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Where does the General keep his armies?

In his sleevies!

So You Want to Hire a Contractor (Part 2)

Awhile back we covered the initial stages of hiring a contractor and now, we’re back to dive into part two of what you need to know. This time, we cover some basic logistics around payment, documents, and communication.

Getting on the same page

If you’ve found a contractor you like, you’ll want to make sure you’re on the same page. That not only applies to start dates and payment, but the actual logistics of bringing them onboard.

Before they get started (or within the first week of when you’re starting), have a kick off meeting that covers the logistics below.

Ideally, you’ll have all of the paperwork you need saved in a folder in advance (organization is key!), so you can easily send copies to them before they start work. Then, the kick off meeting to cover the ins and outs of the work itself, as well as focus on your deliverables timeline.

Project management

As we all know, it’s easy for things to get lost in the shuffle. When you’re working with a contractor, especially if you do not have a designated project manager, knowing how they’re going to report to you and track deliverables is crucial.

Hopefully, you asked what kind of project management tools your contractor is familiar with to make sure there won’t be a steep learning curve when they get started. If you’ve asked them to get on board with what you already use, you’ll want to make sure they are invited to it immediately.

We use Breeze, which is a Kanban style board that makes it easy for all of us to collaborate, communicate, and see where we are in the project process. There are a variety of other tools available; if you aren’t picky, ask your contractor if they already have one that they’re using. If you aren’t already using a PM tool, get on it!

Money, money, money

Remember: taking on a contractor means you’ll need to handle not only their payment, but you’ll need to keep things organized for their taxes (and potentially yours) and keep solid records for your business. We use Gusto to handle basically everything, from payroll, to taxes, to essentially all of the HR organization needed to keep employee/contractor information easily accessible and organized. It’s not just for full-time team members, but also great for paying contractors, too.

We also want to stress the importance of paying people on time. This doesn’t just apply to employees, but to contractors, too.

Communicating with your contractor

This is always a bit of a struggle, as everyone does something a little bit different.

When I was contracting, being invited to the company Slack (plus whatever communication was needed through the project management tool we used) was always the best way to communicate. It’s what Zao does in general, too–we have Slack rooms for each project, and invite whatever contractors or partners we’re collaborating with into those rooms. It makes the most sense, as it’s archived, easily accessible, and transparent.

It also means we don’t lose things in our inboxes, then are left wondering what happened.

You’ll also want to make sure you have all of their appropriate contact information in one place. That’s another benefit of Gusto: contractors will need to enter in all of their contact information there, including mailing address, birthday, email, etc. This allows you to easily organize and access their information, which makes your life easier as well.

Our communication reponsibilities

We want contractors who are communicative, which means we also aim to make our communication clear and timely. It would be hypocritical to expect contractors to respond quickly if we don’t do the same, so we do our best to make sure they have everything they need to get the work done and answer their questions.

If we don’t communicate with them, we are responsible for things not getting done, in the same way that if a client doesn’t communicate with us, they are. All of these things are collaborative processes, so we make sure we’re delivering on our end, too. Make sure your communication is on point to ensure your responsibilities are covered, and your contractor is supported.


Now that you’ve got your contractor on board and all those little ducks in a row, you are good to go! Make some money, people!

Have any questions about the start of this process or any burning questions about hiring contractors? Let us know!

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