7 Questions You Must Ask Before Hiring a Freelancer

by | Freelancers, Small Business

Questions to ask a freelancerIf you’re considering hiring a freelancer for a project then this post was written for you.

Small business owners come in all shapes and sizes but there’s a common experience every business owner can relate to…

Unfortunately that experience is known as “chaos.”

And freelancers can be an effective way to reduce the amount of chaos in your life and business. Finding the right freelancer is a dream come true for a business owner. But hiring the wrong person will only make matters worse.

So here are seven questions to ask a prospective freelancer BEFORE you hire them. These are questions you MUST answer if you want to find the right freelancer.

1. Can I see a sample of your work?

If the freelancer you’re considering is unable to immediately direct you to an online portfolio then move on. Yes, I’m sure they have a very good reason why their website is down. And chances are they will have an equally good “reason” as to why they can’t meet your deadline.

With tools like WordPress it doesn’t take a lot of work to showcase a portfolio online today. And if they can’t accomplish this simple task imagine what would happen when they run into a problem while working on your project.

So if there’s no portfolio then move on.


2. What do other people say about working with you?

I know this question is direct, but who cares? You need to cut to the chase or else you’ll waste unnecessary hours interviewing candidate after candidate only to find out later they’re not a good fit.

As the person in charge of the project it’s your responsibility to ask direct questions early on in order to eliminate the wrong freelancers. Remember, this isn’t a self-esteem boosting exercise. If you’re afraid of being direct (which doesn’t mean be a jerk) then you will waste both your time and the person you’re interviewing.

Back to the question, “What do other people say about working with you?”

The ideal freelancer will gladly point you to a list of testimonials from satisfied clients. If they’re unable to provide this you could ask, “Well, what did your last client have to say about working with you?”

If they reply with something like, “Oh my last client was horrible. You know he was just so demanding, so after we finished the project we sort of went our seperate ways.”

That’s code for “go your separate ways now.”


3. Can you meet the deadline of [DATE]?

If your project is time sensitive this should be one of the first questions to ask. Remember you’re trying to weed out every canidate who isn’t a good fit. If you know you need a website done by next month then be clear about that.

And if the prospect answers this with, “Maybe” ask them to please tell you, “Yes” or “No.” Maybe doesn’t cut it. And you don’t want to maybe count on this guy to screw up your project. It’s pretty simple… “‘Yes I can meet the deadline” or “No, I can’t.”

Also remember to be clear about time of day you expect it delivered and which time zone you’re in. If your freelancer is in Portland, OR and you live in London that’s an eight hour difference. So end of business day Thursday in London would be 5:00am in Portland.

A side note here: the good freelancers are typically booked out at least one month. So if you’re looking for quality work I’d giving yourself plenty of time to find a good freelancer. The freelancer who has nothing scheduled for the next week makes me wonder, “Why not?”


4.  Will you be sending me a formal bid letter?

A formal bid letter is a great way to avoid any confusion over what’s involved in the project. A phone call – which we’ll talk about next – can help accomplish this also but there’s too much risk for misunderstanding when it’s not in writing.

And as the one hiring it’s your job to communicate exactly what you need done. If you need someone to write all the copy for your site don’t just say, “How much would you charge to write the copy for my website?”

A better way to ask this would be, “I need copy written for the following pages: Home, About, Services, Our Team. I need headlines on each page and will also need meta-descriptions written for each page using our keywords of Muscle Cars for Sale.”

Be specific. And get it in writing.


5. Can we setup a 15 minute phone meeting?

Get your prospective freelancer on the phone. There’s so much you can learn from a phone call. And it starts before they say the first word… if they keep their word and call you at the appointed time that’s a good sign. People who are punctual are generally always on time. Same goes for those who not.

Not only can you find out if this person is punctual or not but you can also get a feel for who they are by talking to them on the phone. Do they sound professional? Is there loud music blaring in the background? Are they a good listener?

Remember, a mark of a good listener is the ability to paraphrase you. Not in an annoying recorder-like-fashion but in a here’s-what-I-hear-you-saying-main-points way.


6. What’s your process like?

If someone doesn’t have a working process they are either brand new or unorganized. Either way, move on.

The last thing you want is to hire a freelancer who is so unorganized that they can barely remember their own name let alone the project you’re working on.

The flip side is the person who has a process that’s too time consuming. If you are required to be involved with every little aspect of the project then you’re talking with someone who is afraid to make decisions. They lack confidence and it will show in their work. You need to work with a professional who is confident (not arrogant or proud, but confident).

Ask yourself this, “Would you trust a doctor who was always asking your feedback on a procedure? “So, do you concur?”

Now I realize copywriting or graphic design isn’t the same as practicing medicine but I think you get the point. The freelancer should be an expert in his or her field and therefore be bold enough to say, “This would work best.”


7. Do you have any questions for me?

If the answer is, “No” then one of two things happened.

1. You did a remarkeable job communicating every little detail of the project to your prospective freelancer.


2. Your canidate is afraid to ask questions (which is not good).

Now understand this: asking lots of questions up front and asking lots of questions throughout the project are two different things.

Let’s go back to the doctor example. What does a doctor do when he first sees a patient?

That’s right, he asks questions… lots of questions. Direct questions. And when you answer he follows up with another question that draws more information out of you.

He doesn’t just listen to you, send you home with a prescription and then call you every day to ask more questions. That would be annoying and a sign of an incompetence.

Same is true for freelancers.

If your prospect doesn’t have the wherewithal to ask the necessary questions upfront then be prepared for a crappy final product or a series of phone calls that will take you away from the work you’re trying to get done (you know, the work you planned to focus on while your freelancer was doing the other work?).


So remember to ask these questions in order to avoid the freelance nightmare that befalls so many business owners.

By the way, I realize this is an incomplete list. If you would like to add another question or two in the comments section below be my guest.

About Josh Monen

Josh is a direct response copywriter and marketing strategist who makes a living by achieving remarkable results for his clients. His unique understanding of human psychology and marketing principles make him a valuable asset to the clients he serves.