A habit I’ve picked up is to follow the deaths of famous authors (the NYT will feature one on regularly on their home page). When that happens, I like to read about their life and oeuvre and pick up one of their most famous books, which is usually both very interesting and worthwhile.
You can also just go to Barnes and Noble and wander around. Find the genre you like, poke around, and you’ll probably recognize some of the titles or authors, which is often a good sign.
If you have some favorite authors, look up their lesser known books! The fact that you liked their other work is a good sign.
Over time, you will develop a long list of books on your list so you can start getting more selective. Check the Goodreads reviews. Try to understand how this book fits into the bigger picture and whether it or the subject seem significant to you.
Honestly, it’s hard to go wrong early on. Imagine you were just being exposed to film/tv for the first time and you ask for recommendations. ‘I dunno, Breaking Bad? The Godfather? Titanic?’ Even though there’s a lot of trash out there, the best books, like the best movies, are easy to find and there are tons of rankings and compilations.
Don't just read books because they have a good reputation in general.
Business oriented: try your hand at any of the best books on x, by forbes. Google the list "forbes list of best books". Its prob circa 2010ish. They put books on leadership (annapurna, great read), entrepreneurship, product (beijing jeep), etc etc. Some really solid stuff
Pulitzer lists: Just go on wikipedia anf look at winners by year. For example, controversial but interesting : guns germs and steel.
Reco engines: I think i used tastekid a loog time ago. Type in a book, it would give you recommendations on books you might like. With advances in ML, I'm sure there are tons of engines doing the same now
Sorry, but ick. A less popular viewpoint of this is "Triumph of the West" by Roberts. "Connections" by Burke is very good, too.
This is just like the great of life - don't fear failure.
Reading a book you wind up hating is way better then spending that time trying to optimize your process to avoid bad books.
If you do want to look for more promising things, reading is still your best tool.
I used to use what I called the two-minute test:
At a bookstore or library, pull a book off the shelf, read it for two minutes, then put it back.
Often you'll find you really don't want to put it back.
If so, then give it a shot.