What You Don’t Know About How Long it Takes to Hire Freelancers

Can I be honest? Most of the hiring advice I see out there for bloggers and online businesses is total crap.

And maybe you’ve tried what other online business owners have recommended before… like one big-name educator who swears by hiring team members in three days based on gut intuition alone, or a speaker at a conference I attended last year who recommended starting to build a team by hiring family and friends first.

Some people advise finding the cheapest freelancer you can find; others recommend hiring full-fledged employees. Then, there’s what I refer to as the bandaid approach: hiring a VA because someone said they’re great and can handle allllll your miscellaneous needs.

Listen: While these approaches might work for some people, most of these success stories are highly anecdotal. They’re usually the exception, not the norm.

Truth: Hiring for your online business takes some time.

You can’t call your bestie, ask her to take over your content calendar, and expect for all your problems to be solved. You also shouldn’t anticipate finding your next dream hire in three days.

And, while virtual assistants, affordable freelancers, and employees might have a place in some people’s businesses, I’d be willing to bet you need a specialized freelancer who knows what they’re doing to handle a specific piece of your business.

How do I know? Because that’s what most of us in the online entrepreneurial space need.

And while it doesn’t happen overnight, I want to walk you through a realistic timeline for hiring a freelancer that’s RIGHT for your business.

Here’s a realistic sample timeline for hiring a freelancer.

It all comes down to my philosophy, “Hire slow, fire fast.” Even if you are DESPERATE for support and need help, like, yesterday, rushing this process only leads to management messes and wrong picks down the line.

Try following this timeline instead:

Week 1: Develop the job posting

It might sound obvious, but you have to start with a super attractive job posting. This may sound extreme but it’s true: Your job posting determines who applies and who doesn’t. 

Most of my research on understanding freelancers has centered around what’s attractive to high-performers. And I’ve found the best freelancers are very selective about the jobs they apply for and incredibly savvy at spotting red flags. 

The most important things to have in the job posting are: 

  1. The title of the role

  2. List of responsibilities

  3. Preferred qualifications

If you’re wondering where to start with drafting a fabulous and attractive job posting, check out this article

Week 2: Edit and refine the job posting

Give yourself some extra time for editing and refining the job posting. Taking time to be thoughtful and intentional here can save you a lot of time and energy down the road because you’re more likely to have more high-quality options applying to your role. 

Is the job title appropriate for the responsibilities? 

One of the biggest mistakes I see bloggers and online entrepreneurs make when it comes to hiring is looking for a virtual assistant when they really need a writer, social media manager or project manager. 

If you’re thinking about hiring a virtual assistant, project manager or online business manager, check out this article for additional guidance

When you look at the responsibilities, are you expecting one freelancer to cover three positions? 

If the answer is yes, don’t beat yourself up. If hiring were simple and easy, everyone would be doing it. 

And it’s important to strike the right balance. All too often though, online businesses put out job postings that have unrealistic expectations. Here’s an example of expectations for ONE position that I recently saw posted in a Facebook group: 

  • Manage Contact List/Tags on Kajabi

  • Update Sales Calls/Leads Spreadsheets

  • Research speaking/networking opportunities

  • Schedule Podcast interviews

  • research podcast guests

  • Create content calendar (email, social, podcasts)

  • Repurpose email content for blog posts

  • research keyword optimization for blog posts

  • SEO

  • Create PDF guide freebies

  • Schedule Emails (kajabi)

  • Social media trends/hashtags research

  • Facebook ads research

There’s no way one person can do all of these responsibilities part-time, AND do them well.

Are your preferred qualifications too vague? 

The other danger is being too vague. If you only have one to three tasks in the position, it’s going to be hard to attract top talent. 

Week 3: Post the position

Where you post your job depends on the role and your objectives. Most people start with Facebook groups, LinkedIn, or freelance platforms like Upwork.

There are advantages and disadvantages to each… Some platforms are more expensive than others. Some are set up better for communicating with candidates.

Week 4: Review applications and collect work samples. 

If you don’t want to review applications until your eyes are ready to fall out, go through all of them and give each a quick thumbs up or down.

Aim for about 15 thumbs up regardless of the number of applications. And then, spend a few hours reviewing those applications in depth to decide who proceeds to the next step. 

Week 5: Review work samples and schedule interviews.

Traditionally, the hiring process involves deciding whom to interview based on the applications. 

What they don’t tell you is that most people who are chosen for interviews know someone who knows someone… usually the recruiter or the hiring manager. 

When it comes to hiring freelancers, I like to squeeze in one step between reviewing applications and interviewing your favorite candidates to help narrow options down further and see who really would be a solid fit for the responsibilities.

The next best step is to ask the top 10 candidates to submit a work sample. This increases your chances of selecting the best candidates for interviews. And it also helps prevent wasting time on the duds. 

Week 6: Conduct interviews and make a decision.

I know interviews can be the most dreaded part of the hiring process, but they’re absolutely vital.

It allows you to pick up on cues, chemistry, and details that just don’t translate on paper or via email. Plus, you can get direct answers from candidates you’re on the fence about to make your decision a little easier.

Nothing can replace the human-to-human aspect of interviews, but if you’re nervous or not sure of how to conduct one, this article lays out everything you need to know.

Week 7: Make the offer and decline the other candidates.

Yay! Now you know for certain who the right fit is based on their application, work sample and stellar interview.

It’s time to make your offer, AND decline those who didn’t get it by sending an email. This is an often-forgotten piece of the hiring puzzle, but it’s important to leave everyone who interacted with you and your brand with a pleasant experience, even if they didn’t get the job.

To learn about what to say when declining candidates, check out this resource.

So, how long does it take to hire a freelancer? 

Can you hire a freelancer in three days? Maybe. 

But, hiring fast also increases the risk that you’re not going to have enough time for the best freelancers to find your posting. Or you’ll feel rushed to pull the trigger on someone you’re not crazy about (been there). 

Even if you have a large following and can generate a lot of applications quickly, you won’t have enough space to give the applications, work samples and interviews the time and attention they deserve. 

That’s why I advocate for the philosophy: Hire slow. Fire fast. 

I know the timeline I’ve outlined in this post seems long. Maybe even ridiculous to some. But, when you take your time to be thoughtful and intentional throughout the hiring process, you’re much more likely to find a talented, high-performing team member who sticks with you for the long-term. 

Want more feedback, support & guidance in your hiring journey?

In The Hiring Fix, you get direct coaching from me plus a detailed plan to hire a team with ease.


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