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I am in charge of delivery and operations, any issues the team have when helping me deliver work have to go through me, I then bring it to the attention to my boss. My colleague, a developer lately has started to become harder to work with. So to summarise:

  • Since the company cannot meet his salary expectations, he has requested to work from home one week in a month. We have agreed to this, but now has requested that he would like to work 2 weeks from home. Both my boss and I feel that he is pushing his luck on this matter and have in private agreed to not do this. I have told him that if my colleague wants more time away from the office, he should book a holiday and take time out.

  • As time has gone on, he is increasingly becoming harder to manage, if we would ask him to do something, he would end up questioning why it has to be done a certain way. I do not want to get confrontational, but sometimes it is affecting the work flow since developments are now taking longer to complete because they have to be redone to how my boss originally wanted it. Other times the changes make sense, but the problem is things are becoming less streamlined. When I bring this up, he is now starting at times to ignore my advice, and does things his way because he thinks its the best way to do it.

  • I am starting to feel that as he is gaining more influence, he knows for example that right now we need him quite a lot, he is using it to his advantage.

Short of becoming confrontational, I do not know how to diffuse the situation from getting out of hand. My boss yesterday told me that he may need to start having words with the developer, letting him know that there is a limit to what we can give him. Should I let my boss handle it, or should I step in?

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    His boss should handle it. Are you his boss? – Erik Nov 10 '16 at 11:11
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    You need someone a lot, but "can't" pay adequately? That's the problem you need to solve. The attitude your current developer has developed is a symptom and a secondary problem. – Roland Nov 10 '16 at 12:16
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    @bobo2000 Your assessment of remote work is incorrect. You just seem to have an issue with this person working remotely. Anyhow, the real problem you have is that your company needs a decent hierarchy. It's a common problem at startups but having everyone report to the CEO is sheer mismanagement once you hit a certain staff size. – Lilienthal Nov 10 '16 at 13:53
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    I am sorry, but I find your and your companies attitude quite terrible. If I would have a reasonable request like asking for working from remote and you give such a snippy answer ("book a holiday") I would be pissed. Of course you can say no, but whats so wrong about the request? Also I can't find something wrong with a developer asking why some stuff is done a certain way - It is actually part of the job description to do that. If you can't explain your reasoning, most likely his questions are on the spot. – dirkk Nov 10 '16 at 17:02
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    If I wanted to work remotely and my boss told me to "take a vacation" instead, I'd be incensed. It shows that my boss doesn't view remote work as "real work" and that vacations and remote work are somehow interchangeable, whereas the reality is is that remote work and on-site work are the interchangeable ones. In addition, your theory that it's more important for work to be "streamlined" and quick instead of a lead developer understanding the product and more crucially for YOU to be aware of all alternatives is a massive red flag. Your company culture sounds like it sucks, period. – A. McDaniel Nov 10 '16 at 19:03
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My boss yesterday told me that he may need to start having words with the developer, letting him know that there is a limit to what we can give him. Should I let my boss handle it, or should I step in?

You should let your boss handle it, since he is this worker's boss too. You aren't in a position to do anything positive here. The boss has already signaled that, since "it is harder to replace good developers" that they can push the boundaries and get what they want. That's going to be a challenge to undo, but the CEO is the only one who can really try.

In addition, I think you need to start planning for this developer's leaving. He is signalling that if he doesn't get everything he wants, he will leave. I suspect he is already looking elsewhere.

And I think you should be looking for your next job. Since joining this company, you have written questions indicating that it is dysfunctional and that you don't want to be there.

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    I think the last paragraph is uncomfortable in the extreme and verging on creepy, sorry. Tracking specific user's questions and learning about them is something that should be 100% off-bounds, sorry (i saw that happen at Parenting and it was a large reason many people stay away from that site) – user13655 Nov 10 '16 at 22:39
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    The final paragraph is sound advice, and its not like you need special privileges to view a users previous questions. – CaffeineAddiction Nov 10 '16 at 23:02
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    @DVK how is checking post history here (or on parenting) different than on SO or SU to see if someone has asked something similar or have ignored advice given several times? I'm not arguing with you, to be clear. – Raystafarian Nov 10 '16 at 23:04
  • @CaffeineAddiction - Just because you can, doesn't mean you should. – user13655 Nov 10 '16 at 23:17
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    @DVK - "because people reveal personal information here" and "Just because you can..." actually that is exactly why you should point this out to people. As long as the capability exists to see the data publicly then people need to realize that posts do not exist in a vacuum and can be easily linked to other posts. Besides, the community (which you are free to leave) obviously disagrees with your statement "should be 100% off-bounds" since the capability clearly exists. As you point out, if the community had a problem with it they would "stay away" as they did with the site you mention. – Justin Ohms Nov 11 '16 at 16:14
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[...] any issues the team have when helping me deliver work have to go through me, I then bring it to the attention to my boss

You pretty much answer your own question, in my opinion.

Talk to your boss, if you're not this employee's manager it is definitely the right thing to do.

He'll tell you if he thinks this is something you have to handle, or he'll tell you that he'll take it from there, which he should, if you believe this behavior is causing problems.

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My boss yesterday told me that he may need to start having words with the developer, letting him know that there is a limit to what we can give him.

If your boss is ready to step in then yes let him step in.

If anything be more firm with expectations and document what you have told him to do. If he ignores your instructions then go to your boss with documentation.

3

You guys for all your overall success, are struggling to pay competitive wages, and this employee, who knows he has an ace up his sleeve, is trying to run the show. Quite frankly, you're out of luck here.

He is dissatisfied, and probably only wants to stick around because he gets to push you guys around and make his own schedule. However, even with his expertise thrown into the balance, his attitude and compliance issues are making things more difficult for you.

The only way I can imagine this working is if you lay down the law and tell him you'll let him go if he doesn't start complying with instructions. I mean .. if you have to redo his work then why pay him in the first place?

However, beware! He sounds like he's half-way out the door as it is, so once you crack down, he's likely to quit, or start sulking/disobeying even more.

Start planning on hiring a replacement - maybe some young guy with little experience who won't mind working for beans in exchange for experience (aka any recent graduate).

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Your boss is the ultimate decision maker. Let him step in and as far as you are concerned, get out of the way, make sure you look great and play nice. This is a high stakes situation and it's good that your boss is willing to take charge. Your services may be needed post-confrontation to help defuse the situation.

It is unclear to me if you and your boss have thought through the consequences of being confrontational. Your employee and you have professional differences regarding salary and working conditions and you probably don't want the expression of these differences to escalate into a clash of wills and egos, especially since you need him, at least for the time being.

Joe Strazzere is pointing out that your developer has one foot out the door and Joe is probably right. Which means that you are going to have to do some serious contingency planning to make do without your developer. Hopefully, you have more than one developer on the staff.

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