friend of a squid
Getting the Most Out of Contractors

Contractors are very often the most effective way to get stuff done. Over the years, I’ve developed my grand unified theory for getting the most out of contractors. Most of what I’m about to write here can apply to getting the most out of people you work with in general, but I prefer to think of if in the context of contractors.

What’s a contractor?

First—quickly—what’s a contractor? Roughly: a contractor is an individual with a specific skill brought onto a project who is not employed full-time by your company. This definition is designed to exclude:

  • agencies/consultancies where, in theory, the work is done not be an individual, but by a collective
  • regular employees whom you generally work with every day

The Equation

I’ve found there are three main attributes that contribute to the quality of work you get from a contractor:

Quality of Work = Proximity to the Contractor x Skill of the Contractor x Quality of the Brief

Let’s explore each component a bit.


This is something we all intuitively understand. The closer you work with someone, the more “in sync” you’ll become. Proximity also breeds collaboration. The most there is collaboration, the less likely the contractor is go down the wrong path for a long time, resulting in exactly the thing you didn’t want.

Don’t forget that proximity is a continuum. Having someone sit at the desk next you is best, but having someone in your time zone is still better than someone with a 16 hour time difference. Optimise accordingly.


This one goes without saying. The better the skills of the contractor, the more likely the outcome will be what you want. However, what’s important to remember is you you can get quality results even with a lower skills (and presumably cheaper) contractor if you’re will to invest in proximity and the brief.

The Brief

I  have an MBA. Nobody taught my how to brief. Getting the brief right for a highly skilled contractor is so critical yet is so hard to get right. How many times have you thought you gave someone everything they needed to know to do a good until to receive something completely off what you were expecting? It’s not you. It’s all of us.

Sometimes, you may find the brief is doing the project to 80% completion (“I want my UI to look like. Now change the font.”). Sometimes, you may be purposely vague. After all, this is an expert and he should know what to do be better than me. There’s not right answer of what to do, but you do have to understand how it fits together with the other two components.

Finishing Up

Hiring contractors requires some thinking. It’s not a question of fire and forget or you will be disappointed. Spend the right amount of time on getting someone close to you, with the right skills and give her the appropriate brief and good things will follow. Good luck.