I would advise the person to network with people in the industry and ask how much a Masters is worth in that particular industry to advance within it.
Then I would carefully consider how much in-depth knowledge of the industry I'd need to advance in my industry. If it is a more technically demanding industry, you might need to go for the degree, but in most instances, a few courses might be more than sufficient.
The important thing is to develop your core competencies. IE, if you're a programmer, focus on that and take one-off courses on industry specific items that would strengthen your base knowledge of the industry.
If you're in finance, for example. Going for your series seven license might be of more value than a masters. A few accounting classes might be of use, but more than that would be overkill
If you're in the shipping industry, a good general knowledge of tarrifs, bills of laiding, et cet would be far more valuable than any degree.
So, it does vary by industry, and while industry specifi knowledge may be useful, a formal degree that is appropriate for the industry may not be.
But again, network with people, and research the industry as well as individual companies.
In my own experience, I've run the gamut. I'm a self-taught hacker that went to a trade school. I never graduated college. For most companies, that's not a problem at all, for some, it will halt my advancement past a point, and some have hard and fast education requirements. I found it mildly annoying when one company ignored several decades of experience in favor of a degree, but that's how it goes.