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4 Things You Must Know about Working with Freelancers and Remote Teams

June 21, 2016

It is one thing to assume that people who work for you will abide by your organization’s rules. But when it comes to working with freelancers and remote teams, the rules of collaboration change, or at least, they must. This isn’t something I am spelling out from the covers of some human resource report. I have been a freelancer and I know first-hand how different things are when working with full-time employees and when working with external contributors.

During my freelancing days, I worked with 3 companies and 11 projects in total. And none of these 3 clients functioned alike. For one, they all had very different attitudes towards us freelancers. While one raved about how I’d bring in a fresh, outside perspective to the way of things within his organization, another actually happened to tell me that their “brand voice is sacred, and I may not be able to ‘get’ it since I don’t work within the ecosystem that others do.” To which I asked why did they need my services in the first place, only to be told that the company is going through a resource crunch and they needed somebody take on the load of content requirements that were that piling up. *There you go!*

Not only does this qualify as a bad reason, frankly, it’s perplexing to come across such an attitude. And it even made me doubt my capabilities more often than I’d like to admit to. I did ponder over it for quite some time and realized that the difference lied in the way these clients chose to include me in their little universe. One was more open, willing to share helpful feedback, and positive about my inclusion on a broad level while the other was seemingly doing it out of a necessity, and with no incentive or motivation to offer helpful feedback. Given that this second client had no formal authority over me, the least he could do was give me just enough push in some direction to remain excited about the work, especially since I wasn’t even demanding (nor was I entitled to) dental and bonuses, like the other full-time writers.

In a sharp contrast, the first client was very happy to give me a performance review [of sorts] after every month much like what they would do with their full-time employees. And it wasn’t just me. These guys were making use of a large pool of agile talent across functions — tech, operations, and finance included. As an organization, they accommodated all our individual schedules, communicated in a crisp and clear manner, seemed open to giving and receiving feedback, and kept us engaged with the full-time employees, so we all pretty much knew everybody else we were working with. And when I asked why this was so, I was pleasantly happy about the answer that came my way.

“We love that you guys challenge what we think is perfect and doesn’t need changing.”

It’s great when you work with an organization such as this. As a freelancer, it motivates you more to push the mettle and do the best that you can. It’s true that navigating your relationship with individual contractors and remote teams cannot be done with rule books.

Today, when I collaborate with freelancers and remote teams, here’s what I keep in mind:

Be clear on why I need the services of an outsider

Understand what kind of expertise you require for fulfilling a task and make clear how you will employ this expertise. You can choose to get them on a retainer basis, have them contribute on a broad organizational level or just employ their services to address something immediate and pressing. Whichever might be the reason and the approach, be clear about it right from the start.

Never be ambiguous about what’s expected of them

No matter the size of the job you are hiring a freelancer for, it is essential you break down the project into mini goals and deliverables with clear timelines. Even if you have been lucky getting an expert to work for you on a contract basis, never assume they will just “get” it. Define their role, spell out the budgets, and the scope of tasks to be addressed by the agile talent. Be clear about what’s expected of them in terms of quantity and quality of work and how the exchanges will occur.

Avoid collaborating over emails

Not that there is anything wrong with the good old electronic mail, it’s just that it’s increasingly easy for a piece of communication to get lost in the laundry list of emails that pile up like incompatible Tetris blocks in your inbox. Especially when an organization is of a complex nature with too many collaborators and contributors, emails prove to be quite cumbersome. Email are good to kick start the communications and onboard a freelancer to a project, but beyond that it is advisable to have them transition onto a wider project management and collaboration tool. This helps you track all processes pertaining to your project at once and from one source of contact.

Never treat freelancers like outsiders

Alignment. I like this word and for many reasons. It suggests balance and harmony; a ‘merging’ that adds value to the object it belongs to. When it comes to freelancers, the only way to build meaningful working relationships is by ‘aligning’ them to the organization; its strategies, culture, and the people — much the same way you would for your full-time employees. When you onboard external contractors this way — when you try to see if they are the ‘right fit’ for the organization — you stand to reap more valuable work from them. Because this way you suggest that you are genuinely interested in their services, and are happy to have their expertise help the organization achieve some desirable results.


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