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I've accepted a new job and given my required month's notice to my current employer, both are startups. My employer asked me if I could stay a little longer, as they're going through an investment round, and I'm the only expert in my particular area and so they'll need me to stay or find a replacement before due diligence starts.

I asked my new employer if they would be happy for me to start later than a month, but they're not for understandable reasons. I'm to help them achieve an upcoming deadline, and I obviously agreed to a start date on accepting the job. I've informed my current employer, but they're pushing me hard to try and re-negotiate with my new employer.

My current CEO is someone I've known a long time, and I don't want to make things difficult for them, but I also don't want to make a bad impression with my new employer. I didn't deliberately time my departure badly, but my current employer keeps investment plans and our financial runway very close to their chest, and therefore we never really know what position the company is in.

Has anyone else ever been in this situation, and what advice can you give?

Clarrification Clarifying a couple of things, due to feedback on my question. I have a months notice, as this is what is required by my contract of employment. This is normal in the UK, where I’m based. It’s possible for a company to require several months notice, if they include it in your contract.

I don’t want to work two jobs at once, as I’ve young kids.

Update Just an update for those of you who are curious. I told my current employer I will not be extending my notice period. They have now asked to be put in contact with my new future employer, to negotiate my leaving/start date with them directly. I have of course said no, as it seems to me to be completely unprofessional to even ask me this. I now feel I'm in a fight to stop them actively trying to sabotage the relationship with my future employer, for their own perceived short term gain.

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    Ask yourself this; whose goodwill is more valuable to you - your new employer's or your old employer's? I appreciate you're not looking to hurt your old employer, but are you willing to hurt yourself in order to help them? – Jonathon Cowley-Thom Apr 20 '18 at 13:39
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    "Lack of planning on your part does not constitute an emergency on my part". If Joe Blogs were that critical, the current employer should have offered a contract that treated them as a critical employee, setting longer notice in exchange for higher pay, as well as actually hiring more people in that area of work. – Patricia Shanahan Apr 20 '18 at 14:10
  • Comments are not for extended discussion; this conversation has been moved to chat. – Jane S Apr 23 '18 at 21:28
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I've never been in a situation like this, but I would stick to the required notice period (ie: one month) and move on. You even went above and beyond (IMHO) by asking the new employer if you could push back your start date to accommodate the old employer's needs.

In a perfect world, you'd be able to make both employers happy and not burn any bridges, but if push comes to shove you need to choose your new employer's needs over your old employer's needs, because that's where you'll be working for the foreseeable future.

You didn't do anything wrong - you adhered to the contract you signed. Ultimately, it's your old employer's problem that the timing is bad here, not yours.

I would explain this to him (the old CEO) professionally and calmly, and then move on. Something like:

Sorry Old Friend, but I've already asked my new employer about pushing back the start date and they said they can't do it. I know the timing is bad here, but I didn't have any way of knowing what was happening, and I've already made decisions and commitments that I can't back out of. I hope you understand that it's nothing personal, it's just bad timing.

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    I'd suggest that what the OP needs to do is choose his own needs above either employers' needs, actually. But in this scenario, his needs happen to align with his new employer's needs. – Jonathon Cowley-Thom Apr 20 '18 at 13:42
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    This seems reasonable, and is the way I'm going to go. As mentioned in comment above, I've tried to offer other things to help. I haven't spoken to them again yet, but I find these conversations really difficult. – Joe Blogs Apr 20 '18 at 13:58
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    @JoeBlogs: Tip to make the conversation easier and less stressful: write down what you want to say and memorize it. Anticipate questions and push backs they are likely to ask and write down some answers to those up front. If all fails, go with "I'm sorry you feel this way". – Hilmar Apr 20 '18 at 14:06
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    +1, This is the correct answer. Imagining the opposite might help the OP even further. If it was your old employer who was letting you go or firing you, and you asked them to keep you on for a month because you need time to find a new job and you will have trouble paying your bills, do you think your old boss would keep you employed for another month? No, he wouldn't! – Fixed Point Apr 20 '18 at 15:55
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    I'd also like to add that any good manager will manage around the bus-factor. @JoeBlogs try not to feel too bad for them. – John Hamilton Apr 20 '18 at 17:02
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Agreed, stick to your 30 days notice as that's your future income stream. If you wanted to put in some extra effort to mitigate any burning of bridges, an excellent idea would be to open a negotiation with the old CEO as far as part-time, after-hours consulting on what you did in your former position.

Figure out what the hourly rate should be (recommend at least 2x your previous hourly rate, preferably only in four hour blocks), and start negotiating from there. This accomplishes you 'checking the box' that you're not going to completely ditch the old employer, honors your notice to your new employer, and sets the expectation to your old employer that they can't call you for work with an expectation that you'll drop everything and work it for free or real cheap.

Good luck.

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    I would amend this to say, select a rate that gives you an after-tax return at least twice your current (ie new) before-tax rate. Reason is that you want to be paid enough to make completing the work a pleasure, despite being on top of your new position's requirements. If your old boss declines that rate, then it is him saying "no.", not you - an important distinction. Never say no - just quote an appropriate (and fair) rate. – Pieter Geerkens Apr 20 '18 at 19:29
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    @PieterGeerkens: I like such an answer but I can't do 60 hours anymore so it's not always feasible. – Joshua Apr 20 '18 at 23:09
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    Or the new employer can sell OP as a consultant to the old. – Thorbjørn Ravn Andersen Apr 20 '18 at 23:18
  • The first few weeks on a job are a bad time for moonlighting. The OP may need to do some studying in the evenings, and should be getting plenty of rest to help with the stress of a new job. – Patricia Shanahan Apr 21 '18 at 14:32
  • But do not make this open-ended If you do after hours work for your old employer, give it a specific end date (not even that you will accomplish X,Y or Z, just a date). – user8036 Apr 23 '18 at 13:53
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First of all, do not upset your new employer. As you've already asked and been declined regarding a later start date, your hands are essentially tied. The problems of your old employer are exactly that: their problems.

While it is both polite and friendly to help others, you are responsible for your own career development and financial health. Your old employer should understand that, and there are potentially risks being hidden if they are extremely tight-lipped about business finances. From personal experience, upper management usually hushes financial details when they are afraid of how the employees will respond.

Full-time employment is not the only option. You could work under contract in your off-time. Note that this may require the consent of your new employer depending on the terms of your employment. At a minimum, expect the new employer to demand scheduling priority if work is required outside of normal hours.

There are tax implications for so-called "1099 work" in the US if you are paid as an independent contractor, so read up on that. It's not very complicated, but you will be required to report that income when you file your tax return.

Investment activities aren't your responsibility. The corporate officers are responsible for staffing and other requirements. A responsibility on their part does not create an obligation on yours. Professionally, they should not give you a bad reference because they could not fulfill their responsibilities easily--but they might. You cannot control that, so you will have to accept it.

It is possible that a contracting arrangement may allow them to demonstrate the necessary expertise. If this is workable, I strongly suggest you look at standard rates for your field and negotiate on that. Remember that you will be dipping into your free time and sacrificing quality of life with each billable hour.

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To add to existing answers:

  • The old employer is gaining a considerable amount from your work (namely, the company will be more valuable, and therefore, their equity will grow).

    If your efforts/presence there is so critical to that goal, a good position would be to request some equity - instead of salary - if you were to put in any effort towards helping them reach that goal.

    The benefits are:

    • Tax benefits. Equity now would probably be cheap, and therefore not cause extra ton of taxes; and if it gains long term, will only be taxable (at least in USA) under far lower capital gain tax rates.

    • There's very little downside (company goes belly up so you lose a bit of extra equity) vs lots of potential lower probability upside (company sells out to Amazon, you can retire, maybe).

    • As CEO is likely to be far more loathe to lose a share of the company (see above financial reasons) as opposed to pay you another month of salary, they may tell you "no, thanks, we will just hire an outside consultant instead" - thus freeing you from their demands.

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First off - congratulations on the new position. It is fantastic that you have two employers that value your skills.

That being said - you are leaving your current employer for a reason. Those reasons don't change because they would like you to stay around for a bit longer.

The most likely scenario is that they set the terms and conditions of your notice period. You are merely honouring the commitment you made to them, and when you negotiated the conditions of your new offer it most likely was based on the requirements of your previous employer. Now is the time to honour the commitment you made to your new position, and lets be honest, your own career.

Politely explain to your CEO that you were unaware of the impending investment round, however you need to honour the commitments you have made. Explain that over the next month you will work with them to identify the priorities in transferring your projects/skills etc. so that your departure is as seamless as possible.

I would recommend against working under contract or on the side with your previous employer unless this is standard in your industry. In my own industry it is expected that when you move to a new employer some of your previous role will follow you for a time - but this was openly discussed during negotiations. Working for your previous employer on the side/part-time is likely to make new employer question your commitment to their role and dedication to the company. I am assuming here that you have a full time contract with your new employer, or you requested part-time for reasons other than holding down another job.

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I've been in this exact situation, and I answered with:

I'm sorry, I've committed to a start date already.

and

How can we make best use of the remaining 2(4) weeks ?

That carries the message of "its happening, its non-negotiable, lets do what we can in the time that remains"

I was also offered a 20% pay-rise to stay on, but even the biggest pay rise they could offer was less than my new starting salary.

You've decided to move on for your own reasons, your employer's lack of preparation is not your responsibility. Look after and prioritise yourself first.

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I would tell my old employer that they should have kept me closer in the loop.

Beyond that, if this investment round is make or break for them, I would say that I had no idea I was so critical, explain I should have been told, and demand equity and access to the business plan in order to stay on.

Another route I would consider is whether or not the two businesses could synergise. If so, I would suggest that a solution could be an overlap period where you work on something useful to both businesses while taking double pay.

I have been in a similar situation a few times and my experience is that a) you should never walk on a project you committed to b) you should leave employers for new ones if the pay is higher and conditions better long term, where you are not on a contracted project

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One point not mentioned in existing answers:

One strategy I have found to be effective when someone starts pushing me is to make it someone else's problem.

In this case, that would mean that you tell your employer that you cannot postpone starting your new job, but that you would be willing to work for them for some more days as a contractor, if your new employer agrees.

Advantages:

  • You stick to your agreement - one month notice to old employer, punctual start with new employer.
  • Your old employer gets a chance to keep your a while longer, if they can convince your new employer.
  • Most importantly, you don't have to play middleman between the two.

Realistically speaking, your new employer will probably not send you back, but if your old employer offers enough money, they might. And if they don't, then getting you back probably wasn't that important anyway.

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