I frequently experience that my external monitors do not wake from sleep when paired to my MacBook Pro using Lenovo's USB-C docking station.
Often my monitors would never get a signal to wake after sleep-mode unless I first disconnect and reconnect the USB-C cable to my MacBook.
After some digging around, I found that it had nothing to do with my monitors, nor the Lenovo USB-C dock, but the DisplayLink Manager software. Once my MacBook wakes from sleep mode, the DisplayLink UserAgent simply fails to reconfigure the screens. However, if I restart the DisplayLink Manager software it fixes the problem.
Growing tired of reconnecting the USB-C cable I wrote a small script that restarts DisplayLink Manager, which runs when my MacBook Pro wakes up from sleep.
Here is the Apple Script to do it:
tell application "DisplayLink Manager" quit end tell delay 2 -- Wait for DisplayLink Manager to close tell application "DisplayLink Manager" to activate
Using Apple's Instruction tool, you can even paste the above script and export it as an executable app using "Export" -> "Format App" and then copy the generated app to your Applications folder. This way you can also manually run it by simply running this app from a single click.