Most chess engines are much too strong for beginners. Chad's Chess is a weaker engine which can be used with Winboard to allow the human player a better chance of winning!
1. Extract the contents of the download zip file to the same folder as you have installed Winboard
2. Run the installation program (InstallCC.exe).
3. Play Chad's Chess with Winboard by opening the "WinBoard Startup Dialog" and selecting "Chad's Chess" from the pulldown menu.