How can I monitor Conversations handled by Sidekick?
For granular details as to how Sidekick replied at the Conversation-level, you can view and filter all recent Sidekick interactions in the Sidekick Conversations Page.
Here, you’ll see details like:
How Sidekick responded (Resolved, Handed Off, or Did Not Respond)
The Channel and Customer details
The reason for handoff, if applicable
Conversation history is retained for 30 days, giving you a quick way to audit performance and spot improvement opportunities.
Learn more: Sidekick Conversations Page Overview
What happens when Sidekick generates a response that doesn’t meet quality standards?
Before sending any response, Sidekick runs built-in quality checks to ensure accuracy and reliability.
If a response fails for reasons such as:
Missing context or incomplete information
False or inaccurate statements
Policy violations or unverified promises
Sidekick will handoff the Conversation to an Agent instead of sending a reply. The reason for the handoff, and all the steps Sidekick took leading up to the handoffs, appear in the Conversation Review.
How do I improve Sidekick’s effectiveness over time?
Regular review and optimization help Sidekick get smarter and more efficient.
To continuously improve:
Review Suggested Answers generated from handoffs.
Add or update those Answers in your Public Answers repository.
Use the Guides and Answers Performance Dashboard to identify trends and gaps.
Refine your Guides and transfer workflows based on what you learn.
Explore the Guides Performance Detail Report and the Answers Performance Detail Report for more granular insight into how Sidekick is engaging with Customers.
Following these steps and explore the above reports and dashboard to ensure Sidekick provides a high volume of high-quality resolutions.
How do I interpret the metrics in the Guides and Answers Performance Dashboard?
The Guides and Answers Performance Dashboard shows how Sidekick uses your content to assist or resolve Customer inquiries.
You’ll see metrics such as:
Resolved: Sidekick answered without Agent involvement
Assisted: Sidekick responded but then handed off
Guides & Answers usage: Which content is most frequently referenced
Reviewing these trends week-over-week helps you spot optimization opportunities and understand Sidekick’s real impact.
Learn more: Sidekick Guides & Answers Performance Dashboard
Can I customize how Sidekick behaves when it hands off a Conversation?
Yes. You can define when and how Sidekick transfers a Conversation, and the messaging provided to Customers, by configuring transfer conditions within the Guides interface.
To do this:
Add transfer conditions in the ‘When to get more help’ tile, or
Modify the handoff message within the ‘When to get more help’ tile.
Which Channels does Sidekick support?
Sidekick supports several digital channels, allowing you to automate responses across your Customer experience.
Supported channels include:
Chat
Email
SMS
Facebook Messenger
Instagram Direct
This enables a consistent experience for customers no matter where they reach out.
Learn more: What Is Sidekick
How many Public Answers should I have for the Sidekick ‘Questions and Recommendations’ Guide to perform well?
When leveraging Knowledge Sources within the ‘Questions and Recommendations’ Guide, Sidekick relies on your Public Answers to deliver accurate and helpful responses.
While there’s no strict minimum, Gladly recommends:
Starting with at least 100 Public Answers
Continuing to expand (many high-performing teams have 600+)
More coverage means fewer handoffs, faster responses, and a smoother Customer experience.
Learn more: How to write AI friendly Answers
Can I set up Sidekick to skip replying to a specific inbound email, and hand off immediately?
Yes—there are a couple of ways to do this, depending on your preferred workflow:
Option 1: Route to an inbox without automation
Send these inbound emails to a support address that does not have Sidekick automation enabled. This ensures Sidekick won’t attempt to reply.
Option 2: Configure Sidekick to transfer automatically
You can configure Sidekick to recognize certain inbound messages and transfer them to an Agent instead of replying.
Sidekick will still send a handoff message, visible to the Customer
Sidekick won’t send a Customer-facing reply, but it will generate a handoff message indicating the transfer.
To set this up:
Add the transfer scenario under the ‘When to get more help’ tile, or
Build a transfer rule directly into individual Guides.
For both transfer set-ups, don’t forget to configure the handoff message that will be sent to Customers.