I recently had the good fortune to re-negotiate my academic job offer as I now have a joint appointment between Comparative Media Studies / Writing and the College of Computing (!). Here are some lessons I learned from re-negotiating my offer, and the differences between my approaches with the first and second round. I think being able to re-negotiate is an enormously privileged position in many ways, but one thing that was especially helpful about it was the fact that I got to try out some stuff that I wish I had done the first time around.
Negotiating in person vs. in writing
In my first negotiation, I wrote down all of the things that I wanted and made an appointment with my department chair to have a more prolonged conversation (the whole thing maybe lasted around an hour and a half). This conversation had two purposes: I was going to do some information gathering to see what was possible, but mostly I was going to relay my requests. My chair took very attentive notes and confirmed some of the numbers that I had asked for so I knew he was taking the right numbers to the dean. I left feeling pretty encouraged by the situation, honestly, and felt like I had done a good job both learning how the department (and my chair) worked, which I wouldn't have gotten with a written negotiation. I think I also felt better about it because it felt more like a conversation rather than me demanding things, which helped me a great deal psychologically to internalize this as an exercise in teamwork rather than an adversarial encounter. I did this approach partially because I feared the shadow of the rescinded offer, which I know was a severe outlier, but I also didn't know the departmental norms and wanted to get an immediate sense of how reasonable my asks were and follow up in writing.
With the second negotiation, the information gathering / establishing common ground via conversation seemed less important since I had already done it once, and I had enough questions that I figured it might be worth doing it all in writing (which also gives both parties time to think before responding). In the second negotiation, I sent a list of questions that were mapped to specific parts of the offer letter via Google Doc, and my chair answered the questions one by one via comment. After this initial question asking phase, I sent a 3-page letter (4 with the appendix, which was a short outline of my requests) that justified some of the new requests. Objectively, the second negotiation was more successful in the sense that I felt emboldened to push for a lot more (especially since I already had a job...in the same place), but also I simply felt more comfortable with what I knew I wanted. It definitely felt like they were negotiating in good faith, since the salary had also increased substantially to the level that I had requested in round one.
Overall, I'm really glad that I did everything in writing this time, especially since it's a big relief to not have to answer in the moment if you need more time to think about something. (As a friend of mine said, "I did everything in writing because I know that if I negotiated in person, I'd end up owing them money," which is a pretty good descriptor about the perils of negotiating). It was also good in that it gave my other mentors something to review and give feedback on (compared to the table I had prepared for my oral negotiation), and crucially it gave my department chair something to circulate to the deans and other decision-makers. I genuinely think that everyone was acting in good faith here -- an assumption that can't always be made -- but you're always going to lose context and details if the requests are made like a game of telephone. The written method therefore leaves less room for error in terms of relaying specific numbers and requests, which also helped because I felt pretty good about taking a step away from it after writing a first draft and coming back with fresh eyes. If I were to do it again, would I do it in person or in writing? The latter, undoubtedly -- not just because it was more successful, but because it felt more controlled. It did take about a week for me to solicit and incorporate feedback, but I do think it was all worth it. That being said, I think that the written one was successful at least partially because I had a sense for what the department could give (and because I'm generally familiar with how MIT works) -- that came from a conversation, not through email.
I think I also did a better job of outlining the universe of things that one can ask for in a job offer letter (see my post about that here), which I was primarily able to do by asking generous colleagues, many of whom voluntarily shared their offer letters with me. This is a type of solidarity that I do not take for granted at all, but hopefully the aggregated post I made helps those who may not have access to the same resources. While my original offer already had a start-up, I asked for more specific things, like money to create a conference on a subject of my choice (in this case, computing in the Global South) and administrative assistance.
If I were to make a short list of how to go about the negotiation after you get the offer letter, it might look something like this:
Before doing any negotiating, schedule a time to do some synchronous information-gathering, which can serve as a good introduction to the department (and your department chair) and can help you get a sense for what is possible.
Prep for said session by thinking about what you might possibly want to ask for in the offer (see these resources), and orient the conversation as a collaborative endeavor, where you are both working towards setting you up for success in your position.
Follow up on the conversation in writing, either with your asks or with further questions that you might have about the position (e.g., tenure expectations, types of support available for faculty outside of start-up).
Create a letter that outlines what you would like the dean(s) and your department chair to consider, with written justifications about why this will help set you up for the kind of professional success you seek.
Send the letter and stop there: don't qualify your asks, don't caveat in additional emails. Stop. Talking. Let them respond.
Remember that them giving you something in an offer is not charity, but an investment. They see the value in your work (which is why you have an offer!), now is the time to let them put their money where their mouth is.