Check the match stats, passing ratios, key passes, shot ratios, mistakes etc
Putting him on set pieces will wrack up his key passes and match rating
You can rewatch the passes and things he's misplaced in the analysis
Inverted Wingers tend to stay wide, then cut in when on the ball, so check his movement off the ball. You could always ask him to sit narrower or roam from position and see how it plays how
If Bailey's playing well on the right, switch the roles so Countinho is the IF and Bailey the IW