7 Tips for Working Successfully with Contractors and Freelancer
I've had the opportunity to both work as a contractor and hire them for various projects and roles within our company.
From social media and customer service to design and web development, the flexibility and expertise that freelancers bring can be a game-changer for small businesses looking to scale.
Contractors can become an essential part of your business, providing specific expertise for one-off projects or ongoing, reliable support, without the overhead associated with full-time employees.
How to Find the Right Person
Whether you’re looking on Upwork, Fivrr, or within your own network, my recommendation is to conduct a test project with multiple contractors.
While you can get an initial idea of someone’s fit through interviews and their portfolio, nothing beats working with them directly on an example of what they’ll be actually doing for you.
The test project should be paid to value the freelancer’s time and so that you can use the results they produce.
When I was looking to hire a writer to create social media content for Forte Labs, I interviewed multiple candidates and asked two of them to conduct a test project, which was creating one week’s worth of real content.
This way, I was able to compare the quality of writing and it became clear who to move forward with.
7 Essential Tips for a Great Working Relationship
Once you’ve found your ideal candidate, here are the critical steps to enhancing your collaboration with your new contractor.
1. Sign a Statement of Work (SOW)
While paperwork is certainly the least fun part of running a business, it ensures a smooth working relationship from the start. This document should outline at the minimum:
Scope of Services: Clearly define the contractor's responsibilities and deliverables. What happens when you might want to increase the scope?
Compensation Details: Specify how much they’re going to get paid and when.
Assumptions: For instance, the contractor will bring their own software and hardware to conduct the work.
Confidentiality: Protect your business information!
You can draft an SOW with the help of legal counsel (or ChatGPT). Once you have one, reuse and adjust this template for future contracts to speed up hiring.
2. Set Communication Expectations
Next, you’ll want to establish how and when you will communicate with your contractor. Setting these expectations early helps integrate them into your team seamlessly.
Synchronous: Would you like them to be present at team meetings? Will you have regular 1:1s?
Asynchronous: Through which tools will you communicate regularly? For example, email, Loom videos, or instant messengers like Slack and Google Chat. What response time are you expecting and can they provide?
At Forte Labs, we use Google Chat as our main communication tool with staff and most contractors. But there will be exceptions…for example, our web developer, who sets up dedicated Slack channels with all of his clients. Depending on who you work with, they might bring their preferred way of communication to you.
3. Provide Necessary Tools and Access
The last essential step to getting your contractor started is access to the resources and tools they need.
I recommend keeping a list of all tools you use in your business handy, so it’s easier to identify which accesses a contractor might need.
Tool Access: Add your freelancer as a user on the necessary platforms and tools (watch out for the right permissions). If that’s not an option (additional users often cost extra), you can also share the general login via a password manager. We use 1Password and set up different “vaults” for contractors which contain the accesses they need.
Email Address: Will your contractor need their own name@yourbusiness.com email address? If they communicate externally on behalf of your business, then yes. Otherwise, not necessarily.
Dedicated workspace: I recommend setting up a dedicated Google Drive folder, Notion page, ClickUp doc, etc., for your contractor to keep all of their work in one place. For example, I’ve set up a “Social Media Hub” in Notion where our social media writer can find all information and resources to create content for us.
Product Access: I found that the better contractors know your business and its products and services, the better they can work for you. We’re giving our contractors access to our online courses and community so they know what it’s all about.
4. Give Them a Heads Up on Your Needs
As you start working with your contractor, keep them informed about upcoming projects even if the details aren’t finalized yet. That way, they can mark their calendar and manage their workload with other clients. You’ll also prevent disappointment if they have to turn down last minute requests.
For example, I’ll share as early as possible with our web developer when we need a new webpage for an upcoming launch and by when he can expect my draft for implementation. The last thing I want is postponing a launch because the website isn’t ready.
5. Create a Repeatable Workflow
Consistency in workflows helps you and your contractor manage your time and expectations effectively.
Ongoing Work: Set specific weekly/bi-weekly/monthly deadlines by when your contractor delivers the work. For example, I know that I can expect to see our social media content for the upcoming week in Buffer every Friday morning. And a YouTube thumbnail will be ready for feedback every other Monday, ahead of the publishing date on Thursdays.
Project-Specific Work: Get clear on cut-off times. By when does your contractor need to be informed to be able to deliver the work in a certain timeframe? And by when do you need to tell them if requirements change (e.g., you don’t need their services any longer)? For example, if I cancel on our videographer only one day before a scheduled shoot, he’ll still charge us for the day, of course.
6. Get Them Invested in Your Success
When contractors feel involved and valued, they're more likely to contribute significantly to your success.
Performance Metrics: Share your KPIs and results regularly. How did their work contribute? Where are they falling short? Trust me, the best contractors want to know because they’re eager to develop and improve. They also want you to be their best case study to show potential new clients what they can do.
Future Planning: Discuss how their role fits into your broader business strategy and long-term plans. Most contractors will be happy to contribute their ideas.
7. Recommend Your Contractors to Others
While it might seem counterintuitive, recommending top-performing contractors to your entrepreneur friends benefits your business. You help your contractors expand their skill set through diverse projects and foster a community of thriving professionals who are motivated and loyal.
If You Part Ways…
Whether your needs change or your contractor moves on to other projects, there are a few things to keep in mind to ensure a smooth transition:
Secure all original files they worked on—not just PDFs—to allow for future modifications. No company assets should be permanently stored on their end.
Revoke all access to tools. This is easier if you wrote down what access you gave them in the first place.
Ask your contractor for the best way to contact them should questions arise.
