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Writing a letter is a formal and respectful way to approach your boss with a personal request. Whether you're asking for special time off, sponsorship for an activity that isn't work-related or a change in your schedule to accommodate personal issues, take the time to carefully plan your letter. The way you word your request, as well as when you submit it, can mean the difference between being granted what you want and having your request denied.
Make Your Case
It's important that your letter proves you've thought your request through. Be detailed rather than general; for instance, instead of saying, "I'd like to start a social club for the employees," outline exactly what sort of program, how your employer can accommodate it, and where and when the program would take place. Explain why you believe your request is important and, if applicable, how it will benefit the company. Your employer is more likely to consider your request if you show that you've already looked at it from all sides.
Acknowledge the Downsides
Depending on what your request is, it may harbor the possibility of creating a need for adjustments in the way work gets done. It behooves you to think these possibilities out ahead of time and brainstorm solutions for them. Don't leave this for your employer to do. For instance, you may be asking for something that could put stress on the company budget, but if you can find a way that your request can save the company money or create a return on the investment, spell this out in your letter.
Make sure your request follows company policy on the matter. If you need to, consult your employee handbook before you write your letter. If you're asking for additional time off, for example, check the guidelines on how much notice you need to give, how long you need to be employed before you can ask for extra time off and how seniority affects requests. Any request you make shouldn't negatively impact your ability to do your work. Show how you'll accommodate your employer's needs if he grants your request. Also, be sensitive about your timing. If your employer is under unusual stress or you know the company is in a bind, wait until the atmosphere improves.
No matter how well you get along with your boss, it's best to make your letter professional and polished. Address your boss by his title. If you work for a large firm, you may also need to identify yourself and your job title. Avoid slang in your letter; stick with a formal tone, and use proper grammar and spelling. Mention that you understand your request might have to be declined for reasons that aren't personal. On a side note, if you're requesting reasonable accommodation for a disability, your employer is legally obligated to work with you according to Nolo. He can still ultimately reject your request, but only if it would bring undue hardship for the business and only after trying to reach a suitable compromise.