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I work in a small business - it's me and my boss. He generally handles support calls and sales while I am a mixture of web dev, database admin, windows mobile developer etc. basically all aspects of computing and software.

I spend most of my time fixing bugs and doing stuff with data, and developing the odd thing. Without me, the business would be screwed after a while, although a lot of clients could chug along OK without support.

my boss wants me to begin a massive rebuild of our windows mobile platform and basically rework everything to work on android. I keep trying to make it clear that this is a big project, especially since I have next to no experience in android development. I can certainly do it, but it'll take a long time.

The big problem is, I want to tell him I'll be leaving within a few months. I have a job opening up with a family member soon that I really want to jump on. I thought it would be best to give my boss as much notice as possible to find a replacement, but I am just finding it so difficult to tell him for various reasons:

  • before he hired me, he struggled for months to find someone. he took a chance on me as an inexperienced graduate who was unemployed for quite a while

  • he feels more like someone who is my dad's friend than a 'colleague'. I feel guilty about leaving because he'll probably have to pay a LOT more for someone new, and it'll take time to find them which could hurt the business

  • he's always been a very generous boss. i work from home and i am paid well for how little work i actually have to do. he's extremely flexible and lenient with things like sick days and holidays etc.

  • he's worried about our platform not being supported in windows 10 and many of our clients upgrading soon, which is why he wants to do the android rebuild. if I leave and clients begin upgrading, he could lose a lot of business in the meantime and it could hurt the reputation

  • if his business is hurt bad enough it could screw his family over

is it a case of just ripping off the band-aid? I am certainly not intending to pass up on the good opportunity as I'm pretty bored of this job after almost 4 years.

marked as duplicate by gnat, Chris E, Mister Positive, Masked Man, David K Jan 30 '18 at 18:29

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  • 3
    This might be better suited to the Interpersonal SE. – user Jan 30 '18 at 16:48
  • The sooner you tell him, the sooner he can arrange some knowledge transfer with a new start and minimise the impact of your departure. – user34587 Jan 30 '18 at 16:59
  • If he's going to have to pay "a lot more" for someone else to do the job, that suggests you're not being paid enough and is a pretty good reason for moving on. – Jonathon Cowley-Thom Jan 31 '18 at 10:29
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You should probably wait a bit. It is typically a bad idea to give notice before you have a written offer in hand.

A few good reasons for this:

  1. Even in the case where the new opportunity is with a family member or close friend, you never know for certain whether you will get the job offer until you have received said offer in writing. What if your relative comes across someone much more qualified for the job you want? Do you expect them not to hire that person? That's may be a lot to ask...

  2. Once you've received the new offer, what if you find its terms unacceptable? What if you like your current position better? It would be easier to turn that offer down and stay if you had not already quit your old job.

  3. The notice period can be very uncomfortable for both employer and employee. Especially when you regard your employer as a friend. Right now, your best case scenario involves working side-by-side with this guy for 3 months after you tell him you are leaving. Why would either of you want that? This is exactly why the typical notice period (depending on your location) is 2 weeks.

Once you've accepted an offer from another company, you should give the standard notice (2 weeks in USA), document your work for your eventual replacement, and in your case, maybe offer to help write the job posting for your replacement. Anything further is exceedingly generous.

  • thanks for the response! I was actually thinking of giving my boss 'notice' of me leaving but not my 'notice to terminate employment' if that makes sense. my contract requires 1 month of notice and I wouldn't intend to give that until I had secured the next job, but I would like to give him more 'notice' that I'm leaving so that he can find a replacement and perhaps do a handover period – Ross Campbell Jan 30 '18 at 17:14
  • Please be aware that your boss may not see the distinction between the two. For some employers, expressing intent to leave in the near future is the same as giving notice. YMMV. – djohnson10 Jan 30 '18 at 17:58
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Let's go point by point:

before he hired me, he struggled for months to find someone. he took a chance on me as an inexperienced graduate who was unemployed for quite a while

Yes, and it was cheap, and he has gotten a lot out of it

he feels more like someone who is my dad's friend than a 'colleague'. I feel guilty about leaving because he'll probably have to pay a LOT more for someone new, and it'll take time to find them which could hurt the business

If they'll have to pay more for someone like you... they shoyld be paying a lot more for you, and he isn't. So much for being a friend and he's underpaying you?

he's always been a very generous boss. i work from home and i am paid well for how little work i actually have to do. he's extremely flexible and lenient with things like sick days and holidays etc.

Are you actually sure you want to leave that behind? It's sounds great!

he's worried about our platform not being supported in windows 10 and many of our clients upgrading soon, which is why he wants to do the android rebuild. if I leave and clients begin upgrading, he could lose a lot of business in the meantime and it could hurt the reputation

He could take it as an opportunity to get someone onboard with android dev experience...

if his business is hurt bad enough it could screw his family over

This is certainly not on you. His business, his profits, his loses... It's the way it works!

  • thanks for your reply. you see, I am underpaid in terms of my responsibility, but way overpaid in terms of the difficulty and volume of my work, and my experience level. that's why I haven't made an issue about it, i feel i've been very well compensated while he probably feels he's got a good deal too. it's a win-win working at home and doing very little has gotten extremely boring, and most of my work is very repetitive now. I actually WANT to be out there busting my ass on something! and since the new work will be at a much higher hourly rate rather than a salary i'm very keen – Ross Campbell Jan 30 '18 at 17:17
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    +1 for "His business, his profits, his loses... It's the way it works!" If he's created a business that will fail if his singular underpaid IT person leaves, that's on him. With that said, it doesn't sound like anything you're doing will actually make or break the company in the near term. Any responsibilities that could actually crash and burn the company (such as the website goes down and only you know how to bring it back up) should be documented anyway. Nothing in the company should have a "bus factor" of one. en.wikipedia.org/wiki/Bus_factor – Chris G Jan 30 '18 at 17:34
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Your not wanting to leave him is admirable. Giving a long notice shows you to be a conscientious employee.

However, it is his business and his responsibility. The businesses failure to plan for losing an employee has been called the 'hit by a bus' scenario. At the end of the day it's his business and his responsibility.

One possibility would be to give notice but then help your current employer hire your replacement and do a knowledge transfer with the new hire.

  • A long notice without another job in hand is foolish. Sometimes places just replace you immediately. – HLGEM Jan 30 '18 at 19:37
  • that was basically my plan - do a handover if he finds someone in time – Ross Campbell Jan 30 '18 at 19:45

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