ThinkReservations can send emails and text messages to guests at key points in the reservation lifecycle - automatically. These emails and texts are called "transactional" messages, as opposed to "marketing" messages. This chapter we will also discuss the personalized upsell portal and digital registration tools that you can use with those emails and texts.
Automated Emails
Review the email rules you have in place with your account now. Those can be found in ThinkReservations > Settings > Email Rules.
Consider best practices:
✉️ Confirmation Email - Sent immediately after booking.
Guests have a right to expect that when they make a reservation, they will receive a confirmation email immediately. This email should contain booking and payment details and the cancellation policy.
Review your confirmation email in full. If you look at the email and see that it is very long, you might not want to read it. Your guests may feel the same way! If you have a lot of information that you would like to share with the guest, consider putting that information on your website instead. You could create a page on your website that guests only get to when they click the link from your email. This approach ensures that the critical details of your confirmation email are not lost in a sea of other information. Another option is to use a digital guidebook from a dedicated provider.
✉️ First Reminder Email - Sent two weeks before arrival
The first reminder email should be sent around the same time that your cancellation policy kicks in, or around two weeks before the arrival date. It needs to be sent far enough in advance so that a potential mistake with the arrival date can be corrected. The objectives of the first reminder email are to reconfirm the reservation details, notably the arrival date, and remind the guest of your cancellation policy. This email should be short and sweet. There is a bit of a misconception about transactional emails. When you send long emails, you might feel that you are giving the guest a lot of value with all of this information. However, it's often hard for the guests to see the value; they might just see a wall of text.
✉️ Second Reminder Email - Sent 3-6 days before arrival
The second reminder email should be sent a little less than a week before arrival. The objectives of this email are to share arrival instructions such as directions, where to park, and room key code and to upsell them. Short and sweet applies here as well.
Your guests won't feel like they are getting "spammed" or inundated with your communication - even if you are sending what you feel is a lot of messages - if the content of the messages are relevant, helpful, and on the shorter side.
What is my Upsell Portal? Why should I upsell Items?
When guests make their reservations online, they are presented with upsell options after they select their room and rate. The Upsell Portal is a separate page guests navigate to after the fact that focuses on upselling. It gives guests another opportunity to review your enhancements and add to their stay.
Because of the time separation between booking and upselling, you will have more success in getting your guests to spend on their stay in order to enhance their experience. This works because of the two-purse psychology: guests mentally separate the money they spend on the room from what they spend to enhance their experience. Once the cost of the room is committed, guests are more willing to dip into their “fun” or “experience” budget for add-ons, making them more receptive to upsells in the portal. The longer the time between booking and being upsold seems to help. Add that to the fact guests get excited about their stay when it's "this week", and you can understand why we recommend to send the second reminder with the upsell portal link 3-6 days before arrival.
Whether or not you have ThinkMessenger, you’ll want to include the Digital Registration link in your second reminder email. If you don’t have ThinkMessenger yet, the Digital Registration tool works on its own. And because it can optionally include the upsell portal, there’s no need to include both links.
✉️ Thank-you Email - Sent 1-2 days after check-out
Your thank-your email is your opportunity to truly thank them for the business, ask them to return, and share feedback with you. Sending this within a day or two ensures the guest's experience is still fresh in their mind. And a prompt thank-you is simply good hospitality manners on your part. It's also an ideal window to gently ask for a review or feedback.
If asking for a guest review, consider the review site you currently need an increase in, as opposed to sending them a link to each site. If you give them too many choices, surprisingly, they may not take any action. Giving more choices also seems to reinforce the feeling that the review is more about you, and less about the guest.
If you are uneasy about sending every guest a link to write a review, you could instead send them a link to a private survey from a service like surveymonkey. This way, you collect the feedback and have an opportunity to correct any problems or issues before they leave a public review.
Automated Text Messages
ThinkMessenger is the tool that allows you to communicate via text messages with your guests. It's an add-on feature, so please let us know if you don't yet have it enabled when you are ready to move forward.
Please review your text message automations by navigating to ThinkReservatoins > Settings > Message Rules. The automated text messages that you send should complement the emails.
🗨️ Confirmation Message - Sent immediately after booking
Use: Optional (if not already covered by email confirmation)
Best Practice: Keep the message short and reassuring. Simply confirm the reservation and include contact info if the guest has questions. Avoid restating all reservation details. Some clients like to use this message to simply introduce themselves and let them know they can opt-out by replying "STOP."
🗨️ First Reminder - 3–6 days before check-in
Use: Recommended
Best Practice: Include check-in time, parking info, and room key code (if applicable). This is where you would include the link for the upsell portal or digital registration. Aim for friendly and informative.
🗨️ Second Reminder - 1-2 days before check-in
Use: Recommended
Best Practice: Reinforce arrival details, and let them know you're looking forward to hosting them. No need to repeat everything from the first reminder.
🗨️ Third Reminder
Use: Optional (useful for longer lead times or if you have a high no-show risk)
Best Practice: If enabled, send several days ahead of arrival as an initial heads-up. Keep it very brief.
🗨️ Day of Arrival Message (morning of arrival)
Use: Recommended
Best Practice: Welcome the guest and remind them of check-in time and contact info. Keeps communication warm and proactive.
🗨️ Check-In Message (triggered after check-in is pressed)
Use: Recommended
Best Practice: Send about 15–30 minutes after check-in. Ask if everything in the room meets expectations or if they need anything. This message helps identify and resolve issues early. We recommend you to consider using a survey template here.
🗨️ Multi-Night Message (sent the day after check-in for multi-night stays)
Use: Optional
Best Practice: Great for stays of 2+ nights. Check in briefly to ask how things are going and if they need anything. Keep tone light and service-oriented.
🗨️ Check-Out Message (morning of check-out)
Use: Recommended
Best Practice: Remind guests of check-out time and offer help with bags, transportation, or luggage storage. Keep tone polite and helpful.
🗨️ Follow-Up Message (1–2 days after check-out)
Use: Recommended
Best Practice: Send a warm thank-you and let them know you'd love to host them again. Highly recommend you use a survey template.
General Text Message Content Guidelines
Tone: Keep it professional, friendly, and concise. Make sure to match your brand!
Length: Aim for 2-3 short sentences. Avoid large blocks of text.
Personalization: Use first names and only include reservation details that are relevant and helpful.
Links: Make sure to not use public URL shorteners.
Frequency: Be thoughtful not to overload guests. Generally, 4–6 well-timed messages per stay is a good balance with the emails. Keep the content relevant, helpful, and informative so your guests don't see it as spammy.