The best way to negotiate options, in my opinion and experience, is to choose a number that you want your options to be worth in 4 years. For example "Hey CEO/Boss, if I work here and blow it out of the water for the next 4 year, I want the options you give me today to be worth at least X number" - This is a fair way to structure the conversation for a few reasons.
1. It sets up a timeline that is inline with your realistic amount of time at the business. If I tell you your options will be worth 100k for example after we IPO for 3B, that is not realistic or fair to you - it only justifies me shafting you today because I'm talking 10 years out and best case scenario.
2. You can walk through the future states (ie 1 to 2 funding rounds) and project the current value out based on expected increases of valuation at these subsequent fundraising rounds.
3. You set the number that you think your effort is with.
4. it is not talking about % points which people have weird biases around due to internet
Note: Assume 20% dolution at each fundraising round.
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My rec's: If its your first startup, tell your boss after 4 years you want your equity to be around 200-300k. This gives you a way to walk backwards to today and come up with a real number of options to hit it.
If its your second and you want a home run be in the 750k-1m range
If you're an exec/leader - aim higher and talk it over.
VP at early stage are coming in around .8-1%