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So You Want to Hire a Contractor… (Part 1)

If you are running a small development or design agency (or working solo, but looking to grow), you may wonder when you’ll be able to actually hire employees. Hiring a team–even one person–can be intimidating.

You may be worried about taxes, whether you can afford it, or how you’re going to find someone who is a good fit. You might be panicking at the amount of work you have piling up while knowing it simply is not possible to hire a team member and offer them the full benefits of a regular employee. You know you need additional hands on deck, but you’re not sure you can start fleshing out a team of full time employees

That’s when it’s time to hire a contractor.

Getting started

One of the easiest ways to find someone who is a good fit is an obvious one: ask around. It’s likely someone in your industry has a solid lead on who can help you out.

You can contract for whatever help is needed the most.

Here are a few things I’ve seen developers hire contractors for in the past:

  • Development
  • Design
  • Social media management
  • Content management
  • Writing
  • Customer service
  • Tech support
  • Project management
  • Virtual assistance

Word of mouth is a great way to find folks, as is reaching out to any professional communities you’re involved in for recommendations.

While trying to find someone within your network is a good start, it’s also worthwhile to put out a call to online job boards (or even just a call out on your site). While we’re all inclined to invest more trust who is only a few degrees of social separation away, you want to have options. You never know who is lurking out there and will jump at the opportunity to work with you. Maximize your opportunities to create an amazing team by utilizing both your network and platforms that expose your call for a contractor to a new audience.

Vetting

A huge aspect of productivity and success is having an incredible team. Although someone may not be formally joining your company, working with them even on a part-time or short-term basis means that you are working as a team.

A part-time or short-term team member can still have a huge impact on the work you’re creating and your clients’ experience. You want to make sure that they’re a good fit! If you don’t put the effort into finding a contractor that will enhance your team, you’ll wonder why you bothered at all. A bad personality or work style fit can create stress and unrest, and diminish the overall quality of your work. You want someone who is going to work well with you and deliver the goods.

Do your research

Do they have a website with samples of their work? Resumes are great, but often incomplete–especially if they’re performing a specific kind of work (development, writing, etc.). You need to see samples of the work they’ve done in the past.

Keep in mind: if the work is live on a client’s site, it may be different than what the contractor intended. How many times have you recommended something to a client, only to have them shoot it down? Or, worse, go in a completely different direction that you think is questionable (at best)? We’ve all been there, and as we know, clients get veto power. They’re hiring us to create what they need and want, and sometimes we disagree on the best way to accomplish that.

You may come across a sample that makes you go, “Buh? What is that?” Make sure you compare other pieces of their work to that, and look for consistency. Ask yourself, “Is this a deviation or a norm for their work?” You want to make sure that you’re not judging them based on decisions that weren’t entirely their own.

If you find a sample that makes you go, “??!?” to be anomalous, you can bring questions about it to your interview.

Doing this research gives you a fantastic starter for your first conversation with them, as you can ask them how they created this work, what kind of challenges they experienced while doing so, and other relevant questions. These questions offer insight into not only the work itself, but how they conduct themselves professionally and when facing adversity.

Ask for references

And make sure you check them! Even if you get a word of mouth recommendation, make sure you ask for a few additional references and follow through on tracking them down. You want to know that your contractor can consistently deliver good work and maintain relationships. Several good recommendations can give a lot of insight as to who they are and what they’re like to work with.

For example, what most of my references will tell you about me (both good and bad):

  • I’m a consistent, open communicator.
  • I’m also an overcommunicator, meaning I check in a lot and tend to follow up with the persistence of a hungry bed bug out for blood (or a puppy looking to play ball, if you’d prefer a less disgusting analogy).
  • I work hard to make sure what I’m delivering is the best it can be, and have an eye for additional opportunities (don’t get them started on how many times I’ve said, “That’d be a great blog post!” in the middle of a meeting).
  • I’m opinionated and outspoken, which surely can be annoying, but it comes from a place of advocacy and wanting things to be as high quality as possible.

Does this mean I’m a good fit for everyone? Surely not! A good fit for some, but not for others. It’s good information to have either way. A “good fit” is entirely determined by your personality and working style.

Another example:

If you find out that your contractor is a bit lackadaisical with communication, but always delivers work on time, you’ll have to determine what’s the most important to you. Would you prefer someone who communicates well but is sometimes flexible on deadlines? Or would you prefer someone who doesn’t communicate as much, but always shows up exactly when they say they will?

Of course, ideally you’ll find a candidate that checks off all of your boxes, but people are fallible creatures. If you know what your values are, you’ll be able to parse the information recommendations provide and apply it to your dream team scenario with ease.

Conduct an interview

Get on the horn and talk to your potential candidate! Even if most of your communication while working will be done virtually, take a moment to hop on a call. You want to get a sense of who they are through their tone and the way they verbally communicate. You’ll want to use this time to set your expectations for them. This is also an opportunity to ask questions about their experience and the way they approach problem solving and conflict.

Make sure you’re upfront about who you are and how you work, too. Give space for them to ask questions. Remember: This interview is their opportunity to interview you, too. It’s about finding a mutually beneficial set up, not just about you finding a crony. It needs to work for everyone.


In part two, we’ll cover what you need to get organized and logistics for hiring contractors.

Have any questions about the start of this process or any burning questions about hiring contractors? Drop it in the comments!