6 Ways To Speed Up Your Contractor Onboarding Process

If you’ve stepped foot in a store recently, you might have been surprised at the holiday decorations already hitting the shelves. It’s the most wonderful time of the year…and it’s often the busiest for the self-employed workforce: when surveyed, 84% of Found users said they expect to work as much, if not more, during the last few months of the year.

That’s because the fourth quarter is often a make-or-break-it time for many small businesses. With holiday promotions, end-of-year projects, increased customer demand, and employee vacations, you likely have more on your plate than you can handle alone before the year ends.

In this hustle and bustle, bringing on additional help may seem like the ideal solution to lighten your load. But hiring a full-time employee just for a short sprint doesn't make financial sense. For instance, if you're an e-commerce shop running a Black Friday or holiday promotion, you might temporarily need help with Facebook ads for your advertising. This is the magic of 1099 contractors. You can tap into their expertise for a particular project or time frame, which is often a more cost-effective solution than bringing them onto your W-2 payroll.

But here's the catch: Rushing and hiring the wrong contractor can create a nightmare for you. So, how can you speed up the contractor onboarding process without compromising the quality of work? Here are six ways to successfully onboard your contractors in record time.

Create a central knowledge base 

When you are your business, it's easy for all your business how-to's to live in your head. But you don't want to be a bottleneck for your contractors, especially when you're on a tight deadline. Before you even hire and onboard your contractor, take some time to create a source of truth for your business. This folder or document can be the go-to spot for any new contractor to watch tutorials, review guidelines, and familiarize themselves with standard tools in their own time.

Your new contractor will inevitably have questions as they get used to your systems and workflows. If you can't respond immediately or are spending valuable time explaining the basics, you slow down both you and your contractor–which is the opposite of what you need in the final sprint of the year.

So, what information should live in your knowledge base? Start by identifying the basics they'll need. Gather existing documents and resources and organize them somewhere easy to share and access. Here are a few ideas of what to include:

• How-to videos: Is there a specific software you use that your contractor will need to access? Create a walk-through video using a program like Loom. These are ideal for visual learners, who can rewatch them as needed.

• Glossary: Every industry has its own jargon, and ensuring your contractor speaks the same language as you is crucial. A dictionary of your business's terms, acronyms, and colloquialisms can be a handy reference tool. You can also include information about your business structure or other key stakeholders they should know about.

• Brand guidelines: Your brand voice is unique! If you’re hiring a contractor to help with content, you’ll want to make sure they sound like you. Include examples of previous communication for them to reference.

• Previous documentation for projects: Is your contractor working on a campaign or project you’ve done in the past? Provide context for those projects, including what went well and what could have been better. Include links where you can.

• Templates: Templates help save your contractor time and provide a consistent look and feel across all communications.

Get in the habit of regularly updating documentation as needed. As your business grows, you’ll want to be able to bring new contractors on board all year long quickly. 

Set clear expectations from the start

Clear communication is the foundation of all working relationships. Onboarding new contractors goes smoothest when expectations are clear from the beginning. Before you even begin interviews, create a detailed job description that outlines exactly what you need the contractor to do. Include things like:

• The specific deliverables and output you expect

• Project timelines with milestones and deadlines

• How you will track progress and performance

As you’re interviewing prospective contractors, talk through these things in detail. Make sure each candidate understands and agrees to the expectations. This allows you to find the best fit before onboarding begins. Once you’ve found the best fit, get a written contract that documents everything you talked about. Specify deliverables, timelines, tracking methods, and consequences if expectations aren't met. Setting clear expectations upfront ensures you and your contractor start on the same page. 

Develop a system for onboarding and paying contractors

Onboarding new contractors can be a major hassle, especially during your busiest season. Collecting tax forms, keeping track of payment schedules, and staying on top of year-end tax reporting requires a systematic approach. Doing this manually, not to mention for multiple contractors, can add up to hours of administrative work. Let's face it: This is the last thing you need during your busiest season. 

That's where tools like contractor management software can help. Sure, you could send an email asking your contractor for their W-9 form, keep tabs on if they've sent it, and remember to follow up. Or, with just a few clicks, you can request a W-9, check to see if you received it, and then store a digital copy in your account until tax time rolls around. Sounds much better, right? 

But it’s more than just organizing tax forms during onboarding. You’ll also need a system for paying your contractors for their work. 1099 payroll software can handle payments for your independent contractors or freelancers and ensure you’re tracking those payments correctly so those end-of-year 1099-NEC forms are accurate.

Assign a dedicated work buddy 

Even if you have the most robust knowledge base, there will still be questions. That's where having an assigned point of contact comes in handy. A work buddy can help answer any contractor's questions, navigate through challenges, and offer support throughout the project's duration. Maybe it's another long-standing contractor who has supported your business for years. In many cases, that work buddy might be you. 

Whomever it is, you'll want to figure out the preferred means of communication early on. Is it Slack for instant messaging and collaboration? Maybe email is your preferred way to get project updates? What if something urgent comes up? Are you comfortable with your contractor texting you? The key lies in identifying a communication method that works best for both you and your contractor and sticking to it.

Start with a trial assignment

Time is of the essence in Q4, so starting with a trial project may seem counterintuitive. But when done correctly, a smaller, limited-scope project means your contractor can learn the ropes in a controlled environment before you put that big project in their hands. It allows them to familiarize themselves with your systems (using that knowledge base you've already created) before they hit the ground running on that more extensive project. Not only will this save you time in the long run, but it will also help you determine if they're a good long-term fit. Otherwise, you'll need to return to the drawing board to find someone new.

Schedule recurring check-ins

Remember when we said clear communication was the foundation of all working relationships? That applies to more than just interviewing. Regular check-ins help you keep the project on track. You can use these touchbases to walk through progress and address important issues that might pop up for your new team members.

For your check-ins, it's helpful to use multiple methods of communication. Real-time check-ins, like live video chats or in-person meetings with your contractor, make problem-solving, addressing blockers, and providing quick feedback easy. But you'll want to come into those meetings with an agenda. A post-meeting email recap or shared document will give both of you a place to jot down discussion topics and action items. These can come in handy when you and your contractor have different schedules, are in different time zones, and can't meet as regularly as you'd like.

Streamline your 1099 contractor onboarding with Found

Working with contractors is a fantastic way to get expert help and work smarter instead of harder in the year's final stretch. Finding, hiring, and managing great contractors and freelancers can take time and know-how, but is well worth the investment.

A tool like Found can be a huge help when managing the financial aspects of dealing with contractors. From easy onboarding to tracked payments, our user-friendly platform simplifies the nitty gritty of hiring. No toggling between apps: Manage contractors and your business finances, all in Found. Unlike other contractor management software, Found's contractor tools are free with no monthly or per-contractor fees. You can instantly pay your contractors for free with a Found account. Paying is as easy as sending a text, and they can choose from a range of flexible deposit options. 

Simplify contractor management, and sign up for Found today.

The information on this website is not intended to provide, and should not be relied on, for tax advice.