Communicating with Contractors: How to Start the Relationship Off Right

Communicating with Contractors: How to Start the Relationship Off Right

3 min read
Drew Sygit

Drew is a classic overachiever, bringing intensity and passion to everything he does. While in the mortgage business, he rose to a VP position at the first broker he worked for and then started his own company.

In the pursuit of excellence, Drew obtained several mortgage designations and joined mortgage and several affiliate association boards. He also did WebX presentations and public speaking engagements. It was during this time, he started personally investing in single family rentals, leading him to start Royal Rose Property Management with two partners. He also joined the board of a local real estate investors association, eventually becoming its president.

The real estate crash led to an offer from the banking industry to manage a Michigan bank’s failed bank assets they acquired from the FDIC. The bank went on to eventually acquire four failed banks from the FDIC, increasing from $100MM in assets to over $2B while he was there. After that he took over as president of Royal Rose Property Management and speaks at national property management conventions.

Former board member of Michigan Mortgage Brokers Association, Financial Planners Association of Michigan & Mariners Inn (nonprofit)

Former taskforce Member of Michigan Association of CPAs (though not a CPA)

Involved in mortgage business for over 18 years, obtained mortgage designations: Certified Mortgage Planner, Certified Mortgage Consultant, & Certified Residential Mortgage Specialist

Board member of Real Estate Investors Association of Oakland; President since 2012

2009-2012 Shared-Loss Manager for Talmer Bank (now Chemical Bank) handling FDIC failed bank loan loss strategy, reporting, REO management, collections, & gap analysis

Started investing in real estate in 1996

President of Royal Rose Property Management since 2001

Drew received an MBA from Wayne State University, concentration in Finance & Marketing.


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Like most property management companies in our area, we don’t have a stable of permanent contractors that work for us. What we do is deal with a relatively short list of contractors with whom we’ve established relatively mutual trust. Over time, we’ve learned the hard way that nothing is ever 100 percent in the property management game—we’ve had our share of relationships with contractors that ended badly and one that is being closely monitored in recovery mode at the moment.

The point is, we’ve communicated with contractors more over the past year than 99.9 percent of the greater population and would like to think we’ve got some experiences you can benefit from.

Getting a Response

The first big hurdle you have to clear when talking to a contractor is getting a response from them in the first place. If you’re talking to a genuine professional organization, the kind with an office and staff, they may not communicate as fast as you’d like, but they do communicate. You will pay for this kind of professionalism, though, with higher prices. If you’re a DIY landlord or your property just isn’t worth dozens of thousands of dollars, you probably aren’t looking to indirectly pay this type of contractor’s office and advertising expenses.

So, if you prefer to get pricing by working with smaller contractors, the likelihood of them calling you back quickly is dependent on factors like:

  • How many jobs are they currently juggling?
  • How much do they trust you to be worth their time?
  • How easy (or “easy-per-dollar”!) does your scope of work sound?
  • How much work are they likely to lose out on the future if they ignore you?

Related: How to Work With Contractors and Manage a Job Site as a Flipping Newbie

It’s easy to think, “Well, I can’t control whether or not the contractor calls me back,” but if you look carefully at that list, there’s only one item that is entirely out of your control—or two if you don’t have a standing relationship with the contractor. The presentation of the job and the presentation of yourself are entirely within your control.


Selling the Scope of Work Itself

Of course, there’s a delicate balance to be struck, because if you go overboard on selling the job as easy (/per dollar), you’ll end up ruining their trust in you when it turns out to be a pain in the backside. You have to be honest about the details of the job—what you don’t have to do is include any amount of non-factual commentary on how negative you feel about the job. Just present them with the basics honestly, and if there are any positive side-comments you can make, feel free.

Related: 4 Reasons You’ll Never Find a Good Contractor (Insight From an Investor/Contractor)

A Professional First Impression

If you want to present yourself as trustworthy to a contractor you don’t have a standing relationship with, the best way to do that is to present yourself as a long-standing professional:

  • Introduce yourself as a landlord/property manager with x units/years of experience,
  • Present the scope of work on business letterhead (or in an email with a professional signature, with the attachment formatted in a professional manner),
  • Speak confidently and knowledgeably about the work required, about the contracting industry in general, and about the property/unit in question,
  • Have a website and a phone number the contractor can investigate on their own to establish your level of professional commitment to your properties,
  • And effectively present all of the same kinds of background details that you would look for in a potential business partner to figure out whether or not they were professionals.

By presenting yourself professionally and putting an honest-but-positive spin on the scope of work, you can dramatically improve your chances of getting a call back from a contractor—even one you’ve never contracted with before.

So we’ve covered everything up to the first “touch back” from the contractor—but of course that’s literally just the beginning. Check our next post for quite a bit more.

How do you start off relationships with contractors?

Weigh in below!