Educator stories: How to teach online classes that engage teens
An educator on Outschool shares how she connects with teens in her online classes and follows their lead as they direct their own learning.

Kathy Wilder’s teaching toolbox includes a handful of strategies that have helped her build rapport with teenage learners and grow her online teaching business.

She mainly teaches philosophy classes to teenagers—with a few sessions for younger learners—as well as literature, banned book, and art history classes for teens. Kathy has taught on Outschool since 2019 and currently offers ongoing courses and a few multi-day ones. Most of her learners are homeschooled in the U.S. or from Asia and other parts of the world. All told, she has taught learners in 37 countries.

Kathy often puts classes on her Outschool calendar a few months in advance so that learners who might want to join in a couple months can see what classes will be available then. She has generally scheduled her classes at the same times for the last few years. That way people know her regular class schedule. She ends up with a lot of last-minute enrollments, but she also has had learners who have attended her courses for a couple years.

We asked Kathy to share how she has created class environments that welcome teens and encourage them to return. She talked about six approaches that have worked for her.

Present yourself authentically when teaching teens

As Kathy says, teenage learners in particular can spot inauthenticity a mile away. “It’s about authenticity,” she says. “They know if you’re faking it. They want somebody who’s authentic.”

For her, being authentic includes sharing stories about her life. For instance, in a discussion with learners about whether kids have rights, she shared how she told her then 2-year-old son that the coffee cake had coffee in it. When she and her learners talked about whether this was the right thing to do—she really just didn’t want to share her coffee cake—all the learners said, “No, that wasn’t right.”

Kathy tells stories to signal to learners that they can take risks and share too.

“I’ll share stories about myself, about things I’ve done,” she says, “which I think encourages them to be more open to sharing things that they have done.”

Allow cameras off, if possible, in your virtual classroom

Kathy is fine with teenage learners keeping their cameras off (after she has verified that they are an enrolled student), which can be a choice that learners of this age will make, if allowed. She understands that for some classes it’s important to see what learners are doing, but in Kathy’s classes she’s able to give learners autonomy and the freedom to decide how to participate.

“I do not care if the cameras are on, as long as they’re participating… however they are more comfortable,” she says. “Some have the cameras on. Some have the cameras off. Some I have never seen again after the check-in. They like being able to have that sort of autonomy.”

Kathy is open to various ways to participate, such as emojis (very popular) and hand gestures. She tends to leave chat as an option for communicating with her directly.

She says it can initially be uncomfortable when learners have cameras off because you don’t have eye contact and the ability to see if you are making a connection. Keeping some line of communication open gives her “some sort of acknowledgement that I am speaking, that I know that they are there,” she says, “and did not just go into the kitchen.”

Have a framework for a respectful class environment

Kathy uses the “circle of inquiry” framework as a guide for her classroom interactions. This sets the standard for how learners will explore ideas, learn about themselves, and be respectful of others at the same time.

“In a circle of inquiry, do we talk over people? No, we do not. Do we raise our hand? Yes, we do,” she says. She adds that although she prefers that learners raise their hands so everyone can hear what each person has to say, she understands if learners forget and just speak out. Learners tend to self-regulate after a few times, Kathy says.

The concept of a community of inquiry comes from Matthew Lipman and is part of an educational approach called Philosophy with Children. Kathy started using the framework in her philosophy classes but says it can apply to a wider set of classes.

Let teens direct their learning

Kathy chooses to let students lead as much as possible because then they’re more likely to participate, to become invested in the class and topic, and to learn. It’s all part of an inquiry-based approach where learners explore questions.

“I really try to have my classes be student-centered rather than teacher-centered,” she says, “because that gives them some control over the process.”

Kathy says she treats her teenage learners like young adults and respects their ideas and insights. “That gives them that freedom and that feeling of, ‘I can say this and I don’t have to worry that someone’s going to make fun of me. I don’t have to worry that someone is laughing. I can say this.’ “

She notes that people often dismiss teens’ ideas because they’re coming from kids. Her attitude is: “No, your ideas are worthy, and they have merit. So this is the place to share them.”

Teens like questions that challenge them, Kathy says, and creating a safe emotional space is important for discussions where they need to consider multiple points of view.

Bring humor to your classes

Keeping the mood light and using humor often is a hit with teens, Kathy says. For example, teens love to give a thumbs up or thumbs down, which some people may think only appeals to younger learners.

Another example comes from one of Kathy’s art history classes, where learners looked at paintings and discussed: “Has this person ever seen a baby?” Kathy explains that in many old paintings, babies look like little old people. There’s actually a religious reason for it, she says, but in today’s world it can look ridiculous.

People may think that learning about philosophy means discussing the ideas of “a bunch of boring old dead guys,” Kathy says, “but that’s not what we’re doing.” In her classes, learners might talk about happiness, for instance, and what makes a person happy.

It’s not just educators who can bring humor to a class. Teens like to be funny too, Kathy says. “They come out with some stuff, and you’re like, ‘That didn’t even occur to me.’ “

Relax and enjoy teen learners

The bottom line is that Kathy really enjoys teens. From them, she’s learned about current teen culture, including some up-to-date teen slang, which she sometimes throws into her classes. When she says “that sounds ‘sus’ to me,” that tends to bring a few laughs.

She likes hearing what teen learners have to say, too. Her class icebreaker questions include: Why is six afraid of seven? Would you rather be a bee or a bear? Would you rather someone write a book or song about you?

In response to the last question, a lot of teens say “song,” which initially surprised Kathy. They tell her that they haven’t done enough in life to fill a book and a song is shorter.

“I love the teens. I really do,” she says. “They’re just so fun.”

To learn more about how Kathy develops classes that teens enjoy, check out the full interview with her.

More from Outschool

From the classroom to the campfire: Offering summer learning with camps

Learn how to increase enrollments on Outschool by offering engaging summer camps to learners in the United States, the U.K., and East Asia.

How to price your Self-Paced classes

Learn the formula to maximize your passive income opportunity by pricing your Self-Paced classes for success.


Teach on your terms

Set learning free