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I am relatively new at a company (< 3 months) and am working in a development capacity. Despite the current climate, I still would like vacation time even if that means sitting at home. I am however encountering an issue with my requests not being approved on time by my manager, let's call him Jon. The company guidance regarding notice is usually double the amount of vacation requested (e.g. You want one day off, you must request the leave two days in advance).

I have requested vacation through our HR system twice now and it has never been approved in time. On both occasions I supplied plenty of notice (1+ week notice for 2 days off) and sent a couple of emails and IM's to Jon but never received a reply. This resulted in me cancelling my leave in both instances. I was slightly irritated it had come to that since I had followed protocol.

I am aware Jon is a busy person and perhaps doesnt have that much time to be approving vacations but at the same time, I would like some time off. How can I approach this situation in the future? I dont want to just take unapproved vacation time and come back to a disciplinary.

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    Has Jon responded to why he's being so slow and what you should have done instead? Approving your requests is basically part of his job, so it sounds like it's him failing at doing his job, busy or not. – Erik Apr 17 at 8:43
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    Did you talk to Jon in person? – Bernhard Döbler Apr 17 at 8:45
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    He hasnt responded to any of my messages at all, no. We have standups on video calls which he attends for a few minutes a day but thats about it – nagrom97 Apr 17 at 9:00
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    By cancelling the leave, do you mean you just went to work because it was not approved or you stopped the request in the system? It might me helpful to keep the expired request to create a paper trail, else one could claim you're causing unnecessary work by requesting leave you not really want to take. – Chris Apr 17 at 9:25
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    "This resulted in me cancelling my leave" At whose request? Couldn't you have just taken that leave under the assumption it would be approved? (This won't fly in all companies of course!) – Lilienthal Apr 17 at 9:42
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My guess is if he'd had a problem with the leave request, he would have rejected it right away but, because he had no objections, and was too busy - or possibly too disorganised (approval can't take more than 30 seconds right?) - he let it slip through the cracks.

Your first step should be to talk to him. Explain how you've been unable to take days off because he has been slow in approving them. Hopefully he'll see how you have been impacted and get a bit more organised.

A solid backup strategy for scenarios like this is to contact the person in question with an email worded in such a way that only requires them to take action if they have any objections or concerns. Then, a non response equates to tacit approval.

For example: "Hi Jon, I know you have a lot on your plate and may not have time to get around to processing that leave request. Just let me know if you have any issues with it".

If you don't hear back take your day off. If he happens to challenge you about it on your return, you have the email (and the fact he never approved or rejected the leave) to back you up. It is unlikely to happen the next time.

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    And copy that email to hr... – Solar Mike Apr 17 at 9:23
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    It's up to you but I'm not sure I'd copy HR right away. What you're trying to do here is (a) work with his lack of organisation so you can take annual leave, (b) provide cover for yourself while doing so and (c) subtly highlight his tardiness. If you include HR it risks coming across as complaining and belligerent and you may make trouble for him and impact your working relationship. I'm not suggesting this couldn't be escalated to HR at some point - just that now is not the time to do it. (Best to try to handle it yourself - like mature adults). – amcdermott Apr 17 at 9:44
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    I would call Jon on the phone and request the leave be approved – Donald Apr 17 at 11:59

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