Learn to communicate with automation for short term rentals

How to automate messages to rental guests (without sounding too robotic)

1. Brainstorm and type! Write out a plethora of messages to your guests before you even consider automating them. Assume questions they will ask and include in the messages. What do they need to hear from you? Think about the timeline of your stay. From the beginning communication, during the stay and checkout. Try to make it flow like in conversation. This can feel a little odd for someone who isn’t necessarily a creative writer. Also, remember not all guest are going to be savvy tech wizards. Over communicating process or instruction is better than under.

2. Save. When you feel like you nailed a message (or part of a message), and it was better than average, SAVE IT TO A FILE. I repeat, SAVE IT TO A FILE. You are not finished though. This is just the first rough draft.

3. Time to edit. Here is where you can really transition from robot to real human. Check out the following tricks:

• Use local sayings. Don’t be afraid to use phrases and sayings that give the guests a sense of place. If you say y’all in real life, say it in your messages. If you say thanks more than thank you, use that too. Never close correspondence with the word “sincerely”. The closing can be interpreted as too formal and stuffy. Your guests are on vacation, and you are taking care of them. I personally use, “all my best”, “best” or “warmly” among other sweet, conversational closings during the first message to a new guest. Then, the following automated messages will end with just my name and no signature. This practice subtly indicates a shift from semi-formal to casual, friendly communication. 
• Emojis are your friend. A picture really is worth a thousand words. Keep it short and casual with a smile. If something funny happens, laugh. If they are frustrated, show that you are empathizing with them too.  Emojis are just fun anyways. We should all have a little fun running our STRs!
• Expressions that relate to what they’re feeling go a long way. “Yay! you’re booked” “whoops, there’s an issue with your payment” “woo-hoo! here are your check in instructions” Connect with your guests emotionally in a way you would if you were there looking them eye to eye. 
• Short and sweet. They are not in grad school, keep the writing simple like a trashy summer romance novel, not an engineering textbook. 
• No grammar Nazi’s allowed. And if you want to start a sentence with “and” because it sounds like a conversation, DO IT! And put to rest everything your high school English teacher taught you. And.…ok, don’t throw out all the rules. But, you can relax the rules here and there.

4. Save. Can you tell I may have had a bad experience with this!

4. Speak the messages out loud. Grab a spouse, your friend, co-worker and put them to work. Give them the automated scripts and have them speak the messages out loud to you. It should sound like a conversation not a monologue. Guest messages should read as if they are standing in front of you, and you are explaining things in person. Messages should not read like a user’s manual. The more personal and friendly you make them, the better they will connect with you and your short term rental. 

9. Revise & publish: ta-da! You are done. Of course, there will be tweaking over time to your communication. Here is to you freeing up some time to do the things in life you work so hard to enjoy.