Communicating with Contractors: How to Express Expectations & Move Jobs Forward

Communicating with Contractors: How to Express Expectations & Move Jobs Forward

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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In Part I, we talked about what it takes to sell yourself to a local contractor (in a way that will inspire them to actually get back in touch with you in a reasonable time frame). Of course, just getting a call back is hardly the end of the process. In fact, it’s literally just the beginning. You still need to get a bid from the contractor, potentially haggle over costs, approve the bid, get them started on the work, get them to update you about the work (if it’s a longer-term job), and get them to tell you when they’re done.

Communicate Your Expectations

The best thing you can do to make that process flow easily is communicate your expectations in terms of your desire for return communication. Each time you send anything to a contractor, that communication should include a mention of what you’d like to receive next — and when.

Related: The Investor’s Complete Guide for Hiring a Trustworthy Out-Of-State Contractor

For example, when you first reach out to a contractor for a bid, be specific. Include in your work order a line like, “Please provide a rough date for when you can provide an estimate, and approximately how long it will take you to complete this job (understanding that both are flexible by nature).” This line has a lot going on. First, by asking for a date for the estimate, you ask the contractor for a commitment. You can put the day after that into your calendar with a note that says, “Remind the contractor you need an estimate on X job.” Furthermore, it requires that the contractor get back to you with the date. This establishes a pattern of communication.

Keep Things Moving Forward

When you follow up with the contractor the day your calendar reminder pops up (because very few contractors will get back to you), you’ll reinforce the pattern by requesting that they get back to you again.

The email you send out in response to their estimate and completion time (after you’ve approved the estimate) should include a similar line that says, “Please confirm when you can start this job.”

Also, if you’re working with anything less than large-scale, corporate-level contractors, warn them now that you’re going to require them to submit pictures and/or video of the completed work for your records.

Related: Communicating with Contractors: How to Start the Relationship Off Right

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Tracking the Job to Completion

Once the work starts, you’ll want to monitor progress. If you don’t, you may get stuck last on the contractor’s priorities list. This is where you want to be careful — no one likes to be micromanaged, especially contractors! Use the completion time they submitted to determine if it makes sense to check in once or twice per week. You may end up just checking in once at the end if it’s a short job. Set yourself a new calendar reminder each time you check in with the contractor. This way, you don’t get busy and forget.

Once the job is nearing completion, politely remind them that they agreed to provide you with video or pictorial evidence of the quality of their work (and that you will be holding off on paying the invoice until you receive them, if necessary).

Once you have their evidence (and their invoice), you can send the final — and in some ways most important — of the messages to the contractor. That’s the one that says, “This is how I felt about working with you.” And if that feeling is positive, “and if you felt similarly about working with me, I’d like to continue to offer you occasional work in the future. Would you be willing to take my calls?”

Because ultimately, an ongoing relationship with a good contractor is one of the best things a landlord can have. It’s worth all of the effort put into effective communication.

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Do you have any of your own tips for communication with contractors?

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