How to Stay Smart When Hiring New Contractors! 5 questions to ask yourself before you start your search

When you’re hiring new team members, it’s easy to slide into the personal instead of focusing solely on the pragmatic.

If a contractor is warm and funny and you totally love her vibe, you may end up glossing over her stellar-but-inapplicable qualifications. She’d be a great addition to your team personality-wise, but doesn’t bring the right skills to the table.

If a contractor comes highly recommended by colleagues, it can be tempting to hire her even if you can’t afford her sky-high rates for more than a few months. It’s easy to forget that a team member is only a good fit if she’s both qualified and within your price range.

So how do you strike a balance? How do you make sure you hire accomplished contractors who fit your needs and your budget?

I’ve got 5 questions you should ask yourself before you even begin searching for new hires, and all of them can help you track down ideal team members!

New here? I also have the following posts to help women entrepreneurs outsource their business tasks like a boss:

And of course, you should definitely take my free quiz to find out the #1 task that you need to outsource to not only free up your time – but to give you the space to focus on revenue-generating tasks in your business.

Which tasks will this contractor own?

When large companies hire new staff, they always create a list of both qualifications applicants should have, and the job duties they’ll be expected to perform. Solopreneurs can and should do the same. Before you look for candidates, determine exactly which tasks and projects you want to outsource.

Do you need someone to handle correspondence, social media, and other communications-heavy work? Or do you need more help with graphics, Instagram staging, and design-focused tasks. Be sure the workload you’re handing off is comprised of non-income generating tasks that are currently sucking up your time–ones that need to be done but not by you, personally.

Once you’ve charted out the tasks, list the associated skills needed to tackle them properly. Using these two lists, you can pore over contractors’ past experiences and capabilities to find a perfect fit for your current needs.

What’s your budget?

Naturally, you want to hire team members who are talented, competent, and enthusiastic. You want the best you can afford. But it’s important to be honest with yourself about how much you can spend on an ongoing basis.

Decide what your budget will be, keeping in mind that this new contractor will handle non-income tasks and allow you to focus on the money-makers.

This means you may soon generate a slightly higher income overall … but don’t assume you’ll get a huge bump in revenue right away. Add a modest amount to your current average monthly income, and work backwards to determine what you can afford.

Need help? Try using this simple ROI tool to calculate how much you’ll save, and how much you can reasonably spend on contractors.

Do you have more time, or more money available?

I would never advise you to knowingly hire sub-par freelancers! That said, you don’t necessarily have to hire super-experienced, highly skilled folks right out of the gate. Especially if the tasks you need help with are relatively simple and easy to learn, it can be well worth the effort to hire a relative newbie and train her rigorously.

This is especially true if you have a tiny trickle of income and lots of time: You can’t pay big bucks, but you can train intensively. Hire a smart but inexperienced contractor at a low hourly rate, and balance your budget against your available time.

If you have no time to train or aren’t clear on how to explain your processes in detail, you’ll need to pay a higher starting rate for someone who has done similar work already and will get up to speed faster.

Who is your ideal contractor?

Now that you’ve determined which work will be assigned, how much you can pay, and how experienced you want your contractor to be, create a team member avatar.

Much like you’d create an ideal client avatar, consider what you want your new hire’s aptitudes, interests, and personality traits to be. This information will help you hone in on exactly what you’re looking for, beyond the hard facts and qualifications.

Who do your colleagues trust?

Naturally, you’ll need to take this information with a grain of salt.

Your fellow entrepreneurs may have wildly different needs and budgets, so their “ideal” contractors may be your worst nightmares!

But they may also be able to shorten your search for amazing team members by recommending current or past hires of their own, and can even give you the inside scoop on their strengths and weaknesses as freelancers.

You’ll want to screen each candidate using the information you compiled using the previous four questions, but consulting trusted colleagues for recommendations is a great shortcut to finding quality contractors.



I’m Melissa. I’m an entrepreneur, mom to two teens and a dog, and married to the love of my life.

I’m an outsourcing strategist for women entrepreneurs who are sick of struggling to get everything on their to-do list done while also growing their business and income. Hiring help will free up more of your time to focus on your big vision and the actual creation of your dream business. You’ll be able to earn more, reach more, and have the freedom you crave.

Obsessed with: adventure, camping, books, and essential oils.

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