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I work at a very small software development firm (6 people, not including the boss) where the accumulating dissatisfaction with the workplace is forcing me to start actively looking for alternative opportunities. The problem is that not only I'm quite possibly the most valuable employee here, but also, another very skilled and arguably the most hardworking coworker has a similar plan. The two of us are quite close, and informally we discussed at length the idea of leaving the company, and came to the conclusion that it's the best way to go.

We are not coordinating our job hunts (as we have different priorities and preferences for an ideal new job), but there is a high chance of the two of us announcing our resignations at approximately the same time. Because the company is so small, I am afraid the damage of two key workers leaving at once will be severe, if not catastrophic, since the business is already struggling.

Do the two of us need to carefully work together on our departure plans somehow, to avoid resigning simultaneously (and as a result attracting a double amount of negativity from the boss and the remaining coworkers, because of apparent "conspiracy")? Or do we just individually go through with our plans and leave it to the company to deal with the potential damage?

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    If you separately intended to leave, then if the timing matches on your departure it's not your issue. – Jane S Aug 31 '15 at 22:36
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    @VincentAdultman If asked, you can honestly answer that you had separately. Whether you discussed it with each other after that is irrelevant. – Jane S Sep 1 '15 at 0:06
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    @Gideon But most people would much rather believe a conspiracy than coincidence, no matter how many facts are available. – CJ Dennis Sep 1 '15 at 4:01
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    You're not responsible for the success or failure of any company that you're not in charge of, regardless of how valuable you are. If your departure is not a wake-up call to the owner about making sure employees are happy, then the company should have serious trouble and possibly go out of business. If it is a wake-up call, then you will have actually helped the company in the long run. – Todd Wilcox Sep 1 '15 at 12:06
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First, should you feel bad?

The reality is, stuff like this happens. A few key employees leave at the same time. It's not your fault. Companies which fail to plan for employees leaving end up hurting. But that's a management level problem for failing to plan.

Are you actively lying to your boss? Is your boss doing surveys to understand what employees want (and actually taking action)? Are you paid market rate or above? Is your manager good? Do you have a good work environment?

If the answers to these questions is "no" then it's clear your boss isn't doing what he can to keep you around.

Don't let yourself feel guilty because of your boss's negligence.

Negativity compounds

Be careful to avoid you and your friend commiserating and making things worse. A negative spirit can be pretty powerful. I have worked with someone before who could find great reasons to complain about everything - this person had a disproportionate impact on me disliking my situation. Be careful that you don't "talk up" how bad the situation is and then leave because of that.

What should you do?

Hopefully you have communicated at least some of your concerns with your boss previously. If that has happened, your boss will not be super surprised. Leaving unexpectedly, having voiced no concerns, will leave a much worse impression than having tried to reconcile them.

If you haven't talked with your boss, that alone will probably be a negative on your relationship. It won't destroy it, but it probably will hurt it some. In this situation, if you aren't being candid about your reasons for wanting to leave prior to resigning, I'd strongly avoid talking too much about why you are leaving in details. Something like, "I just don't think this is the best place for me and am excited about this other opportunity" can answer most questions.

People may press the "why did both of you leave?" but realistically you can't stop this question from happening. People love to speculate/gossip. Keeping it professional and not badmouthing the company (or them) is your best bet.

Minimizing damage(s)

Because the company is so small, I am afraid the damage of two key workers leaving at once will be severe, if not catastrophic, since the business is already struggling.

A few thoughts here, too.

First, you can't prevent all the damage and you may not be able to even prevent most of it. A company losing 1/3 its employees is going to have problems, especially if they are the top employees as you say.

You can do a few things to help though. One possibility is to focus on preparing for getting hit by a bus. I asked that question for nearly the exact same reasons, I was part of a small team and was the sole technical contributor. Documenting your work, and documenting what your next steps are can be helpful. You can start doing this even now (and realistically it's helpful for your current work, too).

Next, if you have flexibility on your notice period, this may help to have a longer period. Some managers might say, "oh you took a new job? here's the door cya now" but others may appreciate a longer notice period.

Your mileage will vary based on whether this time is used effectively to transition or more to "do as much work as you can get in before you leave."

When talking with your new company, I suggest verifying they would have flexibility before offering a 4-week notice period to your current employer. The last thing you want is to have a 2-week notice period, offer 4 to your current employer, and be out of a job for that period (well, maybe this would actually be ideal, depends on the person I guess).

  • While this is a generally good answer, I feel it focuses too much on the "Letting your boss know you aren't happy so he can plan" aspect, and could do with a "Do as much as you can now to ease the transition" section to round it out. – Jon Story Sep 1 '15 at 11:45
  • @JonStory the asker wasn't as concerned with that part, given how the question is worded. The reality is, if two people leave a company of six it's going to be rough (especially if those two are carrying the company). There's not really any level of planning that can prevent that from being a problem. It's unfortunate, but as I say at the beginning, you can't feel guilty about that problem. It's an inherent risk with starting a small company and not doing your best to keep employees. – enderland Sep 1 '15 at 13:56
  • It appears to me that the OP was concerned with that part to some extent, as it relates to the potential negativity they would receive: planning well for your departure reduces the perceived negativity of the departure. I'm certainly not saying your answer is wrong, just that I think it could perhaps be more complete with that addition – Jon Story Sep 1 '15 at 13:59
  • @JonStory good point. I added a bit at the end for that. – enderland Sep 1 '15 at 14:25
  • I did something similar when I was leaving a small company, where I was the only back-end developer and very unhappy. Yet I did the courtesy of telling my employers I would leave the company in 3 months. It was a calculated risk, where I could get fired. But I knew the company, the people, and they wouldn't do that. It was ample time for them to prepare, yet they didn't. I ended up leaving and they got hit by a bus anyways. Regardless, think very hard before doing this. It can backfire. – harsimranb Sep 1 '15 at 17:20
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Let's say you, your colleague and three other guys in red shirts are at the company picnic and stand next to the gas barbeque when it explodes.

That's a risk the company needs to plan for, so "only" the two of you leaving should be covered, too. If not, it is in no way your fault and if the working conditions are that bad, it was to be expected.

Also, don't overestimate your importance, any system you have build could be either learned or rebuilt by a new set of developers. Been there, done that. :)

If you want to be nice, try to document as much as possible for the new set of developers and stay available for questions later. Emphasis on questions, not work. And agree on the terms how much, at what hours, which response time, what you get for it, and so on.

For the conspiration part, Mohair is right, check what your work contract defines as "one employee hiring another".

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    +1 for both redshirts and, more importantly, talking about how to ease the transition. The single best thing you can do when job hunting is start documenting everything clearly for whoever takes over your role. The more information you can take from inside your head and put clearly on paper, the better – Jon Story Sep 1 '15 at 11:46
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If they really cared, the management would already be doing things to address the problems which are causing dissatisfaction among the staff.

The most generous thing you can do, if you haven't already done so, is to constructively engage in a dialog about possible solutions to these issues. This way, when/if you do leave, no one involved is blindsided about the real reasons why. In other words, if you handle this right your boss won't have reason to ask "Why didn't you say anything ?!" when you do leave.

If constructive dialog fails then it is absolutely OK for you to plan your own exit without regard to coordinating timing with others. Just be a gentleman when you announce your departure and everyone will understand or at least get over it in time.

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If you are both job hunting independently of each other, then I don't think you have any issues. The one thing that could get you in trouble is if you both end up at the same new job. Often, your company will have you agree not recruit anyone for a year after you leave. So if you both end up together somewhere else, that could be easily interpreted as one employee recruiting another.

  • Worth noting that any post-employment agreements should come with some sort of compensation. If they want you to agree not to recruit, then what are they giving you in consideration for that? If the answer is nothing, then you have no reason to sign it (and really shouldn't). – Allen Gould Sep 1 '15 at 20:58
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If your boss pays you for the work that you are doing, and at some time either you or your boss decide to cancel the agreement, so that you are not working for him and he isn't paying you. At that point, you have no obligations towards each other (except not badmouthing each other, not giving away any trade secrets, returning stuff that is in one's possession but owned by the other, probably some record keeping etc. ). Your boss won't be concerned with how well you are doing financially and emotionally if he cancels the employment, nor do you have any reason to be concerned with how well your boss will be doing financially and emotionally when you are leaving.

Your boss would only have a legal reason to complain if you intentionally did something in order to damage the company, that is with the intent of damaging it. If damage to the company is an unavoidable side effect of you leaving, then that is not your fault. So the two of you have no obligation at all to time your leaving to minimise damage to the company. Even if you had looked for a new job first, found that a company is looking to hire two new employees and you told your colleague - after working hours to be safe - there is nothing the old company can do unless there is something explicitly in your employment contract.

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    "At that point you have no obligations towards each other" - while true (with the exception of the kinds of contractual obligations you point out) legally, I feel this is more a question of ethics or at least professionalism: ie "How do I handle this scenario, which I know will at least be tricky for my current employer, as professionally as possible". – Jon Story Sep 1 '15 at 11:48
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    On the ethics side, how many companies care whether you can pay the rent when they lay you off? – gnasher729 Sep 1 '15 at 18:20
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I was in the very same situation almost 2 years ago.

Me and my colleague were "conspiring" to leave, until both of us found another place to work. My bosses, which are good people and I am still in touch with them, also had the fear that they wouldn't find more people to work.

It was my first job. I started working there as a trainee in the very first months of the company. I stayed there for 2 years, but I was way underpaid and they said "they couldn't pay me more". The company's financial situation was not great, and I knew it. So I could choose to stay and help them grow, or to leave, get more money and experience.

But I was feeling that I had not evolved in my professional carreer for months and months. My friend was in the same situation. Also, my opinions were being ignored because "some specialist told us not to do it". So, even though they cared for my person, i felt they didn't really cared for my work, so I decided to find another job and left. And so I did.

Months after it, I visited them and... they were doing great. When I left (turns out that they didn't miss my other friend), they knew that they sould reorganize their processes, be more productive, and then they got some more trainees, which became employees. Hell, even some of my ideas were implemented (just one, but hey, it's already something).

It was a blessing for them that I left, and it was a blessing for me that I left.

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Even if you were planning your exit together that wouldn't be a conspiracy, since what you're doing isn't illegal[1]. And really, how far apart would you have to stagger your departures? The answer is how long it would take for the first replacement to be up to speed, which is too long. Don't burn any bridges, but you're under no obligation other than to give your contractual notice period. At that point it becomes somebody else's problem.

I once had a boss who knew I was dissatisfied. He actually accused me of trying to persuade another guy (who felt the same but better at hiding it) to leave.

I simply pointed out that the other guy was a big boy now and perfectly capable of making his own mind up.

Within six months we'd both jumped.

[1] unless you're planning to violate any applicable non-competes, or pinch IP etc.

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