>python -m prodigy ner.print-dataset an_ner_date_01 | less -r
'less' is not recognized as an internal or external command,
operable program or batch file.
Are you on Windows? I think the problem in the first command is that your shell doesn't have the less command. It allows you to go through large output page by page, but it's not strictly needed – but if you are on Windows, you should be able to use more instead. So: | more -r.
What terminal are you using? The colors are only shown if your terminal supports colors.