Better get written permission before doing that. Bring up all the concerns mentioned here to your boss. The first word out of my mouth would be "liability", the second two "probably illegal".
Some bosses dont like to hear that stuff. I dont care. If I can save my employer from royally hosing up, I WILL mention it. Besides, doing work twice is the most aggravating thing to me. Do it right the first time.
Is this also a power pole? If so, I seriously doubt you will get permission to do what you are asked. I have seen thousands of poles, not one to my knowledge has customer (private) lights on them.
I seriously doubt you'd get handcuffs, however I suspect a HIGH chance of tearing it all back down/off, sinking your own pole, and redoing the work. jm2c.