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How to find great contractors for your online business: 5 steps

October 25, 2022

Business Planning

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how to find great contractors a pinterest image with people lined up to interview

If you’ve been following along in our hiring series you’ve now reached the point where you are ready to hire, but now you’re wondering how to find great contractors for your online business.

If you’ve missed our earlier lessons check out the following:

Why you should hire a team for your small business: 5 great reasons

What not to outsource in your online service business: 11 critical things

What you should outsource first: the 5-step process to help

As a brief reminder, thinking about how to find great contractors should be approached as a thoughtful and intentional process. You want to find the perfect fit and it is better to not hire at all than hire the wrong person just to get the work “done”. That’s the whole reason why you want to know how to find great contractors right? Not just anyone but great!

My 15+ years of financial and operational experience compels me to remind you that turnover costs your company a buttload of money! The more often you must do this because you didn’t know how to find great contractors, the more money you will waste.

Turnover happens but it should NOT happen because you lack the skills necessary to hire effectively and know who you really need in the job.

How to find great contractors – Step 1: The job description

The secret for how to find great contractors starts with the job description. The main way that people fail at writing job descriptions is they write something general and broad. I find that women struggle with this most because they have been conditioned to not seem demanding or needy.

But if you aren’t clear on what you’re looking for – the people applying for your job won’t be clear on whether the job is for them. You will lose out on great candidates who can’t picture themselves in the role and get applications from people with no standards who literally applies to everything. These are not the people you want.

Your how to find great contractors job description must address the following things:

  • Company culture
  • Specific expectations about things you value (like attendance, responsiveness, quality, communication, etc.)
  • Specific deliverables
  • A timeframe for how many hours the person should expect to put in
  • Any personality items that are important to you

I also feel compelled to remind you that you should not (nor are you legally allowed to) discriminate against someone based on race, age, gender, or religion.

How to find great contractors – Step 2: The job posting

Now you may think that the best practice when considering how to find great contractors is just to blanket job postings everywhere. I disagree strongly. Posting jobs on Facebook, Indeed and other places like that will get you a bunch of fluff and junk to sift through for maybe one great candidate.

So how to find great contractors?

Upwork. Upwork is a pool of people intentionally seeking contract work (not always true in other places) and provides several key features. First, you can see their ratings from other businesses that have hired them. Second, Upwork has protections in place for you as the hiring entity that you don’t have to pay if you don’t get your work. There is a screenshot captured work tracking, and weekly time tracking with time limits so you can keep costs under control. It’s a great place to find hourly help and you WANT hourly help.

Why do you want hourly? Because you are test driving (which we’ll get to in a minute). You want to really know if the job description you made is correct, the scope of work is right, the time scope is on point and the person is worth it. Hourly work allows all that without a long-term commitment.

So, post your job description on Upwork and see what kind of applicants you get. If you need inspiration for how to write your post do some searching on Upwork for how others are titling and tagging their job descriptions and see what kind of traffic they are getting. You don’t need a million applicants, but you want options. Upwork is basically a goldmine for those who want to know how to find great contractors.

How to find great contractors – Step 3: The Screening

how to find great contractors man saying "No, I hire good people who give a shit"

Now, you’ve had some folks apply and it’s time to start screening. The screening process is one of the most overlooked components when business owners are thinking about how to find great contractors.

But hiring is a lot like dating. It is a good idea to create a set of non-negotiables before you start the hiring process so that it’s easy to weed people out before you meet them.

I will use my own business as an example, but you should create criteria for screening that matters to your business. Because really, while I’m giving you all kinds of advice no one can tell you how to find great contractors if you don’t know what you’re looking for.

Since I own a financial firm, accuracy is one of the most important qualities I look for. I also look for people who are open to feedback and can follow sets of instructions that may contain multiple steps. Responsiveness is the last key attribute that I look for.

I also don’t hire for experience as much as motivation. Why? You can’t make someone want to do a good job, but you can easily teach them how if doing a good job is naturally important to them.

So, my how to find great contractors criteria are as follows:

  • Spelling and grammar must be correct – including capitalization – again, I’m looking for accuracy and attention to detail so if their resume is full of typos or they didn’t capitalize their own name (this has literally happened to me) I will not hire them
  • Did they answer my written questions in Upwork fully? I usually ask multi-part questions in Upwork to see if the person will pay enough attention to read the questions and address each part. This is my version of seeing whether they pay careful attention to all the words in the instructions.
  • Have they done something to advance themselves at each job they’ve had? I don’t care what job it is, have they done their best to excel? One of my best hires was at my corporate job and the gal I hired had no clinical experience at all. In fact, she worked in housekeeping. She was clearly very young and smart and could have been doing lots of things and most people would treat housekeeping like a job you shouldn’t try at. I mean, cleaning bedpans at the hospital is not glamorous by any means. On her previous review in that job, she was given a “Far exceeds expectations” which, after all my years at the company, I knew was hard to achieve. I immediately wanted to meet her because if someone gave their all at a thankless job like housekeeping, I wanted to see what she could do for me. I did hire her, and the recruiter said that this gal had been trying to get work in the clinical side of the company for two years, but no one would hire her without experience. Their loss, she was fantastic!

After they pass this test, I give them a call or email and they have 24 hours to respond. If you are actively applying for jobs 24 hours is completely reasonable. We live in the age of cell phones and constant connection and there are few places you can go where you literally can’t respond to a call.

This is the time to be strict, not give people grace. You WANT to screen people out here. You don’t want to start by cutting people slack, that always ends badly. They need to earn slack once you’ve hired them and you know they are great!

How to find great contractors – Step 4: The interview

After you’ve screened them, I recommend a two-step interview process. When you’re trying to determine how to find great contractors, you want to first start with a phone interview.

Why? So that you can tell how they sound over the phone. It also gives you an opportunity to screen them again without seeing them. If someone sounds gruff or like someone who doesn’t fit with your idea of customer service, or the vibe is just off then you can simply not invite them back for a video interview.

Have a few questions ready for the phone interview. I recommend ones like this:

  • Tell me a bit about yourself
  • Tell me what interested you about this position
  • How do you see this job fitting into your overall vision for your career

These questions will help you assess them on a personal level, whether they have a clear understanding of what the job is and if they are even thinking about how this position fits into their long-term plans.

This process again should screen some folks out. Because the key to knowing how to find great contractors is a stellar screening process. By the time you get down to video interviews, 2-3 candidates are ideal.

If you already have a team, it’s a great idea to involve them in the video interview so that they can provide feedback about the fit of the new person into the team culture. Multiple sets of eyes and ears help weed out things that you may not notice but others will.

The questions I like to ask in this interview center around the candidate giving me specific examples of how they’ve handled certain situations. It’s a challenging type of interview style but it works super well. I’ll give you some examples below but what I’m looking for is a specific example and if they say what they “would do” or give a general statement of how they “would” handle things then I know they didn’t really listen to the question.

Some examples of these questions are:

  • Tell me about a time when you gave exceptional customer service
  • Tell me about a time when you had to solve a problem that you didn’t feel you had all the information to solve
  • Tell me about an experience you’ve had working with a diverse population
  • Tell me about a time you made a mistake, how did you find out about it and what happened
  • How do you actively manage your stress
  • Tell me about the best and worst boss you’ve ever had

For the question that is “tell me about a time” you should get a specific story and it should have a happy ending – like it should all turn out well. I can’t tell you how many times I’ve asked those questions and in the end, the customer was still unhappy. That’s your customer service example? Pass!

I ask about diversity because inclusion is important to my business, and I know it’s so much more than race or language (things people typically focus on).

Finding out how they relay a story of them making a mistake is also very telling. I know that mistakes happen so if they say they’ve never made one. Red flag! If they made one, caught it, and then put a system into place to prevent it from happening again? Gold star.

If they do not have an active strategy to manage stress – they need one.

And lastly, I just like to hear them describe bosses because they have no idea what my management style is like and I will know which category they would put me in based on their description.

Always complete all the interviews before you hire and be thoughtful about it. The key to knowing how to find great contractors is to take it slow and put them through a rigorous hiring process.

How to find great contractors – Step 5: The test drive

how to hire great contractors a girl with open arms and the words "you're hired!"

Finally, we have come to the hire! You’ve selected a person and you want to hire them. It’s time for the test drive.

This gives you both a chance to assess whether it’s a good fit without feeling like you must continue if either of you is not feeling it after a month or two.

I suggest having a strong scope of what will occur during that trial period. They will complete x tasks or a specific test project of sorts and then you will both come together and reevaluate. It’s always good to go more slowly than you think is necessary so that you don’t invest more time/money into someone that ultimately won’t be a good fit.

Conclusion – How to find great contractors

I hope you’ve found this guide helpful to wade through how to find great contractors with intentionality and confidence.

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Hey, I’m Sarah, Your New CFO.

I help take the confusion out of finance . 

I've spent more than 15 years working in both the corporate and small business sector helping businesses both large and small find creative and new ways to save money while increasing value and profits. 
And nothing gets me more excited than helping small business owners create more profitable businesses.
Why? Because I know exactly what that means for you. It means more time to call your own, more trips, more time with your kids, less time worrying about money. 
I founded Leo & Vern in honor of my grandpa, my favorite person ever, who used his knowledge as an accountant to leave a legacy behind for our family. So to me, carrying on his legacy of helping others create their own legacy? Priceless.






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