Holiday Preparation Checklist
  • 18 Oct 2022
  • 5 Minutes To Read
  • PDF

Holiday Preparation Checklist

  • PDF

The holidays are inevitable events that happen every year. While it's one of — if not the busiest — time of the year, it's also a time when many companies ramp up temporary hiring, see how well operational processes are performing, as well as stop operations for a few days to have your team spend time with their families. 

We put together this guide to help you think about items to review and complete during the holiday season to ensure operational efficiency. 

Plan for the holiday rush

Hiring and Training

  • Onboard seasonal workers early – aim to have them fully trained by end of October.
  • Use Gladly Academy to train and certify your new hires (it's free!)
    • Don’t miss the different offerings under ‘Trainings’ and ‘Paths’ to help you brush up on specific functionality and Agent soft skills.


  • Conduct a Rules audit, specifically those for spam and reassignment (e.g., make sure emails don't get stuck with an Agent if they are offline). Check out our Sample Rules Library here. For other Customers, they prefer Conversations to remain with the same Agent regardless of them going offline. You can choose!
  • If not already included, add hyperlinks to your email auto-replies and/or Agent signatures to direct Customers to important FAQ documents or other web pages.
  • Use Business Hours Rules for email/SMS/social messaging to incorporate holidays by using exceptions. You can have different automated messages go out at any time during the day using business hours.
  • Consider shortening your Conversation Reopen Window (default is 24 hours) so more Conversations are treated as new. This may help manage your backlog.


  • Make sure your IVR holiday hours are accurate, if different from regular business hours.
  • Update your IVR recording to mention high call volume, if applicable.
  • Consider adding an SMS or voicemail option in your queue IVR for Customers waiting on hold. You can do this yourself, or you can contact Gladly Support to scope an SOW if you'd like assistance from our Professional Services team.
  • Utilize Proactive Voice to send bulk messages to your Customers about shipping delays, carrier changes, or delivery status.


  • Make sure you have auto-throttle enabled for chat.
  • Ensure your Sidekick throttled message includes alternate Channels to reach you if chat is not available (SMS, email, etc.). Have the contact channels clickable with a hyperlink so it's one tap away!
  • Activate a Priority Boost for chat using People Match if chats are waiting too long.
  • Reduce cart abandonment by activating Proactive Chat on your checkout page and/or activating chat payments to help drive revenue. Contact Gladly Support or CSM to activate chat payments.
  • Consider shortening your auto-end (not auto-close) times for messaging (default is 15 minutes). This gives your team more throughput by spending less time waiting for Customers to reply before new messages are routed.
  • If you use Sidekick, consider Quick Reply buttons in addition to Quick Actions as a way to streamline your Customers’ chat experience and also customize routing, if needed.
  • Utilize Proactive SMS to send bulk messages to your Customers about shipping delays, carrier changes, or delivery status.


  • Revisit the email setting going back to same Agent (temporarily or permanently).
  • Save precious time! Automatically apply topics based on keywords or Entry Points using Rules.
  • Audit your auto-replies and make sure they include alternate Channels like SMS and are clickable using a hyperlink.
  • Utilize Proactive Email to send bulk messages to your Customers about shipping delays, carrier changes, or delivery status.


  • Sidekick Self-Service: Use Quick Actions proactively to get ahead of questions you anticipate like shipping delays, new promotions, advertising new product lines, etc. You can change your Quick Action content easily so it can be dynamic based on your market needs.
  • Pull Sidekick Answer Search and Sidekick Answer Usage reports on search results/answer usage. Use these insights to update Quick Actions, Keyword Groups, and/or create new Answers. Think if there are any holiday-specific phrases, like Black Friday or Cyber Monday, that you want to link to your promo/discount Answers.
  • Remove additional contact numbers from truly self-service processes.
  • Check the order in how you list your contact channels on your website. It makes a difference! List your most efficient and less expensive channels first.
  • If you don’t have one, establish a Help Center on your website so Customers can quickly get and search for answers to their top holiday questions.

Blocking Contacts

  • Get familiar with ways to block contacts if you see spam or inappropriate messages.

Monitoring Trends and Volume

Measuring Performance

Review Gladly Support Access and Procedures

  • Make sure to give the appropriate folks Team Manager (or Administrator) access in Gladly so that they can contact Support.
  • Review the list of support priorities and how you should use them! 

Before you leave for the holidays

Close the phones

Set up your IVR so that Customers who call while your team is out for the holidays to hear your greetings and messages during your holiday hours. You can even set up the IVR to have callers leave a voicemail so you can call them back during non-holiday hours.

See How do I close our phones to learn how.

Close Chat

Hide the Chat option on your website for days that you are closed and allow Customers to use your self-service options for Sidekick (If Self-Service type is used for Sidekick.

  1. A week before the day(s) you are closed, check the Closed box next to the days you are closed for the week coming up on the Sidekick configuration page. Click Save when you're done.
  2. As soon as the holiday(s) pass, go back to the Sidekick configuration page and uncheck the Closed box if you are open on those days.

Set up auto-replies for email

While you can't stop Customers from sending an email, you can set up your email auto-reply to let them know your holiday hours.

  1. Create an email Answer.
  2. Create a Rule that uses the email Answer you created to send an email reply to Customers containing your holiday message/hours.
  3. Be sure to activate this Rule. You can deactivate this Rule when it's no longer needed.

Set up auto-replies for SMS

Like emails, you can't stop Customers from sending an SMS, but you can set up your SMS auto-reply to let them know of your holiday hours.

  • Create a Messaging Answer.
  • Create a Rule that uses the Messaging Answer you created to send an SMS reply to Customers containing your holiday message/hours.
  • Be sure to activate this Rule. You can deactivate this Rule when it's no longer needed.
Tip - Utilize Business Hours for Messaging Channel
You can utilize Business Hours alongside Rules to customize your messaging based on date and time.Contact Gladly Support

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