How To Work With An Illustrator | Part One

How to Effectively Initiate an Illustration Project

My very first ever client/boss/charity-case-worker used to always say I should write about how to work with an illustrator. I was like — wat? You mean, like, other than what we’re doing right now? And does this mean I have to get wordpress? Because I am so not down with PHP. Can’t someone just invent some, like, really pretty minimalist writing platform already? Anyway, somewhere over the course of some unruly number of freelance clients, and on the heels of an internal Shopify talk about how to work with the illustration team — I see what he was talking about.

Illustration — and illustrators — often get put in a black box. Some combination of not-quite-technical not-quite-artist that requires tip-toeing, soft voices and “oh but I don’t want to stifle your creativity” that ultimately leads to a decisive yes or no moment instead of a collaborative process. I’d like to assert once and for all that illustrators—despite all the pretty colours, and peculiar smells—are not all flowers poised to wilt in a gentle breeze. Kill the myth of “the creative.” Illustration is no longer a talent unique and unreachable but to a select few. Rather, just series of steps and approaches refined over years of just doing the thing: attainable to anyone with the time and desire to try. With that in mind, let’s do this: how to work with an illustrator.

Signs You Have an Illustration Project

Okay I’m going to skip over the obvious ones. If you’re having prints made, just finished a children’s book, or have dreams of a pirate-penguin mascot, hopefully you’ve figured out you need an illustrator before now. In product design, it’s a little bit trickier. You probably have an opportunity for illustration project if..

◊ Your users are frustrated, or don’t know what to do next
◊ A feature is being bypassed, misused or underused
◊ There is too much text; the text is not being read/understood
◊ You want another means of speaking directly to your user

To that end, you probably have a larger problem that needs to be addressed first if you are contacting an illustrator because you want to fill up space or decorate.

Getting To Yes

So, you know that thing, where you’re answering emails, but you kind of have something else you want to get to, so you just flag the important ones thinking that you should wait until you have time to send a proper answer—and then that time never comes and you end up neglecting only the most important emails? That’s where your email goes when it’s open ended. Sorry for the delay, email is hard, yadda yadda yadda. It’s not intentional, it’s just those questions you asked—What’s the quote? What’s your availability? What’s the timeline?—are kind of really hard. Like, hang on, so what did I charge for a similar project? Was that reasonable? and did I already up my rate? Wait didn’t I promise myself I wouldn’t take anything like this. Okay so if this other project finishes up when I think it will—which it never does—then I should be available aroooound… oh wait that lands on Thanksgiving… carry the 2..

It’s not a great reason, but it’s just how it is: if you’re sending open ended emails, they’ll probably get procrastinated, some might get forgotten.

Instead, make it easy to say a definitive yes or no (or yes, but…). Save us both a whole lot of time and email headaches and put all the details necessary for a quick decision in the first email: size and number of illustrations, context, timeline, and budget.

So: instead of…

Hey Supa-Star,

I love this that and everything, btw look how important I am, I’m basically featured on every website ever. I am hoping to get an illustration style defined for our soft launch that is someday soon-ish. Just wondering what your availability is, and what you’d typically charge for something like this?

Email Mc-drag-it-out

I’m being a bit of a B here, that’s actually a totally reasonable email to send someone, it’s just that it’s hard to answer, and will probably result in a lot of back and forth.


Hey Pizza-Lover

I invented a pizza ray gun that turns anything you point at into pizza. We need a hero illustration as well as 3 smaller illustrations for the feature call-outs. We’re launching on May 04, and I’d like to have the illustrations finalized within at least 2 weeks of launch. The budget is $9999.

Cheese-crustedly yours,
P. Roni

I’d also add that I know a lot of people feel like they’re giving up their hand when they say the budget. To that I say, eh, that’s your call. You’ll probably end up around the same number, and skip the back and forth. FWIW I think we could use more transparency in design budgets, and the only thing you really stand to gain is taking advantage of a new designer in not paying them what they’re worth.

A bonus detail is why you think this project plays to our strengths. It’s not totally necessary to get to a yes/no, but dang it goes a long way in communicating what you’re looking for with the lowest word count.

Internally, it’s a little trickier..

but the principles remain the same. Get as much information out as possible for the illustrator to give you a decisive answer. I’m being intentionally vague here—’cause I don’t know how your company companies—but consider what criteria they are making their decisions on. That is to say, they are probably trying to prioritize, probably trying to decide how much time your project will take, how much impact it will have, and how much time it will take away from the other projects put on a team that will perpetually have more work than resources (read: every team). And hey, maybe I’m projecting here, but they’re probably trying to practice saying no—since that’s what everyone ever is supposed to be working on—and they’re scanning your conversation to see if this is a good chance to prove they can do it, too.

So, the most important thing you can provide is context. Not just context for the problem, but context for your team, your project, and the potential impact it has both internally and externally. Prove why it’s the most important thing to the company right now. Or, just as valuable, why it’s not. Make it easy for the illustration team to say no immediately, so you can move on to find someone else.

That is, instead of..

Hey we need some icons for the sauce picker.


Hey we have a big marketing push for the choose your own sauce feature launch, and we really need it to be polished before the next issue of Chipolte Montly comes out.

And then, of course, don’t forget to add all the crucial dimensions for moving forward—size, number of illustrations and timeline—to make everyones lives easier and get it in one place. But honestly, once you’ve got commitment to the project, getting details is no biggie.

The point is: cut to the chase. Everybody is over extended, and you can save both yourself, and your illustrator a helluva lot of time if you just start at the important details.

Up Next: Expectations; Getting Started and okay fine we can talk about money too.

Does thinking about process, how people work together and building systems around those ideas like this sound like fun to you?

Shopify is hiring designers in leadership roles. Get at me.



Draw for $$$

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