Calendly/Redtail/Outlook sync issue: Bosses’ schedules getting combined

Hi ​@carterg 

In order to be able to help you, please attach some screenshots of the current setup and explain the workflow in more details.

Hi @carterg,

It sounds like Zapier is having trouble distinguishing between the two calendars. I’d suggest setting up separate Zaps for each boss, making sure each one is pulling from the correct Outlook calendar. You can also try adding a filter step to separate their schedules more clearly.

If that doesn’t work, reaching out to an expert might be a good call! Let me know if you need any more help.

See my screenshot above of the “Steve Outlook Zap”. This is just for one boss Steve; I have the other one set up identically for Robert, except the “searchterm” under the “Find Calendar Event” step says Robert instead of Steve. I'll explain more below; I’ll start off with my process of building this and give you some explanation.

First, I used Retriever Cloud to move Redtail events to my bosses' Outlook calendars. Then, I had to connect the bosses’ Outlook calendars to the Outlook step in each of their Zaps. Afterwards, I linked their Outlook calendars to Calendly. 

This seemed to block off meetings accurately, but not exactly how we’d like it. It essentially combined the entire redtail schedule into one for both advisors. But it is weird because it works in some specific cases. But another example is that on both of their schedules, an entire week I have blocked off on Redtail for my vacation is blocked off for them on Calendly. Through speaking with Zap support, we figured out the search term is the area that keeps messing up. See below for more explanation: 

The Zap support team told me that I needed to change the actual event names in Redtail/Outlook so that the “searchterm" is found. So what I did was make one Zap’s search term “Steve” to align with his schedule and the other Zap’s search term is Robert. But this makes my job extremely complicated because that means I have to manually edit every single redtail event to say “Steve” or “Robert.” Can you confirm what the search term is exactly looking for within an Outlook event? And do you have any advice on a better way to help manage what I’m trying to accomplish? I went back and forth with a Zap support team member for weeks and wasn’t able to figure out a solution. I’m contemplating reaching out to an expert as this is very complex. 

Hi ​@carterg,

Thanks for the detailed explanation and screenshot; they help clarify the situation. In the “Find Calendar Event” step for Outlook, Zapier uses the Search Term to scan fields like the event’s title, description, location, or attendees, so including “Steve” or “Robert” there is essential for matching. However, manually editing every event isn’t scalable. Instead, consider using advisor tags or custom fields in Redtail to identify who each event belongs to. You could then use a filter or a Path in Zapier to route each event to the correct calendar. Alternatively, if Redtail doesn’t support tagging, use a Formatter step to automatically append “Steve” or “Robert” to event titles before being added to Outlook. This avoids manual updates while still supporting your logic. If each advisor has their calendar, direct events there without relying on search terms. And if applicable, try “Find or Create Event” to reduce duplication and simplify matching.

Im a little bit confused though, why not just link the Outlook calendar directly in Calendly?

I was able to link the two advisors’ Outlook calendars to their Calendly accounts. It is blocking off certain events, but not everything. Some days are accurate, and some aren’t. For example, on 7/22, Robert’s redtail/outlook schedule has a meeting at 10:00 AM; however, there are time slots on Calendly for the whole day. Steve only has two meetings that day, yet his calendar has two available time slots. 

In other words, something is occurring where Calendly is not detecting the Outlook/Redtail schedules accurately. I thought Zap would be the glue to put this puzzle together. So far, I have only gotten more confused and have hit a brick wall on this project. 

This seems like it could work: 

“Alternatively, if Redtail doesn’t support tagging, use a Formatter step to automatically append “Steve” or “Robert” to event titles before being added to Outlook. “

How do I do this? 

Hi ​@carterg,

If you're facing issues between your advisors' Outload and Calendly. First, confirm that each advisor's Outlook and Calendly accounts are properly connected, with availability settings in Calendly configured to check the correct calendars. If you're using Zayou'reo help differentiate events (for example, by appending "Steve" or "Robe" rt" to" titl" es), y "u can set up a Zap that triggers from Redtail or Outlook, uses a Formatter step to append the advisor's name, advisor's updates the Outlook event. Test and monitor the Zap to ensure it's working smoothly. Let us know if you need help fine-tuning it!

Feel free to ask if you need further help or have additional questions. We're here to help.

I can confirm that both of their Outlook accounts are properly connected. I worked with them on a call to do this. How would I use the formatter step? 

Hi ​@carterg,

Thanks for confirming both Outlook accounts are connected. I'm glad the initial setup is working! To use Formatter by Zapier, add a new step to your Zap, choose "Formatter," and select an action like Text, Number, or Date/Time based on your need. Then configure it by mapping the relevant fields from earlier steps, setting up the transformation (like split text, find/replace, or format dates), and testing the output. Once you're happy with the result, use the formatted data in your next step. 
Feel free to share if you have a specific case, and we'll help tailor the solution.

Do you know where exactly the formatter step would go in my image above? I may need to provide further screenshots. Also what would I make the “search term” on the “find calendar event” step?

Hi ​@carterg,

To integrate the Formatter step with the "Find Calendar Event" step in your Zap, place the Formatter before the calendar search, especially if you need to adjust dates, text, or numbers first. In the Formatter, choose the right action type (for example, Date/Time or Text) and set up the transformation needed. Then, in the "Find Calendar Event" step, use a dynamic field (like a formatted title or date) from the Formatter or trigger as your search term. Finally, test the setup to ensure the Formatter modifies the data correctly and the event is found as expected.

If you have any further questions or need additional guidance, feel free to ask. We're here to help.