April 22, 2019

The Five ‘C’s’: What to Consider When Working With Contractors

Working with contractors can be of great value, regardless of the stage of your business. In effect, you’re utilizing a minimal viable labor force that enables you to attack a lot of different projects with specialized, scalable resources. This is particularly beneficial at the early stage.

The Five 'C’s': What to Consider When Working With Contractors

Working with contractors can be of great value, regardless of the stage of your business. In effect, you’re utilizing a minimal viable labor force that enables you to attack a lot of different projects with specialized, scalable resources.This is particularly beneficial at the early stage. While great in theory, there are some things to consider to ensure that working with contractors is actually beneficial in practice. These are tradeoffs you want to understand and manage through.


Contractors are usually working on multiple projects concurrently, which means you may find yourself questioning their commitment to your project. It can be hard to not take it personally and blow up in frustration. After all, your project is of paramount importance (to you). Otherwise, you wouldn’t have spent the time to find someone to execute on it, and you sure as sh*t wouldn’t be compensating them to do so.Of course, your contractor is not as passionate about your project as you are. They’re trying to pay the bills and build their own portfolio. But this is really no different than managing full-time employees, many of whom are basically trying to do the same thing as the contractor.At the end of the day, you truly can’t hold anyone working on your projects to the same standard you hold yourself. If you do, you’ll constantly be disappointed, you’ll burn them out and your progress will suffer. What you can do is work to understand just how much all of these people have on their plates and how good they are at juggling priorities and delivering what’s expected (within reason).


(If you read nothing else here, read this.)If you can’t communicate, you can’t collaborate. Figure out a clear communication cadence with your contracting partner.

  • How do you both want to manage the project? What systems will you use?
  • How do you keep track of progress?
  • How do you adjust / maintain scope?
  • How do you keep things cordial and productive in the face of misaligned views and pressures?

You’ll need a consulting services agreement with statement(s) of work in place to govern your relationship. These are the rules of the road and what you can point to along the way to make sure everything gets done as expected. There should be specs (write them all down!), milestones, acceptance criteria, and more.You’ll also need an agreed upon transition plan; after all, this person is not likely to work on your project forever. There will be more work to be done, code to be updated, designs to be tweaked, numbers to be updated, etc. Whatever it is, it will evolve over time, and you need to have the foundation in place to ensure you don’t get stuck.When you invest the time upfront to build this foundation and commit to communicating consistently, you will find that things go a lot more smoothly, and you’ll have a replicable framework you can utilize across your contracting relationships.


All projects go through periods of great productivity alternating with weeks of waste. What you want to try to do is smooth the course of productivity.Maybe you have a manic developer who pulls a weekly all-nighter to deliver a significant piece of the project seemingly out of thin air, then goes dark for the next seven days.Or, you get a flurry of content (hello, 6 blog posts!) when you had seen nothing for the past two weeks and had a stale blog and social feeds. Great, you have some content now, but it sure would have been nice to have had something to drip over the last 14 days.The point here is you don’t want your project moving in fits and starts. While ultimately you’re getting some deliverables and value, this shotgun approach to productivity will wear everyone out and leave you with anxiety around the ultimate performance of your efforts.So, whether it’s three commits a week, one blog post, or 3 campaigns launched and measured over the course of the month, spell it out and hold your contractor accountable to the delivery timeline.


Your contractor is not a full-fledged part of your team / organization. As such, they will not be in your all-hands meetings, will not be pitching strategic initiatives and will not be building support within the company for cross-team collaboration. If any of these is happening, hire this person outright or retain them as an advisor.What they should be doing is excelling at delivering on a self-controlled project that does not suffer from corporate distractions and externality risk. This is the contribution to be expected.You need to feel like you’re receiving valuable contributions from your contractor, just don’t be unrealistic with your expectations. If you’re not seeing the value, cut the cord. That’s one of the benefits of utilizing a contractor. The breakup is less complicated.


Everything we’ve touched on up to this point painted the strokes for how to “control,” or really manage, a contractor relationship. If you do these things, you can maintain control without needing to micromanage or feel like you have to bad cop your way to a successful project.So, find yourself an experienced, self-starting contractor who is comfortable charting the course with you and driving the bus to get the project done to your satisfaction. You won’t need to backseat drive. Rather, you can copilot by checking in on status, consulting the map (your agreement and statements of work) and redirecting as necessary and providing the support your partner needs to succeed.