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Amanda works at HubSpot, and she came with a unique auto respondent that asked her contacts to guess where she is. To give background, she flew down to Boston to attend a Red Sox training game in the spring with her father. She chose to ask her contacts whether where they think she might be, and also this played some wonderful use of litotes here:

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Thank you for your email. I’m out of the office and into the cookies and eggnog right now. I’m celebrating the holidays with my loved ones and will not be checking my email until [return date].
With technological advancements, you always have access to your work and contacts, making it difficult to be offline even when you are not physically present in the office. However, it sometimes becomes a necessity to step away and treat yourself to a vacation. .

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When one of my colleagues went on vacation, he sent an out-of-office message that was both clever and smart. First, he sent the recipient on an imaginary scavenger hunt to “the highest peak of the tallest mountain.” He used humorous absurdity to make it clear that he would not be checking email while he was away.
An old boss had a pet peeve about this so I became very conscious of making sure that I listed out who to contact on what day… before the group email. So it looked something like this:

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In this image, you're letting people know you're OOO with a "Missing" notice on a milk carton. Genius. Just be careful — this sort of autoresponder is best for internal emails, not for autoresponders that get sent to prospects and clients.
In our company it is very much the norm (though some don’t and it’s not looked down on. It’s just we kinda know every handles the ridiculous amounts of email we get in different ways that suit them). And it’s the norm of the people who so to put that in there because 1. if you go anywhere north of where we’re at, you’ll get zero reception and 2. other people we work with know you normally do.

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Remember, your email signature is as important to your company as all of your other corporate branding. Update any marketing promotional banners with seasonal offers. When the holiday season is over and your promos have finished, make sure you are no longer using a Christmas themed banner.

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. If the out of office assistant will turn off on the day and time you selected, do not send automatic replies audio button, else the messages will continue to get delivered.

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    Thank you for you message. Our offices are closed until [insert date] and I am out of the office. Our entire staff is reflecting on a wonderful year, resetting, and recharging for 2018. We will respond promptly after the holidays, but in the meantime we will be busy doing the following:

    It got bad enough that others began begging someone to cull the list. Reply all, of course (thankfully it didn’t turn into an explosion of replies all). Someone finally did remove the email from the list.
    A clear, thoughtful out of office message saves the caller from troubles and inconvenience caused by your unavailability as they know what they should do next. Such a system avoids the negative impact that could come from the inability to respond to calls and messages. Your clients would likely try and contact you again and again, getting frustrated and losing trust in your business.

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    3.) Welcome to the John Doe AG. Our offices in Berlin are now closed for a holiday. You can reach us on working days from Monday to Friday from 9am to noon and 1pm to 6pm. For general inquiries you can also send us an email to [email protected]. Thank you very much. We wish you a nice day - your John Doe AG.

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    It’s wise to check they aren’t though. A colleague once had an out of office from an academic that simply said ‘on fieldwork’. Just those two words.

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    Ta-da, you are done! You are one step closer to your vacation. Remember, just because you are away, it doesn’t mean you cannot make someone’s day with a funky OOO email!

    I will be away from (Date) until (Return Date). For urgent matters, you can contact (Contact Person).
    So, because I want you to be able to enjoy your time off, I’ve put together these two email templates to help you make it abundantly clear that you’re not around for the next 24 hours.

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    Here are five ways to help prepare your business and your clients for your vacation or time off. Schedule your absence ahead of time. Set the expectations with clients. Send a “last call” email the week before you leave. Don't take on new clients or tasks right before you leave. Stand your ground when you are gone.

    Seriously, literally, anything but a voicemail. I’d take “sharpie on a dirty napkin delivered by carrier pigeon to my island vacation” over voicemails. I can’t flag voicemails for later. And also, we have this cool new feature where you can see missed calls. I do not need a voicemail just saying “Hey its Bob, call me back.”
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Ta-da, you are done! You are one step closer to your vacation. Remember, just because you are away, it doesn’t mean you cannot make someone’s day with a funky OOO email!

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I thought it was funny but could never get away with using something like that at my org. I loved the “competent people who work for me” part – I make this joke all the time. We have some people who feel that they should have a manager personally attend to them and, at least in my case, my highly competent team is in the weeds of that work a lot more and are not rusty (like I am).

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Or they work with one or more of those people that call you 5 minutes after sending an email if you don’t reply.

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4. You snooze, you lose! The [holiday name] sale will end soon. Even though holiday sales last for quite long, some of us still have trouble finding something special for themselves or their loved ones.

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