Is there any way to find out if a guru is in fact enlightened? What are the external signs of enlightened gurus?

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There are two things being asked about here. Enlightenment and gurus. It’s easy to tell if someone is a guru. A guru must be able and willing to, off the cuff, give spiritual answers to personal questions.

A bit harder is to tell if someone is enlightened. You need a certain familiarity with the space and, preferably, exposure to someone you are pretty darn sure is enlightened. This way you can measure one person against the other.

The person that set the bar for me was Osho. I read Osho when I was in my late teens, through one of the Rajneesh Bibles. I highly recommend getting a copy of one of these if you’re at all interested in hearing what enlightenment sounds like “off the cuff.” Osho got me interested in the space and so I started reading some of the material from other teachers Osho talked about.

Osho wasn’t a fan of J. Krishnamurti. But Osho didn’t claim that JK was unenlightened. Instead Osho had problems with his style. He’s plenty enlightened, he’s just not a very good teacher. He doesn’t break things down for lay audiences. Which is a bold thing to say because JK is revered throughout the East, way more popular than Osho even.

He was more of a fan of UG Krishnamurti. He found UG’s style to be way more in line with his teachings, unlike JK’s. I couldn’t get through a single JK book, but I devoured everything on UG I could find. UG is practically a nobody in the world of Eastern mystics.

Osho was able to paint a picture of enlightenment by giving examples of what enlightenment didn’t also give you. Just being enlightened doesn’t magically make you a good teacher. You have to work on that separately.

This, to me, is the hallmark of what you want out of a teacher. They have to be able to reduce the amount of mystery behind that which they’re teaching. Someone doesn’t have to be enlightened in order to be a good teacher, even of enlightenment. Not all football coaches had great football careers.

Also through this exploration I was able to make the determination that the amount of attention a guru gets is usually inversely proportional to how useful their teachings are to understanding enlightenment yourself. UG’s enlightenment was extremely authentic, more authentic than Osho’s even, and far and away over JK’s. UG experienced, intensely, the crazy presence that enlightenment brings, and didn’t mute it at all for the sake of being relatable to ordinaries. Osho did some of the dumbing down, JK did it so much there was nothing left.

Another thing you need to realize is that a guru can only help you understand enlightenment, reading a book or even sitting in an enlightened person’s presence and absorbing their wisdom or energy will not make you enlightened yourself. You must still do the work. And if you’re reading the wrong things from your guide, then you’ll never get there because you’ll forever be moving in the wrong direction.