain available for:
- Warranty support
- Maintenance planning
- Future capital improvements
- Ongoing property needs
At Landmark Associates, many of our projects lead to long-term partnerships because clients know they can rely on our team when future needs arise.
Final Thoughts
Hiring a general contractor is about more than price.
It’s about choosing a team that communicates clearly, manages risk proactively, and delivers predictable results.
The right contractor helps protect your building, your budget, your tenants, and your timeline.
At Landmark Associates, we’ve built our reputation on being the contractor property owners and managers can trust — delivering high-quality work with clear communication and dependable execution across every phase of the project.
If you’re planning a renovation, repair, restoration, or capital improvement project, our team is here to help.
Contact Landmark Associates today to schedule a walkthrough or discuss your upcoming project.
๐ 508-482-0104
๐ www.landmarkassoc.com
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