How To Work With An Illustrator | Part Two

Above all: Set Expectations

Okay, cool. So we’re doing this. You need an illustration; I need a project. This is really for sure definitely happening. Everyone comes in bright and shiny: armed with the experience of all the other times that projects were less than room-temperature-butter smooth; and an unbending determination that this one will be different. We’re going to take our time. We’re going to do things the right way. This is going to be GREAT.

Of course, miscommunication happens. Things get lost. People are hard. I’ve heard radical candour so many times that I’m pretty sure you’re just making sounds now. Radical candour. Radicalcandour. Radicandour. Raticandor. Rat I can or. Brat I can more. That I pander. What? What. Nothing. And when you’re in the thick of it I say: get over it, everyone is trying their best. But if you haven’t started yet HOLY FLIP SET ALL THE EXPECTATIONS YOU CAN.


Types of Illustration Projects

Actually, there’s too many types of illustration projects to name, and they’re hella nuanced and unique (read: quoting is hard). Where I draw a line on the art board leaves us with two: service projects, and design projects. It’s important to be clear in articulating what type of help you’re looking for when starting a project, not just for the illustrator, but for yourself. 
The expectations of deliverables, regularity of communication and level of collaboration are so dramatically different that to not mislabel them leaves project with the gas pedal down and the gearshift stuck in neutral — everyone just trying to catch up to they think the other person wants.

Service Projects
A service project is a well defined project, with clear deliverables, probably fitting into a larger overall design. Hey I need to visually explain how this works. In 800px. In Blue and yellow. Probably in this style.

Something feels gross about admitting you’re a service team, like when Vivian Ward turns on I love Lu — you know what, never mind. It’s just something designers need to get over, if you ask me. You don’t need to reinvent the mail icon on every project just to justify your twitter bio. Jumping in to an existing problem, getting up to speed with the existing parameters and helping another designer execute on their vision is an awesome way to spend your time. You can continue to think critically, solve problems, tell stories — or whatever the next phrase we latch on to is — but you can also trust that the designers who got there before you gave you all the information you need to do a good job.

Design Projects
A design project is open ended. Not open ended, like “hey are you available”, but open ended like “I don’t know how I should do it, but I know what I’m trying to do.”

We are, after all, story solvers, and we live for this shit. This is when you bring an illustrator in to help you play to an illustrations strengths and decide what warrants an illustration. Or to help you be precise in choosing the voice you’re communicating through. Design projects are heavy on the conversation/exploration, light on the execution — at least in the beginning. It’s easy to get 6 months into a design project, look up and wonder if you’ve actually started yet. Design projects are hard. And frustrating. And potentially friendship ending. What? What. Don’t worry about it, Janet. We hugged it out. But DAMN they are so fun when you start to figure it out.


Know what you want

Start by removing the phrase “I’ll know it when I see it” from your vocabulary. You won’t. I definitely won’t. No one knows how to work with you. Or in more actionable terms: manage your own expectations first.

You don’t have to have a clear vision for what you want your project to look like, but you should have some idea of something. Anything. Without something to aim at, all process goes out the window in favour of the spaghetti wall. Let’s just keep throwing noodles until something sticks. Might stick on the first try; might never take. Nobody knows how long it will be before it’s al dente.

Start with the tangible

Obviously the things you do and don’t know are going to be dramatically different depending on the type of project you’re working on. Regardless, you should consider it your first step to gather as much information as possible. You can start with the easy stuff (read: the stuff you can just look up): dimensions; timeline; budget; brand constraints; printing limitations; how it will be animated; what screen will it interact with. Look for anything you can think of that will lead you to say “oh I like it, but it’s not going to work because of x.” Identifying something that you don’t know, but probably should know (and are asking for help to figure out) totally counts too.

Gather everything, ever, that you like. The more the better. You should be looking for things that you like and are suited for this project. Think of it as trying to Frankenstein your brand new illustration style together. You just need to help find the parts. You don’t need to limit yourself to found illustrations. You definitely don’t need to limit yourself to Dribbble. You don’t even need to limit yourself to images; “you know that feeling? when you let yourself give up for the day, the guilt of binge watching washes away, and you can finally finish re-watch the rest of Firefly in peace” will do just fine.

Gather everything that you definitely for sure don’t want. Potentially more valuable than your previous scavenger hunt. This is the stuff we will not figure out if you don’t directly tell us.

Continuing in descending order of importance, let your illustrator know why you think this project is suited to their strengths. DO NOT say because they had a lot of followers. Unless you invented a pizza-shooting ray gun, then you can say whatever you want. There are so many different illustration styles, unique to each artist. I’m going to be pretty confused if you come to me looking for a 3D or watercolour look (followed by uh.. no..?). Ideally this includes specific references of work that the illustrator actually did, or a style similar to their work, and the reasons you were drawn to it. The more reasons you have, the easier it will be to exaggerate those qualities. It’s the most efficient way to make sure that you both have the same expectations and vision for the final product.

The less tangible (read: art direction)

Hells yes you can be an art director, even without all the debt and h̶o̶r̶n̶ ̶r̶i̶m̶e̶d̶ ̶g̶l̶a̶s̶s̶e̶s̶ (update:) facial hair. Start with ideas that you already have. “I don’t want to stifle your creativity” is bullshit. I haven’t met a single designer who won’t interpret your instructions to suit their own opinions. That is, after all, why you hired the expert. More importantly, I don’t know anyone who won’t i̶g̶n̶o̶r̶e̶ reinterpret your ideas if they think they’re s̶t̶u̶p̶i̶d̶ uninformed. Seriously. Don’t fret about clouding your designers brain with too many ideas before they have a chance to be creative. We’re good. Share your ideas. Even if they’re only half ideas. Especially if they’re only half ideas. You will always have more context on the problem we’re trying to solve. There’s probably something useful in there, if not the idea itself, then the discussion around it. The level of abstraction; the choice of metaphor; which elements you’re gravitating towards—all of them potentially easier to understand through example.

Beyond the ideas you already have, there are less concrete qualities and feelings that you can aim at with your illustration project as well. As an exercise, (and not to imply that it’s the only one, just to say that it’s hard to know what you want, so here you go) before you see the first pass at an illustration: consider the qualities you want in your illustration; which are at odds; and where you lie on that spectrum. This will give you a tool to articulate where you want your illustration to land, as well as a tool for more actionable feedback later in the process.

Just find a common language that everyone on the team can aim at, and measure the success against. There is always going to be specialty/industry/BFF specific jargon, but that shouldn’t exclude anyone from the conversation.

Don’t confuse relevant details with art direction. You can leave the art direction fairly open ended, if you want. So long as you’re comfortable with a wide range of possible solutions. Beyoncé, NY, inky-grunge. Cool. I can totally do that. Ima be legit pissed when it turns out you wanted a survivor Bey when I just finished with Lemonade Bey. That’s not a symptom of an open ended direction, left up to interpretation. That’s just a thing I was supposed to know about.

Ideally, this is all captured in a brief. Realistically, it’s not. Just make sure that it’s all written down (probably in an email). Remember that if you’re working with a contractor, they probably have 10 other projects they’re holding in their brain and it’s easy for bits of conversation to get lost.


The Working Agreement

In articulating what you’re aiming at, and the type of help you’re soliciting, there’s an implied working relationship; a level and schedule of contribution. Close that communication loop by being a grown up and saying it out loud with your words. Ideally, you get it in writing. Realistically, you at least have a conversation.

Equal contributor vs. Resource

Vision needs ownership. Multiple visions = division. Making it clear from the beginning who will be making decisions, and to what granularity is hella important. There’s a lot of feet on the ground, so quick: everybody speak up before toes get squashed. Who has the final say? Actually, who has all the less-than-final says, too? Am I there to help construct the vision? Or am I helping someone else execute on their vision? Is my input just a suggestion or do you need to tell me why you’re didn’t make the change? One is not better than the other, they’re just different roles. Problems only start to bubble up when people don’t agree on where everyone stands.

Equal Contributor
Collaboration in it’s truest form. We either worked together on the vision prior to execution, or we are both aiming at the vision set by another stakeholder. We move forward in sync. Not just in the work we do, but in deciding what work should be done, and what/how the work is presented. I might manipulate the illustration style to fit your product, but hey maybe you can switch up your product to fit my illustrations. We’ll keep reshaping our pieces until they snap together. This relationship is one of give and take. What do you need from me? On it. Here’s what I need from you. Six avatars coming your way; make me up a reports page with zero sales wouldja? I consider it my responsibility to fight for my opinions. If we disagree, be ready to convince me, because I’m not backing down until you change my mind, and I expect nothing less from you.

Resource
This is not my vision, but I trust in yours. Tell me what you need. Advice? Context? Three Facebook ads and a cat? I’m your girl. Here’s my professional opinion. I consider it my responsibility to make sure you understand where my suggestions are coming from. I will make it abundantly clear when I think something is a bad idea, and work to make my point of view as accessible as possible. Beyond that, it’s your call. Feel free to leave it on the table. No skin off my back*.

Time/energy commitment schedule

One of the things that makes illustrators so suited for freelancing is our working schedule. We like to soak up everything we can about the project, and disappear—only surfacing briefly to check in on colours or choice of metaphor. When you’re working on a service project, this schedule works great. Hand off all the constraints, goals and extra details; sit back relax, your illustration will be here shortly. Damn, that wasn’t it? No problem, BRB.

A design project doesn’t work this way**. There are too many variables that haven’t been solved yet. Sure, I can get my sponge on — soak up everything I can — but by the time I come back the project has hit 3 forks, and it’s gearing up to get on the highway. Now I have all this work that doesn’t fit; and we’ve taken three turns without considering the constraints of illustration. Set the project up such that everyone understands and agrees to the amount of collaboration up front. Don’t try to kick off a design project while you’re still wrapping up your last project. Instead, find a way to get everyone in the same place (mentally or physically), with the understanding that their attention should not be divided.


But, literally, how are you going to work together?

What needs sign-off/check-ins?

What is the first thing you’re expecting to see from your illustrator? Is it a full illustration? Or is it just the colours they’re using. Do you want to talk through the ideas/use of metaphor? Or are you more interested in seeing the style? A quick conversation about what level of granularity you’re expecting—or the illustrator is planning to do—can go a long way to prevent miscommunications.

How, exactly, are you going to collaborate?

This is particularly important on big projects with a lot of people working in parallel. Are you all contributing to one master? Is one person collecting pieces and editing them to fit together? Are you all working on your own pieces and talking through the inconsistencies? Are the files provided with the purpose of viewing or editing? Do you need to be in the same room?

I like to start these conversations around how people are already used to collaborating. You know, since it doesn’t matter what you say, everyone is going to be trending back towards their own habits anyway. How you approach collaboration should be a clean slate, informed by what has worked well for you in the past, but not beholden to it. It should be a little different every time; custom designed to fit the project, the team and the level of trust.

If you’re a new team working together for the first time, your goal should be to over communicate. It’s jarring to see your work edited without knowing it’s coming, or the reason it was changed. The smaller the change, the bigger the slap in the face. A change paired with a heads up—I was working on accessibility and changed some colours—goes a helluva long way in keeping that project running smooth. Even better, remember that you’re working with designers, and they love it when you come to them with the problem you’re facing, instead of the solution you’re applying. Just tell them why you’re thinking about making a change and the rest will solve itself.

The longer you work together, the more intimate you can get with someone else's files, but take the time to build the trust. Over communicate why it made sense for you to make changes 10 times, and the 11th time your good intentions will be implied.

When is something no longer flexible?

Big fat juicy design projects, with everything up in the air and everyone working in parallel: pick your milestones, and lock them in. A schedule is nice; all hands in 1–2–3 THIS-IS-OUR-GREEN works too. 6 months into a project, I don’t want to see inspiration from the internet that is totally out of left field but, like, can you 3D? Try your best to keep it an iterative process. Here’s what’s working; here’s my hesitations. It’s okay to say nothing is working, but hopefully you’re having those conversations up front.

I like to organize my work by confident; WIP; up next and ask for feedback accordingly. If I’m confident, that’s the work that we have collectively landed on. It’s just an FYI, or reference for consistency on the rest. Obviously, I still want your feedback if you have any, but if you see something glaringly wrong in the confident section, it’s our communication that has gone sour. It doesn’t always have to be literal design files. It can be just written down,or talked about we’re going to work more with negative space; we want more large headlines; here’s a list of places where the background colour can change. When everyone on the team agrees on what we’re confident on, it creates constraints for everyone to align to, and for everyone to push their own elements around. WIP & up next is where I want every thought that runs through your mind. Good? Bad? Totally unrelated? Sure. Why not. Both are equally important for different reasons. Yeah, obviously it’s important to get feedback on the work I’m actually doing, but it’s just as important to make sure that whatever I plan to do next will be the most useful way to inform the entire project.


Setting and managing expectations is a trucking hard part of being a designer, but a crucial one. It’s easy to get excited about a project and run with it before you’ve laid the proper ground work, or assume that everyone sees it the way that you do. It’s easy to skip steps and hard conversations when a project evolves, and levels of contribution change. However, it’s always worth the extra time and effort to make sure that everyone is on the same page, and understands their role in the project. Setting expectations is not a skill that comes naturally to everyone, so be understanding when they are not set perfectly. Instead, remember that everyone is trying their best, and internalize how expectations can be set more effectively in your own pursuit to become a better designer.


✌️ That’s it for now! Up next: Illustration feedback

Oh, and if that pizza-ray gun thing seemed kind of out of left field, here’s part one!


*I reserve the right to rage text at least Justin before I move on. I won’t use names tho, k?

**You can pull it off, it’s just really hard, for no good reason.