4 min read

Keeping it real: working with contractors

Before I get started…

Have you ever been in a relationship where you were not fully sure that the other person was 100% committed? Paranoid that they were kissing someone else behind your back? If yes, I hope you weren’t married. Or, I hope that it turned out you were just paranoid and nothing was going on. In any case, if you are familiar with that feeling of paranoia, you might understand where I am trying to take this really lame analogy.

It’s a fact: when you work with a contractor or freelancer, you are working with someone who has his or her own business interests in mind. You’re a client; maybe even one of many. That person is there to do their work and get paid, but not advance the work of your company or your team. It’s an in and out situation in many cases. Unless, of course, that person is contract-to-hire or is looking to keep working with your team on a project basis. For those reasons, and for the fact that I have (and do) work with many amazing contractors, I had a hard time writing this post. I'd never want my contractor/freelancer friends and colleagues to think I think they're whores. I get the business, I do! I just always have my projects in mind. So I went with my ideas anyway, because I think that if you’re managing projects with contractors or freelancers, there are some obstacles to think about. So I'm here to offer some thoughts. Let me know what you think.

My thoughts on working with contractors and freelancers.

I’ve managed many projects—both successful and umm…mildly successful. I wouldn’t say that the success of those projects sits on my shoulders completely, even though I tend to feel that way. A project’s success always lies on the shoulders of the entire team. What makes that dynamic difficult, at times, is working with contractors.

I’ve had the pleasure (?) of working at an agency where most of our resources are staffed in-house. So, as luck would have it, project teams would be assembled somewhat easily on a resource plan (yeah, that’s a topic on its own). In the instance that we were understaffed, we’d be able to bring resources in from other offices or talk to contractors. That was never my first choice; here’s why:

The budget: You’re never able to keep the project budget the same when you bring on a contractor or freelancer. The rate is never the same as your in-house rate, and you’re pulling actual dollars out of your budget to pay someone.

The working dynamic: Unless your contractor has tons of experience working with your team, there is always going to be a period of time where you need to adjust to one another’s working styles. Things (both big and small) like standard company practices, meeting culture, file formatting and communication come in to effect.  Then there’s the idea that they’re in the project for just the engagement, not for the long-terms affects the project can have. Of course, I recognized that there is never consistency from person to person, and you can always work around these types of issues. Going in to the situation aware of the differences is always helpful.

Location: Unless you’re lucky enough to have a contractor take a desk in your office, working full-time as a part of the team, location can be issue to think about. I’ve had it both ways (contractor sitting in the office and outside of the office), and there is an obvious preference for me. I’ve been burned too many times with missing people or late deadlines due to other commitments that were not communicated to say it’s easy enough to have a team member working from another location. It’s the worst when you’re waiting for someone to respond or pick up the phone and you’ve got an antsy client waiting on them. The worst.

Meetings and collaboration: Aside from the fact that I very much dislike scheduling people in several different locations, there are other problems. I’m realizing more and more that my teams benefit from collaborating across disciplines (not a problem!). If one team member is out of the office, the product and the team could suffer.  So if a contractor wants to work outside of the office, away from the group, there is a chance that a detail may be missed.

In the end, I know it’s something that we all deal with. There is no real answer to the issue, because every company operates on a different model and sometimes, you just need an extra hand. And, yeah, sometimes contractors and freelancers are great! But having one (or several) on a project requires a little more love on the project management end. I have a few very quick tips to help make things run smoothly:

  1. If you have the luxury of doing so, check out your contractors’ resume and talk to them on the phone. You can be a huge help in determining this person’s fit on the team. Don’t be shy about wanting to know qualifications—you’re going to have to answer to the client and deal with this person for the term of the project.
  2. Be clear about the project hours that you have available for all of the work that you’re contracting and keep tabs on those hours on a week-to-week basis. (If you can, have the person enter their time in to your own tracking system.)
  3. Set expectations about working hours and deliverable times.
  4. Schedule check-in meetings with your team and the contractor (seems like a no-brainer, I know)
  5. Be clear with your clients about the contractor’s working relationship with your company. There’s no need to hide that you needed some trusted help! (Unless your boss tells you not to. Duh!)
  6. Schedule in some extra time for review of the contractor’s documents—at least until you are 100% comfortable with the work product and are sure that it’s in line with what you’d deliver (format included).

One more thing: What about when you’re the contractor?

Oh boy. It happens quite often, but I wouldn’t want to be in that role unless I were working as a full-time contractor on a specific project with a defined team. I’d also want to be sure that I could contact my team via IM, iChat, phone, etc all day. Can you say "separation anxiety?" But, hey, I don’t have much experience in this realm. If you do, I would love to hear your perspective on it!