can I resign but still ask for severance?

by Alison Green on April 3, 2025

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.)

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{ 57 comments }

{ 57 comments… read them below or add one }

    1. Palmer*

      I expect severance is a topic because this is a higher up position see the “lack of executive presence” line. Leadership/upper management positions can get much better compensation and off-boarding.

      I definitely see LW skipped the “Finding other roles within the company I could transition to” step. Awful corporate culture is a big reason to leave.

      Honestly this is a good step by LW, don’t burn the VP bridge since you aren’t the right fit. Hopefully get a smooth exit.

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      1. Defying Gravity*

        But upper management / executive positions often have contracts, which almost always include severance provisions. LW doesn’t have that, so she’s likely not high enough in the org for severance to be a reasonable expectation or likely part of a separation discussion.

        I agree that severance doesn’t sound likely in this scenario.

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        1. nnn*

          Most american workers don’t have contracts, even management positions, so you can’t conclude anything from that.

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  2. MK*

    I am very surprised that severance is even on the table here. Frankly, I don’t see any messy situation that requires a clean break; OP isn’t satisfied with the job and the company and it sounds like the company isn’t satisfied with her performance either, them parting ways makes sense. In fact, I think it’s even less likely if, as I understand it, the manager handpicked OP for the job rather than her hiring going through their process; the manager is in a rather awkward position with the company, if that’s the case, and not really in a place to advocate for OP, even if she wants to. Unless there is some other factor, it would look ridiculous in any workplace I know.

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    1. umami*

      That is my thought, too. It could come across as a bit out of touch to essentially say, this isn’t working out, but you can pay me to go away. I would worry that it would affect getting a positive reference down the road.

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      1. Sloanicota*

        Agree. I don’t think it’s *wrong* to ask, but I would … certainly appreciate OP’s chutzpah if they did.

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      2. Decidedly Me*

        It definitely feels out of touch with the situation to me, too. I don’t think asking would help with leaving on good terms vs asking for a smooth, mutual exit without that.

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    3. Ann O'Nemity*

      I think it’s only possible if the VP/mentor is feeling incredibly guilty. I can imagine a scenario in which the VP mentor lures the LW away from a good company into a toxic one and then feels terrible about it. The VP may have the budget and authority to try to make things right with a severance. But given the performance issues, I don’t think a severance is likely.

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    4. Cordelia*

      Yeah I don’t get it. If I hired someone who turned out to be poor at the job and have a negative attitude that was having repercussions for me and the company, and then they came to me saying they disliked the job (and therefore had no intention of trying to improve) I’d let them go – I certainly wouldn’t be paying severance. I don’t think it makes any difference that OP was “sent for” by her previous mentor – she chose to take the job.

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    5. Tiger Snake*

      I had the same initial feeling: I am used to severance being specifically tied to when you need to stand down people unexpectedly. This isn’t what’s happening here.

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  3. Ann O'Nemity*

    Severance is possible, but I think it’s more realistic that you can negotiate a runway to leave. You’ll get time and flexibility to find another position. And your company gets time to rehire and doesn’t have to worry about keeping their search confidential or having a coverage gap. I think you will only get severance if your mentor is feeling incredibly guilty about the situation and wants you to leave in good shape.

    Still, any attempt to negotiate a clean exit is risky. They may decide to just push you out early. You really have to know your boss.

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    1. Lily Potter*

      That’s a really good point, Ann O’Nemity. I’ve seen this a few times in my corporate career, especially back in the days of everyone working in-office. All of a sudden, a co-worker wouldn’t come into the office anymore and everyone was told that they’re “working offsite on another project.” In reality, they’d been given a couple of months where their “job is to find another job” – full pay, benefits, and PTO accrual while they job search. Opinions may differ – some might prefer a clean break with a cash severance – but in my industry it’s far easier to find a job while you’re still employed, so this set up was of a benefit to those that got it.

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      1. Bbbbbbbbb*

        In this economy, this ain’t happening. If you haven’t tried to find a job, or looked at a listing since Jan 20, … well, each job has at least 100 applicants if not more and disappears within a day. So unless your skillz are mad sought after-no-one-else-has ’em, best to not mention a word, keep your head down and search search search for new. If you leave on your own… unless there’s a trust fund in your bank… Just. Don’t.

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      2. pomme de terre*

        I’ve been in a similar situation. I was not thriving, and they gave me about three months to look for a job, during which time I had a lot of “personal appointments” and random WFH days that my (terrible) boss did not question one bit.

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    2. Sloanicota*

      Yes! And this can look like returning your mentor’s kindness, because you’re not leaving them in the lurch / with an unfilled position. You can suggest you stay until they get a new hire up and running if you like, or just give more-than-usual notice and start job searching. Hopefully you’ll get something that’s a better fit for you before you have to leave this job. And you might feel significantly better knowing it’s over, a lot of stuff will hopefully be coming off your plate, etc. That to me is a best case scenario.

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    3. el l*

      Well said. Honestly, the best I would expect would be that you would say a few things and get a somewhat longer and definitely defined timeline to find another job. Like, “Well, we’ll keep you on for another 6 weeks, and if you don’t have a job lined up by then, we’re letting you go without severance.”

      And as so often, it’s vulnerable to some guy in suspenders who doesn’t like the deal.

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  4. I'm just here for the cats!!*

    Keep in mind that if you get severance you might not qualify for unemployment.

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    1. Lily Potter*

      This is likely state rule dependent; it would be good for OP to investigate the rules for their state. In my state, getting severance doesn’t make you ineligible for unemployment but it does delay it. When I was laid off during Covid, I got two months’ worth of severance and while I applied for UI immediately, I didn’t get any UI money for two months.

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      1. Ann O'Nemity*

        Yeah, same. And it depends if the severance is a lump sum or paid out like salary. My last org paid severance out like a salary, so employees couldn’t get unemployment at the same time. Often times, the severance lasted long enough for someone to get another job, so the company wasn’t on the hook for unemployment benefits.

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      2. Don't You Call Me Lady*

        In Massachusetts, at least the last time I was laid off (Covid) the rules were that if I was paid the severance in one lump sum I could get UI immediately, but if it was paid every other week like normal payroll, I would have to wait ’til that ended.

        Luckily my employer at the time was able to the lump sum

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      3. I'm just here for the cats!!*

        Oh I definitely meant that it’s state dependent and OP needs to look at the rules for it.

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    2. Ask a Manager* Post author

      Severance doesn’t make you ineligible for unemployment; generally it would just kick in after the severance stopped “covering” the salary. (So if you get the equivalent of 3 weeks of severance, the unemployment wouldn’t kick in until those 3 weeks were up.)

      Reply ↓
      1. I'm just here for the cats!!*

        that’s interesting, thanks for the clarification. I wonder, what about if they pay out vacation time or something? Would that count as a severance? Or would it be better for them to pay out the vacation time and then the OP could file for unemployement.

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  5. Lily Potter*

    If you are not eligible for unemployment until April, wait until May before bringing up any hint of this conversation with your employer. It’s possible that, once you tip your hand, that they’ll fire you immediately. You don’t want to be fired on 4/15 if you’re not eligible for unemployment until 4/30.

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    1. PenguinWrangler*

      +1 to this. If they’re at all frustrated with you, protect yourself and your options as much as you can.

      Similar situation: I worked at a company with an incredible 401k match and profit sharing program, but you needed to be there 6 years to be fully vested. I worked there 5.5 years without a merit raise before I brought one up. In that meeting they denied my raise, and I said that was disappointing because of all the reasons I had brought up, and that it made me question my ability to grow in the organization. They laid me off 3 months later, 3 months before I was fully vested in the program, which was like 7 or 8 grand, a lot of money for me. I think they said, this person isn’t happy here, let’s get them out before they cost us more than they have to.

      Reply ↓
  6. PenguinWrangler*

    Can someone help me with this phrasing: “my gap in executive presence has had repercussions and has also created tension with my boss for making her look bad.” What is a ‘gap in executive presence’? From context I’m guessing that the LW is not ‘fixing their face’ in these meetings and it’s rubbing people the wrong way…

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    1. MK*

      Either that, or OP isn’t showing up on occasions when it is expected from an executive/with executives.

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      1. PenguinWrangler*

        Or if they were expected to stand in for their boss (who is leaving a gap) but they aren’t showing up or doesn’t have or isn’t exercising executive authority in those situations.

        I guess I’m finding out that my issue is with the word “gap”

        Reply ↓
    2. Don't You Call Me Lady*

      It’s vague but I interpreted it as OP was hired to be somewhat senior, and isn’t living up to that either in performance, attitude, or both

      Reply ↓
      1. PenguinWrangler*

        Ah, so the “gap” would be between the title/job description and what the LW is delivering, I could see that.

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    3. RIP Pillowfort*

      So I Googled executive presence. It’s a term for leadership. So gap in leadership capabilities?

      Like if OP were brought into lead and they are finding their skills aren’t there- that’s the gap.

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        1. GammaGirl1908*

          Serious jargon. I gathered that LW was not effectively delivering something she was hired to do, but it was unclear whether that was face time, actual presence at events, professional bearing and attitude, or something else.

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      2. Cordelia*

        wow, I completely misunderstood that then. I thought OP was not physically present at events and meetings that she should have been at as an executive

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    4. Moths*

      Kind of similar to above, but I’ve always heard it in reference to how you act/how people perceive you more than just straight leadership skills. Meaning, do people perceive you to be acting like you are an executive/leader (remaining calm in meetings, not getting flustered, presenting information clearly and well, making others feel confident in you and the projects you’re leading, sometimes even clothing and grooming, etc)? So more even than if you have the skills, it’s a reflection of if others are perceiving you to have the skills. That is, do you have the presence of an executive? Or, at least, of the ideal type of executive, since we all know true executives that may not live up to those things themselves…

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  7. Eldritch Office Worker*

    This isn’t the case here, but may be relevant to others who are drawn in by the headline: I’ve also had a lot of luck negotiating a severance when I know a RIF of some kind is coming, or otherwise can see a net benefit to the company for letting me go.

    For example, at my last company, they were clearly going under. I was HR, and there were less humans around as the company shrunk, but they still could’ve used me and weren’t planning to get rid of me anytime soon. I just would not have enjoyed the tasks I ended up with. So I made the case they could get those tasks covered by someone a lot less expensive than I was, and that I would be happy to take a voluntary layoff if they gave me a severance and didn’t protest my unemployment claim. Win-win.

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  8. Elara Harper*

    In my company, the best she could hope for in terms of severance on a voluntary quit is not having unemployment contested, but that’s still worth a conversation. On one occasion (in 18 years) we did agree to cover medical an extra month if they would move their final day to after an all hands event.

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  9. Dido*

    I don’t really think the LW should hold out hope for a severance in this scenario… it doesn’t even seem like she’s tried to job search yet, I don’t understand why she wouldn’t just try to get a new job and then quit

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    1. GammaGirl1908*

      In LW’s defense, the more senior you are, the longer it can take to find a job. I read somewhere that for every $10,000 of salary you are replacing, you should expect it to take a month of job searching. So, finding a new $120,000 job can take up to a year. Obviously this is not 100% perfect (and inflation, and cost of living, and blah blah fishcakes), but … the basic point stands that the more you get paid, the longer it takes to find a comparable job. New executive-level jobs don’t tumble out of the sky.

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  10. PickleJuice*

    A planned transition where unemployment would be available would be VERY generous of the employer! From the things described, it almost feels like the employer would be happy to part ways, but I can’t imagine hoping for extended benefits when the LW attitude is so bad that it’s already been addressed and still hasn’t improved.

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  11. MaxPower*

    OP, why quit without something lined up? Most people find something new before resigning when they find that their current job isn’t a good fit for them. Besides the fact that it’s going to make you more financially secure not to have a period of unemployment, hiring managers often assume that someone who quits without something lined up were actually fired, but allowed to call it a quit to save face. Unless the job is absolutely untenable every single day (which this doesn’t sound like it is), focus on finding something new first.

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    1. PickleJuice*

      I agree!
      I know it’s a tough market, but planning your resignation around when you can receive unemployment is not sending a great message!

      Reply ↓
  12. municipal*

    I was in this exact situation once. I had moved across state lines for the job and within a few months it was clear that I just didn’t mesh well with the company culture. Moving meant selling my old house and the real estate market was rapidly softening. The house offer I got was not what I had expected, and I was afraid I would be compounding my mistake if I did not have a house to go back to.

    When I told my boss it was not working out, he was relieved. Also, unbeknownst to me, there had already been talks about a PIP that nobody was hopeful about and a severance in the likely scenario that I would be fired. My boss had me finish out the week and paid me for the next pay period after that, too, as severance. It was less expensive for them than paying me through the PIP period and then paying severance. I did not need unemployment because the job market was still very hot in the area where my house was.

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  13. MSD*

    I don’t understand why the OP thinks they’ll get unemployment. You don’t get unemployment when you quit your job.

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    1. Ask a Manager* Post author

      That’s why she asked about “a smooth exit that they initiate” — she’s asking if they can negotiate the departure in a way where she’d be eligible for unemployment. Some employers are willing to do that if it saves them from having to go through a potentially messy firing (or any firing, for that matter).

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    2. GammaGirl1908*

      I was able to negotiate this last time I left a job. It wasn’t working out, and both sides had a number of very valid complaints. I agreed to leave and not sue or badmouth them IF they agreed not to contest my claim for unemployment and give a neutral reference.

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      1. Smarter ow*

        This is kind of a site issue, but I took a job years ago that I wasn’t sure was going to work out. It was with a former boss, but in a totally different sector than I had worked in before. I put in my employment letter that if for any reason, the job didn’t work out, he would agree to lay me off. It didn’t work out and he did lay me off, but only because we had an agreement to do so. I don’t know what heavenly presence was smiling on me that led me to negotiate that upfront, but I’m so glad I did.

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        1. MK*

          He laid you off because he could and wanted to. I seriously doubt that letter was legally binding, or that the company would honor it if they were against the lay off.

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    3. Meep*

      I took it as OP knows she is on her way to a PIP plan or termination and is afraid they might terminate before she is eligible for unemployment.

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  14. Budgieman*

    For large organisations that regularly slash positions it’s not uncommon to have a quiet word to your boss that if any retrenchments are coming you wouldn’t put up a fight… it saves the bosss from having to have unpleasant discussions if someone is willing to fall on their sword.
    In a similar vein one colleague went to talk to our boss many years ago with a written resignation in his hand. He walked in the bosses office and shut the door. The boss’s radar was on, and he said “Stop. Don’t say anything. Can this meeting happen tomorrow morning instead”… and had the redundancy package in place by the next day. Definitely a Win-Win!
    My own situation, my boss (same guy – knowing I had been there for decades and was ready to go) said to me “I have to lose somebody next quarter. Are you interested?”.
    Basically… I’d start by putting out feelers… you never know your luck!

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  15. NotSarah*

    One of my favorite expressions that guided my early career search was “slow to hire, slow to fire” – you want to work for a company that work toward a healthy and fair separation.
    But…unless you have some passive income or you’ve really dialed in your finances, this doesn’t seem like a market to be jobless in. The mass layoffs of federal workers definitely impacted our community and it was a little scary to think “what if that happened to me?”.
    I wonder if the OP can fake it, dig deep to find a better attitude, and wait it out.

    Reply ↓

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