Rate talk with a repeat customer took me 8 months to crack
Had this one client who kept asking for a discount every single contract renewal. I tried saying no nicely, then tried sending a rate sheet, even tried the silent treatment. Finally figured out she just wanted a line item breakdown so she could justify it to her own boss. Took me 8 months to realize she wasn't cheap, she was stuck. Anyone else have a client where the real blocker was internal politics, not the actual money?
Eight months of back and forth over a discount because she had to justify the line items to her boss? That sounds more like you two just weren't talking to each other right than some big internal politics thing. If all she needed was a breakdown, that should've come up in the first call or two, not month eight. Maybe the lesson here is just to ask what's really going on earlier instead of treating every pushback like a money problem. Not every client who haggles is playing three dimensional chess with their own company, sometimes they just aren't saying what they actually need.