If you’ve ever had to chase employees to retake the same compliance training, you know how much time gets wasted. Automating this stuff in Lessonly saves headaches, keeps auditors happy, and lets you get back to work that actually matters. This guide is for anyone managing training—HR, compliance, IT, or whoever got “voluntold” to own this—who wants to make recurring assignments run themselves, without a bunch of manual effort.
Here’s how to set up recurring training in Lessonly, what works well, what to watch out for, and when you’ll need to get creative.
Why Recurring Assignments Matter (and Why Lessonly Makes It Harder Than It Should Be)
For compliance-heavy roles, you don’t just assign a course once and call it a day. Most regulations want you to prove that people keep up with their training—year after year, sometimes more often.
The problem? Lessonly doesn’t have a true “recurring assignment” feature built in. There’s no magic button that says “send this lesson again every 12 months.” But you can work around this with a combination of smart assignment rules, groups, and a little calendar discipline.
If you’re hoping for a native recurring feature, stop here—Lessonly doesn’t have it (yet). But you can get 80% of the way there with some planning.
Step 1: Organize Your Content for Recurring Use
Before you start fiddling with assignments, make sure your training content is set up for repeatability.
Here’s what works:
- Use Lessons and Paths: Build your compliance content into “Lessons” and group them into “Paths” if there’s a sequence (ex: Security Awareness Path).
- Version Control: If you update your training each year, don’t just overwrite the old lesson. Instead, duplicate lessons for each cycle (e.g., “2024 Security Training”).
- Naming Conventions: Name lessons and paths with the year or cycle (“Q1 2024 Harassment Prevention”) so it’s obvious which version is current.
What to ignore: Don’t try to cram recurring logic into a single lesson or path. Lessonly doesn’t track when someone last completed a lesson, just that they finished that version.
Step 2: Build Your Learner Groups
Recurring assignments only work if you can target the right people, every time.
Best practices:
- Use Groups for Compliance Cohorts: Create groups in Lessonly that match your compliance needs (e.g., “All Employees,” “Managers,” “New Hires”).
- Dynamic Groups: If your HRIS integrates with Lessonly, set up dynamic groups that update automatically as roles change. If not, plan to update groups manually.
- Test Group Membership: Before you automate, double-check who’s in each group. People get missed all the time.
Pro tip: Keep group logic simple. If you start nesting groups or adding lots of exceptions, you’ll hate yourself in six months.
Step 3: Set Up Assignment Rules (the Manual Way)
Since Lessonly doesn’t do true recurring assignments, your main option is to create new assignments at the interval you need (monthly, quarterly, annually). Here’s how to make that as painless as possible:
- Go to the Lesson or Path you want to assign.
- Click “Assign.”
- Choose your Group(s).
- Set a Due Date: Pick a realistic deadline—compliance auditors don’t care about “ASAP.”
- Customize the Message: Remind folks why they’re getting this again. (“It’s that time of year…”)
- Send the Assignment.
Repeat this process for each cycle (e.g., every January). Mark your calendar or build a recurring reminder in your own system.
What doesn’t work: Don’t try to re-assign the same assignment to the same people. Once someone completes a lesson, Lessonly marks it as done for that assignment—reassigning won’t force them to retake it. You must create a new assignment each time, ideally with a new lesson version.
Step 4: Automate What You Can (With Integrations or Zapier)
If you’re lucky enough to have Lessonly hooked up to your HRIS or an automation tool like Zapier, you can cut down on the manual work.
With HRIS Integration:
- Some HR platforms (like BambooHR, Workday, or Namely) can trigger assignments in Lessonly when someone joins a group (e.g., “New Hires” get assigned mandatory training on Day 1).
- For recurring cycles, you’ll still need to push out new assignments, but at least group membership stays up-to-date.
With Zapier:
- You can set up a Zap to create assignments on a schedule.
- Example: Every 365 days, Zapier creates a new assignment in Lessonly for a specific group.
- This isn’t foolproof—Lessonly’s Zapier support can be spotty, and you’ll need admin access and some patience.
What to ignore: Don’t expect full automation unless your organization invests in custom scripting or a third-party training management system. For most people, a calendar reminder and a 10-minute assignment creation once a quarter is easier than overengineering it.
Step 5: Track Completion and Remind Slackers
Compliance only works if people actually finish their training.
How to stay on top:
- Monitor Assignment Reports: Lessonly’s reporting is straightforward—just pull up the assignment and see who’s done and who’s dragging their feet.
- Send Reminders: Use Lessonly’s built-in reminder function, or nudge people directly if your culture allows.
- Export Data for Audits: Download completion data as CSVs for those inevitable “prove it” moments with auditors.
Pain points:
- No “Automatic Reassignment”: If someone misses a cycle, Lessonly won’t automatically roll them into the next one. You have to keep an eye on stragglers.
- Reporting Gaps: If you’re duplicating lessons for each cycle, you’ll have to pull reports from each one separately. There’s no master “John Smith has done every annual security training for five years” dashboard.
Step 6: Archive and Update Old Content
Regulators and auditors may want proof that you don’t just use the same stale training every year.
- Duplicate and Retire Old Lessons: When you roll out a new version, duplicate the old lesson, update the content, and clearly mark the year.
- Archive Old Assignments: Don’t delete old lessons or assignments—archive them so you can show historical completion if needed.
- Document Your Workflow: Keep a simple log (Google Sheet, Notion, whatever) listing which lessons were assigned, to whom, and when.
Real-World Tips and Gotchas
- Don’t Overcomplicate: You’re not building a spaceship. For most orgs, a recurring calendar invite to assign new lessons is good enough.
- Communicate Clearly: People ignore “mystery” assignments. Always explain why they’re getting the same training again.
- Get Buy-In from Managers: If compliance matters, managers need to back you up when folks ignore reminders.
- Keep It Auditable: If you ever need to show a regulator your process, clear records and naming conventions will save you hours.
What doesn’t work: Don’t expect Lessonly to do all the work for you. If you need airtight, automated, multi-year compliance tracking, you’ll hit its limits. But for most companies, this manual-plus-calendar approach is more than enough.
Wrapping Up
Recurring compliance training in Lessonly isn’t “set it and forget it,” but it’s not rocket science either. Keep your content organized, your groups tidy, and your reminders consistent. Start simple, automate where you can, and improve your process each year. The less time you spend fighting your training tool, the more you can focus on what actually matters—keeping your people (and your company) out of trouble.