7 Strategies for Hiring the Best Freelance Help

Small businesses are increasingly using freelance help, and the reasons aren’t hard to understand – there’s a large pool of freelance experts out there, with a wide range of skills, willing to start work pretty much on the spot as you need them.

This means you can complete projects quickly, and using freelancers can be very cost-effective, because you’re not paying health care and other employee benefits. Freelancers are also available in pretty much every field – from IT through design, writing, and website creation, to basic labor.

Hiring Best Freelance Help

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They are also a flexible asset, which probably explains their increasing popularity – rather than having someone on the staff filling a niche you rarely need, they can be brought in on an ad hoc basis for a few hours as required. This also helps you to order and minimize your cash-flow.

There are some important strategies to consider when hiring good freelance help, seven of which we will look at below. Let’s get going!

1. Define the Type of Help You Need

The first thing you’ll need to consider when hiring a freelancer is the type of help you need. If you’re planning to use an online freelance resource, knowing exactly what type of help you need is a basic step.

Break your project down into its basic elements to understand what you need, and write out a brief clearly stating what needs to be done. This will help you to clarify the type of help you require, and will also help the freelancer when they come on board.

Bearing in mind that most freelance websites are international, it will pay to stipulate that you need someone fluent in English (or your own main language) to avoid misunderstandings. Clear communication is really important, so the fewer obstacles you put in the way, the better.

2. Evaluate Resumes and Portfolios

Never start by looking at prices – you should be evaluating resumes and portfolios by searching for experience relating to the kind of work you want to have done.

Remember, you usually get what you pay for. There’s a market price for work, and if someone is very much cheaper, there is usually a reason. It pays to look through any documentation very carefully, and particularly samples of work, to get a feel for the skillset of the person or people you’re evaluating.

If you’re looking at a series of resumes and portfolios, try to create a tick list of must have qualities and experience, and check every freelancer you’re interested in against them.

3. Look at Their Sample of Work

It’s not a bad idea to ask freelancers to agree to undertake sample work (a short blog post, for example), which will give you at least some idea of whether their work will fit within your setup.

A word of caution, though – freelancers won’t take kindly to being asked to do anything lengthy for free. Be aware that they quite rightly expect to be paid for their efforts, and while they may be happy to take on a short demonstration, they won’t want to produce anything substantial.

If you ask to check their work (and this can be wise, because in some fields such as journalism, final copy can be heavily edited), don’t ask for something that takes more than 20 minutes to complete.

4. Ask the Right Questions

If you decide that you really need to judge your freelancer face to face (either by video chat, or in person if they live locally), you’ll need to think carefully about the questions you ask.

Crucially, you need to make sure your freelancer will be able to deliver by your deadline and to your standards. Explain the level of guidance available, and find out what they expect. If there are gaps in their resume, ask questions to fill them, and find out in their own words how they think they fit with your project.

You also need to make sure they are willing to take on your company’s values and practices – if you have particular procedures that they need to adhere to, now is the time to make this clear.

5. Obtain Realistic Recommendations

If the freelancer offers contacts for recommendations, take them up – but bear in mind they’ll almost inevitably be choosing people that they know will praise them and their work.

If you have access to a resume, you may want to check the references against their most recent work. If the referees are not on that list, it may just mean they’ve moved on – but it could also be a red flag.

You should ask your freelancer to provide a contact for a recent employer as a matter of course. If they’re not willing to provide one, treat them with caution.

6. Consider How to Interact With a Freelancer

Because your freelancer will likely not be working in your office, you’ll need to make regular progress checks, particularly if this is the first time you’ve worked with an individual.

The freelancer will also appreciate any feedback you are able to provide. You will find they also enjoy the security of knowing their work is meeting your expectations, rather than getting to the end of a contract only to find their contribution is not what you’d hoped for.

It’s a good idea to draw up a contract that protects both your interests and those of the freelancer. Spell out what you want to achieve, any intermediate targets that should be met, a timetable, and how payment will be made (e.g., project-based, with a retainer fee), as well as who owns the rights to the work.

Include a clause protecting you in the event that the freelancer leaves the project, perhaps by stipulating that final payment is due on project completion, for example. Stipulate that the freelancer is expected to work for a particular period of time, or until the work is completed.

You also need to make sure that the way you’re using your freelance help doesn’t mean they are technically considered as employees under US law – there’s a good post here that goes into the details. Specifically, you should issue a Form 1099 for any independent contractor.


For small businesses, using freelance help is an increasingly popular way to get work done quickly and cost-effectively. However, to make sure you get the best help out there, bear these important points in mind:

  1. Analyze your project to understand the type of help you need.
  2. Create a checklist of experience and qualities you want in your freelancer.
  3. Ask the freelancer to complete a sample task (but make it short).
  4. Ask freelancers about any issue you feel is relevant to your project.
  5. If you’re concerned about references, contact a previous employer.
  6. Provide your freelancer with regular feedback.
  7. Draw up a contract that protects you and the freelancer

Have you ever hired freelance help, and what did you think about the experience? Let us know in the comments section below!

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