A Collaboration Cheat Sheet for Business Owners

Have you ever tried to work with someone but it was an utter disaster? And maybe you wrote it off as a bad match-up or a clash of personalities. But most likely, a series of miscommunication, power struggles, or lack of trust was to blame. These are the most common reasons collaboration fails.

As the workplace grows increasingly remote, collaboration often means long-distance collaboration. Many companies now employ freelancers because it’s less overhead. And when you’re talking about collaborating with a freelancer you’ve never met face-to-face, collaboration gets even more complicated. So here’s your personal collaboration cheat sheet.

Extend Some Trust 

Many successful individuals find it hard to let go of control. Self-confidence and self-reliance are handy traits for entrepreneurs, but they’re a hindrance when working with others. 

If you’re used to doing everything yourself, collaborating with a freelancer can be a big change. Remember that freelancers are often experts in their fields, so give them room to do their part. Working with others requires give and take, but the end result is worth the hassle!

Give Constructive Criticism

The “Golden Rule” works well here. Don’t say anything you wouldn’t want to hear. And give feedback with the “compliment sandwich” trick. 

Example: “Great work on the audit, Joan! I did notice, though, that the Accounts Receivable was off by two digits. You’re such a whiz with numbers, and we rely on you so much. Do you need help with anything?”

Notice how the feedback is neatly sandwiched between two compliments?

Clearly Designate Tasks

Make sure your freelancer knows what they’re expected to do. Otherwise, you miss essential tasks or waste time duplicating work. For remote work, try collaboration software such as Trello. Or, create a Google calendar just for things you outsource.

Ask About Their Personal Life

When you work in the same office as someone every day, you really get to know them. You start to understand their personality, how they work, and intimate details of their lives. That type of camaraderie is harder to build with someone you’ve never seen in person, but it’s still possible!

Treat every freelancer you work with as you would an employee. Be friendly and make a little small talk. You may find a freelancer you love working with, and this makes it more likely that they’ll also want to continue working with you. Even if you only work with a freelancer a handful of times, a little friendliness goes a long way. People want to do a better job for someone who’s friendly!

Communicate Well & Really Listen 

When someone talks, do you really listen? Or are you already thinking about what you want to say in response? The next time you’re having a conversation, practice active listening. Give the speaker your full attention. And when they’re done, reiterate what they said before responding. 

Example: “So, you’re saying, Maddox, that we don’t have guest speakers lined up for episodes 3-7. I can get on that right away. Expect an update by next week.”

When you don’t listen and communicate well with one another, mistakes happen, production falls behind, and the overall quality of work suffers. So don’t assume things, and always ask if you’re unsure.

With this handy guide, you can collaborate with anyone, anywhere. If you need help with a specific task, our Gig Gurus are happy to help. Just set up an account to start posting gigs!

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