How to design for obstacles in your online course

Creating an online course isn’t just about making your content look pretty. To create an online course that changes lives, you’ve got to consider those very lives.

Like where your learner is when they start your course (mindset, emotions, skill-level) and where they want to end up. This is called your learner journey.

Your target learner’s journey is important, but there’s a key aspect of that journey that’s equally important yet often overlooked: obstacles.

Learning isn’t a straight line, especially when the subject matter is complex.

There’s habits to contend with, environmental constraints, technology issues, etc. Not to mention trying to finish your course while dealing with kids, a full-time job, aging parents, and all the other stuff that tries to 💩 on your goals.

Why learning obstacles matter

Let’s say you create a great course. You validated it so you know your audience wants it. You even did a pre-sale and sold a bunch of seats before the course went live. Sweet!

When you open your course up, everyone is so excited to start! But three weeks in and you start to notice that engagement begins to drop.

Like any good instructor, you check progress rates (easy to do if you’re using Thinkific or WP Complete).

And that’s when you realize that no one has gotten past the first lesson. Cue the friggin' violins.

A bunch of things run through your mind at this point:

  • If your students get stuck they won’t finish your course.

  • If your students don’t finish your course, you’ll have a hard time getting testimonials.

  • If you don’t get testimonials, you’ll have a hard time getting sales the next time around.

Holy crap! So this is why obstacles matter?

Ultimately, if you want to create a course that changes lives, it’s your job to anticipate your student’s learning journey. You can’t make people finish your course, but you can find out where they’re getting stuck.

Here are some ways to do that.

Discover obstacles BEFORE your course begins

One of the simplest ways to find out where your students are getting stuck is to use a survey. 

For example, in my interview with Halley Gray we talked about how she uses surveys in her course, Be Booked Out, to find out where her students are struggling early on. 

using surveys as pre-assessments

Halley uses the built in survey feature in Thinkific (which is great by the way).

She uses a pre-assessment at the beginning of her course to help her get a clear picture of where her students are and what they’re struggling with before they even start.

This helps her to understand her learners better and anticipate their obstacles. 

Pro Tip: Ideally, you want to use built-in or embedded surveys/ quizzes to avoid sending your learners out of the course environment. If you don’t have this option, you can link out to a survey--just be aware that distractions may keep students from returning to your course.

Using customer interviews 

Another way to discover obstacles is to schedule customer interviews before you create your course. This is great for getting qualitative data.

  • If you have a mailing list, email your subscribers to find participants.

  • If you don’t have a mailing list (or it’s not very engaged) find participants via forums, Facebook groups, meetups, or LinkedIn groups you’re part of.

Discover obstacles DURING your course

Let’s be honest--most of us are not self-motivated. We often get distracted. Sometimes we prioritize the new flashy thing over the thing that feels like work.

Your learners are no different.

Even if you plan for obstacles before your course, there will be times when your students will get hung up or just don’t want to do the work. 

Sometimes the issue is motivation, sometimes the issue is information, sometimes the issue is life.

You can work around this by creating check-in points during each lesson. For instance, adding a quiz to the beginning or end of your lessons is a great way to check student understanding of the material and keep them engaged.

Pro Tip: Got a Facebook or Slack group? Pay attention to what questions people are asking and at which points in your course they’re expressing frustration.

Discover obstacles AFTER your course

So far we’ve talked about how to find obstacles before students take your course and while they’re taking it, but what about after they’re done? Is that a thing?

Uh, yeah!

You can—and should—send out a final survey or do an exit interview to find out what worked and what didn’t. 

Pro Tip: This is also a hack for gauging completion rates if you’re using a platform that doesn’t track that. Aaaaand, you can use final surveys to get testimonials because those bastards can be hard to round up sometimes.

What to do after you find learning obstacles in your course?

Okay, so you’ve identified the literal sticking points in your course. Now what?

Fix ‘em.

Learning obstacles usually stem from an issue with motivation, information, demonstration or application.

Your students need regular check-ins, clear & simple information, examples, and lots of practice.

Tips for eliminating learning obstacles

  • Keep your content simple. We almost always make things more complicated than they have to be. Try to solve one problem per lesson.

  • On the other hand, make sure you haven’t left any key information out. If so, add it. (This is why beta testing comes in handy.)

  • Use examples. Examples necessary to drive home a concept should be in the course. Examples that are supplemental should be in email or the resources section.

  • This isn’t common, but if your course is heavy on examples and light on instruction it can leave your students wanting more. If this is part of your student feedback, consider moving your in-course examples to email.

  • Doing is what distinguishes a course from a book. For transformation to occur, add activities to your course to give your students the opportunity to practice what you’ve preached.


As a course instructor, it’s your job to find out what might get in the way of student success. You can’t make people do the work, but you can (and should) design with obstacles in mind. This is what separates courses that change lives from those that don't.

You can get started by keeping information simple, adding examples, using surveys and quizzes to check-in, and providing opportunities for application.

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