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Outsourcing for Business: How to Hire a Winning Freelancer

Outsourcing for Business: How to Hire a Winning Freelancer

You shouldn't be doing everything, and delegating is a key part of being successful. Outsourcing is great, but is also something that many people have tried and failed at! In this article you'll learn how to not suck at it, and hire top talent.


 

Know exactly what you need.

First off, one of the biggest mistakes that people make is that they have some idea of what they need, but they just throw up a job and expect the freelancer to know exactly what to do. You could not be more wrong.

Imagine someone came up to you and said 'Hey, you're an architect. If I pay you, can you design my house?' with barely any extra information. Do you think you'd nail it? I doubt it very seriously. You would give it a go, but it is almost impossible that you'll do it exactly the way the had imagined because they hadn't even told you what they want.

Before you hire anyone, get really clear on what you actually need. Don’t assume someone will be able to read your mind, you need to know exactly what you want if you want it done right.

 

Write a killer job description.

Once you know what you need, you need to describe it simply and clearly in a killer job description. Don’t be vague explain everything they need to know with all the info they could need. You also want to make the job seem fun and exciting so you can attract better freelancers. Include things like:

  • A summary of the job.

  • The key responsibilities and activities that will be carried out.

  • The key skills required.

  • The type of personality you’re looking for.

  • Who they will be working with or report to.

  • Compensation and working time zone.

  • Examples of what you need done (if relevant).

  • A little bit about your company.

  • Why it's a great opportunity for the right person.

 

Request a cover letter.

On UpWork you have an option to 'Require a Cover Letter' before an application an be made. Definitely do this, you can see straight off the bat who is clever and genuinely interested by the way they submit it.

A cover letter will weed people out straight away. You’ll be able to see who is clever and genuinely interested by the way they submit it, vs some generic copy-paste response without personality.

 

Ask specific questions.

On top of a cover letter can also make freelancers answer compulsory questions. I recommend this as well, because the way that they answer the question is another indicator for how good they will be.

Asking smart questions will weed out people even more. Their responses are often a good indicator of how they think and their character. Don’t ask yes or no questions, ask something that requires thought. Things like β€˜if you were _____, what would you do?’ are much better. For example when hiring a social media manager I'l put:

  • Add a link to the best post you ever wrote.

  • Add a link to your favourite page that you follow.

  • If nobody knew who you were, how would you build a following?

 

Do trials.

Don’t just go for the cheapest person. Run a short trial of the task you need done. It’s unlikely they will refuse, you're looking for someone that really wants to work with you anyway. Provide them with an example task (or training if you have it) and what you need them to do. Let them know how many spots there are available to create scarcity and some healthy competition so they do a great job, fast.

 

Hire for personality.

Now is where you can look at the results, look at their rate, and then make a decision on who you want to hire. Keep in mind their price does not always directly reflect their talent. Whilst I don't recommend getting someone just because their rate is higher, in my opinion I think it's always worth paying for quality. If someone is a clear winner and their hourly rate is slightly higher, it's worth hiring them. 


Now this is important… β€œSkills” jobs can be a trap. When you hire someone who has the skills already, it means they are walking in with the baggage of their past work, and likely won’t do it your way which leads to confusion or you redoing the work. Hire people with a get-it-done attitude, high energy and a good cultural fit.You can teach skills, but you can’t rewire their DNA or teach someone to not be a jerk.


Note - sometimes you might even end up hiring an extra person. Don't waste good talent - seriously if you find someone awesome just hire them and find work for them later, good talent is hard to come by!

 

Hire them and set expectations.

Time to make someone's day! You've checked the results, you're happy and it's time to hire the winner. Welcome them to your business and make them feel special. Tell them that you are a team, that they are working WITH you, not just FOR you, and you are exciting to have them on board. A friendly company culture is important. They will be happier, and they will do a better job for someone they respect. 


It’s important to set expectations from the start. When you need them to be available, when they get paid, who they will work with, what will happen if work is not up to standard, the next steps etc. It’s also important to share your core values right away and get everyone on the same page from day one to remove any possible confusion or frustrations.

Confirm the KPIs.

These are in the job description, but it’s still a good idea to have a super-simple list of their roles and KPIs in an obvious place, so you can easily visit it to check performance, and hold them accountable. If problems ever arise, you can visit this list. You agreed to pay them XYZ, and they agreed to complete these tasks. If they aren’t being completed, this simple list removes the he-said she-said.

 

Teach them, but stretch them.

This is very important. Once they come on board, walk them through everything that needs to be done because even if you made a process they won't know exactly what to do right away, and they will often be too shy to ask.

Train them, don’t assume have everything they need. You need to give them the tools and resources they need to get the job done, but at the same time you don’t want to spoon feed them. Let them run into obstacles to see how they react, what they come up with and how they think on their feet.

Be available to answer any of their questions (I recommend adding them on Skype or Slack) and understand that it is a learning process. They will make a few errors, but so do you. They will get more efficient as time goes on.

 

Look after them.

If your freelancer is doing an ongoing role, make sure you look after them. Treat them with respect, give them a bonus when they are doing well, if they are in a tough part of the world make sure they can look after their family. If somebody is working with me I consider them as part of my family, and family looks after each other. 

 


 

So there you have it! With these tips in mind, you can now go out and hire a great freelancer. Check out UpWork and get started today - hit me up on Instagram @mitchills and let me know how you went! 

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