I work in procurement. That means I negotiate with suppliers all day, every day. I’m the one the team calls when they need something fixed, and want something better than using a big hammer or lighting everything on fire.
The absolute best tip was courtesy of my first boss in the field:
"Always be prepared to walk away and say ‘No, thank you’. "
You won’t look weak (except to the wrong people). Instead you’ll come across as empowered, that you know what you want, have no tolerance for games, but also can be trusted. Very few people like people who always say yes, no matter what anxiety says. In order to be here, it’s important to have options and choices you can accept. Be ready to jump rails if it looks like you won’t get your first choice. That’s how good negotiators in my field do it - they have several acceptable options.
It’s still not easy to do. It requires perseverance and flexibility. Allow yourself to practice in lower-risk situations.
Selling.
The HOA changed management companies about three months before I moved out. New one couldn’t be bothered to provide the condo docs and required legal paperwork to me, the seller, my lawyer, or either realtor for the transaction, despite repeated requests. (My copies from my purchase were not enough for the bank.) Without it, the transaction could not close. We made it, barely, but their sluggishness almost destroyed the sale and the purchase of my next home, as the transactions were all dependent.
It took my realtor camping out in the HOA office to get copies. According to her, she showed up and was waiting for them and sat there for two hours while they photocopied, printed and generally fucked around pretending it was too hard to find.
They tried to claim I was behind in my dues too, but I’d anticipated that strategy, and emailed my realtor pictures of the cancelled dues checks AND the notarized statement from the outgoing management company saying I was paid in full at the time of handover.
I was glad to move out. Apparently they didn’t get better as I saw a lot of units for sale in the next year.