Questions Every Owner Should Ask Before Hiring a General Contractor

Caroline Brodsky • May 26, 2026

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.


📞 508-482-0104

🌐 www.landmarkassoc.com

✉️ info@landmarkassoc.com


By Caroline Brodsky July 10, 2026
As housing needs continue to evolve across Massachusetts, more homeowners are exploring Accessory Dwelling Units (ADUs) as a way to create additional living space , increase property flexibility , and prepare for future lifestyle changes. Whether you're considering an ADU for aging parents , adult children , rental income , guest accommodations , or simply making better use of your property, understanding the planning process is the first step toward making an informed decision. At Landmark Associates, we believe successful construction projects begin with education, realistic expectations, and careful planning. This guide brings together many of the most common questions Massachusetts homeowners ask when exploring ADUs and serves as a central resource to help you better understand the process. What Is an ADU? An Accessory Dwelling Unit (ADU) is a secondary residential living space located on the same lot as a primary residence. Unlike a traditional home addition, an ADU functions as an independent living space with its own kitchen, bathroom, sleeping area, and private entrance. Common ADU types include: Detached backyard cottages Garage conversions Basement apartments Attached additions Above-garage apartments Because every property is different, one type of ADU may be more practical than another depending on available space, utilities, zoning considerations, and construction costs. ➡ Accessory Dwelling Units (ADUs) | Landmark Associates | Within 90 min of Hopedale, MA. Why More Massachusetts Homeowners Are Exploring ADUs Interest in ADUs has grown significantly throughout Massachusetts over the past several years. Many homeowners are discovering that an ADU offers long-term flexibility without requiring them to relocate. Some of the most common reasons homeowners build ADUs include: Housing aging parents Providing independent living space for adult children Creating guest accommodations Establishing a dedicated home office Planning for future caregiving needs Exploring rental income opportunities Increasing overall property functionality As housing costs continue to rise and multigenerational living becomes more common, ADUs offer a practical solution that adapts alongside changing family needs. For a closer look at why this trend continues to grow across the state, read: ➡ Why More Massachusetts Homeowners Are Exploring ADUs Could Your Property Support an ADU? One of the biggest misconceptions homeowners have is assuming every property can accommodate an ADU. While recent state changes have expanded opportunities, each property still requires an individual feasibility assessment. Some of the most important factors include: Lot size and available building area Existing setbacks Driveway access Utility connections Drainage considerations Topography Existing structures Building code requirements Professional feasibility evaluations help identify opportunities early while reducing costly surprises later in the project. Understanding what's possible before investing in architectural drawings can save significant time and expense. For a more detailed explanation of the evaluation process, read: ➡ Could Your Property Support an ADU? Understanding Massachusetts ADU Regulations Massachusetts has recently updated regulations that have increased awareness and accessibility surrounding ADUs. However, many homeowners mistakenly assume that these changes mean every property automatically qualifies. In reality, successful ADU projects still depend on: Local permitting requirements Building code compliance Utility capacity Site-specific conditions Construction feasibility Statewide legislation has opened new opportunities, but every project still benefits from careful planning and professional guidance. To better understand how these changes may affect your property, read: ➡ Massachusetts ADU Rules Have Changed Five Questions Every Homeowner Should Ask One of the best ways to avoid delays and unexpected expenses is by asking the right questions before beginning the design process. Consider: Why are you building an ADU? Who will live there? What is your realistic budget? Will utilities need upgrading? What timeline are you hoping to achieve? These conversations often shape the entire direction of the project. Homeowners who invest time in planning generally experience smoother construction and fewer unexpected changes. For a deeper discussion, read: ➡ 5 Questions to Ask Before Building an ADU Before You Build an ADU Even after deciding to move forward, there are several important planning steps homeowners should complete before construction begins. These include: Understanding project costs Reviewing financing options Evaluating construction timelines Hiring qualified professionals Confirming permitting requirements Preparing for inspections Early planning often leads to better budgeting, fewer delays, and a more efficient construction process. Before taking the next step, we recommend reading: ➡ Before You Build an ADU Can an ADU Increase Property Value? Another common question homeowners ask is whether an ADU will increase the value of their home. While no contractor can guarantee future property values, many buyers appreciate homes that offer additional flexibility. Potential benefits include: Space for extended family Home office opportunities Guest accommodations Long-term housing flexibility Rental income potential Greater property functionality The impact on resale value depends on many factors, including location, construction quality, neighborhood demand, and overall property layout. To learn more, read: ➡ Could an ADU Increase Property Value? Can an ADU Generate Rental Income? For many homeowners, one of the most appealing aspects of an ADU is its potential to generate supplemental income. Depending on local regulations, market conditions, and individual property characteristics, an ADU may provide: Long-term rental opportunities Housing for traveling professionals Additional monthly income Greater financial flexibility Better use of underutilized property While rental income should never be the sole reason for pursuing an ADU, it can be one of several long-term benefits homeowners evaluate during the planning process. Understanding local regulations, operating costs, and property-specific limitations is an important part of making an informed decision. Learn more in our article: ➡ Can an ADU Generate Rental Revenue? What If Your ADU Application Is Denied? Receiving an ADU denial can feel discouraging, but it doesn't necessarily mean your project is over. Many applications are denied because of challenges such as: Setback limitations Utility constraints Lot configuration Drainage issues Placement conflicts Building code concerns In many situations, homeowners are able to move forward after redesigning the project or exploring alternative ADU configurations such as: Garage conversions Basement ADUs Attached additions Smaller detached units Professional feasibility assessments often identify solutions homeowners may not have initially considered. Learn more here: ➡ Denied for an ADU? You May Still Have Options Bringing It All Together Every ADU project is unique. No two properties have the same layout, utility infrastructure, permitting requirements, or homeowner goals. That's why successful projects begin with education—not construction. By understanding your property's limitations, asking the right questions, evaluating current regulations, and working with experienced professionals, you'll be better prepared to make confident decisions throughout the process. Whether your goal is creating space for family, improving your property's flexibility, or planning for future housing needs, careful planning remains the foundation of every successful ADU project. Why Work With Landmark Associates? For more than 20 years, Landmark Associates has helped homeowners, property owners, and commercial clients throughout Massachusetts navigate complex construction projects with confidence. Our approach is built around: Clear communication Professional project management Honest guidance Experienced construction oversight Quality craftsmanship Rather than rushing homeowners toward construction, we focus on helping clients fully understand their options before making significant investments. Our goal is simple: Help homeowners make informed decisions and build with confidence. Schedule an ADU Consultation If you're exploring the possibility of adding an ADU to your property, the best first step is understanding what's realistically possible. A professional consultation can help you evaluate your property's feasibility, identify potential challenges, and outline practical next steps before investing in design or construction. Whether you're just beginning your research or ready to move forward, Landmark Associates is here to help you navigate the process with confidence. Contact Landmark Associates today to schedule an ADU consultation and discover what's possible for your property.
By Caroline Brodsky June 30, 2026
Can an ADU Generate Rental Revenue?
By Caroline Brodsky June 30, 2026
What Massachusetts Homeowners Should Know if Their ADU Plans Hit a Roadblock Receiving news that your Accessory Dwelling Unit (ADU) project cannot move forward can be discouraging. After spending time researching, planning, and imagining how additional living space could benefit your family, a denial may feel like the end of the road.  Fortunately, that's often not the case. Many homeowners who receive an ADU permit denied in Massachusetts discover there are alternative paths forward. In some situations, a revised design, a different ADU configuration, or a more thorough evaluation of the property can help overcome challenges that initially seemed impossible. Every property is different, and understanding why an application was denied is the first step toward identifying a solution.