How To Work With Freelancers

Disclaimer: I schedule these posts months in advance, so if we have beef now, we didn’t when I scheduled this.

            Oof, it feels weird to write this one. I mean, it’s not exactly “Throw out their grain every night no later than six. They’re used to me coming home at 5:30 so they’ll get grumpy if they get too hungry.” But there are a whole lotta things I wish I knew before I got thrust into positions of leadership, much less positions where I had to make decisions. Hopefully, I can keep someone else from making the same mistakes, and just for spice, I threw in the habits of some of my least favorite bosses.

            They’re just people, bro. Maybe they’re not available right now because they’re taking the kids to Disney Land! Every people comes with baggage. Sometimes that thing is late because they’re fist fighting a land shark, or more likely, doing something like dealing with a family emergency. Yes, you need the thing, and you need it on time, but you also need empathy and compassion if you want to keep that talent in your corner. Another thing that will help you is to keep track of their time zone, that way you’re not asking for urgent work at their 3am.

            Be clear about what you want. If you want a drawing of a guy, playing a fish shaped banjo, on The Great Wall of China, then you need to tell your freelancer that you want a guy, playing a fish shaped banjo, on The Great Wall of China. Don’t just say “Some person, on a wall, playing some sort of oddly shaped instrument.” that’s hecka up to interpretation. If you’re not clear you could get some lady, sitting on a garden wall, playing a heart shaped guitar. Which, then you will be sad because that is not what you wanted.

            Be clear about when you want it. This one gets tricky for me. I’ve worked on an “as you’re able, and I still have money to pay you” basis, but as the event I needed the work for got closer, it got hairy. You know what it’s like when a person with three feet of hair starts loosing hair from stress? Not fun. And you’ll find it in your food. Don’t do this to me, Joe. Pick a deadline out of the air. Even if it’s “within the next six months” it will help a lot. And if it is “soon”, “soon” is not a real deadline. “By the last day of the month” is. To be honest, I’ve done it to others too. You need solid dates you can nail down on a calendar. It will help you, and the team stay on track.

            Come with a napkin drawing. You remember banjo fish guy? I promise you, if you show up with a stick figure drawn on a greasy napkin, your freelancer will be excited. A really crappy version of what you want is better than no version of what you want. I can tell you from experience, as a free lance social media manger, that it’s a lot easier to adjust a message from a newsletter, and change it to a Facebook post, than to wonder “Is this right? Am I allowed to say that? Is this too edgy? This is what they meant, right?” Because with social media management, you’re often turning three paragraphs into three sentences at most. (Yes, I am taking on new clients. Message me for more information.)

            Stop hovering. Micromanagement drives me batty! Either you come with “I made this [rough sketch of fish banjo guy] but I just need you to clean it up.” or you stop telling them how to do their job. I had a boss that would try to stand over me while I was working on the company newsletter and try to dictate to me like I was a scribe. “Tell them that…” It was very distracting, because often times we weren’t even working on the same place.

            Eventually my patience wore thin and I said “Why don’t you make a draft of what you want to say in your office, then email it to me?”

            I feel I was polite enough, but I believe he got the message because he blushed and said “No thank you. You write in your off time…” then went to his office.

            I had another boss that would physically stand in my way to survey me while I worked on an assembly line, then complain when my productivity went down. Other times, she’d take the work out of my hands, try to show me how to do it, do a much worse job than me because she hadn’t been doing it 100 times every day (I’m not exaggerating) for the past few months, then, once again, act surprised when productivity and quality went down.

            I understand. The people under your employ and the things they produce are a reflection of you. But you hired them because you trust them. If you don’t, why did you hire them?! Admittedly, I have had to go behind people I’ve worked with and make slight adjustments (now everyone I’ve ever worked with is going “Omg, was it me?!”), but it’s a lot better than having to present the world your napkin drawing.

            Don’t say it’s good when it’s not. Sometimes, you shouldn’t make that adjustment yourself. “Can you change the font? That’s a little hard to read.” is completely different than hovering. That “Well, what do you think?” usually means the freelancer showed you work for feedback before finalizing it, and they want your input. It’s completely different from standing over someone while they work!

            “I will certainly take a look at this for you before you finalize it” > “What are you doing now?”

            Get it? The difference is they asked.

            Communicate, communicate, communicate! That’s it. That’s the secret to any relationship. Communicate.

            But you have to watch how you communicate. You also have to learn how they communicate. I ran into that with a boss I friggin’ adored, and accidently made a mess of things. Some people need direct, clear, communication. Some people need a gentler approach my Germanic butt is still learning. Paying attention to how someone needs you to communicate with them is the hardest part, but you’ll learn as you go, and you get to know them.

            Use contracts where you can. Gentleman’s agreements are all well and good. My friends and I are just generally happy to work for each other! But even so, contracts set those healthy boundaries, and give a sense of expectations on to both (or all) parties.

            Throw out their grain every night no later than six. Oh wait. They’re not horses. Don’t do that.

            They are your partners, not your slaves or servants. I’m going to tick off a lot of employers by saying this, however, someone has to say it. You, an employer, hire talent because that person either has a talent you don’t have or because you don’t have enough hands, or hours in the day, to perform that talent. Be it a cover artist, or a ranch hand, you needed them. And you know what? If they’re worth their salt, they’re going to be snapped up by someone else if you mistreat them. They don’t owe you butt kisses. Treat them like a partner; keep them in the loop, communicate with them, tell them what you need and what you expect. You didn’t buy them from some online slave auction, and they can and will leave if you mistreat them. Do not abuse your role in their life. They are not horses.

            Pay them on time. For the love of all that is holy, PAY THEM. I’ve seen more than one friendship ruined over that. Whether it was cash, farm fresh eggs, your first born, or that weird braid on the back of your head you only think no one knows about, you need to pay them what you promised them when you promised it. If life punched you in the jaw, tell them so! “Can you please hang on to this work? I’ve hit a hard time financially, but I hope to pay you within the next three months. Thank you for your time and dedication.”

            Or, alternatively “Hey bro. My mom found The Neck Braid and made me clip it. I need time to grow you another one, but The Neck Braid will live again!”

            And no. You don’t get the work until you pay for it. Don’t let them give it to you either. That’s immoral. No one wants to work for free. If you run off with the work in hand, you’ll forget you haven’t paid them. But you should also give them a general idea of when you think you’ll be able to pay them. Maybe you’ll be paying them a little each month until it’s paid off!

            All in all, just remember they’re people, not horses… Much less robots! And you hired them because they know what they’re doing, but you also need to communicate and tell them what you want. Set up the expectations of your professional relationship, then actually pay them. You’ll be fine. There will be hard days, but that’s the biz, kid.

            Can’t get enough of Helen’s ramblings? Love this blog and wanna help keep it running? Subscribe to Helen’s Patreon to access this content early, and a ton of poetry and short stories! A portion of proceeds go to Helen’s secret neck braid.

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Helen M. Pugsley

Helen M. Pugsley comes from a small town of twenty in eastern Wyoming. They have been passionate about writing since they were small. Helen has been working on The Gishlan Series since she was 14, and 'The Tooth Fairy' was a pleasant side effect of surviving a global pandemic.

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