Was your software already tested with Wine by other users ?
Before to waste time, please look into https://appdb.winehq.org ('Browse Apps').
Doing a manual installation is the hard way to use Playonlinux/Playonmac.
The easy way is to use a script already wrote by someone else (do search first into the 'Supported software' list, then in the forums), because the application that you want to use may need some additional libraries and it is very hard to know which ones.
At the bottom left of the window, click 'Install a non-listed program'.
Lots of steps
... Details about the Playonlinux packages (in the wiki, called 'Category: Features').
Shortcuts for the software installed
At the end of the manual installation, POL show you the list of .EXE files found in order to make shortcuts. Take the time to select carefully the files needed (you will be allow later to delete the useless shortcuts).
If a application do not work, do not forget that you can try a other (install a newer) version of Wine. This is very useful for the old tutorials found on the web.
- www.gamersonlinux.com/ : Many examples of manual installations (called there 'step by step')