7 Common Hiring Mistakes and How to Avoid Them

When it comes to hiring freelancers, I’m willing to admit that I’ve made my share of hiring mistakes. 

Even with 10 years of corporate experience in managing and hiring and a master’s degree in industrial and organizational psychology, it wasn’t enough to prevent wasting time, energy and money on making a few mistakes. 

One that stands out the most was in the fall of 2017 and it went like this… 

I had created my first digital course and wanted to hire an instructional designer to help me improve it so I could scale it. 

One of the candidates had an impressive resume of digital marketing strategy and was confident he could create an email marketing funnel for my course. And I thought, “I want one of those.” 

The interview went well, so I hired him.

Unfortunately, it fell apart after a couple of weeks.

When I received my first automatic charge of $632, I almost had a panic attack. I was paying $30 an hour… what was this guy doing for 20 hours a week? 

After the second week and another $674 fee, I asked to see where he was at and discovered that he had basically done nothing. 

After 40 hours of work and $1,300 in two weeks, the contractor had created a PowerPoint presentation of recommendations.

Yep. A bunch of slides of his recommendations. 

That’s when I ended the contract. Because I could see our working relationship wasn’t going anywhere. 

It was painful at the time and still a bit embarrassing to talk about. 

But, this was the key experience that led me to set out to really understand freelancers. 

Now, I know I didn’t have to conduct an autopsy on my mistake. But I was so afraid of repeating it that I had to know what I did wrong. 

What are the most common hiring mistakes?

If you’re wondering how you can prevent some of the most common hiring mistakes in your own business, you’re in the right place. 

While most hiring mistakes aren’t exactly fatal, they can end up hurting your business, and your sanity, over time if you aren’t aware of them. 

And, these can happen to anyone! In fact, many of them I’ve made myself early on in business, which is what led me to start working to find a better way to hire.

Keep reading to discover the top 7 hiring mistakes bloggers and other creative entrepreneurs make. 

1. Hiring a family member or friend to make it "easier."

Hiring a family member or friend can be an okay plan, until it’s not. 

For one, it can be hard to give feedback to friends and family because they may take it very personally coming from you. Over time, resentment can easily grow, causing damage to your relationship.

They also may not respect deadlines or your requests as seriously because of your close relationship, in which case they likely won’t take the work as seriously as you do.

If you do want to hire a relative or friend, vet them the same way you would another candidate. Interview them, ask for relevant experience, and lay out your expectations for the role. 

Hiring within your circle doesn’t have to be a disaster, but be sure they’re actually the best fit for the position (because, by the way, firing a loved one is NO fun).

2. Writing a vague job posting.  

The most talented freelancers are highly selective about which postings they apply to. And they stay away from vague job postings because these postings don’t look like credible opportunities. 

In my early days of hiring, this is a mistake I made myself. I posted in a Facebook group in 2016 that I was looking for a virtual assistant to do some writing and editing who was “sparkly and reliable.” 

Instead, you want to be specific in your job posting. What do you need help with on a daily, weekly and monthly basis? What kind of experience or background does your ideal team member have? 

Providing specific details allows the best candidates to decipher whether it’s the role for them.

Check out this job posting template for more on how to craft a posting that will attract dozens of highly qualified candidates. 

3. Not being clear on what you want.

As the job poster, you need to articulate the kind of freelancer you want, the projects they’ll be contributing on and how much work they can expect. Some freelancers may try to upsell you related services if you’re unclear (or unconfident) about what you want and need.

And… It’s easy to be swung when you’re not really sure what you need. I know it’s easy to doubt yourself and feel like you don’t know what you’re doing, or that someone else has more experience and answers in some topic (email marketing, SEO, social media, etc.).

And maybe they do. But, you can always hand over more responsibility and tasks after you make a hire you trust to do the things you need done right now. 

Don’t make a hire because you feel pressured that they must know better than you do about what you need. Get as clear as possible on the tasks and work you need assistance on the most.

Read more about what the best freelancers are looking for in their clients. 

4. Expecting one person to do everything.

As an entrepreneur, you’re probably a generalist, which means you can handle most tasks in your business pretty well most days. Partly because you’re wired that way and partly because you have to. 

But freelancers, on the other hand, are typically specialists, which means their expertise lies in one or two more narrow areas. 

I used to think it was better to hire one person because I thought it would be too overwhelming to manage multiple freelancers. But I was always disappointed because no one seemed to be able to handle as much in my business as I could. 

To avoid this common hiring mistake, consider hiring two people for two very different areas of your business. In the long run, this likely will save you time and money because they will be able to focus on their skill sets and you can more easily manage them.

5. Hiring the first person you talk to because it feels right.

Your intuition is a powerful thing, but it becomes a problem when it’s the only tool you use in the hiring process. Definitely listen to it, but it’s not the only factor to take into account when you hire.

Instead, try rating candidates objectively so that you have another way to confirm what your gut is telling you. This also increases confidence when the person you connect with really well also fits best with the role. 

6. Going with the cheapest option.

Cheaper isn’t always better. A writer who charges $20 an hour may spend three hours working on a blog post for you, and a writer who charges $50 an hour may only need one. In this case, you would actually be saving $10 by going with the more expensive option.

Focus on fit first and then budget. You could always hire the candidate who is the best fit, and may cost a little more, but start with a couple hours a week or a handful of hours a month. 

7. Selecting the most "qualified" option on paper.

So often, business owners go with the strongest resume or most qualified candidate, even though they don't really know or like them on a personal level. If you're collaborating with and managing them, you should also like being around them.

Again, go with fit first, and I mean the all-around best fit: the person who fits the role, complements your brand and vibes with your personality best. They might not have the most impressive background or most experience, but none of that matters if they can perform well and support you best.

Minimize hiring mistakes by getting specific and thinking long-term

While none of these hiring mistakes seem inherently "bad," each has the potential to go really sour. When you hire, think about being as specific as possible about your ideal team member, what hole they'll fill in your business and how to draft a job posting that attracts exactly that kind of contractor.

Money and qualifications and chemistry are important, but they're not everything. Take your time, and be vigilant in your vetting.



Additional Resources

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Take the Mystery Out of Hiring Freelancers with Work Samples