The Control Freak’s Guide to Working with Freelancers

by Jackie

At some point in your business you’re going to realize there’s something you just can’t do. It may be creating graphics for your website, it may be installing a piece of software you just don’t understand, no matter what it is, it will happen. When it does, you’ll have to find someone out there in the big old internet to do it for you.  When you find just the “right” person and you hand over the reigns to whatever it is you can’t quite do you’re probably going to freak out.

There may be minor anxiety spells or all out panic attacks, there may be unprovoked lashing out on innocent nearby family members, there may even be uncalled for working out ~ in an effort to get rid of some of the excess anxiety energy you’ve got going on.  While those are some of the ways to release some of this yucky I don’t have control over this piece of the puzzle energy ~ they probably aren’t the best ~ well working out’s probably good, but sheesh, who wants to do that. :)

There are ways to handle handing over the reigns of your super awesome business pieces to someone else without losing your cool.

When you finally find your Mr or Mrs Right freelancer make sure you talk to them. If this is your first time hiring someone else to help out in your business act like it isn’t. (at least in your head) It’s super easy to make up all kinds of crazy bullshit in your head when you focus on the fact you have no experience whatsoever doing this. Act like you do it all the time.

Just because this is your first time doesn’t mean you can’t ask for what you want and what you need. Not only for the project at hand, but for your mental well being as well. It might seem scary but go ahead, channel your inner Donald Trump. You own this business… you can ask for what you need. The worst that can happen is they say no ~ and maybe that tells you this isn’t the right person for you to be working with after all.

So what is it you need to ask for?

It depends on what the project is, but let’s look at hiring someone to do something artistic for you. This could be a header, or a new theme, or even just an image to put on your website. Artsy stuff can be tough because you may have an idea how you want it, a picture in your head how it’s going to look ~ and that’s hard to get out of your head and into the artists head. I mean if you could just draw it, you would right?!

So try to explain in as much detail what you’re looking for. The color, the feel, the layout. Make sure you know in YOUR head, what are must have elements.  Also identify in your head what is flexible and where the artist can run with something. The thing that rocks the socks about artists is that well, they’re artists. They have all kinds of awesome arty tricks up their sleeves, things you, as a rockin’ business owner ~ but non artist know nothing about. It’s important to let them have a little room to work ~ so they can create you something completely awesome.  AND it’s super important you know where you’re going to draw the line between what you want and their artistic awesomeness.

State this line clearly in your first conversation. No, it’s not bitchy ~ really it’s not. It’s you being clear so you can walk away from the conversation without heart palpitations. The clearer you can be with the artist the easier it will be for them to wave their art wand within your lines to create something you’ll both be happy with.


Set a timeline, deadline or whatever you want to call it. Make sure you and your freelancer know when this needs to be done, finished, in your hands complete. Do not say “oh around the middle of the month” when you need to launch your awesome thing on the 30th. The middle of the month may look different to you than it does to an artist. Give them a date, a time. I’d like it by the end of the day on the 15th. This way if the 15th comes and goes you know you stated yourself clearly and you don’t have to feel “bad” when you say to them ~ “Hey, where’s my stuff? I thought we agreed on the 15th.”


You’re getting ready to hand off this project ~ it’s something big, or something little, but it will no  longer be in your hands. You will sit around fretting about whether the freelancer is really working on your stuff, or whether they’re taking a nap or drinking Tequila until all hours of the morning instead.

Talk to your freelancer about their process. How do they work, how does the project move to completion. This will help you better understand what’s happening on the other side of the computer screen.

In line with this communication thing, set up check in days. If  you’re going to sit there wondering, freaking out, creating minor or major anxiety attacks for yourself wondering if it’s really getting done ~ set up check ins. Ask your freelancer to send you an email every couple of days to let you know how things are going.

It may seem crazy ~ and you may feel that’s revealing a little too much of your crazy ~ but I guarantee you, these little check ins will allow you to keep moving forward with the pieces of the puzzle you DO have control over. It’s really easy to stop working on the project because the piece someone else is working is so crucial that if it isn’t done, or isn’t done “right” the whole project will have to be put on hold or started over. Yeah, it’s easy to go there, so just ask them to check in. Ask them to let you know the project is moving along.


This runs along the lines of communicating with your new freelancer. Ask for updates. If it’s art related, ask them to send you a peek of what’s going on. This way you don’t have to feel scared it’s not going the way you want. You can see if it is, and if it’s not you can ask for changes in the early stages where it will still be possible ~ and not cost you any extra money.

If your project isn’t art related ~ but it’s more concrete ask them to send you some numbers. What have they done. This way you can feel good knowing things are getting done, and you can go about your work.


Talk about how and when payment will be made for their services. Also make sure you know what will be extra and how they will talk to you about it if they see something’s going to go over. Also make sure you talk about what happens if you don’t like their work ~ or it isn’t what you wanted in the end. Do you still pay? Do you pay half, a quarter?

The money, especially if you’re a new business owner with not a lot of it, can cause some extreme anxiety through this process ~ especially if you haven’t set it up so you’re hearing from your freelancer regularly. It’s really easy to start making stuff up in your head… don’t. Be clear from the get go, so you know exactly what will happen, and how. :)

How to do this without coming off as a total control freak crazy person.

Well… :) Just kidding. Be nice about it. Speak politely to the other person. Talk to them like you would talk to a friend. It might even help to tell them you’re a bit of a control freak, and this will help keep you off their back during the process. If you let them know how much you appreciate the work they’re doing for you, and be nice about it, it will be ok.

I think you’re probably being harder on yourself than they are to tell you the truth.

So there you have it, the control freak’s guide to working with freelancers. The first time you do it is the toughest. It gets easier from there, and the more you’re able to hire out the parts that would take you forever, the better. Your time is much better spent doing what you’re good at than trying to learn how to do everything so you don’t have to give up control.  Take a deep breath, and hand over the piece to someone who knows what they’re doing. It will be ok.

I’d love to hear any other tricks or tips you have for not losing it when working with freelancers. Please, feel free to add your tips to the comments section and share them with the class. :)

image credit: Her Wings


Enhanced by Zemanta