Identifying Red Flags and High Risk Projects as a Freelancer

February 22, 2017

Identifying Red Flags as a Freelancer

A few weeks ago when I was writing my Business Lessons Learned in 2016, I realized there was a spin-off post waiting to happen.

I’ve come to recognize many “red flags” as a solopreneur, and not every red flag is created equal.

A red flag in freelancing is not necessarily a sign you should immediately cancel a project. It’s more of an early warning sign that a project may not run smoothly, that a client might be difficult and that I should adjust my expectations and proceed cautiously. I don’t have any regrets about any of the projects I’ve worked on and I think it’s important to share what I’ve learned from my past mis-steps.

Red flags aren’t necessarily Deal Breakers

So what do I mean when I talk about red flags in freelancing? Occasionally, a prospective project will come my way that sounds interesting… but also a little “sketchy”. It’s hard to describe exactly what triggers the “this is sketchy” response in my brain, and this certainly isn’t an exhaustive list. Over the last year and a half I’ve learned to recognize some common red flags and how to proceed accordingly:


  • Red Flag 1: The client hasn’t worked with a designer or developer before.

    This is NOT a dealbreaker, but it’s really good to know so that I can help guide the client through the project and I can make sure to be extra communicative.

    For example, every now-and-then I’ll get a client inquiry for a project sounds really disjointed or unfocused and this is often the reason why. If people have never worked with a designer or developer before, they don’t know the expectations. It’s your responsibility as the designer to manage expectations and help your client understand exactly the work you can do, how long it takes, and how much it costs. Pay attention to the language your client is using, if they keep talking about their iPhone app, but you thought you were making a browser-based web app, make sure you keep getting them to clarify and keep explaining the terminology.


  • Red Flag 2: The client refuses to sign your contract.

    This is an obvious one, but it’s surprisingly easy to get manipulated here. The way my process works, I send a proposal / contract, we review the proposal together, the client signs off it, and then I send the first invoice. If they don’t sign the contract, they’re in no way obliged to pay my invoice. Even if they say, “Hey, don’t worry about. Send the invoice, of course I’ll pay you, but I don’t have time to sign the contract and send it back”, I don’t send the invoice and start the work. If they don’t sign my contract, I don’t have a legal leg to stand on.

    I’ve been caught off-guard by this one a few times and this is a definite dealbreaker. This is also one that I find a little painful personally, because I’ve had this happen with potential clients who I’ve really liked and trusted. It’s so disrespectful for a potential client to refuse to sign-off on a contract that protects both of us.  


  • Red Flag 3: The client gives you just a general bad feeling

    This is the toughest red flag for me, because sometimes it’s a deal breaker and sometimes it isn’t. There are times when I have a meeting with a prospective client, they don’t make the best first impression. I like to give people the benefit of the doubt, so when people come off as a bit abrupt or verging on rude, I brush it off at first.

    When this happens, I make sure I have a few follow-up emails, phone calls or meetings with a client before agreeing to a project with them. This is a bit more of an up-front investment on your part, but it helps you stay away from getting involved in a bad situation. It’s helpful to remember that people who seem curt or abrupt on the phone might be warm and welcoming in person and vice versa.

    Also, SO IMPORTANT when it comes to giving people the benefit of the doubt: do not force your client to only communicate with you through email. I was surprised to hear a few freelance pals say that they’re put-off when a potential client wants to immediately jump on a phone call or schedule a meeting. To me, this is where you have to be accommodating for your client. Email isn’t the only way, and there are so many reasons why your client might be email adverse:

    • The client might be from a different generation than you and find hopping on the phone to be easier than typing a long email.
    • The client might be dyslexic or have a disability that makes writing emails difficult.
    • The client might want to make sure they’re reaching an actual person. Having someone actually answer the phone can be reassuring to someone who’s about to hire you.

      I know some of these examples sound like a bit of an edge-case, but you’d be surprised with how common this is!


  • Red Flag 4: The client speaks poorly of their last designer or developer

    Have you ever had a client tell you that their last designer / developer was awful and just fell off the face of the earth after trying to contact them?

    I have no doubt that there are some freelancers out there who, as I like to say, “design and dash”. There are freelancers who don’t follow up with their clients and believe that by going silent on a client, the client will eventually figure out that they’ve been fired. Those few freelancers who design and dash give the rest of us a bad name. Clients who come to me after having a bad experience with another freelancer have major trust issues, and who could blame them! I would be furious if I paid someone to build a website for me and they didn’t complete the job.

    This is another area I like to give the client the benefit of the doubt. If they’ve had a bad experience with another freelancer, it’s my job to make sure that this project runs smoothly and the client can trust me.

    However, if a client speaks insultingly, makes rude personal remarks about their former designer or developer, or if they’ve hired and fired several freelancers, this is my cue to get out of the project before it starts. At this point, it’s not a problem of a client getting burned by freelancers, it’s probably a problem with the client being difficult.


In general, when it comes to red flags, my new policy is to check my gut, and then proceed with caution. I try not to rush closing on a project deal because I want to be certain that this is going to be a good fit. I’m way more careful when creating client agreements and try to plan for things going wrong (because spoiler alert: something always goes wrong!).

I’m also very transparent with my clients when I feel like a project isn’t going well. The reality is that if you’re having a problem with client, the client may not even know until you tell them. It’s not worth ruminating on and getting anxious about, if you’re not going to talk to the client about it. These are definitely difficult conversations to have, but you’ve got to do it! Often, it’s just a simple misunderstanding and you can remedy things without harming your relationship.

I hope this helps you if you’re a freelancer just starting out on your self-employment journey or if you’re a seasoned freelancer still navigating some murky client relationship waters. If you want more freelance business tips, check out The Freelance Friday, my email newsletter where I share my favourite articles on design, freelancing and business every Friday afternoon. 



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Jessica Suhr - February 23, 2017

Definitely some good tips in there! And I agree: any client that wants to pay me before signing the contract for their own protection is not someone I want to be in business with!

Julienne - February 23, 2017

The Tina Fey meme is everything! Great post.