The Biggest Hiring Mistakes Business Owners Make 

So, you think you’re ready to hire some help?

There comes a time in most small businesses’ operations when they need more hands on deck to help them grow. You’ve got a full client load and can no longer devote time to being all of the things in your business. You’re ready to become a full-time CEO, and you know you need an extra set of hands, or two, to help you get there. 

But before you jet off to scrape together a job listing for LinkedIn, you need a solid strategy. Modge-podging a job description will not get you the candidates you want. 

I know that once you’re ready to take that step of making your first hire, it seems urgent. You’ve got a lot of things to do in so little time. However, one of the biggest mistakes you can make in your biz is flying through the application process. 

So, stop and take a breather before you go live with a job posting if you want to avoid these four big hiring mistakes.

Mistake #1: You don’t create a clear job description

Many people hire VAs or contractors but get stuck on what to assign them. A mistake I see several businesses make is forgetting a job description altogether or not making it clear enough.

Know what kind of help you need and hire for that. Don’t overload the position with an eclectic range of duties. 

Your job description needs to clearly outline this role’s expectations, including a task list. I recommended creating an outline of a task list with daily, weekly, and monthly tasks so your new hire has an idea of what to expect and for you to prepare their onboarding. 

If you hire someone right away and don’t know what to assign them, chances are you are wasting time and money — and those are two things you cannot afford to lose in your business. Setting clear expectations keeps you from assigning “busy work,” which doesn’t get the ball moving. 

These guidelines are vital, even to contractors. Just remember to be flexible. Because contractors are not employees, there is only so much you can expect from them and control you can have over their work process.

Be clear about what the role is to you

I’ll be honest: Titles don’t matter. They’ll help get your posting found by your target audience, but it’s more about what role the position will fulfill within the business. A “doer” on your team will have different responsibilities than a project manager. A doer will get things done — think copywriting, designing, accounting, etc. — while a project manager will reign in your team and ensure you stay on task. 

Make it clear what you want them to do or your job description will read like it’s asking for two different roles. Remember: people can do anything, but they can’t do everything. 

Here’s an example: Someone who is an expert in ActiveCampaign and can execute email campaigns is completely different from someone who can outline the strategies, write the emails, or get a project plan in place. 

Expecting someone to do all of it will create overwhelm and you won’t have (much-needed) checks and balances in your business. You need a checks and balances system in place more than you need to “just get the work done.”

Mistake #2: You don’t have an application process

Hiring is a lot of work. You can’t expect that once someone is interested in the position, contractor or not, they’ll be able to start immediately and that you’ll see results instantly. 

All too often, the application process is too focused on what you need and doesn’t include any of the standard stuff. Job functions are important, but providing these logistics for the potential employee or contractor is a great way to feel out if they are a good fit for you. You need to include things like:

• Expected hours: Will they be working 9 – 5? How many hours per week do you expect them to clock in?
• Per project or hourly rates: For contractors, note if this is hourly work or not. Many contractors, especially in the creative industries, work on a project basis only, so you must have this sorted out before posting. 
• A benefits section: Are you offering health insurance? Paid vacations? Sick days? 

The bottom line is this: You need to have what you will be offering this person — whether that’s benefits or something else — mapped out before you go live with the hiring announcement. If you want someone to stick around and be a team player, you have to remember it’s just as much about you as it is about them. 

No one wants to work for someone who doesn’t have their systems together. Disorganization within an organization is a major red flag. Don’t let quality candidates slip through the cracks because you didn’t plan first. Taking the time to slow down and do the process correctly and thoroughly will always pay off.

Mistake #3: Treating contractors like employees 

When it comes time to hire, one of the first questions you’ll probably ask is, “Should I hire an actual employee, or should I contract this out?” Contractors are a great investment for your business and an easy way to dip your toes into the hiring waters. They give you a set of expert eyes and clear your schedule to work on projects you otherwise wouldn’t have time for. 

But keep in mind: Contractors are not employees. Because contractors are considered “free market agents,” you don’t get to dictate their working hours, their turnaround times, or how they deliver content. While many contractors are happy to work with your needs, it’s important to know the rules. (I recommend reading the IRS’s rules on independent contractors vs. employees.)

Another thing to know about contractors: They often require a big-time investment upfront in the form of project fees or upfront retainer payments. And just like any help you hire, it’s going to take time for their work to pay off. 

When you’re a solopreneur, you can easily work on an idea, all the way from cradle to grave, without waiting on anyone else. When you have a team, it doesn’t work the same (even if they aren’t a contractor). 

You have to communicate your ideas and work together to bring them to life. Realize that you will have to leave space for them to work. If you hire a contractor, also keep in mind that they will not be available 24/7. They likely have numerous clients at any given time, so you’ll have to wait a bit before you can pivot into a team.

Mistake #4: Assuming your team can “do it all”

A common complaint I hear from business owners is that their VA, content creator, or other team member isn’t able to help them come up with ideas or strategize on the direction for their business. 

That’s because that’s not their job. I’ll say that again and again until it *clicks*. It is NOT the job of your VA, OBM, copywriter, etc. to come up with the ideas for your offers, products, and content and then execute on it. 

YOU are the visionary and the brand leader, so lead it. 

Their focus and strong suits are getting things done, not creating high-level strategy. You can’t shoe-horn someone into a role that 1.) they’re not hired for and 2.) aren’t comfortable with.

If you want someone to help you flesh out your ideas and plan to move the business forward, you don’t need a VA. You need a strategic partner who can help you turn your ideas into action, evaluate the internal resources of your business, and create a plan to move forward. They’ll help you look at the big picture and assess the overall performance to determine points of improvement. 

You’ll also get sound advice on whether or not your newest idea is the next big thing or if it’s just a distraction. This is where I hear most business owners struggling because they want their team to offer feedback they’re not qualified or paid to give. Also, remember that their livelihood is based on having a good relationship with and keeping their client happy. A strategist with experience will know how to navigate a conversation like this.

If you want to tap into the resources a strategic partner can offer your business, my 1:1 sessions are a great way to do so. 

With monthly consulting, you get two 30-minute strategy calls, weekly check-ins for accountability, and real-time Voxer access to ask questions and get feedback as you implement your projects and ideas.

Space is limited, so book today if you’re interested.