Key questions to vet every freelance prospect
How a prospective client's past experience with freelancers can be a green flag—or a warning sign
The first time you meet with a freelance prospect, they’re vetting your skills and experience. It’s a mistake, however, to think you’re just there to impress them and get the gig. It’s also an opportunity to do some vetting of your own.
Beyond gathering information about the project and company, the most revealing line of questions is to ask “Have you worked with freelancers before? How did it go? Were there any issues?”
In my experience, the responses will fall into one of three categories:
They’ve had great relationships with freelancers.
Usually a green flag. You can follow up by asking specifics of what those freelancers did right that you should emulate.They’ve never worked with a freelancer before.
Not an automatic red flag, and needs to be viewed in light of how much business experience they have in general. Since it’s unfamiliar territory for them, be clear about expectations, timelines, and your process.They’ve worked with freelancers, but there were difficulties.
Here’s where follow-up questions are key. Ask them to describe what went wrong, while keeping in mind you’re only getting the client’s side of the story (and the freelancer might have a different perspective). For example:
“The freelancer missed deadlines” vs. “The client gave me the source material two days before the project was due.”
“He turned in poor-quality work” vs. “I did 15 rounds of revisions and the client still wasn’t happy.”
“She’s too expensive” vs. “The client asked for a discount after they signed the contract.”
You’ll need to rely on your instincts to determine where you think the truth lies. Does the client seem to have an objective explanation of what happened, or is it possible that you’ll be the next in a long line of freelancers who ended up having issues with them?
Past Experience Isn’t Foolproof, But It’s Your Best Early Indicator
The earlier you can assess a prospect’s history with freelancers and get a sense of their work style and expectations, the better you’ll be positioned to decide if it’s an engagement worth pursuing.
There’s no foolproof method for uncovering if someone is easy to work with—and sometimes red flags only start flying once a project is underway. But asking these questions (and following up as needed) can give you a valuable head start on making smarter decisions and being aware of possible danger zones.
In the comments:
Have you ever asked a prospect about their past experience with freelancers? Depending on their answer, did you end up taking the project or running in the other direction?