The Quick Guide to Hiring a Contractor in Your Online Business


4 August, 2022

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Podcast manager by day, reader, crocheter & introvert by night, and all-around lover of everything business. From tips and tricks to insights and inspiration, we'll explore the wild world of podcasting and entrepreneurship together. Let's make some magic happen!

Hi, I'm Lauren!

Read on to find out the answers to why, what, when, who and how or listen to episode 002 – “Begin the scaling process by hiring your first team member” below!

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For some people it’s a dream. For others, it’s an absolute nightmare.

What am I talking about? Managing other people! For some entrepreneurs, having others complete work for you and your clients feels like you’ve really made it. But, if you feel scared at the prospect, or don’t want to eventually have your own team, that’s fine too! The beauty of running your own business is you can literally do whatever you want, and nothing is ever the “right” thing to do.

However, if you’re in that exciting phase of being ready to hire your first team member and you’d like a bit of guidance and advice, keep on reading!

Why would I want to hire someone?

Now, this question might seem like an obvious one. But there are a few reasons I wanted to cover that might cause you to get the ball rolling with the hiring process:

  1. You don’t enjoy certain tasks and want to stay doing the ones you love – in your “Zone of Genius”
  2. You want to increase your income but you’re short on time – freeing up some extra time by outsourcing would allow you to take on another client or two
  3. You want to scale your business up to a point where you don’t need to be involved in the day to day running of it
  4. You want to be able to time time off more easily or frequently

Basically, hiring people comes down to two reasons ultimately – time & money.

What role should I hire for?

Sometimes this will be really clear to you – for example, if all your time is taken up by replying to customer support emails to the point where you can’t create anything new, you need to hire someone in a Customer Support-type role. However, if it’s not so clear cut for you, my biggest tip would be for a week or two track every task you do and how long it takes you. If you’re using a project management tool like ClickUp this is so easy as you can do it straight inside the task! You might be surprised at how long some things take you. But, to get you started here’s a couple of ideas of roles in the online business world that you might want to mull over and see if that’s the right hire for you.

  • Virtual Assistant (General): To handle customer support, admin, sending invoices
  • Virtual Assistant (Tech): Course creation, email funnels, sales pages, website edits, CRM/PM setups & management
  • Online Business Manager: To handle the day to day running and management of your business, working on operations, systems, project management – some offer other services like tech too
  • Copywriter: To write anything in your business – a sales page or website copy, Instagram captions or blog posts
  • Graphic Designer: To design your brand, website, social media graphics, graphic-based emails – these people may have different titles too!
  • Social Media Manager: To manage all of your social media – it may be your entire presence or just one platform, but they usually create graphics, write captions & provide engagement services, too
  • Podcast Manager: To produce your podcast from start to finish
  • Content Repurposer: To take what you’ve already created and turn it into something new on different platforms

When should I hire someone?

“Hire before you’re ready” is the quote that’s always thrown around. And I do agree with that, because you’ll have the time and the capacity to onboard them properly, provide them with all the SOPs (Standard Operating Procedures) they’ll need to have a great start in your business, however you don’t want to hire an assistant, and then after two weeks have no work to give them. You’ve got to be realistic that you have a workload that you could offload to somebody else and find that balance between early enough, but not too early! Look forward in your calendar to what projects, discovery calls and other commitments you have coming up and consider if you feel that you could do with some help by the time you get there!

Also don’t forget, that some roles are easier to onboard than others and will be very led by the person you’re hiring – for example if you’re hiring a copywriter to write your sales page, they will arrange to have a call with you or give you an onboarding form you just need to make the time to complete. Whereas someone like a general VA who’s going to manage your customer support inbox will need a lot of training, standardised emails and will have lots of questions in the beginning (particularly if your business is a bit messy!).

Who should I hire for that role?

Firstly, once you’ve chosen the role you’d like to bring into your business, consider if anyone jumps instantly to mind. Someone who might come highly recommended, an acquaintance who you know is killing it or someone whose name you just seem to see everywhere. Ask your business friends for a referral of who they’ve liked working with. Check them all out, see what they offer in terms of their packages & pricing and be sure to add them to a list.

Now, I wouldn’t necessarily recommend hiring a friend who’s also a business owner, because unfortunately you never know what’s going to happen with a business relationship. Not to be negative, but all sorts of things can go wrong and you really don’t want to be losing a good friend over it.

Next up would be to create an application form for your role. Consider what you feel you are looking for in a role:

  • Are you looking for quick turnaround?
  • Do you want to hand out a task and have it done that day or the next day?
  • Or do you not mind that much at all really?
  • Do you want someone who’s going to be actively responding to you and active in Slack daily?
  • Or do you not mind sending them an email and getting a response in three days?
  • Do you want someone who is going to fully take charge of something in your business? (ie, a podcast manager who would almost completely take over that entire process for you)

And also, what are you not looking for?

  • Would someone on a different timezone not work for you?
  • Are you looking for more experience/higher price or less experience/lower price?
  • Are there any personality traits that would be a turn off?

The Application Form

I’d recommend creating your application form in Airtable. It’s like Microsoft Access, Excel and Zapier had a weird baby (you’ll have to check it out for yourself 🤣). Basically, you can create an application form in there, create automations based on particular criteria in your form and have responses populate into a database for easy viewing! In your database, I’d also create some sections for you to write thoughts and notes about the people who have applied and create some sort of ranking system so you can easily see who to invite into the next round of your process.

Make sure to share your application form around in places where people who might like to work with you would be:

  • Slack groups
  • Facebook groups
  • Your social media
  • Your business friends can also share on their social media
  • Your website

Make sure to get on a call with anyone who you’re seriously considering. I believe you can always get a good feel for if you’d get on well with that person, which is super important in business – don’t forget, skills can be learned but a personality clash can’t really be fixed!

Another way to help work out who you’d like to hire is to ask your top 3 candidates to complete a test piece of work for you – make sure this is paid! Ask them all to complete the same task and then you’ve got a really easy way of comparing them and seeing who you feel is the best fit.

Finally, you’re ready to hire! Let your chosen contractor or team member know that you’d like to work with them, and then it’s over to them! Hopefully they have a great system where you’ll receive everything you need from them, and then you can begin the next step in getting them ready to work with you – onboarding! Definitely a post for another time as this is such an important part of working with somebody.

So, let me know in the comments below – what role was your first hire? Or what role are you looking to hire for right now? I’d love to know!

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