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I work for a very small company, I'm currently the only employee besides my boss. In the past we have had more (but not many) staff, but due to other job offers or other circumstances, all of them have left.

I have been giving my employer a few months to find someone and hire them, but it has already been three months and he hasn't done this.

How do I strongly imply he should hire someone else before I leave without making it clear I'm going to leave? I feel letting him know could make the working environment very awkward.

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  • Have you made up your mind to leave, or is there something your boss could do that would make you happier to work there, and stay? Have you discussed this with him/her? – Kent A. Nov 3 '15 at 19:51
  • Give him a leaving date (within the contract). Otherwise he is going to think this is just a bluff – Ed Heal Nov 3 '15 at 20:03
  • No, nothing. I've been at the company for years, it isn't growing, and there's no way to move up. I can earn nearly double what I'm making now, elsewhere (I have been offered previously). – Joe Smentz Nov 3 '15 at 20:04
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    Your title suggests that IF your boss hires someone else, you WILL stay. Is this accurate, or are you going to leave anyway? – AakashM Nov 4 '15 at 8:53
  • @RonD: If things are as you describe them, why are you still there? – gnasher729 Nov 4 '15 at 8:56
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It is not your responsibility to tell your boss you are thinking of leaving/they need to hire another person. I'm assuming you have a notice period in your contract and if so, this is there for their benefit as much as yours.

As you quite rightly say in your post, this could lead to an awkward relationship/atmosphere which is another reason to look after yourself first. Plus, what if you do broach the subject and then do not find another position for a while? The awkward atmosphere would have to be endured for far longer than you probably anticipated.

Keep quiet. Let them do their job and look after yourself!!

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I assume that you are unwilling to let your employer know that you are leaving until the notice period (e.g. two weeks or whatever it is) before you actually leave arrives.

If that is the case, I would line up another job first. Once that is in place, give your boss your required notice and then leave. This option offers you the maximum protection, but at the (potential?) cost of negatively impacting your relationship with your current employer. (Edit: see comment below.)

If that is not the case, and you are willing to let your boss know that you are leaving in the (not too distant) future, then have a face to face conversation with him/her and make it clear that you are planning to leave but that you won't do so until you are confident that your employer has found a suitable replacement for you, UP TO a specified maximum time. So for example, you could say, "I need you to search for my replacement in earnest. I will stay with the company for up to three months while you look. If you can't find anyone in that time, then I'm sorry, but I'm going to have to leave. If you find someone sooner than that, I will be happy to leave early once that person is trained." This option puts you in better graces with your current employer (whom, I assume you will want as a reference) but makes your job search trickier because you won't have a definite end date. This is a significant risk to take.

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    Welcome to the site Nonnal. Thanks for submitting a good first answer, but let me point out that it's dangerous to give this kind of ultimatum ("I'm going to leave in X months") without having a job lined up. A job search can take considerably longer and saying that to an employer is a good guarantee that they'll replace you as soon as possible. Giving a standard notice period (2 weeks in the US) shouldn't negatively impact your relationship. Nitpicking: letters of recommendation are mostly a relic of the past as your references are normally contacted directly by the hiring manager. – Lilienthal♦ Nov 3 '15 at 22:43
  • Great points, @Lilienthal. +1 for a thoughtful, well-reasoned, helpful, and polite reply. – Nonnal Nov 3 '15 at 22:46
  • You're quite welcome @Nonnal. I don't like being so critical of new user's first posts, especially when they're already of good quality but it was all meant to be constructive. Remember though that comments are temporary on StackExchange so if you want to update your answer to incorporate something that was mentioned in a comment you're encouraged to do so. Don't feel like you can't add something to your answer just because someone said it in a comment "first". Of course, you also shouldn't include things that you don't agree with either. – Lilienthal♦ Nov 3 '15 at 23:22
  • I don't want to make my "new user advice" comments too long, so feel free to join me in chat if you have any further questions or if I was unclear about anything. – Lilienthal♦ Nov 3 '15 at 23:23
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As others have noted its usually a good idea to have a backup plan (an offer letter from another company), before broaching a subject like this.

However I want to ask why, you want your boss to hire someone else (I am guessing it's not that you are lonely and want someone to talk to). More likely you want someone else to take on some of your work load.

Therefore your real ask is that your boss reduce your workload rather than hire someone else, in fact if your boss did hire someone else and the new hire was incompetent, it may not help you.

Therefore my advice would be to ask for what you actually want (reduced workload) and let your boss figure out how (and if) to accommodate your request. Note, (s)he may go in a different direction such as offering you a pay raise, would you accept that? if so how much would you be looking for?

I would also recommend establishing a timeline for when things will change.

Finally, it may be the case that your boss is happy with the status quo and simply refuses to make any changes, so you should be prepared to make the jump...

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This is just like any personal relationship you are in. Imagine that you hint to your girlfriend that things are not working out. She should get the picture that maybe you two aren't a long-term thing. Maybe she starts looking for other guys, but at the very least she's not buying a house and car in both your names.

If you have already hinted at your employer that you might be leaving that is more than enough - really you went too far. If you sit your employer down and make it 100% clear it would be like telling your girlfriend that she is too annoying, too ugly, or too stupid to date you. Any self respecting girl would dump you on the spot. At the very least she is going to be seriously hostile towards you until that fateful day comes (from you or her).

Expect your employer to act the exact same way.

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