Lessons Learned from Years of Workday Expertise

Open enrollment can feel overwhelming, especially when managing multiple plans or providers. However, with proper organization and a few best practices, you’ll find the process easier and more efficient. Here's a guide we put together of the things we have learned to do over the last few years. We hope this helps you navigate open enrollment with confidence.

1. Start Early and Create a Tracker

Why wait? If you're aware of plan changes, start writing down what they are and reviewing current integrations to know where and what Integration Maps, Workday Reports and xslt have to be updated.

Where should you write this info down? We recommend creating a tracker ( spoiler alert you will reuse this tracker yearly so the effort is worth it) that lists all vendors, integrations, and can include technical notes, Note where plans are referenced in your XSLT or other configurations.

*If documentation is lacking, work with your team or a partner like Stormloop to create comprehensive records.* Reminder once you have your tracker, you will use this annually so the juice is worth the squeeze.

2. Talk to your Vendor

Engage with your Vendor early and often.

Key questions to ask your vendors

Are there any changes to the file format
Do the file for OE have to have any special naming convention
When is the testing window
When is the last file for current year due
When is the OE for next plan year due
Not always common but Vendors sometimes will roll out updates for how to present the data on your files. Reviewing updates to their specs to analyze impacts to your integration . You and your team will want to know this as early as you can to add to your tracker and test the updates.

Contact vendors early to confirm testing requirements:

Some vendors require test files or updates to headers in enrollment files.
Include this information in your tracker, specifying which vendors need test files and their due dates.

3. Clean Configuration

Open enrollment reports often include hard-coded dates for the plan year or even plans themselves. Avoid this practice as best you can use calculated fields to reference the next year’s start date dynamically.

Often, you may encounter a use case where an OE report and integration have different fields than the currently running report and integration in your tenant. When this occurs, it is critical to use clear naming conventions for these integrations and reports to avoid confusion.

You can always create clones of the existing integration system if it involves a custom transformation, and copy the report to make the necessary updates. This approach will save you time and eliminate the need to start from scratch.

4. Prepare for Testing

Timeline planning:

Work backward from vendor deadlines to create a clear testing schedule.
Begin reviewing reports and testing files at least a month before test files are due

Test in a sandbox environment to avoid prematurely sending files to vendors.

Confirm that integration mappings point to the test environment. Disable the path to the vendors prodcution.
Manually launch integrations using the correct effective date (e.g., 1/1 of the new plan year).

Validate file accuracy:

The Workday delivered Enrollment Count report is your best friend. Use this report to confirm:

Effective dates.
Correct employee populations.
Accurate plan enrollments.

Test a representative sample:

Select a handful of employees per plan to ensure data accuracy.
Use the enrollment report in your tenant to validate how many employees are enrolled in plans, and that they match with the test files.
When you open the file from test ensure the OE start date is in the file.

5. Manage Deadlines with Calendar Invites and Checklists

Vendors often have distinct dates for turning off current-year files and sending new-year files along with dates when OE files for the new year are due. To manage these dates we suggest

Add calendar reminders for these key dates.
Use a checklist to ensure every step is completed on time.

6. Use Workday Tools for Efficiency

Mass Update Scheduled Future Processes:
This feature allows you to renew the current schedule for the new year. (Mass Update Scheduled Future Processes can be completed before or after deleting the remaining occurrences.) Simply update the end date to the end of next year and select the schedules from the grid below to update them for the upcoming year.

Scheduled Future Processes:
This feature allows you to view the remaining schedule for the rest of the current year.

From here, you can take related actions on the schedule and “Edit the Scheduled Occurrences.”
This enables you to delete the remaining runs in advance. In most cases, vendors will no longer want current-year files to be sent after the OE file has been processed.
These tools allow you to edit and schedule multiple election providers simultaneously, saving significant time.

7. Final Touches: Verify and Execute

Before sending production files:

Double-check where your file is going.
Ensure schedules align with vendor requirements.
Validate that effective dates, headers, and file structures meet vendor expectations.

With proper planning, tracking, and leveraging Workday tools, open enrollment can be a smooth process. By starting early, maintaining thorough documentation, and keeping an eye on deadlines, you’ll reduce stress and set your organization up for success.

If you need help organizing your integrations or creating a robust tracker, partners like Stormloop can provide expert guidance to simplify the process and ensure nothing falls through the cracks.

Open Enrollment Made Easy