I'm an inexperienced software engineering manager and recently I hired an employee (a software developer). The technical skills of the guy look good, but I encountered several things which he didn't mention during the interviews.

Right after we signed the contract he said that he has planned a vacation next month and he wants to take unpaid leave for two weeks. Also, only after hiring him did I find out accidentally that he's working part-time at another job and that he wants to stay there while working full-time for us at the same time. Since he's a remote employee, it's hard to say how much time he is spending on that other job. Also he started asking about changing the payment schedule as an exception for him for the first month despite the fact that we agreed to the schedule in the contract.

I understand that it's my fault that I didn't do the best work during the hiring process, but still I feel that we've been cheated by him a little bit. What would a good manager do in that situation? Should I just not worry about this?

We have set up a probation of 2 months.

We don't have a point about side jobs in our contract. We will need to add it.

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    Comments are not for extended discussion; this conversation has been moved to chat.
    – Neo
    Commented Dec 6, 2019 at 13:37
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    I think you should state jurisdiction.
    – Strawberry
    Commented Dec 6, 2019 at 14:25
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    Did you hire this person as a W-2 employee or as a 1099 contractor? I have to ask because you say he signed a contract. And if you hired him as a contractor, if you take any action to try to prevent him from having other clients who aren't direct competitors you're breaking US federal labor law.
    – tbrookside
    Commented Dec 7, 2019 at 17:59

8 Answers 8


Set some clear expectations that your employee needs to meet in order to pass their probation period.

Right after we signed a contract he said that he have planned a vacation in the next month and he wants to take an unpaid leave for two weeks.

Is this OK for the company? If it's not then say no.

Also, only after hiring I found accidentally that he's working part-time at another job and that he wants to stay there working full-time for us at the same time. Since it's a remote employee, it's hard to say how much time he spend on that other job.

Don't measure your employee's performance based on time, measure it based on results. You can't say how much time any remote employee is putting in, but you can easily measure the results they deliver.

Also he started asking to change the payment schedule as an exception for him for the first month despite the fact that we agreed the schedule in the contract.

Similar to the first point - as a representative of the other party who signed the contract, you can say no if this isn't OK.

Have a meeting with your employee, and let them know clearly that you're not happy with the way they've conducted themself so far. Set clear and measurable expectations for what they need to do to make it through their probation period, given their current conduct.

If they meet those expectations, then great: you've got an employee who can do what you need.

If they don't meet them, then that's what probation periods are for. Let them go.

  • 43
    Don't measure your employee's performance based on time, measure it based on results the caveat for this is that much of employment law and policy is built on thresholds (i.e. if an employee works more than X hours on average, the regulation changes). So - yes - as a manager, you want to measure performance and manage to an acceptable work product. But from the company's perspective, if an employee is "full time" then there is a need to know they are actually working full time.
    – dwizum
    Commented Dec 5, 2019 at 19:10
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    "Is this OK for the company? If it's not then say no" ... OR try to figure something out so that it becomes okay. The employee probably made a mistake by communicating it a bit late, but I would consider it a major red flag to have this specific leave request denied, especially if it's been planned long in advance (or it's non-refundable). You also have to consider whether you'd prefer to need to find a replacement for this employee, and whether you can find one who can start less than 2 weeks from now. Commented Dec 5, 2019 at 19:47
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    @Dukeling both the working a second job alongside your fulltime job AND the late notice of leave are factors that may impact on your ability to perform your duties. I've always been upfront about pre-scheduled vacation plans (if that means that I've lost opportunities; then I've lost opportunities while maintaining my personal integrity). While the employee thinks they are doing the OP a service by taking it as unpaid leave, they have potentially caused issues with the OP's timelines that were made with certain expectations.
    – Aaron
    Commented Dec 6, 2019 at 1:16
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    “you can easily measure the results they deliver” in what kind of perfect world do you live? The effort, quality and impact of work can be very hard to estimate. Sometimes you need a whole week for a simple thing because of tool issues, sometimes a seemingly hard thing is half an hour’s work because you can base it on something else. In addition the manager has to be aware of all the things the employee is currently engaged in (ongoing support tasks, mentoring etc. etc.). You only know what you’ve lost when the employee is gone.
    – Michael
    Commented Dec 6, 2019 at 8:43
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    @Dukeling the issue I see with the leave is that the new employee concealed it until the contract was signed and they started the job, even though they knew about it earlier. I've actually been on the other side of this, and interviewed for a job when I'd already paid for a holiday in what would be my first month of work. I let the company know this while we were in the interview/negotiation stage. I didn't want to start by burning good will that I hadn't even earned yet and risk getting let go during my probation period.
    – Player One
    Commented Dec 6, 2019 at 9:05

I agree mostly with Player One's answer, that this is something that needs to be solved during the probationary period. You need to find a (polite) way to tell him "Dude, you're springing a lot of unpleasant surprises on us. We'll see how it goes during your probationary period, but this is not a good way to start."

Aside from whether you're okay with him having side jobs or unpaid vacations, is that he's undermined trust. This is someone who doesn't tell you stuff that you need to know. That's a big strike against him during his probation.

So I don't entirely agree with setting specific measurable goals to pass the probationary period. Sure, there are minimum thresholds that must be passed. But part of the probation is to be a catch-all for anything you didn't even anticipate (and thus didn't put in the requirements).

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    The part time job might not even be in the same industry, so they might not consider it a conflict. They may also know it ends soon, so a minor overlap to avoid missing a good job is acceptable to them. I'd guess they missed out on other jobs because of these "unpleasant surprises" being admitted to upfront, so now they are avoiding telling everything to get a long term job, instead of potentially having to stick with part time temporary jobs, like I was stuck in for over 15 years. Trust can be re-earned. Commented Dec 5, 2019 at 21:11
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    Side jobs should probably be an interview question. That way, the interviewer can determine for themselves whether it'd be a conflict of interest. "Failing to mention" isn't quite as fatal as actual lying in an interview, but if you fail to mention a lot of things in an interview that you then have to bring up before the ink is dry on the contract, were you really acting in good faith?
    – ObscureOwl
    Commented Dec 6, 2019 at 11:17
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    First of all, side job restrictions are handled via contract terms. None were set by OP, thus it is at least debatable, whether or not this is an issue in itself. I am a bit inclined to argue, that these side jobs are none of OP's business, since the contract does not mention this. But there are caveats to this, specifically, there can be legal implications, e.g. how many vacation days do they get? How many hours are they allowed to work? What about their health insurance and taxes - are these affected too? There are two somewhat reasonable perspectives to this story. Commented Dec 6, 2019 at 11:46

I understand that it's my fault that I haven't done the best work during the hiring process, but still I feel that we'are been cheated by him little bit. What would good manager do in that situation? Should I just don't worry about this?

You cannot travel in time, and instead of trying to do so you have to deal with the situation at hand. And the way I see it you have two issues at hand:

  1. Vacation time. This may very well have been a slip on his part, I sure have done that in the past when only later down the road I remembered that I have XYZ planned and will need to be off. It happens, especially when in the middle of stressful times like job hunting. The best way to handle it is to call the employee and figure out a compromise. In the end of the vacation doesn't derail your company plans, then you should simply allow it, no reason to make a thing out of it for no good reason.

  2. The other job. This is none of your business. You didn't ask, your contract doesn't prohibit it (although those clauses are often non-enforceable anyway, that depends on jurisdictions and details), and you found in some less-than-direct capacity about it. As this is none of your business, don't make it your business and leave it alone.

As for trust, I wouldn't be too bothered. Having multiple jobs at the same time is something "normal" in certain countries and cultures, so just calling it a lie is a stretch. Likely just like you assumed that the employee will have just one full time job, he assumed that there is nothing wrong with having a few, even fault on both sides, or more precisely no fault on either party.

With that in mind, I wouldn't make more of those two issues that needs to be done. Remind the employee about company vacation policy for the future, and make sure to stay on track of whether the agreed work is getting delivered in a timely fashion and to professional quality. If it is, you just got yourself a great employee. If it doesn't, then you can handle it.

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    Spot on. The only concern I see with #2 is a potential conflict of interest. If that side job is working for a competitor, for example.
    – Cypher
    Commented Dec 5, 2019 at 19:56
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    @Cypher, right. Working as a remote digital design artists might not be a conflict of interest, but doing software dev for a competitor would be. The fine line is if they are doing Drupal/WP that isn't actual development, but still possibly related. And doing the same position but in a completely different field is also a fine line and up to company policy, which the OP says they don't really have. Commented Dec 5, 2019 at 21:24
  • Regarding 2. Many contracts actually prevent you from having a job on the side, related or not.
    – Anemoia
    Commented Dec 6, 2019 at 5:52
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    @snake op specifically said that's not the case here.
    – Aida Paul
    Commented Dec 6, 2019 at 9:10
  • About 2. Another job can affect your ability to focus and be available for your main job. I've often seen it specified in contracts. Once I saw that you're not allowed to do more than 8 hours a week for other work... even volunteer work. Commented Dec 8, 2019 at 12:33

Obviously, the vacation part is up to you. Is it okay for the company or not? I had this case once myself. Vacation already payed for. But I told the employer so during the interview (at the when can you start part) so it was not problem at all. Maybe a good opportunity to have a talk to that employee about company culture in regard to vacation (extent and notice period ...)

The second job is more concerning. Where I live, it is customary on full-time jobs that the contract forbids any side gigs unless approved by the employer. This can not only affect his work-performance, but also if it is similar to his main job, generate conflict-of-interest situations you don´t want. If you don´t want your codebase or worse, your clients data be misused, proceed with extreme caution!

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    Downvoting for the last few sentences. It's not worse, or better, just because the employee is remote. It would be the same set of issues if he worked on location in two places, and the supposed codebase is in as much risk.
    – Aida Paul
    Commented Dec 5, 2019 at 12:29
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    @TymoteuszPaul: It´s is easier to copy things when no one watches you. Speaking from experience, unfortunately. OP already voiced concerns over not being able to control the working time, so ...
    – Daniel
    Commented Dec 5, 2019 at 12:53
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    It really isn't, especially when talking about software dev world where I can copy your entire codebase in a matter of minutes onto a thumb drive and no one would ever be any wiser than it has ever happened. If you think that being in the office means that someone cannot steal your code, but they can do so remotely, you are simply unaware of how easy it is to do. Nor that it's germane to this question anyway, as OP already decided to hire remotely.
    – Aida Paul
    Commented Dec 5, 2019 at 12:56
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    @TymoteuszPaul If you can do that with a thumb drive, you employer either trusts you or does not have a very good IT governance. Also it leaves traces, which can be relevant in a lawsuit. Anyways, if I´d show up with a thumb drive in my first workweeks, I know my colleagues would have had questions! I´d be more concerned about data, especially customers/ business contacts though. I know of an occasion where someone had just written down contacts on a sheet of paper - and was caught, because a colleague noticed. Trust is the issue here. OP has been given reason not to trust.
    – Daniel
    Commented Dec 5, 2019 at 13:01
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    Spot on, Daniel. In development we often have access to privileged information, and our moral character and code of ethics matter more than our technical skill in some situations. A knowledgeable, but untrustworthy person is a liability, not a valuable employee. For example, in our company you don't get remote access, production access, or access to your email on your phone until after you've passed probation. Why? Because they've gotten burned before, and now they'd rather not risk it. Undermining that trust right off the bat is a good way to get fired.
    – AndreiROM
    Commented Dec 5, 2019 at 17:11

In my experience good managers tend to be those that are ...

  1. Honest (as much as they can be)
  2. Direct
  3. Adjust/adapt their expectations and practices as new information becomes available
  4. Learn to make (quick) decisions based on objective information (what is happening vs how you feel about what is happening)

Has anything that has happened so far cross a threshold for you (or your company) that would outweigh the possible value they could provide?

If that threshold has been crossed, figure out what you will need to do to re-hire for that position.

If you can see a path forward after this initial learning period; focus on setting boundaries, clearly communicating your expectations, and be consistent. As long as nothing in their contract contradicts the rules you would need to establish to avoid a similar situation in the future, do so.

On a personal note, some of the most difficult experiences I have had as a manager came from managing engineers that provided an incredible amount of value to our company but would test boundaries and complicate my life in ways I didn't realize were possible. I also did everything I could, for as long as I could, to keep them on the team. If an individual does not perform, is not reliable, and impacts the performance of the team (directly or indirectly), thats an obstacle that needs to be removed.

  • A very good answer. There is a difference between being dishonest and having discretion about keeping secrets.
    – spuck
    Commented Dec 6, 2019 at 16:09

Do you have an HR department? If so, you need to get them involved TODAY to protect the company's interests and to make sure you don't do anything on behalf of the company which will come back to bite you.

For the vacation issue, how about: "Sorry, we don't offer unpaid leave to employees during their probation period. What we can do is agree to a new start date after your vacation?" (This is an example of something you need to run by HR; what exactly is the policy about unpaid leave?)

For the outside job part, I don't think this is a valid concern. Sure, you won't be able to track a remote employee's effort level, but you can track their results. Just like you won't know if he is spending time working on his other job, you also won't know if he is sleeping in, watching movies, or washing his dishes during the day.

Unless there is a "your butt will be at your desk and available by phone 9-5 M-F" clause in his contract, what difference does it make if he is working mornings, nights, or weekends for you?

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    A side-gig can be a concern if the other employer operates in the same (or similar) field. It would be possible for the dev to start copying code from one project to another, etc. (other conflicts of interest can also arise). You're right that in a perfect world it wouldn't matter, but when he demonstrates shady behavior from the very start, it raises questions.
    – AndreiROM
    Commented Dec 5, 2019 at 17:17
  • @AndreiROM: yes it raises questions, but what's to stop any employee from starting a side job the week after they start with the OP's company? If they're tending bar, waiting tables, or delivering pizzas on the side, no problem. Working for a competitor is a non-compete or NDA issue. I do agree that this particular hire has enough red flags to make me pass on him...
    – spuck
    Commented Dec 5, 2019 at 17:21
  • What would stop an employee from seeking a side-job is the prospect of being fired if found out. You're right that anyone can pick up a side-gig, but most employment contracts forbid this (unless approved by management), and finding out that your employee lied about such a thing can be a fireable offense. That rule may sound tyrannical, but it's meant to protect employers from a situation like this. As the OP himself states, how certain can he be that that the hours this guy are claiming he worked are accurate? I have no idea if the OP's contact includes this clause or not, however.
    – AndreiROM
    Commented Dec 5, 2019 at 17:27
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    True enough, but also very location-specific. I wonder what actually is in this contract, if it didn't spell out leave, side-jobs, or work hours...
    – spuck
    Commented Dec 5, 2019 at 17:31

I understand that it's my fault that I didn't do the best work during the hiring process

No, it is not your fault.

This is either regulated by the law (in France for instance by default you must be "free to work" for your employer. This is usually part of the contract but if not it does not matter as this is the law anyway), or someone in HR made a mistake.

You have a probationary period. What does the law says about this period? (you are not the one who is supposed to answer this question). Again, taking the example of France this si a time when anyone can say good-buy without providing any reasons.

It would be best if you added a country tag.


It looks like not only you have little experience in hiring, but your company also hasn't mastered the basic things.

The 'planned' vacation - why are you actually asking? Either everyone takes their vacation when they want - and it's not relevant if they work for 2 weeks or 20 years, or you have, hopefully, some procedures and unless vacation is approved there's no vacation.

As for 2nd job, it's the absolute standard for employment contract to forbid any side jobs without the explicit allowance from your employer. If your company forget about such clause, then honestly, you can't blame that guy from not complying to the non-existing rules.

For the future: improve your recruitment process. For the current case: ignore and judge the guy based exclusively on the results, or negotiate, but beware, that you're really not in position to dictate anything that's not covered in the contract.

  • It's pretty common for vacations that were planned before hiring to be approved (at least unpaid) in my neck of the woods Commented Dec 6, 2019 at 23:37
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    @AzorAhai I agree with your comment and would likely have approved the time off. But it should have been disclosed before the contract was signed.
    – Cindy
    Commented Dec 7, 2019 at 10:54
  • @Cindy Fair enough. Commented Dec 7, 2019 at 17:03
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    "As for 2nd job, it's the absolute standard for employment contract to forbid any side jobs without the explicit allowance from your employer." This is very regional, potentially illegal, and in no way an absolute standard.
    – user29234
    Commented Dec 8, 2019 at 16:20

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