Yesterday we hosted a tech deep dive where we went DEEP into what’s possible with conversational courses.  In this post I want to recap what we covered and offer some resources that can help you get started.

One of the more powerful use cases we shared is repurposing old content—Zoom recordings, interviews, presentations—into segmented, interactive modules. Instead of one long video, you break up the content into conversational learning segments with small clips from the original source material.

Usually, this kind of work takes days.  We shared how you can do it in minutes.

We did this recently with a talk from Thomas Hübl.  We used AI to segment the transcript into meaningful sections. Then we designed a conversational experience around those segments. Each section became its own deep reflection.

I’ve put together a step by step guide for how you can do this yourself SUPER FAST.  Check out the guide here.

This is a way of breathing new life into old content.  It’s also a powerful way to partner with thought leaders.  We’ve used this exact strategy to build some of our most impactful partnerships.   Many organizations and thought leaders have old content just lying around.  When you offer them a way to repurpose that content in a conversational format that gives it new life, builds community, and generates revenue at the same time they tend to be very receptive.  I lay out the strategy in detail here.

If you’re interested in more background and context, read on.

How it all started

Ten years ago, we started Sutra with a vision to support meaningful connection and conversation online.

An early inspiration was the uLab program from Otto Scharmer at the Presencing Institute.

One of the most impactful aspects of that experience was the case clinic process, where small groups engaged with each other through a sequence of guiding prompts. It was powerful. What struck me was how adding structure to a group’s interaction could generate deep insight and transformation.

Since then we’ve been prototyping and iterating ways to create this quality of connection and conversation asynchronously online.  We’ve developed a feature set called conversational courses which we believe offer a path to the future of learning.

The Problem with Current Online Learning Models

As we spent more time exploring the online learning space, we noticed some clear gaps. Traditional self-paced courses often have shockingly low completion rates. People sign up, they watch a couple videos, and then they disappear. There’s no sense of connection. No accountability.  No conversation with other participants.

On the other hand, cohort-based courses can be incredibly engaging—but they’re also incredibly labor-intensive. You have to find a new group of people to enroll each time, schedule everything, manage participation, run live sessions. And once the course ends, it’s over.

There’s this gap—an unmet need—between these two extremes. On one side, self-paced courses lack connection and community. On the other, cohort-based courses offer connection but are time-bound and hard to sustain. What’s missing is a format that offers the ease and scalability of self-paced learning while fostering the sense of shared presence and engagement that makes cohorts so powerful.

The Promise of AI and Conversational Learning

AI opens up new possibilities, especially when we think about context. One of the most exciting things about AI is its ability to ask questions and guide conversation. And that’s where we can start to see something new emerge.

I’m not talking about using AI to deliver content or be the main interlocutor in a conversation. That’s not what this is about. For me, the magic happens when AI supports human interaction. When it helps highlight meaningful contributions. When it makes reflection visible. When it enables deeper engagement between participants.

The vision is to combine the flexibility of self-paced learning with the relational richness of social learning. AI can help facilitate that. It can create a space where people feel invited into meaningful conversation—even if they’re not there at the same time.

Key Elements of a Conversational Course

So what exactly is a conversational course? It’s a course format that delivers content one piece at a time. After each piece, there’s a reflection prompt—something that invites you to pause, consider, and respond from your own experience.

Once you respond, you’re given the option to see what others have shared. This creates a sense of unfolding dialogue. AI plays a key role here: it surfaces the most meaningful responses using tools like highlights, summaries, and word clouds. It helps bring the richness of everyone’s contributions to the forefront.

And participation is opt-in. You choose when and how to engage. You can share your response privately or publicly. You can explore the full stream of discussion or just engage with what’s highlighted. The format is flexible, yet designed to create a feeling of intimacy and shared presence.

Real-World Use Cases and Prototypes

We’ve been experimenting with this format in a number of different contexts. We’ve run courses with thought leaders like Charles Eisenstein, Dan Ariely, Jennifer Garvey Berger, Thomas Hübl, and others.

We’ve also explored hybrid models: a self-paced core combined with occasional live sessions. The self-paced content creates a steady rhythm. And the live sessions become these rich touchpoints where deeper engagement happens. What’s beautiful is that the course doesn’t end—it gets better over time as more and more people contribute.

How to Build a Conversational Course

When you go to create a conversational course on Sutra, you’re working with a content editor that lets you build block by block. You can add content, reflection prompts, continue buttons, and more. Each prompt acts as an invitation into deeper reflection and conversation.

You can keep it simple: a single page with a few videos and prompts. Or you can build a multi-module journey with many layers. There’s a lot of design flexibility.

We also have an AI builder. You give it a bit of direction and it generates a scaffold for your course. You can then edit and refine that structure. There are templates too: single-page courses, multi-page experiences, and worksheet-style formats. It’s all designed to help you go from idea to experience quickly.

Less Content, More Conversation

One of our guiding principles is: less content, more conversation. Traditional courses often overload participants with information. But transformation doesn’t come from content alone. It comes from reflection. From conversation. From seeing your own experience mirrored in someone else’s words.

We put a lot of emphasis on crafting good prompts. Prompts that invite people to share something real. Something that matters. When participants respond to these prompts, they’re not just learning—they’re teaching. Their responses become part of the course. And that gives the experience a sense of aliveness.

There’s a kind of generativity in that. You see people realizing things in real time. Naming something they hadn’t named before. And then others resonating with that. That’s where the magic is.

From Video to Conversational Course: A Step-by-Step Guide

In the second half of the presentation, I walked through a full demo of how to create a conversational course from a video using AI tools. It’s a powerful workflow—and I’ve written a detailed guide that walks you through every step. You can find that guide here.

The process starts with downloading your video and generating a transcript. Then you work with AI—whether it’s ChatGPT, Claude, or Gemini—to identify key themes, generate content, and create reflection prompts. You also generate timestamps for your video cuts.

Next, you segment your video using a tool like LosslessCut, and finally you upload everything into Sutra. It’s surprisingly smooth once you get the hang of it. And the results are powerful: you go from a long video to a beautifully segmented, reflective learning experience.

Conclusion

I believe that online learning can be deeply relational and that conversation can be a form of transformation. AI—when used with care and intention—can help us create experiences like this.  In fact, this might be one of the most powerful, and most needed use cases, for AI.

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