7 Mistakes First-Time Employers Make (And How to Avoid Them)

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When done right, hiring a freelancer is one of the best ways to take control of your schedule and grow your business. But like any time you try something new, it’s easy to take some missteps the first time around. Here are the most common first-time employer mistakes, and some tips for getting the most out of the experience.

1. Posting vague job descriptions

The only way to attract the right freelancer is to set reasonable and clear expectations from the very start. You can’t do this if you refuse to give any specifics about your job! Before you even start looking for freelancers, pinpoint exactly what it is you want. What do you want them to do? How fast do you need it? What specific skills and industry knowledge are required? And don’t forget your budget – will it allow for the best of the best, or are you simply looking for someone who can get the job done?

2. Going for the cheapest

Automatically hiring the freelancer with the cheapest rate is a recipe for disaster. Assess each freelancer’s portfolio, profile and ratings as well as their quote. Newbies tend to charge cheaper rates to score more jobs because they are trying to boost their reputation. If you find a newbie with a portfolio that impresses you, go for it! But if your job requires finesse or specific expertise, you may need to hire a more experienced guru at a higher rate. This generally pays off in the long run in terms of turnaround time and the end result.

If you find you aren’t getting the quotes you want, make sure you aren’t making some of these common job posting mistakes.

3. Providing too little information

Different types of industries all have different conventions around hiring. For example, a copywriter will probably ask you for a creative brief, or a short explanation of what you want, your customer avatar, and information about your branding. If you’re not sure what you should be sending the person you want to hire, ask them or ask the Guru community! By giving a freelancer what they need in the proper format, you’re greatly increasing the chances that you’ll get what you want.

4. Having an unrealistic deadline

Don’t try to outsource something very important on a short deadline. You need to allow enough time for any revisions that need to be made, and besides, you never create the best work leaving it till the last minute.

5. Sticking with a freelancer ‘just because’

Nothing says you have to stick with the first person you outsource a job to. If you’re not 100% happy with the work or a freelancer’s attitude or communication, then you can and should look for someone else, even if you are in the middle of a project. You may have to pay for the work that has already been delivered, but sometimes it’s better to cut your losses to move forward with a freelancer who will bring you more value long-term.

6. Undervaluing communication as a skill

When you first start talking to a freelancer, pay attention to how promptly they respond. Do they seem to proactively offer information on related topics when you ask a question? Do they answer all of your questions, or only the first one? The last thing you want is to work with a freelancer who is unavailable when you have a question. Look for the red flags from the beginning, and establish your expectations in your agreement, where you can request updates from a freelancer at set intervals.

7. Making payment before receiving work

It’s never a good idea to pay a freelancer up front when you’re hiring them for the first time. There are just too many things that can go wrong, from simple misunderstandings to outright misrepresentation. Once you’ve paid a guru, your money is with them and there is nothing we can do to help get it back. Instead, protect yourself by asking your freelancer to create an agreement, and fund upcoming hours or milestones using SafePay. This gives your freelancer the assurance that you plan on paying them, and you can rest easy knowing that your money will be paid to them only after you approve the work. In the case of a dispute you can request a refund of SafePay funds and use our arbitration services, if needed.

Don’t be afraid to hire freelancers. But do be smart about it, and reach out if you need help! If you have any questions or concerns about how to outsource your job, let us know in the comments.

You can also learn more about outsourcing 101 and how to simplify the hiring process in the Help Center.


  1. This may have been suggested above, but surely some freelancers (sorry, gurus) have experience with communication. Coming from a software development environment, as well as copywriting and script editing, I believe I could do a better job in communicating requirements for freelancers. I’m sure many of us could. It would require a neutral third party (i.e. not buyer or seller) to mediate between the two parties, without divulging too much information. I’m happy to volunteer for a nominal fee (say, $5:) ) and I think others would be as well. Let’s use the enormous talent pool we have to help buyers specify what they want in enough detail so a guru knows what they’re letting themselves in for. Also, the mediation fee could be split amongst the volunteers, and perhaps (partly) given as a discount to the buyers, to encourage them to use the service. Bad idea? Good idea?

    • In addition to my previous suggestion — and someone remarked on this in this thread — is the poor quality of spelling and grammar in certain posts. If you’re good at spelling and grammar that service should be optionally available to all sellers. Again, a nominal fee (say $2) should apply, but only once the seller has accepted an offer in principle.

    • Interesting idea, Colin! Thanks for sharing your feedback. We’ll consider that as we’re looking for ways to improve the site in the future.

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