New to negotiating….does it look bad if I ask for two rounds of negotiation on different topics? I.e., base and then start date / vacay days? Should’ve done it in one call but couldn’t think on the spot.

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I would try and get all your "want to haves" into one discussion. Typically your recruiter will need to go up the approval chain to modify your offer, so you only want to do that once. Also, a good rule of thumb is you can change the numbers, but not the letters in an offer - which means you can probably only really negotiate salary and bonus, not benefits, and rarely PTO.

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Should be able to do all at once.

Always better to combine a few topics into the same negotiation. But you can still introduce a second topic later if you didn’t discuss it yet.

Its a big decision dont be shy of negotiation, i have generally found recruiters to be ok with couple of discussions

Assuming you started by negotiating on base, once that’s agreed I think you can seamlessly then ask for whatever start date you want.

However, would not open a negotiation on vacation days. That’s typically a hard policy rule and impossible to influence - no point wasting negotiation good will on it.

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