can I resign but still ask for severance?

This post was written by Alison Green and published on Ask a Manager. A reader writes: Last summer, an old mentor from my past company — who led a couple projects I was on but was not my direct manager — took a new VP role and sent for me. I had applied for a role on her team at our former org and didn’t get it, but […]

Apr 3, 2025 - 19:13

can I resign but still ask for severance?

This post was written by Alison Green and published on Ask a Manager.

A reader writes:

Last summer, an old mentor from my past company — who led a couple projects I was on but was not my direct manager — took a new VP role and sent for me. I had applied for a role on her team at our former org and didn’t get it, but was able to create a similar opportunity for me at her new org. I’m absolutely grateful.
The tricky thing is I’m actually not happy here. This company is not my jam overall and I only somewhat give a shit because of my mentor and now boss. But as you’ve written about before, going from a friend (albeit a senior friend) to a manager had unexpected growing pains now that the dynamic is markedly different.
I can sense things going south (i.e., at a recent off-site, I got feedback about my attitude and communication resulting from frustration with the org as a whole, and my gap in executive presence has had repercussions and has also created tension with my boss for making her look bad) and while I still have a sense of duty to someone who has advocated for my career, this company as a corporate entity can go fuck itself.
Here’s where I’m stuck. I’ll be eligible for unemployment in April and will have accumulated enough hours. I’m not interested in resigning altogether (and can’t collect unemployment if I do), and I want to preserve relations with my boss and leave on good terms rather than being a miserable employee and leaving on bad terms. Is it an option at all to have a frank conversation negotiating a smooth exit that they initiate, and with severance?

It’s possible! The severance part is less certain, although it’s possible too.

Since it sounds like your boss knows things aren’t going well and probably won’t be surprised to hear you’re not loving it there, can you have a candid conversation where you lay out your concerns? You could say something like, “I really appreciate how much you’ve advocated for me, so I want to be up-front with you that I’m increasingly thinking Company isn’t the right place for me. I’ve encountered issues XYZ, and I’m concerned I’ve also caused problems for you since you brought me in. I’d like to be realistic that it’s not working out, and I wondered if you’d be open to negotiating a planned transition out of my role, where I could file for unemployment while I look for another job? Ideally I’d hope to discuss severance as well, with the hope of bringing this all to an easy resolution for everyone.”

Your manager might hear this with some relief! If it’s been clear to her that things aren’t working out, it’s easier to have you raise it before she has to and to have you offer a clean solution for everyone.

However, on the severance part: Companies typically only pay severance when they’re firing someone or laying them off. The idea is to give you a financial cushion so your income isn’t yanked away overnight (typically in exchange for you signing a general release of any possible future legal claims against them, whether or not they think you actually have any).

However, there are some occasions where you can try to negotiate severance when you’re leaving voluntarily — like if it’s clear your work isn’t going well but your employer would prefer not to fire you (this might be your situation), or when you moved for a job that turned out to be very different from what you were promised and the employer feels guilty about that, or if the employer is worried you might have a legal claim against them for something otherwise. In your case, you’d basically be asking them to offer severance in exchange for a relatively clean exit from a messy situation. You don’t have a ton of leverage to negotiate it, but you can certainly ask without looking ridiculous. (And if there’s anything that would give you more leverage — like that you left a good job for this one and it ended up being different work than you were told — definitely mention that.)