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Just get then to clean up at the end if that's what works for them. Presumably you want 'visually brilliant' work, foremost. You might lose some of that brilliance if you force your designer out of their intuitive headspace in order to rationalize every decision in their design while they're still exploring.
It's always easier to tighten up a strong idea than it is to inject an idea into a formulaic layout.
ding them in the approval process
ding them to the boss
Stop doing the cleaning after them, and write it in a e-mail, warning there will be consequences.
Devs will follow the sloppy alignments, ask 10 times more questions to the designers about where to find what, deliveries will be late and with lower quality...
Just don’t say «I told you so» and you won’t look like a dick. But if one comes and say it’s your fault, ask them to re read the e-mail.
Well, theres a couple things to address here:
As mentioned above if the designer is in "explore mode" then I think it's ok to break from styles and symbols.
If the system is defined and there isn't a need to explore outside of those perimeters, then you probably want them to keep the system styling.
If thats the case and they are still breaking away, then the issue is probably that they are not comfortable with the tools and workflows that Sketch has. Which is understandable and totally normal for anyone not familiar with the process. They most likely need some tutoring and extra time to adjust.
How you deal with it?
Are you his senior or supervisor on the project?
If so pull rank and lay down the law on how the work needs to be completed. Address the issue by explaining why you're not happy with the way he is completing the work and then teach him. Don't leave him hanging.
It's gonna hurt, he might not like it. its gonna be extra work for both of you. But if you know better and are senior, its your responsibility to train him and make him better.
I'm not saying its easy, but thats what being experienced is all about.
1. Yes, unfortunately. I work on a small design systems team within a design org of almost 200 designers, and even the simple things like a scaling/grid system of 4/8, or aligning to pixel grid is almost never done.
2. Where I've seen most success is in engineers refusing to accept a spec if it's not aligned with the system. If that doesn't help or isn't possible due to timelines, consider cleanly escalating to your manager.
Generally, I've found that policing too hard is a bad idea. I've had a lot of positive feedback from showing designers how things work and why they're important - you'd be surprised at how simple concepts are so alien to some people until you point it out to them.
Also, the Design Systems public space on Slack is a great resource for all things related to design systems. I think there are something like 6,500+ design systems designers in that group.