1. The copy will change.

RIP anyone who is waiting on final copy.

Solution: Always draw to the concept, never to the words.

2. Placeholders don’t work.

No one hears you when you say like this but not this. All they see is an illustration that shouldn’t be there in an otherwise good design, and conclude illustration in general will never work, when it’s actually just the placeholder that’s not working.

Solution: Use ugly scribbles where the illustration will go to get feedback on the design.

3. Every illustrator is a snowflake.

You can make everyone draw the same, eventually, but everyone has their unconscious signatures and tendencies they can’t help but gravitate towards. There is a diminishing return on continually sending their work back with picky consistency issues.

Solution: Embrace every illustrator’s tendencies, and work them into the style instead of trying to force everyone to align to a single illustrator’s vision and style.

4. You will never be explicit enough.

You can and should make illustration guidelines, but act on the assumption that no matter how detailed you are, pieces will be missed or misunderstood.

Solution: Use guidelines as a contract, not a how-to. Everyone agreeing to move forward together, even if they preferred a different solution.

Bonus solution: If you can’t see a tangible use for your time spent on a guideline, spend that time creating re-usable assets, people understand more through intuition of working around your assets than they do your written words.

5. Nobody knows how to work with you.

Not many designers have a lot of experience working with illustrators. They work faster and more confidently with photography, so more often than not, that’s what they just choose automatically.

Solution: Just give ’em a minute. Designers who use illustration as their primary design tool (not to be confused with someone who comes in with the designers are finished and decorates it) are, like, pretty new. A significant portion of your job as an illustrator is education. It’s your job to educate other designers about when the best time to include you is, what the capabilities of illustration are. When you act as a black box, people hesitate to include you: it relinquishes too much control. Instead arm everyone with tools to give illustration feedback—even if it’s not their expertise—and include them throughout the process.

Bonus solution: Do sprints (#MostMisusedWordInTech?) with new teams. Give them a chance to get comfortable working with you by literally sitting next to them.

6. Bad draw-ers will draw.

Hire all the illustrators you want. Make it clear that your company is investing heavily in illustration, and you have found people who’ve made this their craft. Say “Hey, drawing is hard. Please let the illustrators do it, not you” over and over until you’re certain there’s no one left to tell. You will find some illustration in some corner that breaks all your precious style rules. That you had no idea existed. That definitely for sure no one contacted the illustration team about—either because they thought they could do it just fine; the illustration team was too busy; or hey, they just wanted to give it a shot.

Solution: Closed doors don’t work. Instead, open illustration up to everyone who wants to try. That is, if you want to do the work of an illustrator, of course you’re totally welcome, please follow the same review process that the full time illustrators follow. Here’s our channel; reviews are every Tuesday. You’re in it or you’re not: don’t try to do our full time job half way, that’s rude.

7. You are last in line.

Yeah yeah yeah, you can work really hard to get ahead of the work; ask to be included early, remind people that a) we are designers too b) illustrations take a long time. And everyone will work really hard to be respectful of that. But also, there are a lot of moving parts, and visuals get pushed to the last step; illustration is the last step of the last step. Like okay, phew, layout figured out with one day to spare, can someone drop an illustration in there?

Solution: Clear your calendars before any launch. Earmarked for the unknown. I guarantee your time will fill up. Also probably try to teach people about a more integrated workflow, but that’s a solution for tomorrow, not today, and everything is on fire today.

EDIT: I remembered another one

8. Cut off dates don’t work

You can tell everyone that you’re not going to accept any new requests all you want, they’ll just say “cool well we changed the thing, we can still use your old (now wrong) illustration if you want” and you’ll be like FRIG NO. HANG ON.

Solution: Keep a few generic illustrations in your back pocket for when you actually can’t get to it in time, also see: 7

That’s it, that’s all the things I know.

✌️