If you’re staring at a mess of training docs, slide decks, and outdated PDFs, wondering how to get it all into Lessonly without losing your mind—or your team’s patience—this is for you. Whether you’re new to Lessonly or just trying to get better at wrangling content, I’ll show you what actually works (and what’s just marketing fluff).
1. Get Real About What You Have
Before you touch Lessonly, take stock of your content. This step sounds boring, but trust me, it saves headaches later.
- List your sources: Is stuff in Google Drive? Dropbox? Email attachments? LMS exports? Make a list.
- Decide what’s worth keeping: Not everything needs to make the jump. If it’s outdated, redundant, or nobody uses it, skip it.
- Formats matter: Lessonly likes text, images, videos, and PDFs. If you’ve got quirky file types (like old SCORM or PowerPoint files), you’ll need to convert or rebuild.
- Pro tip: Make a simple spreadsheet with file names, topics, and intended audience. It’ll help you spot duplicates and gaps.
2. Map Out Your Structure Before Importing
Lessonly has two main building blocks: Lessons (individual pieces of content) and Paths (ordered groups of lessons). If you just dump everything in, you’ll end up with a mess that’s hard to fix later.
- Think in topics, not departments. Organize content by what people need to learn, not who “owns” it.
- Keep it shallow. Deep folder trees are annoying in Lessonly—stick to clear, broad categories.
- Sketch out “Paths” for key roles. For example, “Customer Support Onboarding” or “Sales Product Training.”
- Don’t overthink it. You can always reorganize later. The main thing is to avoid random uploads with no plan.
What to skip: Don’t try to perfectly replicate old folder structures from your last LMS. Lessonly isn’t built for that, and you’ll just waste time.
3. Clean Up and Prep Your Files
Now’s your chance to ditch the junk and fix what’s broken.
- Standardize naming: Use clear, descriptive file names. “2023_sales_intro.pdf” beats “final_FINAL_v2.pptx.”
- Combine duplicates: If you’ve got five versions of the same sales script, pick one.
- Update formatting: Check for formatting weirdness when copying from Word/Google Docs—Lessonly’s editor is pretty basic.
- Compress videos and images: Huge files slow everything down and annoy learners. Aim for reasonable quality.
What works: Lessonly’s WYSIWYG editor is fine for text and images, but fussy with tables and fancy formatting. If in doubt, keep it simple.
4. Import Content Into Lessonly
Ready to bring content in? Here’s the honest truth: Lessonly doesn’t have a magical bulk import for lessons like some LMSs. You’ll need to do some manual building, but there are ways to speed things up.
A. Start With Templates
- Create a few lesson templates for common types: procedures, onboarding, product overviews.
- Copy/paste content into these templates to keep everything consistent.
- Save time by duplicating lessons when you need similar structure.
What works: Templates help new lesson creators stay consistent (and save you from formatting hell).
B. Use the CSV Import (for Users and Assignments, Not Content)
- Don’t get misled by the “import” option: Lessonly’s CSV import is great for users and assignments, but not for bulk uploading content.
- What you can do: If you have a ton of learners to add, use the CSV template under “Users” to avoid manual entry.
C. Upload Files Directly Into Lessons
- Drag and drop PDFs, images, and videos right into the lesson editor.
- Limitations: You can’t bulk upload 100 files into 100 lessons. It’s manual, but the process is straightforward.
- Embed videos: If you use Vimeo or YouTube, just grab the embed code—saves on storage and works better cross-device.
What to skip: Don’t waste time trying to upload a giant ZIP file of your old courses. Lessonly doesn’t unpack those.
5. Organize With Tags, Paths, and Search
Once your lessons are in, you need to make sure people can find what they need—without clicking through endless lists.
A. Use Tags Wisely
- Add tags to lessons by topic, role, or skill. For example: “onboarding,” “compliance,” “sales.”
- Don’t over-tag. Three to five tags per lesson is plenty.
B. Build Paths for Structured Learning
- Group lessons into Paths for specific training journeys.
- Keep Paths short and focused: People lose interest after 3–5 lessons in a row.
- Assign Paths by role or team so people only see what’s relevant.
C. Rely on Search, Not Folders
- Lessonly’s search is pretty good. If you use clear lesson names and tags, people will find what they need.
- Don’t obsess over folders: Lessonly doesn’t do deep nesting. If you’re spending hours reorganizing, you’re probably overcomplicating it.
Pro tip: Put key info (“How to reset password,” “2024 product updates”) in lesson titles and tags so they show up in search.
6. Test and Tweak Before Rolling Out
You don’t want your first wave of learners to hit broken links or half-baked lessons.
- Preview everything: Use the “Preview” option to see lessons as a learner.
- Check permissions: Make sure only the right people can see each Path or lesson.
- Pilot with a small group: Get feedback on navigation and clarity. Fix what’s confusing before going wide.
What to skip: Don’t bother formatting every lesson to perfection out of the gate. Content that’s clear and accurate is more important than perfect fonts.
7. Keep It Up To Date (Without Losing Your Sanity)
Importing is just the start. Keeping training current is where most teams drop the ball.
- Assign owners for each key Path or topic. Someone needs to be on the hook for updates.
- Set review reminders: Lessonly can send reminders to review or update lessons—use them.
- Archive old stuff: If a lesson is obsolete, archive it instead of deleting. You might need it for compliance later.
What works: A quarterly review cycle is usually enough for most teams. Don’t try to schedule monthly reviews unless you have tons of resources.
Honest Takes: What Works, What Doesn’t
- Works: Templates, simple structure, and clear naming conventions.
- Doesn’t work: Trying to bulk import content, building deep folder trees, or forcing Lessonly to mimic your old system.
- Ignore the hype: Lessonly is good for straightforward, bite-sized training. If you need heavy-duty compliance tracking or complex branching, it’s not the best fit.
Wrap-Up: Keep It Simple, Iterate Often
Importing and organizing training in Lessonly doesn’t have to be a slog. Don’t aim for perfection out of the gate—focus on getting the essentials in, making them easy to find, and building from there. The best training systems are the ones people actually use, not the ones with the fanciest structure. Start simple, fix what’s broken, and keep improving. That’s how you win.