What You Need to Know About Hiring Creatives

In my early twenties, I built a multi-million dollar business without any investor funding.

Initially, SalesFolk started as a service business which helped B2B salespeople and marketers create more effective messaging, with an emphasis on email templates. 

Over the years, I hired hundreds of writers, editors, and other creative professionals to help me scale my company. Many of my early hires didn’t work out, but after the first dozen I started to notice a few patterns with my best creative hires. 

The following advice applies for any role that requires lots of creativity. You could be hiring a full-time designer to make your software beautiful and easier to use, or just a contractor to edit a video or help produce a podcast.  It even holds for creating rap songs and music videos. 

Hiring for these traits will help ensure your projects run smoothly: 

Unfortunately, many creatives don’t have this. This is largely what separates the best creative professionals from gifted amateurs. Many businesses pay consultants and agencies because creative talent is often bad at being clear and timely with their communication.  

I won’t hire someone who can’t be reasonably responsive over Slack or email. 

Beyond his incredible musical talent, I chose my rap producer, Keyzus, because he’s highly collaborative, communicative, and responsive. 

Wrangling creatives can be really hard. Many software developers, designers, and artists hate deadlines, and will fight them tooth and nail. Professional copywriters and editors are usually a little bit better with deadlines, but freelancers will definitely use the maximum time you give them.

It’s true that it’s hard to assign accurate deadlines to complex creative projects, especially if you’re doing something new for the first time. But you should still at least try.

You can ask whoever you’re working with what they think is a reasonable deadline, but use your best judgement. If you can, try to research online what an average timeline would be or ask someone you know who does similar work. You should somewhat trust whoever you’re working with, as everyone’s process varies. 

However, it doesn’t hurt to compare. That’s why I like to try out multiple people for whatever project I’m working on, assuming I’m going to be doing that type of work on an ongoing basis. If you hire a few people to do small projects, you can compare their quality, speed, and price. 

What’s really important is that whoever you hire doesn’t make a habit of missing deadlines. Things will go wrong sometimes, the complexity of a task may be underestimated, and emergencies happen. But consistently missing your deadlines is a red flag, and requires at least a conversation, and potentially a firing.

This is so important for all hiring, but especially creatives. Many people make the mistake of trying to hire the “best” designer, writer, or video editor, without worrying about their willingness and ability to collaborate. 

I can’t tell you how many times I hired someone extremely talented who quickly became a giant nightmare to work with. You and whoever you hire should be open to discussing feedback if there is confusion or disagreement about why changes need to be made. However, a creative simply ignoring or refusing to receive feedback is unacceptable. It doesn’t matter how many awards someone has won, where they went to school or worked if they can’t take feedback.

Try to look for this trait in interviews, but I also highly recommend creating “test assignments” (even paid ones) to see how well someone can collaborate or not. 

This is one of the top traits I hire and fire for. I always try to give job candidates a sample assignment that provides a preview of the work they’ll be doing for my business. Beyond them not doing a terrible job on the task, it’s really important that they carefully follow my detailed instructions. 

Remember: you’re not hiring a mind-reader who already knows everything about your preferences and your business. Try to include all the resources and directions they need to be successful on the assignment, assuming they have the skills and determination to do well. This is time-consuming, and your assignment won’t be perfect the first time you create it, but it will be invaluable if you continue to improve and iterate on it over time. 

It depends on the role I’m hiring for, but these assignments usually weed out 68-95% of potential hires.

Once hired, I pay close attention to whether this person can continue to follow instructions or not. It’s fine if they have questions about instructions, or even to challenge the way something is done if they have good reasons and logic. (Some of the best hires will do both of these things!) But I’ll swiftly fire anyone who simply ignores directions or fails to implement feedback that’s been given at least once.