Questions to Ask Before You Hire a Contractor - Article Banner

Maintenance is getting more expensive, just like everything else. 

Whether you’re paying for a preventative HVAC service call, a minor repair, a major roof replacement, or some updates and improvements during a turnover, your costs are likely to be higher than you anticipated. 

That doesn’t mean you should cut corners when it comes to working with professionals. 

It’s important to continue taking care of the minor issues and the major repairs. This is what protects the condition of your property and increases the value of your investment

How can you do it cost effectively without wrecking your ROI? 

By partnering with a great contractor and their team of vendors and subcontractors. 

Where do you find a great contractor and how do you know they’re the right person for the job? 

You ask for referrals, and once you have those referrals, you do a little research and you ask your potential contractor a lot of questions. 

It’s not always easy to find contractors you can trust, especially if you’ve never worked with them before. We always start by confirming the contractor is licensed and insured. We evaluate experience and qualifications, and we look at the previous work they’ve completed that’s similar to the projects we have in mind. 

And then we come to the point where we want to interview a potential contractor and ask some questions. 

What should you ask? 

We have some great starting questions, which we’re sharing with you today. These questions should lead to larger discussions that are likely to answer even more questions that you didn’t even know you had. 

Before we get into the questions you should ask, let’s talk about why having a contractor you can trust is so essential to the effective leasing, management, and maintenance of your investment property in Cleveland

Aren’t All Contractors the Same? 


Definitely, no.

It matters who you hire, and this is why. 

  • Quality of Work Leads to Better Outcomes for Owners

When your property needs something fixed or replaced, you want the problem taken care of correctly the first time. This is why a licensed, experienced contractor is the best and safest way to go. An excellent contractor will lead you to a team of professional plumbers, electricians, painters, roofers, and other repair people who have the experience and the expertise required to complete all the work you need correctly.  

If something goes wrong or the issue isn’t completely resolved, a reputable contractor will come back to check on their work and make sure they find a solution. Licensed vendors and contractors are committed to keeping their customers happy. They’re going to stand by their work and avoid cutting corners. 

  • Bad Contractors Invite Risk and Liability into your Rental Business

Some minor repairs can likely be handled by a handyman. If you simply need a piece of drywall patched, send your handyman or do it yourself. But, if you have a major project that needs attention, you don’t want to hire someone who doesn’t have a business license or worker’s compensation insurance. 

What if someone you hired to fix the roof falls off a ladder and breaks his back? If they don’t have a license or insurance, you’re likely going to be sued. Not only will you be required to cover the medical expenses, you’ll probably face claims for lost wages and distress. That can be an expensive lawsuit.

It’s not worth the risk. Don’t hire anyone who doesn’t have adequate liability and worker’s compensation insurance. Ask for proof of that insurance before you hire a contractor, and make sure they’re requiring adequate insurance and protection from their subcontractors. 

  • Contractors are also Working with Tenants 

Maintenance impacts your tenant retention rates. Failing to respond immediately to maintenance and repair needs will result in frustrated tenants who do not trust you. When you send over a contractor who is disrespectful, messy, or rude to your tenants, you’ll likely lose those residents when the lease ends. 

Tenants are customers. You owe it to your residents to send high quality, professional workers over to the property. Tenants don’t want to open the door to someone who has not been properly screened. Your residents want to know you’re sending a professional who is licensed, insured, and respectful.  

Ask Questions about How a Contractor Conducts their Business

Some of the first questions you ask should be about how the contractor works and what they look for in a project. Understanding a contractor’s business values and operations will tell you if you’re on the same page in terms of scope of work, logistics, and planning. 

Essentially, you’re asking if you’ll work well together.  

Ask these questions when you meet to interview contractors and get to know them better: 

  • How many years have you been in business?
  • Why did you become a contractor? What did you do before this?
  • What kind of training and education do you have?
  • How do you stay up to date on your area of specialization?
  • Do you work with subcontractors? How are they chosen? Will they be the same every day or are different people brought in throughout the project?
  • Do you offer warranties? How do you stand by your work?
  • What kind of insurance do you carry?
  • How do you dispose of garbage and waste?
  • What are your general working hours?
  • How do you handle it when work falls behind? 
  • What will our communication be like?

You’re asking questions like these because you’re looking for a sense of what it will be like to have your contractor and their team at the property. You need to know if the same crew of people will show up every day or if there will be different workers coming and going. You want to know if you can expect them before daybreak or on weekends. 

Always ask how a contractor handles permits, disputes, and disruptions. What will your requirements be when they’re planning the scope of work, pulling the necessary permits, and scheduling the required inspections? 

Ask How They’d Approach the Unique Needs of your Property

Those initial questions should have you feeling pretty confident that this is a contractor who is dependable and professional. If you didn’t like their answers, you can thank them for their time and move on. But if you did like their answers, you’ll need to ask some questions about how they will handle the type of work that you will need at your property. Whether you need help with a complete rehab or you’re trying to renovate the entire first floor, you might want to ask questions such as:

  • What kind of projects have you done like this? Can you show or cite some examples? 
  • Will you provide a quote? Is it estimated or fixed? Is it itemized?  
  • What is the realistic timeline for this project? 
  • Can you apply for and obtain the appropriate permits? 
  • How do you handle surprises or setbacks?
  • What type of payment arrangement can I expect? Am I paying upfront in full or after the work is complete? 

These questions will allow you to get to know the contractors you’re interviewing. You’ll have a way to understand how they do business and what they can do for you in terms of the work you need at your rental property. Always measure the scope of work against the cost of the project as well, and make sure you’re getting the value you expect. 

You’re looking for a consistent set of systems and business practices, but you also need some flexibility, especially if the work doesn’t go as planned. 

Where to Find Potential Contractors for Cleveland Investment Properties

Finding ContractorFinding a qualified contractor isn’t easy these days, with a labor market that’s struggling and a high demand for the type of work that contractors provide. It might require a little bit of digging, especially if you want to find a good one. 

Use online resources and check for great online reputations and positive customer reviews. If you don’t want to go straight to the internet, you can also talk with your personal network and ask for referrals. If you notice another property in the neighborhood having work done, for example, check in with the homeowner and ask about the contractors. 

We know owners have also had luck, by inquiring at local hardware stores. Talk to real estate agents, property managers, and even brokers and other service providers. Your cleaning crew might know someone who does roofing, or your HVAC technician can probably put you in touch with a contractor they work with from time to time. 

Always verify licensure and insurance. Always do some initial online checking around so you can get a feel for reputation and reliability. Then, have a conversation. Ask all the questions that come to mind, and don’t hire any contractors that are not able to answer your questions. 

We understand the importance of contractors. In fact, we wouldn’t be able to provide our exceptional maintenance and management services without a reliable team of vendors and contractors. If you have any questions about what to ask or where to find a contractor, contact us at IIP Management. We work with owners in Cleveland Heights, Lakewood, Lyndhurst, Parma, Solon, and South Euclid (Cuyahoga County).