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

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

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

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When Should I Hire? 4 ways to tell you're ready financially

You hear about it all the time; your business besties are telling you that you shouldn’t be doing it all on your own, but you keep asking yourself “When should I hire? How do I know I’m ready?” This post will walk you through 4 steps to make sure your finances are ready to hire whether it’s a contractor or an employee.

When should I hire – Pre-work: Know what you’re outsourcing

I know, it seems obvious but I’m going to put it out there anyway because if you are trying to decide if it’s the right time to hire but you aren’t sure what tasks you even need to outsource… First – go read 11 things to Never Outsource Then – go read What you should outsource first: The 5-step process to help Now, have you read them? Like, really read them and done all the steps? Are you still asking yourself "when should I hire?" Great! Okay good. Now you’ve done your prework and you know what you’re outsourcing. Believe me, the reason so many hires go south is failure to address this pre-work. It WILL make or break you. Just sayin'.

When should I hire – Step 1: Know your budget

I know you probably want a magic number here but to give you one would be wrong. There IS no magic number because it all depends on your business, your goals, and what you’re hiring for. Hiring can be scary to even the fact that you are thinking and asking yourself "when should I hire?" is great! I’ll give you an example. I hired my first bookkeeping assistant when I was still at my day job 32 hours a week, maxed out on time but earning less than $3k a month in my business. Some people would say that’s crazy. Hiring her freed up my time to market, finish my website, attend to the higher needs of my clients to make sure they were super satisfied, and I doubled my revenue in just 4 months.  Could I have done that without hiring? Probably not because I had ZERO time to focus on any of the tasks that it took to grow my business. Hiring someone allowed me to make more money because I wasn’t in the day-to-day as much as in the CEO role. I also know people who are making 5-figure months who haven’t hired anyone because they just don’t feel the need. You see why the question "when should I hire?" is not simply a number thing? The reason your budget is important is that I don’t want you to OVERPAY for something that is not directly impacting your ability to reach your goals. Now if you don’t HAVE a business budget, then this is the time to start! In fact, I have created a supremely easy-to-use Business Budget template that will have your budget whipped out in no time! It does all the calculations for you AND it uses Profit First (which if you haven’t read you totally should it’s GOLD!) You can even snag it for $50 off it's normal price!

So how do you know what is the right amount? It depends on what else is in your budget. If you run super lean and have some extra money to play with while still keeping your operating costs under 40% then use that as an initial guide.

When should I hire – Step 2: Act as if

One of the frequent things I hear from folks is that they are nervous to add staff because they are worried about cash flow drying up. They don’t want to bring someone on and then have to let them go because business takes a turn. This is probably the biggest reason people wonder "When should I hire?" My advice? Act as if you have already hired someone for 2-3 months. That means setting aside their salary amount from your budget just as if you had paid someone (putting it in savings is perfect). Why does this help? One, it gets you used to seeing what your budget looks like without that money. Two, it provides a buffer now of pay for that person so that IF you have a bad month, you’re still golden on paying them their due. Remember, one bad month or two isn’t the end. You have to make multiple wrong decisions or fail to take multiple actions in a row in order for your business to actually fail. Like you have to IGNORE a whole heck of a lot of signs flat out for that to happen – and you wouldn’t do that – you would act at the first sign of trouble. So, stop stressing, and act as if for a few months to build up a safety net.

When should I hire – Step 3: Get SOPs and processes in place

Step 2 is actually a great time to be working on step 3. Because you should NOT hire before you have some kind of SOP (standard operating procedures) and processes in place so that the person you hire will have some kind of idea what the heck they’re doing! I know you're thinking, "Sarah, this has nothing to do with when should I hire?" But bear with me. I promise you will not believe how little you realize you’ve hacked together until you go to write an SOP. My favorite tools for this? Tango and Loom. Tango is a Chrome extension that you can use (For free) that will screen grab and actually make an SOP for you that you can then edit a bit and go! It saves hours and hours of time and will help so much! Loom is great for walking people through the SOP process in more of a “live” fashion Since some folks do better with written and some with video instructions my ultimate recommendation is to do both. Next up you need some kind of system for task delegation, review, and monitoring. Whether you use Notion, Asana, Monday, or Clickup you need something that will streamline where your hire can find their tasks, mark them completed, communicate to you any questions, etc. Plus, you want to build checkpoints on the processes as well. Now if that sounds supremely overwhelming, I have recommendations! (As always!) If you have no idea what system you need: you want Ariana Rodriguez If you want Clickup/Dubsado wizardry: you need Leann Forbes Getting this in place does take some time and that’s why using the 2-3 months you’re saving up some salary buffer is an ideal time while you are still doing the work to get all your processes documented and systems in place.

When should I hire – Step 4: Create your perfect hire criteria

Now, just like anything else, I want you to approach this thoughtfully and in advance. Don’t just throw out a task-based job description without knowing the type of person who would be a great fit for your company. Because we've now gotten past "when should I hire" and we've gotten closer to "who should I hire" plus you need to have this part nailed down before you start the hiring process. Take some time to answer these questions: - What kind of person do I work well with? - What kind of person has always irritated me to work with? - What are key work habits that this individual must have to be successful in my company? - Does the person need experience or am I willing to train them? - Are there any things that are 100% dealbreakers for me? Political, personal, behavioral? Really the world is your oyster, and no one is going to read this. If you know you won’t get along well with someone with opposing worldviews, don’t hire someone who has them. Or if they hold fundamental views that are different from the values of your company – it’s not about right or wrong – it’s about whether they are a good fit. Once you have really thought about your perfect fit criteria you can use that as a jumping-off point for your interview questions. This way you know that you are asking questions that help identify whether people are the perfect fit or not. I bet you had no idea this was going to be the route we would go when you first googled "when should I hire" but I promise you will be glad you did! When should I hire – Go forth! It’s time! You’ve figured out your budget, saved, gotten your SOP and processes together, and defined your perfect fit hire. No more wondering, "When should I hire?" Now you can get on to the business of hiring with confidence knowing that you have thoughtfully approached both the operational and the financial components of the hiring process.

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