I’ve always been pretty open about the fact that I truly could not run my business without outsourcing in certain areas. It’s something I learned pretty quickly: if I wanted to save my sanity, I needed HELP!
As women, that can be hard to admit. But I’ve never been one to pretend to do it all, especially as a mom of 4. I share more about how I “balance” it all in this blog post.
But when it comes to business specifically, I’m a BIG fan of hiring independent contractors. Contractors are a great option when you’re not ready or willing to hire a full-on employee, but still need some things taken off your plate. Before you jump in though, there are a few warning signs worth watching for. The five red flags below can help you vet potential contractors and avoid headaches down the road.
Like all things in business, however, there’s a right and wrong way to work with independent contractors, and if you’re not careful, you could find yourself in a bigger mess than you’re already in.
Take it from me: I’ve been on that side of things. And it was reallyyyyy not fun. But as the saying goes, you live and you learn, right?!
That was definitely the case for me, and now I have a very specific set of red flags I look for before working with an independent contractor.
I suggest that YOU look for the same!
What Are the Biggest Red Flags When Hiring an Independent Contractor?
The biggest red flags when hiring an independent contractor include a missing portfolio or work samples, poor communication during the vetting stage, no client references or reviews, refusal to sign a written contract, and pricing or promises that seem too good to be true. Spotting these warning signs before you sign an agreement can help you avoid unreliable contractors and protect your business from missed deadlines, scope disputes, and wasted money.
- No portfolio: a contractor who cannot show relevant work samples may lack the experience your project requires.
- Slow communication: spotty responses before the project starts usually signal worse communication once work begins.
- No references: the inability to provide any past client references may point to difficult working relationships.
- Won’t sign a contract: reluctance to put terms in writing is one of the clearest signs of an unreliable contractor.
- Unrealistic pricing or promises: rates well below market or guarantees of impossibly fast turnarounds often lead to subpar work or surprise costs.
5 Red Flags to Look for Before Working with an Independent Contractor
1. Lack of a Clear Portfolio or Relevant Work Samples
A missing or weak portfolio is often the first sign that a contractor may not be the right fit for your project.
Now, let me be clear: I know that everyone has to start somewhere, and I’m not opposed to working with “newbies.”
However, I do still want to know that the person I’m hiring is skilled in the area and has some sort of experience so that I feel confident hiring them!
If the contractor you’re potentially looking to hire doesn’t have a portfolio or struggles to provide work samples, it could be a sign they lack the experience needed for your project, and it could be a red flag that says it’s not worth it.
Depending on the project or task at hand, you may be willing to take the risk, but 9 times out of 10, if a portfolio that showcases relevant, high-quality work that helps demonstrate their skills and suitability isn’t available, I’m probably going to search elsewhere.
2. Poor Communication or Slow Response Times
How a contractor communicates before you hire them is usually a preview of what the working relationship will look like.
As a business owner, it’s often a little scary hiring other people to do certain aspects of your work for you, but one thing that can really help you overcome that fear is a huge trust factor with the person you’re hiring.
For me, one thing that builds trust quickly is effective communication and fast response times.
Do I expect someone to respond to my emails or Slack messages at all hours of the day and night and on weekends? Of course not! I totally understand having boundaries as a business owner and expect for independent contractors to enforce their own.
But if I feel like the communication is a little spotty from the get-go, this is a red flag that I typically don’t ignore because it speaks volumes to how I’ll likely be treated once I become a client.
When hiring an independent contractor, you want to know that you can count on the person and not feel like you have to micromanage their every move. If effective communication is lacking, it could cause lots of issues with your workflow and defeat the entire purpose of hiring them in the first place.
3. No Client References or Reviews
References and testimonials give you a window into how a contractor actually works with clients, not just what they promise they’ll do.
This goes hand in hand with having a portfolio to showcase their skills, but another thing I always like to look for are references, reviews, or testimonials.
Again, I know that everyone has to start somewhere, but if they can’t provide some sort of reference with people they’ve worked with in the past, even if it wasn’t necessarily for their contracting services, it could be a red flag that they’ve had challenges with past projects or client relationships.
This one isn’t always a deal breaker because I know it can take time to build your testimonial bank as a business owner, but it’s definitely something that I always like to look for and acknowledge, and maybe ask questions about so that I get more insight on their reliability, work ethic, and past client satisfaction.
4. Refusal to Sign a Clear Agreement or Contract
A contractor who won’t sign a written agreement is one of the biggest red flags you can encounter, and for me, it’s a deal breaker every time.
Which should be no surprise coming from a girlie who literally creates and sells contracts for a living.
One thing about business is that you want to have everything in writing so that if any situation ever comes up where the “rules” are questioned, you have a playbook, so to speak, that tells you exactly how to navigate the situation.
A well-drafted independent contractor agreement helps set clear expectations around scope, payment terms, deadlines, intellectual property ownership, and confidentiality. It also helps establish that the working relationship is a contractor relationship rather than an employment relationship, which matters for tax and legal compliance. A contractor’s reluctance to sign could be a sign of unreliability, which is not something I (or you!) want to mess with.
For a closer look at the 5 hardest-working clauses in your independent contractor agreements, check out this blog post.
5. Unrealistic Promises or Overly Low Pricing
If a contractor’s rates or timelines sound too good to be true, they usually are.
And lastly, one of the biggest red flags that always catches my eye are any promises or offers that feel a little sus.
If a contractor makes promises that sound too good to be true, such as exceptionally fast timelines or very low rates, that tells me they may not be realistic about the work required OR they’re trying to do anything they can to get the sale.
Unrealistic promises can lead to rushed or subpar work, missed deadlines, or unexpected extra costs, which are all things I really don’t have time to worry about, and I’m pretty sure you don’t either!
Quick Checklist: Vetting an Independent Contractor
Before you sign on the dotted line, run through this quick checklist to make sure your potential contractor checks the right boxes:
- Portfolio or work samples that are relevant to your project
- Responsive, professional communication during the inquiry stage
- At least one or two client references, reviews, or testimonials
- Willingness to sign a written independent contractor agreement
- Pricing and timelines that are realistic for the scope of work
- Clear understanding of the deliverables and expectations you’ve outlined
Why a Written Contract Matters More Than You Think
A written independent contractor agreement does more than just outline the project details. It helps define the relationship itself.
When you put the scope of work, payment terms, deadlines, intellectual property rights, confidentiality expectations, and termination terms in writing, you create a reference point that both sides can rely on if questions come up later. A signed agreement can also help support the classification of the worker as an independent contractor rather than an employee, which can reduce risk around tax obligations and labor law compliance.
Without a written agreement, you’re left trying to piece together expectations from emails, DMs, and verbal conversations, which puts you on much weaker footing if a dispute arises.
The Boutique Lawyer’s Independent Contractor Agreement template is designed specifically for online business owners and service providers who want to bring on contractor support the right way.
Frequently Asked Questions About Hiring Independent Contractors
What should be included in an independent contractor agreement?
A strong independent contractor agreement typically covers the scope of work, payment terms and schedule, project deadlines, intellectual property ownership, confidentiality obligations, termination terms, and a clause establishing the independent contractor relationship. Including these terms in writing helps protect both parties and reduces the chance of misunderstandings later.
What is the difference between an independent contractor and an employee?
The key difference generally comes down to the level of control the hiring party has over how the work is performed. Independent contractors typically control their own schedules, methods, and tools, while employees work under the direction and control of the employer. Misclassifying a worker can create legal and tax consequences, so it’s important to understand the distinction and structure the relationship correctly from the start.
Can I hire an independent contractor without a contract?
Technically, yes, but it’s not recommended. Working without a written agreement means you have little to fall back on if there’s a disagreement about deliverables, payment, timelines, or ownership of the work. A signed contract helps set expectations and puts you on stronger legal footing if issues arise.
How do I know if an independent contractor is reliable?
Look for a professional portfolio with relevant work samples, responsive communication, and positive references or reviews from past clients. A willingness to sign a clear written agreement is another strong indicator of reliability. If any of those pieces are missing, it’s worth digging deeper before committing.
Your Go-To Resource for Legal Education and Support
Overall, hiring independent contractors for help in your business is a great way to take some tasks off your plate and grow your business in a way that feels good to you.
If you want to keep learning about topics like this in a way that’s actually enjoyable, The Legalzine is your go-to resource.
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Each issue covers a single legal theme and gives you:
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ABOUT THE AUTHOR, AMBER GILORMO – ATTORNEY AND FOUNDER OF THE BOUTIQUE LAWYER
Amber Gilormo is the cool lawyer behind The Boutique Lawyer – a one-stop contract template shop for creative entrepreneurs, online business owners, coaches, and service providers.
From client agreements to digital product terms and everything in between, our lawyer-drafted templates take the guesswork out of staying legally protected online (no legal jargon required).
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