I've perhaps been very lucky and fortunate enough to be picky, but when negotiating for a new job, I've always just made a spreadsheet with a bunch of expected

I've perhaps been very lucky and fortunate enough to be picky, but when negotiating for a new job, I've always just made a spreadsheet with a bunch of expected value calculations and then used that to counter as appropriate. For both my current job and the new offer, I'll calculate total expected compensation after 3 years from now assuming bad performance, realistic performance and best performance. Those numbers alone can be very enlightening. If the offer's realistic projection is less than the current realistic projection, I politely let the negotiator know that their offer will need tweaking to have parity with my current situation. Either way, I'll suggest a counter offer that puts the realistic compensation at least 1.2x current if it isn't already, then play it by ear from there. The composition of salary vs. equity really just depends on my current risk tolerance. The more equity, the higher the best case upside. This all happens after the company is serious about hiring me and I'm serious about joining them. It's nice to have a spreadsheet because it avoids appeals to emotion. I wouldn't share the formulas or numbers, but rather only the high level methodology and the conclusions you've drawn from it. It's your tool and confidential info, not theirs. If you feel like you've made a strategic error and asked for too much, you can easily backtrack and laugh it off with the negotiator by saying you had a typo somewhere. More likely, the negotiator will consult their own spreadsheets or board, and they will tell them that your counter offer is acceptable. One time I simply mentioned to a recruiter that I might need to take out a loan to leave my current job due to AMT (since the options were actually worth something), but I was still trying to find a tax consultant to crunch the numbers. She came back right away with a pre-offer for a larger starting bonus pending approval. I later told her that the AMT worked out okay without it, but she still got me the starting bonus since it got approved. It never hurts to ask politely for something!