What to Do Before Hiring Your First Assistant

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Hiring your first assistant (or even employee) is an important milestone for any creative freelancer. Up until now you’ve been the sole person doing all the work for your business — aside from the occasional contract work.

And if you’re anything like me, you’re a control freak who likes to control every aspect of your business. You don’t want other people ruining all the work you’ve done or messing up your systems.

But now you’ve reached a point in your life where you’re NEED to open up the intimate workings of your business to another person. This is not something to be afraid of, but to embrace head-on. It means you need help and your business is growing!

Before we dive into how to hire a virtual assistant or freelance contractor, let’s find out if you really do need to pull the trigger in the first place.

Do you really need to hire?

Naturally, the first thing you need to do before choosing to hire someone, and taking on the added cost and responsibility, is consider your needs carefully. It’s often much more cost effective to outsource than to tackle certain jobs yourself, but there are occasions where it’s smarter for you (the boss!) to do the tasks.

In the early stages of your business, you don’t need executive level assistants — you need workers who can help with the nuts and bolts of your business.

They need to build, assemble, type, sort, sell, serve, check email, books travel plans and answer phones. If you feel like you need more strategic help or training, or download my free Master List of Tasks to Outsource. 

Although, your business may still be quite small and financially vulnerable, delegating work you need help with is the best decision you can make. So don’t be afraid to seal the deal!

Here are the steps to take when hiring your first assistant, so you can avoid any potential mishaps.

1. Look for the right person

Once you’ve decided that you need to hire an employee, begin the process by writing up the job description. I prefer to focus on the type of person I’m looking for, versus only sharing the details of what the job entails.

It’s easier to teach and outline the tasks than to motivate your team member to turn in their work on time. No matter how flexible and casual your small business is, finding the right person is essential for both you and the contractor to have clear expectations.

List all the tasks that will be related to the job, while being as detailed as possible. Note the work hours and any other requirements — do they need to own a smart phone, have access to email on the go, make deliveries or use certain software?

Finally, take a look at the job description and write a list of what skills, training and education would help a person be successful in the position. These are the things you should be looking for in a candidate.

2. Find candidates through your network

Often the best way to find good candidates is through referrals within your own network. This is how I’ve been able to find all of the awesome team members I work with every day.

If a potential employee is referred by someone you know and trust, there’s a much better chance of that person working out in that position, than a stranger you hire on the basis of a resume and interview.

So, put out the word that you are looking for someone to fill a position. But be careful when hiring friends and family — sometimes hiring your sister or best friend can work out great — other times it’s a total disaster! I like to keep my work separate from my personal.

Remember, you aren’t giving out jobs as a charity. You need employees and contractors who will work hard and dependable. By all means consider friends and family, but don’t hire someone just because they need a job.

3. Prepare a thorough interview

Write down your questions ahead of time. If appropriate to the position, pose scenario-based questions to see how the applicant would solve a problem. Here’s an example of the list of questions I ask potential hires:

  • Did you enjoy school when you were younger?
  • What was your best/strongest subject?
  • Who are your favorite inspirational business men/women?
  • What’s your ultimate goal for your own career/business? All of the VAs I work with are in the process of quitting their day job and starting their own business, or they have already quit and are freelancing now. That drive is a vital characteristic of a successful assistant relationship.
  • What do you do in your spare time? What’s your favorite hobby? I have commonalities with all my VAs because I want to connect with them on a personal level, not just a professional one.
  • What does your schedule look like currently? You want to nail down some idea of when they are available to work with you, and if they have the time to devote to being your team member.

Be sure to take note of the person’s non-verbal cues. How do they dress and speak? Did they show up on time? This not only applies to in-person meetings but online ones as well. We do live in a digital world now!

Anyone can rehearse for interview questions, but in a small business you need someone you click with. Someone you can work closely with and communicate well with.

Remember, if you are interviewing several people you may get confused as to which applicant said what so take notes.

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4. Check references

Many people exaggerate or plain out lie on their applications and resumes. Simply verifying employment history and checking references will help eliminate potentially bad hires.

Also, do a quick Google search on potential candidates — you might be surprised what you find. Check their social media accounts like Twitter, Facebook and LinkedIn. What they share on social could potentially reflect on your brand’s standards.

Background checks are also an important way to weed out bad candidates and protect yourself against lawsuits. Depending on the type of position and responsibility, you may only need to do simple background checks like a credit check.

5. Write up the contract

Once you’ve selected the candidate be sure to do everything by the book. There are many legal requirements when hiring an employee or contractor.

So you always want to have a contract in place. Even if it’s just to list out the exact details of the job, it’s important that there’s no confusion and all the tasks get completed on time.

Your local Small Business Association is a great resource to help make sure you “cross your t’s and dot your i’s.” Congratulations on making this important milestone as a soloprenuer and business owner!

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