How to Avoid Disappointment When Working With Freelancers

All freelancers have a learning curve. Even the best and brightest need a little bit of time to get up to speed, especially if they’re handling multiple workloads! Most of us know this, and expect onboarding to be a gradual process, but what many entrepreneurs don’t realize is that, as business owners and team leaders, we also have a learning curve.

Even the best and brightest of us may hire the wrong person, bungle communication, or overpay for work before we get into a reliable hiring groove. Which is natural and normal … but super frustrating.

Luckily, our learning curve can be accelerated! By adopting a few simple practices—some preventative, some ongoing—we can make sure we always hire smart and never end up disappointed in our team members.

Sounds fabulous, right? Let’s dig in!

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.

Screen Freelancers by Creating an Application Process

You won’t be able to prevent every issue just by filtering through applicants to ensure they’ve got the right skills for the job. Some people look amazing on paper, but are tricky to work with in real life.

However, if you don’t do a little pre-screening of your candidates, you may end up interviewing tons of folks who couldn’t possibly handle the tasks you need done. Plus if a freelancer can’t follow instructions on an application form, you can weed her out right away!

Get Recommendations from Colleagues and Friends

Resumes and applications can only tell you so much, and picking a freelancer based on her social media or web presence can be a bit of a crapshoot. Going it alone can lead to hiring sub-par team members who end up disappointing you.

The quickest shortcut to hiring great help is to ask for recommendations from your peers and pals.

Who have they worked with in the past? Do their current team members have any extra capacity? If they don’t have any recommendations of their own, can they connect you to colleagues who might? Don’t be shy! Ask away!

Find Stellar Freelancers by Doing a Little Online Stalking

Hang on, hear me out! You don’t have to do any invasive sleuthing, just a bit of online lurking to see for yourself how skilled and helpful potential freelancers truly are.

Check out a few virtual assistant groups and pay attention to who is responding and answering questions on topics that are related to your business.

Don’t post in these groups for “help wanted,” since doing so may result in an avalanche of emails from imperfect candidates. Instead, reach out privately to those who look like a good fit.

Avoid Freelancer-related Disappointment by Setting Expectations

This tip comes up frequently, but with good reason: It is SO important, my dears! It’s perfectly fine to demand quality work from your freelancers, but only if they know exactly what you expect from them. Otherwise, they’ll disappoint you and you’ll irritate them.

Establish expectations clearly and early on in the relationship regarding communication, deadlines, quality of work, availability, and other important issues. And don’t just have an informal chat! Codify expectations by creating and signing a contract that clearly outlines what’s expected from both you and your team members.

On a related note, expect and be willing to pay fair rates. For instance, don’t expect a web designer to build your blog for less than you’d spend for a nice dinner out with friends. If you’re only inclined to pay bargain prices, you’ll only end up being disappointed by the quality of work.

Build Slowly by Starting Small

I always want to encourage bold entrepreneurs to trust their instincts … but diving into a massive project with a brand-new freelancer can lead to disaster, even if you absolutely adore her!

Start with small projects at first to get a feel for how you’ll collaborated before committing to long-term work. Easing into the relationship will help you gauge your new team member’s strengths and assign work she can excel at doing.

See? Nothing too complex or overwhelming, just a few best practices that will save you from headaches AND save your team members from letting you down!


PS – My VA Training Templates Library includes access to my own private list of over 100+ fabulous contractors to help you find and build your own dream team!

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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