Hiring contractors

Here is How to Turn Hiring Contractors Into a Simple Process

I’m sure you’ve been there before: You hired a contractor to take on some work for an important project, and they turned out to be completely unreliable.

Everything seemed normal in the interview and the project kicked off just fine.

But just as you needed them the most, they either had some excuse for not getting their work done, or worse, dropped off the radar completely…

…leaving you to pick up the pieces.

(Not to mention, start looking for their replacement.)

The good news is, there’s an easy way to make hiring contractors a simple, stress-free process.

And that’s exactly what I’m going to show you in this post.

I’ll teach you five qualities you should screen for when hiring contractors and how to spot those qualities in an interview.

Intrigued? Then let’s get started.

What Five Qualities Should You Screen For When Hiring Contractors?

I’m sure you have a general idea of how to screen candidates in a job interview.

But I’ll bet you’ve never seen a breakdown of what to look for in contingent workers specifically.

And that’s a problem – especially if you’ve been burnt by flaky contractors in the past.

As I’m sure you know, interviewing a contractor is a pretty different experience than a full-time employee.

For one, it’s unlikely you’ll be conducting several rounds of interviews or that you’ll ever actually meet the candidate in-person as you would for a permanent hire.

But it’s also about the specific qualities that matter most to you for a successful partnership.

And so, here are the five features of a great contractor that you should be looking for when conducting interviews:

Quality of Work and Industry Experience

I’ll admit, this seems a bit obvious.

Of course you want to review previous projects or a portfolio to make sure the contractor’s work meets your company’s standards.

But one thing to think about when looking at a portfolio is the importance of industry experience for the role and project.

You see, industry experience shouldn’t necessarily be a “must-have” for every contractor you hire.

For example, you might interview a good photographer who doesn’t have any corporate branding experience.

But if you look at their portfolio and can tell they have a good eye and understand how to work with light, it’s likely they would do just fine shooting your project.

The point is, try to look past whether the contractor has done exactly the thing you need them to do for your project and instead evaluate whether they have the talent and skill to get the job done.

And while quality of work will likely be the first feature you review in an interview (often because it’s the most obvious), I would argue this next one is truly the most important.


Can you count on the contractor to meet your deadlines?

It’s a tough quality to screen for in an interview, but I’m sure you’ll agree that if you can’t rely on a contractor to hit deadlines, then nothing else matters.

And that’s because missed deadlines negatively impact your business.

Clients don’t care if it’s the contractor’s fault you didn’t complete a project in time.

It’s your reputation (and revenue) that’s on the line, so you need to make sure whoever you hire can deliver on-time, every time.


Often, the biggest contributor to missed deadlines is a contractor stretching themselves beyond the workload they can reasonably handle.

And it makes sense why it happens:

Contractors are running their own business and have a hard time saying “no” to opportunities to make money.

That’s why you need to ask yourself (and the candidate):

Does this person have the bandwidth to take on the amount of work you have for them?

And doing so is actually in the candidate’s best interest, too. As Rikke Dam writes for the Interaction Design Foundation, contractors need to be better about managing their own time to meet client needs:

“[Freelancers] know what they can do in any given time frame, and they don’t overcommit. It’s tempting to take all the business on offer, but you’ll end up with no business at all if you can’t deliver. Learning to say ‘no’ is part of the business owner’s life.”

So while it’s not the easiest quality to screen for, you can remind the contractor it’s not in their best interest to bite off more than they can chew.


Here’s a quality you might overlook in an interview that can have a big impact on the success of your partnership:

Will you enjoy working with this person?

I know it seems a bit nit-picky, especially if a candidate meets all the other criteria.

But you’ll likely be communicating with this person on a daily basis for the length of your project.

And so, it’s important you can see yourself actually getting along with them.

Otherwise, you’ll dread communicating with the person and the partnership will inevitably suffer.

And that can affect the success of the project, the satisfaction of your client and ultimately your agency’s reputation.


And finally, make sure the contractor’s fees are within your budget.

There’s no sense in drawing out an interview process with someone you know is outside your price range.

In fact, that goes for any of the five features highlighted here.

But I’m sure you’re wondering:

How exactly do I screen for those qualities in a candidate?

And so, that’s what I’ll show you now.

Here’s The Right Way to Screen for All Five Qualities in an Interview

Require a Portfolio to Review the Contractor’s Quality of Work

Like I mentioned before, reviewing a candidate’s portfolio will be the easiest way to their quality of work is up to your standard.

But when you dig a bit deeper, a portfolio can actually tell you a lot about their quality of work.

For example, say you needed to hire a web designer to help with the launch of a new online store for a client.

The designer links you to a portfolio like this one from Brooklyn designer, Jamie Kleiman:


(image source)

Here’s what you can learn from a portfolio like this:

Is their design work recent? Or have they not updated their portfolio in years?

If you notice they have an outdated portfolio, ask why. A good contractor should be continuously updating their portfolio with new projects and work samples.

Are the designer’s site designs still active?

Go visit the websites included in the portfolio to see if the designer’s work is still live. Web design isn’t cheap and you don’t want to work with a contractor whose work has a short shelf-life.

A good portfolio reveals quality of work and professionalism in your contractor candidates.

But even with a great portfolio, this next step is an absolute must.

Ask for References (or Scan for Online Reviews) to Check Reliability

If you’re hiring a contractor off a site like Upwork, you should have no problem easily accessing reviews.

Here’s an example for an experienced web developer’s reviews on the site:


Pretty simple, right?

But, if you find your contractors through other means (like LinkedIn, Monster, or any of the other job sites), you may need to ask for references.

And there’s one thing you need to be wary of with contractor references:

Some may try to say they don’t have any because they need to protect client anonymity.

Of course, that may be true for some clients.

But if a contractor doesn’t have one person willing to speak on their behalf, they are either pretty new, or worse…

…they’re lying.

Even still, it’s a bad practice to reach out to former clients without getting the candidate’s approval.

Vicky Morton from Twine.fm explains more:

“It’s important to ask permission from your freelancer if you want to contact their previous clients for references. Don’t charge ahead and do this without their say so. It’s a bad faux pas to do this, and could result in a very angry freelancer.”

So, ask for references, but if the candidate is unwilling to provide them, just cut your losses and move on to someone else – don’t call previous clients behind their back.

Share a Concrete Project Plan to Gauge Availability

Here’s the best way to check a contractor’s availability:

Come to the interview prepared with an in-depth project plan that clearly outlines deadlines and commitments the contractor must meet to be eligible for hire.

Unfortunately, there’s nothing you can do but take their word for it on this one, but your transparency in the beginning can help dodge a lot of problems down the road.

Wind Down the Interview with Some Personal Interest Questions

With limited time and a lot to get through, I’m sure saving time for personal questions isn’t a top priority for you when hiring contractors.

But when you set aside time at the end to chat a bit about personal interests, you begin to get a feel for whether you’ll work well together on the project.

But don’t just drill the candidate with questions – make it a two-way conversation, where you share a bit about yourself and they share some of their own passions and interests.

Ask for a Proposal to Determine Affordability

If the candidate checks the first four boxes, let them know their next step is to put together a formal proposal.

And remember this: it’s your call on whether to be transparent about your budget here or not.

If you’re experienced hiring contractors and know the going rate, transparency can help save time and avoid back and forth of negotiation.

But, if this is your first contract hire, it may be better to hold off to ensure you don’t overpay.

If All is Well in Those 5 Areas, This is the Last Step…

Always schedule a test project before officially signing someone on.

You should make it a micro-version of the actual project and offer full-pay for their work.

But prepare to lose the money on occasion.

Not everyone is going to work out, but it’s better to find out during a test project than midway through the real deal.

In fact, that applies to the entire hiring process.

Sure, hiring contractors can be difficult, but if you screen for the qualities I’ve outlined for you here, there’s no doubt you’ll be well on your way to a successful hire.

Check how Zapty can make your processes simple