Agency Guides Overcoming the 7 Key Challenges Agencies Face when Working with Contractors

What to look for when hiring contractors to work with your agency.

For those of us who run agencies, there are countless challenges we face, including getting work, delivering work, and running the business. This article deals specifically with the process of delivering work. If you’re exploring hiring contractors to help your agency’s delivery, good for you!

Contractors can be a great way to get solid work delivered professionally. But there are, of course, pitfalls. Let’s explore the seven key factors to look for when hiring contractors to work with your agency.

  1. Reliability

  2. Professionalism

  3. Expertise

  4. Experience

  5. Communication Skills

  6. Self-sufficiency

  7. Supplementary skills

1. Reliability


Working with contractors can lighten your workload and improve your ROI, but adjusting to this type of partnership might take time – after all, your contractor is not your employee. The best contractors are in demand; your business won’t be their sole priority. Reliability is never guaranteed.

While trust is something you’ll need to build with your contractor over time, do yourself a favour and ask this question before making a hire: Does the contractor have a full-time job? If so, this might push your work to the bottom of the pile when they get busy – or they might give up on their side gig when the going gets tough. I only work with contractors who do it full-time – no “evenings and weekenders”. My business is too small and I’m too busy to take that kind of risk.

2. Professionalism


Is the contractor good with clients? Can you bring them to a meeting and ensure they won’t embarrass you? Since you don’t get to spend tons of time with contractors like you do with employees, it can be difficult to know how they conduct themselves in-person.

While a contractor’s email and phone etiquette can offer up some insights into their level of professionalism, this doesn’t tell the full story. Instead, go after contractors that have been endorsed by other agencies. Online reviews and freelance talent websites are great; real-life references are even better. Many contractors rely on these references to find work, so why not score some great leads through your network?

3. Expertise


A solid contractor lightens your team’s workload while filling skill and knowledge gaps, giving you more time to focus on your own areas of expertise – but a subpar contractor simply can’t offer the same level of ease and assistance. The next time you bring on a new contractor, ask yourself the following questions: How deep does their knowledge go? Is it commensurate with what you’re paying them? A contractor with deep subject matter expertise can save you many headaches in the long run, despite costing a bit more.

Ideally, the first project you assign your contractor should be a “test” of sorts – something non-essential that will demonstrate if their skillset lives up to their resume. It’s easy for contractors to look great on their website, but the real proof is in the work they deliver.

4. Experience


How long has the contractor been doing their thing? Have they been around the block and made their fair share of mistakes? Contractors who’ve paid their dues and finessed their skills over time have so much more to offer your business – you need someone who’s exhibited true dedication to their craft.

Some businesses prefer bringing on fresh-faced newbies with the intention of “moulding” them into their ideal contractor. However, this approach can be a bit of a gamble – tried-and-true contractors can save you money, stress and screw-ups in the long run.

5. Communication skills


Is the contractor able to effectively communicate with you and your client? Do they use plain English, communicating quickly and simply? Are they in a totally different time zone? These questions can make all the difference when it comes to avoiding communication breakdowns with your contractor.

First thing’s first: Decide how you want to stay in touch. Pick a flexible platform that allows you and your contractor to easily manage projects, like Asana or Basecamp. It’s best to keep all communication threads in one place – the more platforms you add into the mix, the more likely something will get lost in the shuffle.

Remember, communication is a two-way street. Clearly define your needs regarding deliverables and deadlines so there’s no ambiguity surrounding your expectations, and listen when contractors raise concerns. Make sure to provide clear feedback – both positive and negative – and see how your contractor responds. Mistakes happen, but if your contractor can take feedback and grow from it, you’ll know you’ve found a keeper.

6. Self-sufficiency


Sometimes, clients will ask for information or insights that are outside of your wheelhouse – and that’s where your contractor comes in. A good contractor will take the deliverable off your hands and get the job done well. A great contractor will educate you on their process by:

  • Explaining the logic and reasoning behind their recommendations

  • Filling knowledge gaps in your organization, making it easier to relay information to your client

  • Creating accurate project requirements and timeline estimates

When you understand and trust your contractor’s process, it’s possible to completely off-load projects onto them. You can feel confident that the work will get done, and your organization might even learn from your contractor in the process.

7. Supplementary skills


While you want a contractor who’s an expert in their niche, it doesn’t hurt if they bring other skills to the table as well. Many contractors look to gain an advantage over their competitors by adding value wherever possible, often in the form of add-on services. Maybe they’re great at running analytics reports, or perhaps they can help manage their own project. It never hurts to ask!

The best contractors are the ones you turn to time and time again. By exploring your contractor’s skill sets, you can grow their role in your business. With any luck, this will lead to a long and mutually-beneficial partnership.

While there’s no sure-fire method for finding the perfect contractor, you can add these seven factors to your must-have list for best results. Finding a go-to freelancer can be tricky, but your increased ability to deliver incredible products and services to your clients will make it all worthwhile. Happy hiring!

Author Details

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I’m Robin Eldred, the owner here at Wulver. I’ve worked in digital advertising since the turn of the century. I go way back, and have the digital scars to prove it.