Working with contractors and freelancers: A practical guide

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How can you manage colleagues who aren’t actually employees of the company? Learn how to look after independent workers with the help of these effective strategies…

Managing a team of full-time employees can be tricky enough but adding freelancers and contractors into the mix comes with its own set of challenges. After all, they aren’t fully employed by the company, and you have no real authority over them.

But that doesn’t mean independent workers should be kept at arm’s length. They’re a part of the team just as much as your direct reports are.

Like everyone else you work with, freelancers and contractors need communication, trust and motivation to give you their best. But in these kinds of working relationships, you may need to take a different tack.

Here, we’ll take a look at what you can do to make working with contractors and freelancers as productive and efficient as possible.

Set expectations – for both sides

Crossed signals, mixed messages and unwanted outcomes can be common in these kinds of working relationships. Rather than receiving unsuitable or low-quality work, make it a point to set expectations with your freelancers or contractors from the outset.

Draft a document outlining what your desired outcome is and when you need it for so that everyone involved is on the same page. And since you’re bringing them on for their expertise, be sure to welcome their suggestions instead of dictating your ideas to them.

Since these expectations go both ways, be sure to ask them what they want from this relationship too. Why are they interested in taking on this job? Is it money, the chance to learn something new or the opportunity to work for the company? Whatever their answer is, it’s vital you deliver on it.

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Get the important stuff in writing

Along with expectations, there’s a whole host of other important details you’ll need to get in writing too. Things like project scope, overtime and work outside your agreed-upon hours (another thing that will need ironing out) will all need to be mentioned in their contract.

By using a formal contract, both you and your contractors will be protected, avoiding misunderstandings and mistakes surrounding expectations, pay and the length of contract itself.

Don’t be hands off…

There’s an assumption that you don’t need to touch base with freelancers like you would with company employees. And sure, while the relationship is different, freelancers aren’t simply “lone wolves” in it for themselves.

You should still provide them with a supply of drive and direction so you can bring out their best. By taking the hands-off approach, you run the risk of alienating them over the course of their time with you.

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…But don’t micromanage

At the same time, you want to give them the freedom they need to do carry out their duties. Freelancers are natural self-starters who understand autonomy. If you’re constantly checking in with them, you aren’t giving them the space they need to flourish.

Show that you trust their expertise by letting them get on with it. When you have the right collaboration/communication tools or processes in place, it’s possible to check in with your freelancers without micro-managing them.

And don’t forget, there’s a strong chance you’re not their only client. Be respectful of their time and schedule. This is where agreeing on their hours of availability beforehand comes in very handy, especially if they’re based in a different time zone. Likewise, let them know your available hours should they need to get in touch with you too.

Give them feedback

While there’s no need for any formal performance reviews with your freelancers, regular feedback shouldn’t go amiss either. Independent workers won’t know if they’re doing a good job if you aren’t telling them, so be sure to carve out the time to make your feelings known – quality work or not.

Remember, they’ll be used to working their way, not yours. If necessary, let them know of any frameworks, respective working styles of the team and work processes that can help to get them properly up to speed.

You want everyone on your team to work to the best of their abilities, and that includes freelancers and contractors. Whether it’s at the end of a meeting, after a task has been completed or through scheduled one-to-ones, let them know how they’re getting on. They’ll appreciate the time you’ve taken to provide them with feedback.

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Keep communication lines open

When a freelancer goes quiet, it can be a cause for concern. Whether they’re struggling with a project, found work elsewhere or are experiencing some personal strife, a lack of communication can create all manner of roadblocks on the way to success.

Luckily, there are plenty of things you can do to keep in touch with your independent workers and stop the silent treatment from happening.

First, it’s a good idea to let your freelancers know how much work you expect from them in advance. This way, they’re able to plan and prioritise the work you want from them. And if they run into any snags, encourage them to let you know of any delays as soon as possible. This gives you time to make changes to the project or task’s schedule if it’s necessary.

Make sure they have the right tools to contact you too. A project tool like Basecamp or Trello will be an absolute necessity but giving them your (work) phone number can be a real lifeline in the event of bottlenecks.

And even if your freelancer isn’t prone to periods of silence, keeping communication channels open is still a great way of building rapport and trust, and providing them with feedback. If nothing else, you can use your available channels to check in on them at key stages of the project.

Make them part of the team

In their capacity as freelancers and contractors, it’s easy for independent workers to feel a little on the outside. When this happens, there’s a chance they might become disengaged and disconnected, allowing their standards of work to slip as a result. That’s why it’s vital to make them part of the team.

Invite them to important meetings and team lunches. Add them to the team email list. Ask for their opinions on upcoming projects. Although making freelancers seem more like employees can land in a tricky legal grey area if you infringe on any employment laws or HR guidelines, there’s nothing that says you can’t strike up a rapport with them. And by doing so, it establishes greater trust, collaboration and communication as a result. 

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