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I'm going to try painting checkerboard on my warboss's shoulder pad. Is there any special technique that I need to use or should I just be very careful?

Black fine sharpy or a Black color pencil (soft)

draw in the squares then paint in the rest.

Awesome. Thanks for the tip

Probably should mention paint the white first

But more importantly try to put a protective layer of matt varnish on top after the white. (and let it cure properly)

Sharpies and pencils can rub off the last layer if you put too much pressure.

I did mine slightly different. I painted the darker colour first. then did very thin layers of the lighter afterwards. as mine were death skull orks I was able to build the dark blue into a white simply by mixing white in. for black and white I'd do a bronzed flesh (sorry I use old paints still, a flesh colour equal to it would be fine) and apply the white over the top. again very watery layers, allowing mistakes to be wiped away easily. I hope the picture helps. a smaller board is on his wrist.