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About 2/3 weeks ago, I had a one-on-one meeting with my direct superior/manager in which I explained him that I'm considering leaving the company for different reasons (not related to him). He understood, but he also said that he hopes that I would wait for a bit more (about the end of summer). I didn't promise anything back, but we closed the meeting on these (friendly) terms.

Further events happened after the one-on-one, which basically contributed to my 100% decision of wanting to leave the company. Therefore, I'd really like to leave now, which means giving the resignation notice and actually being able to leave at the beginning of June (I'm in Europe).
This would be fine, but I've also heard that in such period the company may be acquired by a bigger one. Since I have some "options/shares" (the company is a startup, it's not on the stock market), I would lose money if I quit before the acquisition.
As further context: I heard about the acquisition thing through an indirect way (a manager told one of my colleague who told it to me), and it may or may not happen (the manager is not even sure about it, but I know that it has not been orchestrated in order to keep me in the company).

The rational thing to do would be to hold strong, wait few months for a probable acquisition and then leave/decide what to do. However, I really have no drive/motivation to go further. I'm continuously looking at my screen, but I'm not doing anything, and if this protracts for a while I may also risk to burn bridges (hence future recommendations).

Should I ask for another one-on-one with my manager? If so, should I be honest about the acquisition thing and everything else (in theory it's a secret).

Also, next week I have a meeting with the CEO (it's a small company). What should I tell him? I don't think I can tell him about the acquisition thing, as he would get furious (he probably told it to few people, and then the news got leaked to few others).

In other words: should I tell my manager/CEO that I made up my decision to leave, but that I'm staying for X months (they will ask why...)?
Keep in mind that I don't have another job as backup, and the reason for not looking yet is because of the acquisition thing (it would be weird to search for it now, and then say to an eventual company that I will be able to join only in 6 months).

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    I would lose money if I quit before the acquisition How much money are you talking about?
    – Nobody
    Apr 6, 2018 at 12:44
  • What makes you think you won't lose money if you leave after the acquisition? Either your shares are vested or they aren't surely? (But that's more of a [startups.se] question). Do you know why your manager wanted you to stay until after summer? Maybe he knows that the aquisition will be done by then? And do you know what amount of money you are talking about? It may be sily to delay leaving for a sum that isn't significant to you.
    – Lilienthal ♦
    Apr 6, 2018 at 12:45
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    FYI @Lilienthal, Startup.SE has been closed.
    – user27483
    Apr 6, 2018 at 12:49
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    And you need to work on that motivation thing. As long as you are accepting a salary you need to do the work whither you are happy or not. You don't have to feel motivated to do work, you just do it.
    – HLGEM
    Apr 6, 2018 at 13:59
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    You do know there are typically requirements, for shareholders, even after an acquisition. So you might have to wait, day(s)/month(s)/year(s) after the acquisition, before your shares mature/vested (i.e. they pay you). Check your contract for the requirements of your shares to be vested/mature, and under what conditions you will be paid, then make your decision based on the facts.
    – Donald
    Apr 6, 2018 at 15:01

6 Answers 6

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My advice is not to leave your job until you have a concrete job offer to go to.

I would ignore the shareholder aspect for 2 reasons:

  1. You are making a life-changing decision based on an unsubstantiated rumour
  2. If you divulge that you waited to leave and gain financially because of this information, then you may be accused of insider trading
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  • I clarified in my original post that the company is a startup, so it's not on the stock market. In such case, is insider trading still an issue?
    – HBv6
    Apr 6, 2018 at 12:11
  • @HBv6: Insider trading laws are not my expertise (and we don't give legal advice on this site), which is why I said accused. But at the end of the day, you don't want to be both unemployed and under legal scrutiny.
    – user27483
    Apr 6, 2018 at 12:20
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    The OP would have to trade for him to run afoul of insider trading. Holding options or delaying a sale isn't insider trading.
    – Lilienthal ♦
    Apr 6, 2018 at 12:48
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    @Lilienthal - As you point out this wouldn't be a case of insider trading, and those laws, are typically only applied to the shareholders making the direct decisions, that result in a price increase/decrease. It does not take the CEO of Google/Apple/Microsoft to know, that the project you are working on, likely will result in an increase to the stock price for Google/Apple/Microsoft. An example of insider trading would likely be, Google/Apple/Microsoft CEO's knowing about the Intel Meltdown vulerability, and then trying to short Intel's stock.
    – Donald
    Apr 6, 2018 at 15:00
  • @Ramhound: If the Google CEO finds out because he employs some very clever people who figured out the vulnerability, without any help from Intel, then it's not insider trading. If he finds out because the Intel CEO informed him, then the Google CEO is now an Intel insider and it would be insider trading.
    – gnasher729
    Apr 8, 2018 at 11:08
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Start looking for a new job and ignore the acquisition rumors. Do your existing job well.

  1. Without a new job that's all just speculation. In order for you to move this along, you need to go actively looking.
  2. You already have mentally checked out and your performance has suffered. This will create problems if it drags out too long. You need to get moving.
  3. You can't make good decision on rumors. You need real data and sufficient information. You don't have that at the moment and there is no reasonable way for you to get it, so it's best to just ignore it
  4. Even if it happens, it may not result in an immediate financial benefit. Many of these transactions have some strings attached to prevent an immediate mass exodus: lock out periods, vesting schedules, pro-ratings, etc. See point 3).
  5. Depending on how your current equity is structured, you can perhaps still benefit, even if you leave right now. If you have stock grants, they are yours. You keep them, regardless of whether you stay or leave. If you have options, you can consider to exercise some right now or shortly after you leave (there is typically a grace period before they expire)
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Simple. If you may lose money then don't let that stop you. If you will lose money by leaving then you need to figure out how much, is it worth your while staying, and you make your decisions.

Don't stop for things that may happen.

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  • Great advice...
    – OncleDan
    Apr 11, 2018 at 15:16
  • +1. I was hoping to find an answer that advised to consider the value of the money versus the value of moving on. I once left a $10,000 bonus on the table because I was ready to move on and no amount of money could compensate me for missing out on KY next opportunity.
    – Kent A.
    Dec 9, 2018 at 14:31
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should I tell my manager/CEO that I made up my decision to leave, but that I'm staying for X months (they will ask why...)?

No.

Decide for yourself if you want to stick around due to the potential acquisition or not. If the former, be aware that rewards for sticking around aren't usually immediate. In every case I have experienced, you'd need to be there at least 6 months post-acquisition to get anything.

Once you have decided then act accordingly.

If you have decided not to stick around, then find your next job, give the appropriate notice, and leave.

If you have decided to stay, then just keep it to yourself until you later decide to leave.

Playing games like "Well I might stick around or might not." or "Well I might stick around because there may be a bonus later." are more likely to backfire than not. If I were your manager/CEO and you proposed that to me, I'd almost certainly tell you to leave now.

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    "I'd almost certainly tell you to leave now." - Or you'd most certainly start looking for a replacement very soon.
    – Dan
    Dec 10, 2018 at 14:18
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Startups often have fake aquisition/partnership/mega customer rumors to keep the morale. I would consider selling my shares to colleagues if possible. Utlimately the question is

How much do you value your time being bored in front of the screen ?

versus

What is probability times amount of money gained in the merger ?

No one can do the math for you

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  • I'd like to see some information regarding fake aquisition/partnership/etc rumors. Having been in upper management with many startups often those rumors are based on reality but deals tend to fall through incredibly often. I've lost count of the number of acquisition discussions I've had. Some sounded like they were just needing the lawyers to finalize paperwork only to have one side back out with no notice. Same with acquiring customers. Things happen, people change their minds. The hard part in management is to not discuss this with the people it may impact.
    – NotMe
    Dec 9, 2018 at 1:36
  • @NotMe , if upper management officially shares realistic info about a possible deal, then it's not exactly a rumor anymore. Now if that info is blown out of proportions and not official to keep the hopes up in a failing startup then there's a fake part in it and it's a rumor. Besides, havings leads going nowhere is a common occurence in all businesses.
    – Manu de Hanoi
    Dec 9, 2018 at 16:59
  • The problem is deals change fast. Not just the likelihood, but even the terms. I remember a 2 week period where we had a company offer to buy us 100%, then change that to a 70% stake, then switch to only an asset purchase deal, then change it to a loan with an option to buy after two years. Every time we got on the phone with them they changed what they wanted to do - and all of that happened before we even got the due diligence phase. My point is that just because someone said something doesn't mean they were intentionally trying to mislead.
    – NotMe
    Dec 10, 2018 at 16:58
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I left a job three weeks before my first options vested. (Best guess at the time was $5000 to $10,000, as this was pre-IPO.) I didn't like the job, and the Director of Engineering was so impressed he made it clear I could come back—even though the quality of my work was career-worst—and that I would have a favorable reference.

However, I had come into a considerable sum of money unrelated to work. Even skipping $10K was not that painful. You will have to balance whether a better recommendation is worth the cost. We don't know what your equity is worth, but you might be able to find out.

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