How to Onboard Contractors to Your WordPress Business

How to Onboard Contractors to Your WordPress Business

After you start to become profitable, you’ll stop worrying about “making this freelance thing work” and start thinking about how you can be more productive—and make more money. You’ll also begin thinking about the tasks you really hate and how outsourcing them might make you feel more fulfilled in your business.

Regardless of your motivation, congratulations on getting to this point! It’s certainly a big step to go from making enough money to support you, to making enough to also support another individual or even a team.

Virtual assistants and contractors might be part-time “employees” of your business, though some may pledge their time to you full-time. Regardless of their commitment, contractors are a lot different than employees. While you have to follow certain guidelines and offer certain things to employees (sick pay, health insurance, etc.), the same requirements aren’t true of contractors. Because of this, working with a contractor is an affordable way to scale your WordPress business.

Once you’ve hired your first contractor, you’ll start to see opportunities to hire others to help you with yet other aspects of your WordPress business. Instead of letting hiring take up all of your time and energy, you’re better off creating templates and processes for managing the entire hiring and onboarding process.

Based on my own experience, here’s how to onboard contractors to your WordPress business.

Create a Job Description

First thing’s first: you’ll need to create a job description that effectively connects you with the perfect contractor for your WordPress business. You’re aiming for something you can create once and use again. Though the nature of what you’ll be working with contractors for will change person by person (and position by position), writing a job description should serve as a template that can be reused as a baseline for any role you’re hiring for.

I’ve found that including the following elements is critical when it comes to attracting the best fit contractors for my WordPress business:

  • Pay: Don’t waste your time on inviting people outside of your budget to apply. Be upfront about how much you’ll pay per hour or over a certain amount of time.
  • Time Expectation: Since contractors oftentimes take on multiple clients, they need to be able to visualize how this role would realistically fit into their existing lives. Similarly, if you’re looking for a full-time virtual assistant or contractor, you need to clearly communicate this to find a good fit.
  • Working Conditions: What do you need from your contractor for this relationship to work? What can someone expect if they decide to work with you? What can you say (and do) to motivate the best to apply? What unique benefits does working with your company offer? Is there a certain working hours expectation that would make it hard for someone in another timezone to effectively work with your WordPress business? The more granular you can get about working conditions, the better.
  • Expectations: What do you expect in terms of deliverables each week for the time you’re contracting with this person? Realize that there will be variability but have some idea of what a certain amount of hours should produce for the average contractor.
  • Skills: Are you hiring a graphic designer? Administrative assistant? Social media virtual assistant? Whatever skills you’re looking for, talk about them in terms of desired specialties and tool expertise.
  • Expertise: Depending on what you need a contractor for, you may require someone with certain industry experience. Make sure to mention this if applicable. If your industry isn’t hugely technical and complicated, know that “expertise” can be taught.
  • Next Steps: How quickly will you be responding to applications? When are you planning on making a hiring decision? What will the remaining steps in the process be? Will there be a paid test? The more you can explain up front, the more qualified candidates you’ll receive as a result.
  • An Easter Egg: Essentially, something to make sure that they’re paying attention. Regardless of what you’re hiring them for, you need someone with attention to detail who can take direction. To put this to use, perhaps instruct applicants to email you an application using a certain, slightly goofy email subject that includes their name (which can also help you to set up an email filter for dealing with applications in a way that doesn’t mess up your email flow).

Set up Onboarding Email Templates

Working with virtual assistants and other contractors will likely get to the point where you either want to hire additional help or you need to replace initial help due to underperformance or even them moving on to another job.

Hiring can be a timesuck if you don’t create a smart process around it. As a best practice, create email templates for the major hiring steps you can expect when it comes to interviewing and onboarding any candidate:

  • Initial interview questions: More or less the basics about what to expect in terms of working together. When I first started hiring contractors for my WordPress business, my mentor suggested questions about their motivations, home life (do they have kids or other major responsibilities), other work, and even technical considerations about their equipment and internet connection. Many of these questions would be considered illegal if you were hiring an employee but aren’t tied to the same scrutiny when it comes to working with a contractor—especially those that are based overseas.
  • Follow up interview questions: In many cases, one round of interview questions will give you enough information about someone to move onto the next round—a paid test project. Follow up questions will probably only come into play when deliberating between two candidates or learning something from your initial interview questions that you’d like to inquire about further.
  • Paid test project: You don’t want to give someone access to your world and the way you do things in your WordPress business unless they can prove worthy of working with you. Trust is something that can really only be built over time and is nearly impossible to determine during initial hiring stages. To qualify promising candidates as best as you can, make your test project representative of the work you’d have them do in your WordPress business. In fact, it’ll be easier to judge if it’s something you need done anyway. Set a flat rate payment (instead of an hourly rate) and a strict due date. If a promising candidate misses it, take that as a sign that they’re really not all that interested in working for your WordPress business.
  • Make an offer: Just wait for them to accept before starting any onboarding stuff or sending additional assignments.
  • Onboarding checklist: What a new hire needs to read, set up, or learn to get up to speed with your WordPress business. More on that below.

The idea behind setting up these email templates is that you don’t want to reinvent the wheel every time you hire someone new. Sure, you’ll have to customize each of these things for most contractor hopefuls but the time spent doing so will certainly be minimal compared to the time saved by creating and using these email templates.

Construct a Contractor Onboarding Checklist

Everytime you hire someone new, you’ll have to do some type of onboarding with them to have a smooth process in place for working together. Here are a few essential items on my own contractor onboarding checklist (which I send as a view-only Google Doc):

  • Official stuff: Like the fact that I need a W9 if they’re a domestic contractor and a basic contractor agreement stating the conditions for us to work together. You’ll also want to consider an NDA (non-disclosure agreement) to protect client information and other behind-the-scenes aspects of your WordPress business.
  • Tools to download: Part of my process for working with contractors includes a workflow that involves the use of certain tools I need my contractors to get on board with to ensure smooth working conditions. I’ll detail those later on in the article.
  • Watch this: I created a number of screenshare videos for how to do certain tasks and how to use the tools required to effectively assist me. Regardless of the role they play in my WordPress business, I have all my contractors watch the Skillshare class I created about writing a kick-ass blog post (and ask them to bill me for their time for this and all other onboarding activities).
  • Read this: I also created a number of text-based articles detailing brand guidelines and other preferences for deliverables.
  • Tracking time: I want to keep track of how long certain assignments take my contractors to do so that I have a benchmark by which to judge the effectiveness of future job candidates. Also, I think it keeps people honest when it comes to billing me at the end of the week.
  • How to invoice me: I have a specific process that I want contractors to follow that helps save me some time when it comes to preparing taxes.

Think of your contractor onboarding checklist as a mix between an employee handbook and training.

Set up a Company Intranet

You might be wondering about how to create a self-sustaining process for organizing and publishing all of these guidelines and training materials. My solution? Google Sites.

On my Google Sites “intranet”, I’ve detailed specific information for completing different types of work, general guidelines for working with me (my “read this” section on the onboarding checklist), and how to use the tools that they will inevitably need to master when working with my WordPress business.

Although I’m well-versed in web design, I wanted to spend as little time as possible on setting up my company intranet—which is not a direct revenue-generating activity. Regardless, spending time on this task is still important for my long-term success (and my sanity, as I hate to repeat myself).

Google Sites is super easy to set up in a bare-bones yet intuitive fashion. It’s also easy to share with a set amount of people, giving relevant parties editing permissions or restricting everyone invited by email to view-only access. Best of all, it’s completely free to use.

Contractor Agreement and NDA

I use AND CO for most of my contracts but they don’t (yet!) have an online contracts tool for working with subcontractors. Because of this, you’ll have to seek out your own template documents for a contractor agreement and NDA.

The best option for creating/customizing these documents is your lawyer, if you have the budget. What I’ve been doing for legal forms (in the US) is LegalZoom, which offers unlimited access to their library of Google Docs/Microsoft Word-editable documents for $7.99/month. It’s really not a bad deal for someone who wants a decent legal document on a budget.

Of course, I’m not a legal professional and don’t pretend to know the perfect solution for this issue. Furthermore, some states/territories will have special stipulations that may nullify part (or all) of a contract that you may not be aware of. The point is that it’s always best to consult with a legal professional before doing anything that has the potential to negatively impact your WordPress business.

Don’t forget to request a W9 from contractors (or the relevant tax form in your country)—you’ll need it if they’re domestic and you spend over $600 with them in a calendar year.

Virtual Assistant Collaboration Tools

Having laid out the majority of my processes for systematizing the process of onboarding contractors to a WordPress business, there’s one last item worth discussing—the tools you’ll need to collaborate efficiently.

  • Google Sites:
    wordpress business

    Google Sites is the tool I suggest you use to build an intranet to use with contractors. It makes it so that you can create onboarding documentation and training once, organize it in an intuitive fashion for contractors, then never worry about it again (except when updates are needed).
  • Todoist:
    wordpress business

    I use this tool for assigning tasks. You can add 5 users to a given project for free, then you have to upgrade to their Premium option if your team expands. Luckily, it’s $28.99/year—completely affordable. Todoist offers commenting, attachments, priorities, and labels on tasks so you can use it like a heavy-duty project management tool.
  • Basecamp:
    wordpress business

    Basecamp is essentially another product management tool. I use it in conjunction with Todoist but you could also get away with using each on their own, depending on which is best for your WordPress business and workflow.
  • Canva:
    wordpress business

    My team helps me create my own daily social media content and we use Canva for branded social media image templates that are stupid simple to customize anew each week. I get by with the free version but there are some perks to the pro Canva for Business version, including the ability to upload custom fonts and a “magic resize” button.
  • Google Drive:
    wordpress business

    Working with a contractor will inevitably involve sharing documents. Google Drive is my favorite solution for this. I do use Dropbox, too, but mostly because clients seem to prefer it for sharing folders with a lot of image assets.
  • Paypal:
    wordpress business

    All contractors invoice me on Paypal, which integrates beautifully with Quickbooks. If they’re domestic, I set them up on Dwolla (also attached to Quickbooks through venDwolla) to give them the gift of no fees (I shoulder a very small fee for the transaction, much less than what Paypal would charge).
  • LastPass:
    wordpress business

    In some situations in your WordPress business, you may need to give contractors access to client account. LastPass makes it easy to share certain passwords and revoke access if necessary. Login information shared through LastPass is encoded so that contractors never have access to the exact login information.
  • Toggl:
    wordpress business

    I ask that my contractors track their time on Toggl and include a screenshot as an attachment on their invoices.

The tools I’ve chosen to use with my contractors don’t cost them anything to use and download—an important consideration for your own WordPress business. Contractors shouldn’t have to shoulder a financial burden for using your tools.

The exception, if you can call it that, is Paypal. For some of my overseas contractors, it’s the only way to pay them in a reasonable maner. That said, I encourage my overseas contractors to research other options and am flexible when they find one that might work better than Paypal.

How to Onboard Contractors to Your WordPress Business

I realize that this is a very high-level look at what is honestly a fairly lengthy process; one that’s difficult to get right when you’re first getting started. So treat contractor onboarding like the learning process it is and give it your best effort now that you’ve taken the first step: doing some research.

Maddy Osman
If you’ve successfully onboarded a contractor or have recently hired a new type of contractor in your WordPress business, tell us about what worked for you and what processes you’d contribute to this list of onboarding ideas.