How to Avoid the Dreaded Contractor Hiring Mistake


by Melanie Benson Strick

Last week one of my new clients called in for coaching, feeling super frustrated that the online marketing service professional she had hired was not getting the job done. Ninety days after her desired “go live” date she still didn’t have a functional website.

This is not the first (nor the last) time I’ll hear this complaint I’m sure. So I started asking her what her interviewing process was like.

Her response is pretty typical of most entrepreneurs.

“Well, she was a referral so I didn’t really interview her.”

Oy. Not following a solid interview process is usually a bad start. About 5% of the time, a referral works out right the first time. But trust me…you don’t want to be in that 95% that doesn’t work out!

Everyone knows they should ask good interview questions. But when you are hiring a virtual contractor to do a specific project or type of work there is a VERY different way you need to evaluate their ability to deliver.

So I’m going to share a few of the tips that I teach all my clients in my Build Your Dream Team system to help you flush out weak or bad-fit virtual contractors BEFORE you waste your time and money.


1. Ask About Their Service Model

Many service professionals have learned how to leverage their time more effectively by building a team of sub-contractors. The problem is, most are not learning how to hire, train and manage these people effectively. So they end up with poor quality control. Or missed deadlines. Or subcontractors who are so overwhelmed that they aren’t able to keep up. Find out if they will personally do the work or if they are having someone else do it. You’ll also want to know if they have a backup plan if they are away from work for a period of time.


2. Explore Work Availability

Believe it or not, if you don’t have compatible work schedules you can go from “excited” to “distraught” within a matter of days. Many virtual service-based professionals are balancing multiple roles (working full time while building the business at night, a full-time parent who only does this work at certain times, or some who only work a few select hours a week!) Make sure their availability to work on your project fits your needs and expectations.


3. Ask About Boundaries

Yep, you need to have THIS conversation. You need to know if they have the courage to push back on you if something isn’t right. Don’t hire someone who can’t say no to you. But you also don’t want someone so stringent that they can’t adapt. Ask things like:

  • If you don’t agree with me what would you do?
  • If there’s a late night or weekend of work, will that be a problem for you?
  • How many other clients do you work with?
  • Do you have a limit to the number of new clients you’ll take on?
  • Is there anything that might happen that would cause you to want to leave?


4. Get to Know their “Energy”

We all have a unique way that we communicate, filter information and see the world. If you hire someone who is just like you but you need them to do tasks that you hate, you are going to be hugely disappointed! On the other hand, someone who is your “opposite” will most likely drive you crazy. Find out what their core processing style is (driver, creative, supporter or details) and how it fits with yours.


5. Vet Their Experience

I know it’s tempting to fill that gap in your team quickly but PLEASE don’t just have a “first date” then get married approach to hiring. A good service professional is trained to sell you on their services. You need to do your “due diligence” and ensure their ability to deliver.  Ask for work samples. Check references instead of just reading their online testimonials. And perhaps even have them perform a sample task for you to see how well it goes. You’ll learn a lot that’s important to your decision by properly vetting out their experience.


Most importantly, trust your gut. If you have a little voice that says, “don’t do it” then listen to it. You might not know why at that time but down the road you will be thankful when you find that perfect person.




Learning how to hire and manage a team isn’t always second nature for entrepreneurs, visionaries and creatives – but that doesn’t mean you can benefit from learning how to leverage the power of other people’s time and talent in your business. Get support, hire a coach, and most importantly, commit to following a proven process for hiring and you’ll end up with much better support teams.



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