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Creator Science with Jay Clouse
#313: How Tom Ross Doubled His Community Engagement and Retention With Training Pathways
00:56:51
Tom Ross is the founder of Learn.Community
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- [00:01]
Tom Ross
People inherently don't know what they don't know, which means if you just dump them into an unstructured community, expecting them to know exactly what they need help with, it doesn't tend to happen. And so I found that having some kind of structured learning was a great starting point for a lot of people.
- [00:30]
Chris
Hello, my friend. Welcome back to another episode of Creator Science. My guest today is Tom Ross, the founder of Learn Community, where he helps community builders design learning experiences that actually stick. Tom's clients have reached millions of people and generated tens of millions of dollars in revenue. And Tom is a longtime member of the lab. His membership is six figures and growing. Tom's been building online communities for two decades, and in this conversation we get into some of the most tactical, counterintuitive lessons that he's learned along the way. We talk about why closing the doors to your membership can make people want in more, why an application process might be the strongest sales lever you're not using, and an innovative approach to onboarding that I'm absolutely going to take inspiration from. But the part of this conversation I keep thinking about is what Tom calls learning pathways, his reinvention of the traditional online course. He rebuilt his own onboarding to fix the completion rate problem plaguing course creator. His own course completion went from 20% to 50%. And he did it by weaving AI agents, worksheets, and even some custom software tools. He built himself directly into the learning experience so people actually finish and actually stick around afterwards. If you're running a membership, a community, or thinking about how online education is changing, this one is packed with ideas that you can steal. We'll get to my full conversation with Tom right after this. This episode is sponsored by ahrefs. Listen, this is gonna sound like I'm joking, but I'm really not. I get fired up about software products that offer a generous free plan. And that is what I get to tell you about today. I've been a user of Ahrefs Free for years. SEO has never been my biggest focus, but I like to know how I'm doing. And Ahrefs Free lets me do just that. With an Ahrefs Free account, you can see your website's backlinks and understand who is linking to you. Check which pages and keywords are bringing organic traffic to your site, use free SEO tools for keyword ideas, backlink checks, website authority, broken links and more. Spot content opportunities for your site, and even look up competitor websites to see where they are getting traffic from. All of this without becoming a full time SEO person. To me, creating an Ahrefs Free account and understanding your search results is a total no brainer. Go to ahrefs.com free. That's a h r e f s.com free. And verify your website today. That's ahrefs a h r e f s.Com free.
- [03:07]
Tom Ross
This episode is brought to you by Facebook. So you were scrolling on Marketplace and there it was, the bike you'd been searching for. You sent a message and it turned
- [03:17]
Chris
out the seller was super chatty, kind
- [03:19]
Tom Ross
of funny, and an avid cyclist. The next thing you know, you're in a cycling crew. Well, a community cycling group. The thing about Facebook, you might find more than what you're looking for from a browse to a bike ride this summer.
- [03:33]
Chris
Find more on Facebook. Tom Ross on the show Overdue. Good to have you here. Excited to chat all things community. You are the community guy. Do you feel like you've settled into that identity like Tom Ross, community guy?
- [03:50]
Tom Ross
I do. Thanks for having me on, man. Yeah, I've been looking forward to this and I kind of see you as the community guy. So we're a couple of community guys today. Having a geek out.
- [03:58]
Chris
Hopefully just a couple of community guys. Which leads me into my first question. What do you think is the prognosis for communities and memberships now, middle of 2026, moving into 2027? Is it too late?
- [04:11]
Tom Ross
No, it is definitely not too late. But I think you and I are probably pretty aligned on this, right? There's been a boom in communities. We've both seen it. But with that comes a boom in communities not done well. So I think there's never been more communities. There's never been more that are struggling. And I think a lot of what I do, and I know you do as well, is how do we help people be part of the 5% that really fly?
- [04:34]
Chris
This is my fear. I'm going off script already, but this is my fear of the new Beehive announcements. Their new community functionality looks thoughtfully designed and it sounds really cool and smart to be like you can just instantly invite your subscribers in and now you know a lot about their reader behavior. I worry that the feature will be so easy to turn on that anybody running a Beehive newsletter will do that. And what we're going to have is a rash of very poor, unconsidered community experiences.
- [05:08]
Tom Ross
Yeah, I would agree. I would also say I've been building communities online for 20 years. I do it day in, day out, and I feel like I'm still learning all the Time. And there's just so much more to get my teeth into. And I think if you're not full time in community, it's a big ask. Right? It's a nuanced business model. It's inherently pretty complex. And I routinely see really big, really smart, really established creators that have nailed core sales or some old school business model, and they struggle when it comes to community because it is a new art form for so many people.
- [05:42]
Chris
Totally. I was just watching a video on your YouTube channel where you talked about one of the biggest failures of retention. And sorry to spoil the YouTube video for anybody who's gonna go watch the YouTube after this, but you said most retention problems are actually failure before somebody comes into the membership. It's a targeting and expectations failure, which I also totally, totally agree with. And that's what we see with a lot of folks who, like, have successfully built an audience. They see community platform exists. I'm just gonna throw these two things together and hope that magic happens. But it just doesn't. At least not long term.
- [06:16]
Tom Ross
Yeah. I think the crux of that video is I kept seeing this pattern where someone would have a community and one kind of member would stick around for years and just be a perfect member. Another kind would invariably churn. Like, no matter what they did, they would show up for them, they would check in, they would bend over backwards, and the member would always still churn. And I'm like, well, if the office the same and the delivery is the same and the care for the member is the same, what is going on here? And it just struck me the biggest variable is who you put in your community. And so I went really deep down that rabbit hole. I started talking to so many community builders, including mutual friends like Tamara, who we both know, who runs PMM camp, but tons of successful community builders. And they're like, I'm seeing the same thing. And it turns out behind the scenes, it's kind of this unspoken retention rule that no one's really publicizing.
- [07:06]
Chris
I do kind of feel like my experience of what I see is I kind of loosely say it's a third, a third, a third, where there's like a third of people who are like pretty inactive. Then you have a third of people who are super users, and a third of people are somewhere in the middle. Those are very rough estimates. But it does seem hard to avoid some percentage of people that just like, inexplicably, you just never see once they join. And the question I get from a lot of folks is like, how do I Fix that. I've started to wonder if that's even the right question. There is to some degree, of course you want to make the product better, but I feel like there's some non zero percentage of people that you're just not going to save and should you put any more time into that segment versus, like, super serving the people who are showing up and doing the work and asking for your help. What's your take on this?
- [08:00]
Tom Ross
I think it depends on your model, but I got a couple of clients, and when we actually ran the math, we figured out if they just never let the people in in the first place who were going to ch to have a happier time because their retention is going to go up, they're actually going to need to sell less slots per launch. It'll take a lot of stress out of their marketing. They can then double down on the right people they let in. And the difference is pretty stark. Like, there's one client I work with in particular, and we figured out when people are referred by an existing member, their retention goes through the roof. They retain very highly because they came in through, like, a warm contact. And then we had a couple of other variables, and it's like, well, actually, people that have those two variables cancel every single time. So it stands to reason. It's like, well, let's bring more of those people in. And we did that. We took referred members from 20% to 60% of all the members they bring in. And then we tweaked the application form and it's like, okay, if these red flags come up, maybe we're just going to say no to those people because it's going to be a waste of time and mental resource trying to serve them. And I don't mean that in a harsh way, but it's demoralizing, right? Because we care about our people. We deeply care about our members. And when you and your team are there, like, doing everything you can and effectively getting ghosted, it's a losing battle.
- [09:12]
Chris
Okay, I love this direction. So let's say it sounds like you're an advocate for an application, because it sounds like for me to selectively say no to people, it kind of seems to suggest there must be an application for that to be true. Is that what you're saying?
- [09:27]
Tom Ross
That's the biggest lever you can pull? The other lever is kind of price and positioning and things like that. But I want to go on record before someone leaves a comment below this podcast. I currently do not have an application, even though I completely believe in that model. But I used to. And when I had it, exactly what I'm talking about here played out. I really vetted people. I let the top people in based on how they scored, and some of them have retained for five years. And it's been incredible. The reason I basically dropped mine is because I had a baby. And I had a baby and I didn't want to be doing launches and reviewing applications. And so I just made the laziest model.
- [10:03]
Chris
And.
- [10:03]
Tom Ross
And I get enough acquisition and I have a healthy enough churn that I can just do that. And members sign up most days and it works. But truthfully, I think I'm going to go back to an application because it's just a stronger model. Okay.
- [10:15]
Chris
Yeah. This is interesting. We're redesigning our tiers of the lab right now. And a decision that I wasn't expecting us to come to, that we're pretty close on pulling the trigger on, is even our lowest tier is going to become application based.
- [10:26]
Tom Ross
Yep.
- [10:26]
Chris
We're not even planning on decision criteria being like a minimum threshold, but also having a maximum threshold of where you are at certain stages to disqualify you from the lower tiers. But the challenge is always when you have an application. I've always thought to myself, we need to have very clear, unambiguous, objective criteria for who is accepted, who is not, so that it's just like, clear, like why the decision was made. But in this world where you're filtering for certain red flags in the application and you see, like, this person's probably not a good fit, how do you message that? How do you tell somebody like, hey, based on your application, we don't think you're a fit if it's not like an objective measure of some kind.
- [11:11]
Tom Ross
I mean, historically, I've always done that with limited spots, and so it's less personal. I think when you do that, that's interesting. And you don't have to say what the exact limit is, but you say, we've got a very select, very limited number of spots each month, and so we absolutely have to say no to the majority. And so you're positioning it as this highly exclusive thing it's hard to get into. You don't feel personally aggrieved if you didn't get in, because most people didn't get in, or at least that's how you get in.
- [11:38]
Chris
That's higher ed.
- [11:38]
Tom Ross
Yeah, exactly.
- [11:39]
Chris
That's interesting. I hadn't thought about that as a lever or a mechanism to pull.
- [11:46]
Tom Ross
Some interesting thing happens. So I had another client, Patrick and he basically opened up his community a little more. And then he closed it again and had an application and he got double the signups, double the interest. It's counterintuitive, right? You're adding more friction.
- [12:01]
Chris
It is.
- [12:02]
Tom Ross
But then people want it more.
- [12:03]
Chris
We've had this experience the last two months because we closed the doors to the lab while we, like, figure this out. Because I'm like, well, if we're going to make the experience better, like, let's just make people wait a month or two so that they have a better experience as soon as they come in. And I track my KPIs, as you know, and we've had almost three times as many applications in the last month as the month prior. And it's like, what, what is that? I'm not marketing it more or differently. It's. It's very interesting. So we've been longtime Evergreen model, and I think we are going to move to a consistent open and close doors message. Tamara has actually been a great model for this. I've watched her changed her structure quite a bit and I've really loved seeing behind the scenes of how she's doing it, why she's doing it. I'm like, I think that'll, that'll make some sense. A big part of that being when you have consistent cohorting of people coming in, it changes the way you can architect the experience of that group coming in. You're no longer having one person slipstream in and saying, here's where you start. You can create group experiences of people joining together, which again, I think is an interesting extrapolation of the higher ed model. Because I remember my freshman year of college or university, my freshman year of college, walking into my dorm being like, I need to make friends now or I'm going to be a loser and I'll have no friends for the next four years. And that's like an extreme teenage example of this feeling. But I feel like when people come into any space, like a membership, like a community, there's some degree of that. I want to solve that for folks. What do you think about that?
- [13:39]
Tom Ross
I think human psychology is fascinating when it comes to this stuff. And it feels like it shouldn't have such a disproportionate impact, but it does. It's like, urgency is real, scarcity is real. This longing for connection is real. Wanting to be part of the cool kids club and this exclusive thing, it all matters. And I know you had our mutual friend Joy Sullivan on the podcast. Yeah, she was kind of plateaued with her community. And then I worked with her, and we doubled her revenue. And one of the biggest levers was we closed it, and people had to join a waitlist. They had to apply, and then we leveraged urgency and scarcity. So when she opened it up, she said, we got this many people on the waitlist, and we have this limited number of spots. And even though she pretty much doubled her price in that time, her last launch sold out in four minutes. So she had her biggest launch ever, and it went in less than five minutes, simply because of these psychological principles. What did not change was the community and the people inside and the offering and the great work that Joy and her team do. All of that was consistent. It's just layering on top the right marketing models, the right psychology, and it's so powerful.
- [14:42]
Chris
Let me ask you this. What do you think is the optimal frequency for doing that? Because on one hand, I'm thinking, okay, if we're going to continue to do a concierge mastermind experience, I'm not going to do that on a monthly basis. It does make sense. I'll maybe do that four times per year. Does that mean that I should only open the door four times per year? I kind of feel like I want to move to at least every two months, but probably monthly. I'm thinking, like, once a month. This is the time. This is when we open the doors. But then I think, is that too often for us to take advantage of any feeling of real urgency?
- [15:16]
Tom Ross
So the example I said where it was open and then it got closed and interest doubled, that was actually monthly. And that was the wild thing to me. I was like, this thing is pretty much always open because you never have to wait more than three weeks. But it still doubled interest. So I think it can work at any cadence. Most people I work with do either quarterly or once every six months. And I think the reason is when they do that, they really market it hard. And they have a big traditional online launch, and they also onboard a big influx of people, have a big welcome party, treat it almost more like a cohort. And they don't want to do that every month or two because it's exhausting and it's a lot of work, and they don't want to burn their audience out with a launch. So I think both can work. But the variables that change are the level of marketing behind it. Because you're not going to want to hammer your audience on a monthly basis. You're just going to have enough supply, demand, tension that you can Kind of drip people into that model monthly, if that's your choice, and then kind of open it up and there's sufficient demand to fill it, and you feel comfortable doing that. But I think experiment, right? It could be one month, it could be three months. Both work.
- [16:20]
Chris
I want to get your take on something else. That's kind of a tension that's still unresolved for me. We're doing this membership cohort right now, and one of the things we're working on is the promise that your membership is making, because I do believe that you should be able to explain the premise, the promise of your membership, and have it be compelling pretty quickly to your target audience. But it seems inherently easier to market, sell, promote a transformational membership than more of a social club. But the tension that I feel is most transformation is like, achievable and then done. And memberships are recurring, ongoing relationships. I know you work with a lot of folks who sell transformational educational, community experiences. So how do you square that circle of like, this is something that can be achieved versus this is an ongoing subscription product?
- [17:22]
Tom Ross
I would push back slightly that transformations are all finite because not all, but
- [17:28]
Chris
a lot of them are a lot of them.
- [17:30]
Tom Ross
But I mean, look at being a creator. Is that ever done? Or building a business or in my case, I help people to grow communities. It's like there's a pretty long life cycle there, at any rate. So what I help people with is they will get the foundations right and they will plan. In fact, I literally have a framework for this, right. So people will start by planning and defining the foundations, things like the promise. They will then build it and design it and make it really intentional, and they will then launch it, and then they'll scale it and they'll look at retention and they'll look at engagement, and they'll look at growth. And often they go right back to the start and sort of tinker on the foundations and improve those. But it is never done. I've been running Learn Community for five years, I think. Similar amount of time as your community. Right. Because I joined right at the start.
- [18:15]
Chris
Yeah. 2022. So, yeah, five years.
- [18:18]
Tom Ross
Do you feel like you're anywhere close to done?
- [18:21]
Chris
Well, the thing is, like, I think it depends on what people expect the outcome when they join, which is what I promised the outcome to be when they join. You know, so there's a version of the lab where I'm like, we're going to help get you to $10,000 a month in revenue. That's like a transformational very achievable, very clear, very sellable outcome. What I like about that is it's very concrete. And so it feels like a promise I want to take you up on. What's less concrete is, hey, this is the group chat that you've always been waiting for. Yeah, to some people that's going to speak strongly to them. And there is a much more long tail, evergreen relationship there. Much less transformational. So this is like the spectrum that I'm playing with of I want the sellability of something that is very concrete but not so concrete so as to limit the length of the relationship.
- [19:18]
Tom Ross
I think you can kind of get a middle ground to some extent. So you are right in that if it's a super finite outcome, I think it can lend itself to a cohort or a course or something like that. Because I work with someone that literally helps people to nail their interview to become a consultant in the medical field. It's pretty finite, right? It's like, you get the job, you're done. So that works really well for her as a cohort experience. But I think what you can do is you can use the bacon medicine approach. One of my clients told me this a while ago. Right. So when you're trying to give.
- [19:50]
Chris
I've never heard this name. This sounds like the chocolate covered vegetable or like, exactly. Bacon covered medicine.
- [19:58]
Tom Ross
They were like, I got a dog and when I want to give my dog medicine, if he's sick, I wrap it in bacon. And so they're like, you know, basically in this analogy, the bacon is the more finite outcome or the more immediate outcome that lures people. And they're like, I want that now. And then people invariably get embedded and they stay for the belonging and the longer, you know, deeper work and transformation that happens there. Now, I deliberately don't want to position my community as like, I'm going to get you to 10k and you're done. But I can position it as well, I'm going to help you build a really amazing business around a community model. And in your case, it's like, I'm going to help you be a really successful creator. Now it sounds like you're saying the tension is that is not finite enough and it's not measurable enough. Maybe it's not appealing enough, but I think you can kind of bake things underneath that right within the offering. It's like, well, we're going to have sprints that get you to these more finite outcomes. We're going to have milestones. And I know today, hopefully we're going to talk about learning pathways. You can get people making tangible progress, that is the bacon. But you can still have the medicine of the deeper connection and belonging and long term transformation.
- [21:05]
Chris
Yeah, we're probably not gonna fully resolve this. Cause I don't know that it's like fully resolvable. But the advice I give to a lot of people is it's a lot easier to sell the functional benefit that you're promising. And the reason a lot of people will stay is the emotional and social benefits that you also scratch. But personally, I like wanna flip that because I'm less interested in selling the concrete thing. And we did this long research, customer interview, member research, we have mountains of feedback now unambiguously, our happiest, most successful members are there for the other people. And like, yes, I could Trojan horse my way into that and maybe that's the way to do it. But there's a lot of shedding in that process. If you're promising like a very concrete thing and what people are sticking around for is the people, the people who come in with the expectation of the concrete thing. When they achieve it, a fair number of those people leave because that's what I promised and that's what they got. And so I'm more interested in changing the perception of what you're getting, but it's just inherently less concrete and there's a tension I'm feeling with that.
- [22:16]
Tom Ross
Again, I think a lot of my favorite communities do both well. So we mentioned Tamara before. I think her specific value prop is like, you're going to be a better leader. But she's heavy on the culture and the kind of people and so on. And I actually think most communities I see are doing the outcome too prominently and then neglecting the human side.
- [22:38]
Chris
I agree. I agree with that for sure.
- [22:39]
Tom Ross
Right. Often when I'm looking at sales pages, I'm like, I have no idea what it would feel like to be a member. And so I'm pushing people to be like, talk about your values and culture on the main page. Pick testimonials and case studies that are more of the kind of soft side and how people are enjoying it and not just outcome related. Have a VSL or a tour video that shows the experience, show photos of meetups, basically show the vibe because people do not like everyone says, I got the best thing and the best outcome and all this programming and all this information. Right. That's become very abundant and very noisy. But I think often it is the vibe, it's the culture, it's the values that are more unique and more compelling for people. And so I have no issue with have a shiny value proposition that helps get people in. But I think absolutely, at the same time talk about those softer, more ephemeral things.
- [23:32]
Chris
I'm a big fan of the jobs to be done framework. The idea with that is that everything we hire is doing three jobs. A functional, an emotional and a social job for us. Some more prominently than others in different circumstances. And I think memberships are really interesting because I do think they hit all three of those things strongly. Social sounds like the thing that it would do the most. But the way social jobs are defined to my understanding is this is how you appear to other people in your social circle. So it's more like external relationship to your social circle. And the emotional job is more the actual community experience. Anyway, it's very interesting because it's easier to sell functional jobs unless people are extremely aware of the emotional job deficiency they have, which I'm increasingly thinking in my space they do have that. That's why I'm really interested in this messaging of this is the group chat that you wish you had. Because I think the people that I'm appealing to don't have that. And if they do, they're probably not going to join the community. That's not the form factor they want. It's interesting. I'm still playing with this, but I appreciate your perspective on it.
- [24:35]
Tom Ross
Yeah. I mean, you serve creators and I think a lot of creators outwardly say I'm very lonely.
- [24:42]
Chris
I don't know. I think this all explodes. I think the less concrete promise explodes in the face of lots of alternatives. I think it's less of a problem unless there's lots of competition and options. And I'm probably going to choose the option in that circumstance, then that's making the more concrete claim. And I think in my space there's more competition all the time.
- [25:03]
Tom Ross
All I can speak from is my personal preference, which is have quite a compelling value proposition. Don't make it finite in any way, but make it the bacon and then absolutely have the warm, richest stuff underneath and try and do both. And I think this actually works pre signup and post signup. So I'm pretty sure you know my friend David Sphinx. I think he's a mutual friend of ours. Right. David's awesome and I love his onboarding framework. Do no fill. And it's basically what members need to know they should do the first action they should take, what information they should know after joining and how they should Feel. And almost everyone neglects the third part. They neglect feel. But it's the most powerful because every community is like, here's a to do list after you join, or here's a bunch of stuff to know. And invariably they make it too bloated and overwhelming. And we could talk about that all day. But the feel part is something that people are sleeping on. And I remember 20 years ago when I was a budding young entrepreneur and I joined a community called Fizzle. I don't know if you ever saw this. It was run by a guy called Corbett Barr.
- [26:08]
Chris
I'm not familiar with it, but it's one of those things where I felt like, oh, I missed the boat. It was before my time. I'm post Fizzle and pre whatever's coming next. But, yeah, I'm familiar. It was legendary.
- [26:19]
Tom Ross
Yeah, it was amazing. So I was a pretty early member there, and that was actually my taste of being a really good member. I think I must have critiqued something like 3, 400 landing pages. It was something ridiculous, just trying to give back as much as possible and ended up getting free membership and all this stuff. But the reason I was so invested is this was pre social media, and it was like the old school community forum kind of vibe. Deeply connective. And at the time, every Internet marketer felt super sleazy, and the Fizzle guys didn't. They felt awesome. So that originally attracted me. I'm like, what is this place? It feels kind of different. And I remember I paid, I checked out, and I signed up, and I had that typical moment where it's like, am I going to get buyer's remorse, or is this going to live up to my expectations? And it loaded for a second, and it took me to a page after my purchase, and this video started playing. And it was the three founders who were basically having like a dance party and I think letting off party poppers in honor of my sale, like, in honor of me joining. They were like, you're here. And they were going crazy. And it was like, deliberately so silly and so goofy. And I paused for a second and I just smiled. And then I burst out laughing. And that was my first experience. It made me feel something. And my first thought was like, these guys are really fun. I feel very aligned. And this is completely different from all the sleazy marketing bros at the time who were taking themselves too seriously. And I hold on to examples like that now because I think these little touch points you can do so freaking much with. I had a member who was like, I'm doing a community for dads trying to get in the best shape of their life. And I was like, cool, what are your values? And he was like, well, camaraderie is a big one. It's a team sport. That's the whole vibe. We're going to rah, rah, pump each other up. And I'm like, okay, well, someone could join your community and just get a default, really lame message. Or you could take the time to film a point of view video from the point of view of the new member and they kind of arrive in this park or something and then suddenly a bunch of your actual members that you've invited to a meetup run up to the camera, AKA the new member, and they're like, welcome. Like, yeah, like cheering them on. What would that do? If you're a dad who joins that group, you would feel part of the gang. You'd feel the sense of camaraderie. It would be like a fun, creative, tongue in cheek touch. And people don't think about that stuff. But I'm really obsessed about it.
- [28:41]
Chris
I love that. I love that. I agree with you. One thing that I've done in onboarding that I'm really proud of, the moment somebody purchases, I actually put a testimonial, like a emotional testimonial at that point. Because in my mind, when you make the purchase, you are at peak anxiety where you have this gap now between I hope this is the right decision and yes, this is the right decision. My thought was I can start to close that if somebody is reassured right at that moment from somebody who's been here for years, who says, this is the best investment I've made in my 17 years of business. But I like that idea too. I think that's a really fun idea to like bring a lot of people in. Obviously we know some of that is kind of cheeky. This was a video, but it's still fun. I love that. I love innovative touches like that.
- [29:28]
Tom Ross
Yeah. One of my values when people join is delight. So my actual framework is delight, Direct, connect. So I want to delight them in some small way. I want to direct them with one single action they should do next. And I want to connect them with one person. So it's not like 10 people who are irrelevant. It's one person that's highly relevant, like a great fit. So to give an example, I had a London meetup earlier this year. Bunch of us are together and I just get a little notification. Oh, a new member joined. Like while we're stood here, this Guy called Luke. And so I'm like, guys, can we do something? Like just bear with me here and kind of go along with it. So I open my laptop and I'm like, hey, Luke. Because I always do a personal video when someone joins. So I'm like, hey, Luke, I'm just at a meetup right now, but I saw that you joined. I just wanted to take a minute to shoot a quick video and say, welcome, I'm so glad you're here. And then I spun it around and suddenly 30 people are like, luke, welcome. And the whole crowd are existing members, right? So boom, delight. And again, if you are intentional about this stuff and you think about it and maybe you have these little frameworks where you can just do it routinely without reinventing the wheel. Every time I don't even think about it now someone joins and I'm like, cool. I got to delight them, got to tell them what to do next and I got to connect them.
- [30:38]
Chris
This is a good segue to one of the things that I found that I wanted to bring up. And we will get to learning paths after this. I want to talk about responsive onboarding. I haven't heard this phrase. I'm like, damn, that's good. That is the stuff. Tell me about responsive onboarding.
- [30:51]
Tom Ross
So I think we've got really good with hyper segmenting things with email marketing and stuff like that, but it doesn't happen so much with memberships and communities. So I've been dabbling with this and I keep turning on and off workflows and trying to get it right. But the basic idea is we both use circle. I think a lot of the listeners do as well. And I love that they have these custom profile fields. So I make them mandatory. And when people join, they basically have to give me a ton of information about themselves. And everyone does it. No one refuses to. Everyone's happy to. And then they get through into the community. And because I have all that context, you can then trigger responsibly a workflow where they get a bespoke onboarding or welcome message. So I know we're going to talk about learning pathways, but let's say someone joined and they're like, oh, I'm just starting out, or like I'm planning my community. It can recognize that and then say, okay, the welcome message needs to be for a beginner and say, hey, so happy to have you here. You're just starting out. You should start with this training pathway. That's the first thing you should do. So instead of getting a generic message they get one that responds to the data they've given at the point of signup and is bespoke.
- [31:57]
Chris
I love that. The other point you made in that video, the distinction, the contrast is like, even if you're good at onboarding, most people who are good and myself is in this camp, linear onboarding is unresponsive and it's assuming that everyone's moving at the same pace. And for most people it's either going to feel too fast and intense or too slow. I've already done this and this frame of responsive onboarding is so good.
- [32:24]
Tom Ross
I'm trying to make it stacked so it's like they get a bespoke first one, but then based on the actions that follow, it starts unlocking more and more and it can get a bit head melting. But you're so right, because what I saw was someone would join and maybe they're really active and they jump in and they're like, hey. And we have a great chat and they go and do all the things and they start consuming everything they can. Day three hits and it's like, hey, you're probably just starting to get settled in. Do you want to do this super basic step? And they're like, well, I did that three days ago. That was like the first thing I did. What are you talking about? And it completely breaks the experience. So I call that linear onboarding. I'm trying to get away from it.
- [33:01]
Chris
I love that. So when you send your first touch point in circle based on somebody's profile fields, is that a direct message? And if yes, is that coming from you or is that coming from an AI agent?
- [33:15]
Tom Ross
Me, but automated. And without fail, I follow up with a personal one. But often I'll be asleep, right. And I don't want them to have to wait 13 hours or whatever to hear from me personally. So the first message is welcome. Super excited. I actually do the testimonial thing as well. It's like, here's what another member's saying and they're really happy and successful and I want that for you. And you made a great decision. You're not alone. We're going to show up for you. Start here kind of thing. So that's the automated one. Normally I then follow it up with a voice note. So it's like we had a member join today and I can see from the profile they're based in London and I can see what kind of community they're doing, et cetera, et cetera. So I'll voice note and be like, hey, I'm really, really happy you're here. Just so you know, we actually do meetups in London every few months. Let me know if you want to be part of the next one. I'll add you to the DM group. So that's where you can go. Like really bespoke and really personalized. Totally, yeah.
- [34:09]
Chris
After the break, Tom and I dive deep into his implementation of learning pathways. I learned a lot from this part of the discussion, so don't go anywhere. We will be right. This episode is brought to you by State Farm. Listening to this podcast instead of doomscrolling. Smart move. Another smart move getting help from one of State Farm's 19,000 local agents when you choose to bundle home and auto bundling. Just another way to save with the personal price plan. Prices are based on rating plans that vary by state. Coverage options are selected by the customer. Availability, amount of discounts, and savings and eligibility vary by state.
- [34:48]
Tom Ross
Hear that?
- [34:49]
Chris
That's now crispy and McCrispy strips meeting creamy Caesar sauce. Sounds extra Crispy caesar sauce at McDonald's for a limited time. This episode is supported by FX's the Shards, a seductive drama from executive producer Ryan Murphy. Set in 1980s Los Angeles, the series follows a group of glamorous, deeply entangled high school seniors drawn into a life of wealth, beauty, parties, and excess. At its center is Brett, whose reality begins to unravel when the arrival of a new student coincides with a series of mysterious murders. FX's the Shards premieres August 5th on FX and Hulu. And now back to my conversation with Tom Ross. How do we get into a learning path and your community and talk to me about the concept of learning paths. This is where I want to go for the remainder of our conversation here.
- [35:50]
Tom Ross
Sure. So I think my pride and joy. I'm in my little home studio right now. I love that we both have our setups. Yours is looking very fancy, by the way.
- [35:59]
Chris
Thanks.
- [36:00]
Tom Ross
But just out of shot, here is the world's biggest whiteboard. And that's my happy space because I love just doing a bunch of strategy on there. And I kept coming back to this issue that courses are struggling right now. I think you've actually done videos about this. Right. And they're sliding backwards. I think on average, 27% year on year.
- [36:21]
Chris
In terms of sales.
- [36:22]
Tom Ross
In terms of sales. And that's across the board, by the way. That's on average for individual creators, massive course platforms and billion dollar companies. They're all kind of going backwards at a broadly similar rate. And I think this Represents the impact of AI massively. I think it represents a decline in people just wanting or wanting to passively consume videos. And I started noticing this with my flagship course in my community. I was like, what's going on? Well, there's a few issues. Completion rate is not huge. I think it was like 20 something percent. About 20%. And you think, okay, well, that's not a ton of people making it all the way through. It was a very long course, but still, I would also notice to our earlier conversation, people would take the course, absorb all the information and then leave. They'd quit the community, they graduate out of it. And I'm like, well, I keep observing that behavior that's kind of annoying. And then the final problem I saw was it would basically be in an isolated bubble. And so people would be in the course and they would occasionally leave comments. You get the comments next to the course videos and I would never see them because the notifications are not great on that and I'd always miss them. And I'd go in a video lesson, I'd be like, oh, crap, I have like three months of unanswered comments. But no one in the wider community would see that comment. They wouldn't get notified. So it lived in this bubble and it felt like a separate entity from the community that surrounded it. They felt very distinct. So all of these things were bugging me and I was like, but on the other hand, people seem to really like the course. It obviously lets me kind of scale and productize my knowledge. So I feel like I want to have some kind of training, some kind of experience here. So, yeah, people inherently don't know what they don't know, which means if you just dump them into an unstructured community, expecting them to have the perfect questions or know exactly what they need help with, it doesn't tend to happen. And so I found that having some kind of structured learning was a great starting point for a lot of people to kind of unpack things for them. So I knew I wanted some kind of guided path. I knew I wanted some kind of training, but I wanted to overcome some of these issues of traditional courses. And so this is where the training pathways came from. I wanted to reimagine a traditional course and I guess kind of modernize it.
- [38:39]
Chris
So how does that look?
- [38:41]
Tom Ross
So I basically split my framework, which is in four parts, into four course modules inside circle. And so that's the backbone. It's like, you do have the standard course material, but I was like, how can I enrich that? And how can I make that better than just a passive course that people watch? So the first thing was I added specialized AI agents, which I think you played with as well. But there was one per training pathway. And they like cute little robots and they got their own names and stuff like that. But instead of expecting people to go and figure that out and proactively message the agent, it triggers when they actually start the pathway. So they will have the agent reach out to them and say, hey, I'm Tinker. I'm going to help you build your community. Here's how to use me. So as you work through this material, I want you to bounce stuff off me in real time and I'm going to be here like your copilot as you go through. And so I was like, okay, that's pretty cool. And people started seeing good results from that. And then what I started hearing was people wanted more resources. So every lesson became less about watching a passive video and more about implementing. So I started putting together really deep worksheets and AI skills and prompts and stuff that people would like as they're learning. They would do it and they'd start taking a bunch of action and that would really enrich the lessons. And I kept pushing this and pushing this. And so it's at the point now I'm actually vibe coding, I guess you would call them like SaaS tools that go within the training pathway. So I noticed there were a lot of limitations with calculators to kind of project your finances. So I built like the ultimate membership calculator, which is like very, very detailed and has all these parameters that most myths. So people can do that as they work through the pricing module or I noticed that I kept giving people similar feedback on their sales page. So I'm currently vibe coding a tool where they drop their website into it and it's like, this will get you 80, 90% of the way there because it's going to point out the common mistakes you're almost invariably making. And this is kind of speaking to a wider point. But I'm on this soapbox at the minute saying I don't think communities are communities anymore, they're ecosystems. Because it is not just a chat forum, it's not just a group of people. It's like often there is cohort experiences and challenges and sprints and in person meetups and conferences and retreats and now SaaS experiences and tools being baked in. It's like this whole smorgasbord of value orientated towards helping the member with their goals. And so I'm kind of thinking about the actual training pathway way beyond. Just like I'm going to watch a video passively in my room and think, how can I cram in a bunch of value? And then I started thinking about this issue of, well, people go in the course comments and they kind of die there. And it's very shut off and separate from the wider community. So I was like, how can I fix that? So I turned off all the course comments and then in the actual training material itself, I direct them back to the community. And I say, like, you're interacting with your AI agent, you're doing the worksheets, you're trying to figure this out, but if you get stuck, go here and get help and support from your peers. And this crazy thing happened. It basically spiked our engagement, where now a huge proportion of our engagement is people seeking help with the various points they're at in the training pathway, like all the time. And these are people I know for a fact they wouldn't be able to muster the perfect question or they wouldn't know exactly what to ask, but they can say, hey, I'm in the defined stage training and I'm kind of stuck defining my ICP for my community. Here's what I've got so far. I've workshopped it with the agent. It's not quite right. What do you guys think? And literally every day there are posts like that coming through and I can see exactly what stage they're at and what pathway based on their question. And other members who are going through the pathways, which is most of them now help because they're going through the same work. And our community managers tagging them, being like, hey, you're at this stage too. You can help this person. You just went through this. So it goes from being this kind of siloed thing to being very connected and very interactive and completely woven back into the community experience instead of shut off, separate from it. And I'm really having fun with this. So it's like I started adding badges and points and some gamification as well. So as they're working through, they're kind of leveling up and getting these cool recognition points and they're again being encouraged to share back in the community. So often people are like, I did this, it's now live, it looks great, I'm really happy. Or I got this result and other members start celebrating with them. So again, just the comparison to, I am watching a course in my bedroom at home and talking to no one to I'M now being brought back into the wider ecosystem. And a final point, in fact, I have many more points. But a final point on this section, a final point on this section is, I'm sure you've seen this. When you have a big archive of replays and workshops and learning content, it's kind of overwhelming for people to navigate and it's very uncommon. They're going to sit and scroll through 400 workshop replays. But this format lets me pick out like cherry pick the best, most relevant ones and weave them into the training pathway as bonus deeper learning. So it's like you've just gone through this pathway. Click here if you want to see a couple of workshops with members that have perfectly executed this training pathway and how they did it and the results they've got. So you can sit for two, three hours if you want. So, like adjacently to the training. So again, it's kind of bringing people back into the community. It's making more of archived content by weaving it into a linear format. I'm going to take a breath at that point.
- [44:15]
Chris
You mentioned that. Okay, so you have this framework that's four parts, and you said you created four course modules. Are those four distinct course spaces?
- [44:26]
Tom Ross
Yes.
- [44:26]
Chris
Okay, that's what I was thinking. That makes sense from an architecture standpoint, I think. I find that a lot of times when I do a thing that solves a problem, there is some new downstream, new challenge that presents itself. So as you've done this, has this created any new downstream problems that now you are trying to solve?
- [44:53]
Tom Ross
Honestly, none spring to mind.
- [44:54]
Chris
Okay, great.
- [44:55]
Tom Ross
And I don't want to say it's been perfect. I would say the biggest challenge has been it's a ton of work because I'm not just recording like an hour of short videos. It's like there's hours of content and all the supportive resources and the SaaS tools and like setting up all the workflows and automation. So it all works. So it's a lot of work. And I view this as a benefit, but also like a, a burden. It's never done. I will always be able to iterate and improve and add new things and link to bonus lessons. It's a living, breathing thing and that excites me, but it's also an ongoing delivery. But it's a scalable delivery. Right? Because I'm building something that's productizing my expertise and crucially, the expertise of the community. Because if we have a guest expert in, it's like I can take lessons from that and weave it back into the core training pathway, or I can link to that as a bonus resource, or if a member has a breakthrough, I'll do the same thing. So I'm kind of capturing the hive mind of our community and then I'm folding it back into the core productized structured training that's there.
- [45:57]
Chris
If I were to try and predict where this might create friction, if I'm a member who joins, who wants to start a community. But I'm very narrowly minded on this goal and I'm going through and I'm putting all this into place and now I'm on stage four, or maybe I've even finished the whole framework and I'm not particularly interested in helping other people do the framework themselves. I'm here to just like run, do get this implemented. Do those people opt out of the work in progress spaces? Are they just turning off notifications? Have they raised the flag of victory? And they're probably going to graduate from here because that's just what they're doing. What happens to that person?
- [46:44]
Tom Ross
Yeah, so I would say that Persona. They often want slightly different things. They often like to teach, actually. So they do enjoy giving back, but it's like they want to jump on with me and geek out. So Josh, who runs Web Designer Pro, he's in my community as well, and he just came on and gave like a killer workshop because he's more interested in that than like navigating the beginner foundations training pathway. I would say masterminds as well. They've been really powerful. It's like a lot of the people who are running six figure or multi six figure communities, they want more to be paired up and connected with other people at their level and put in mastermind pods than necessarily they want to keep going through training material. So there are opportunities to connect people in these various ways. Panels as well. I really like panel events where they don't have to prep. It's like, let's just bring together people at a really high level and have fantastic discussion and really get into it. Which again creates the flywheel. Because then I can AI summarize and be like, what are all the nuggets that I hadn't even thought of? How can we weave them into the core training and then link back to it and cut it up and so on. So everyone's kind of feeding this thing.
- [47:52]
Chris
Yeah, yeah, yeah, this makes sense. I like this idea of developing sass alongside some of these learning things. One thing I'm seeing in this cohort right now that I've never seen before because the tools are just so much more new. I knew that probably an optimal version of teaching this is creating some prompts myself to solve some of these things. But just in the way that I've been teaching and framing things, I'm seeing students taking this, putting it into their own AI system of choice, coming back with really great outcomes. And so part of me is like, yeah, I absolutely should create some prompts. But also, I've just been really surprised in a positive way at how adept these people are just taking it and running with it with their own assistant. It's been really great to see, and the outcomes have been fantastic. So I guess speaks to the same thing of, yeah, this is a magical time of education, and we can do a lot, but our roles as educators now are being small language models for specific problems. And then they can take that to a super intelligent thing and say, okay, how do I apply this to me specifically? But I think there's probably a bound there to be pushed.
- [49:10]
Tom Ross
Well, this is where I love intellectual property and frameworks and our different ways of doing things. Because if you say to Claude, how do I build a community? It's like, boom, right? It's a fire hydrant of anything and everything you could do. Whereas people, like, it's like, okay, nice. I got a nice linear training path where you're going to hold my hand step by step. But to your point of technology, I taught this framework live in a private cohort, and someone on the call I was teaching the thing about, here's all the best practice of structuring your Circle community and how you should do that live. He got the transcript of what I was saying, pasted it into Claude, and this was right when MCP launched for Circle, and it built his entire community structure as per my exact best guidelines and specifications in like eight minutes.
- [49:57]
Chris
We just had the same thing happen now with Circle AI. Someone in our cohort was like, I just took everything that we've been learning and I created my new Circle account. And AI opened up right on the front. And she's like, I pasted all of this in and it created the entire thing. Yep, pretty wild.
- [50:13]
Tom Ross
Which is pretty cool, right? Because I think we can. I keep thinking of it in terms of productizing what we know, right? You and I, we have a lot of lived experience. We've been, like, getting the battle scars and navigating community for a long time. And so if we can take our findings from that, package it up, productize it, and then let people deploy it faster than ever. Through bite sized training, AI assistance, whatever it might be. Isn't that unbelievable for the end consumer? They don't have to go through the years and years and years of trial and error we did. It's like, here you go.
- [50:47]
Chris
Yeah, it's like playing the lens of, well, like a lens or a filter where it's like, okay, you've got this super powered, giant everything intelligence. Now let's put this like small very specific discrete thing on the front of it that is our framework. And through that, what you see on the other side is like magic 100%.
- [51:10]
Tom Ross
My final kind of point of how I set these up is visibility. And this was another issue before people would join the community and maybe float around a little much. Again, they didn't know exactly how to get the help and I wouldn't know where they were at. I'm like, are they taking action? Are they watching the replays, what's going on? But now, because you can track course completion rate and so on, and because people are getting badges and because I set up this really cool thing with profiles where basically as they complete lessons and they do the work, it will update their profile and they're prompted to do so at various points.
- [51:44]
Chris
Oh, it updates the profile for them.
- [51:46]
Tom Ross
Well, it can do both. So a lot of the time I'm asking, asking them to just jump to their profile and update a field. But you can also trigger profile updates with certain behaviors. So their profile acts as like a living, breathing log of how far they've worked through things. So anytime I'm interacting with someone, I'm like, oh cool, they're currently in this training pathway. They've worked through the previous one, they've done all the steps and all the work and they've unlocked the badges and the points and their profile's like one third complete. I can see here's a link to their feature matrix and the features they've chosen for their community. And that links to a Google sheet template that I gave them. And I can just go look at it because it's attached to their profile and so it's like the single source of truth. And that gives me so much visibility. So I can see if someone's stuck, if they're stalling, I can help them overcome that bump or if they're making great progress or if someone else is stuck. And I can say, well, that person over there just did that lesson. They unlock that level of their profile, they can help you out and it's all consolidated in one place.
- [52:48]
Chris
That's awesome, man. So Cool. So now that all this is in place, what is your next frontier of figuring out?
- [52:57]
Tom Ross
So I'm currently rolling out the last pathway, so it's not fully live yet because it's been so much work. So I'm trying to get all of that out ahead of us having our second baby because we're due in September.
- [53:11]
Chris
Yes.
- [53:11]
Tom Ross
And I'm like, frantically, this is part of my motivation. Right. I'm like, these things are amazing, these pathways, but they also can serve people when I'm not there because I'm going to take a break this time, unlike our first daughter.
- [53:24]
Chris
Nice. Oh man. So good, so good. I'm glad we got through a lot of that. Is there anything on this learning pathways point that if we didn't get it out there, we would be letting our listeners down that we didn't touch on, hopefully.
- [53:38]
Tom Ross
I gave an overview of how I've set them up, but I want to talk about the real results that I've had from this. So my delivery has drastically reduced, which has been amazing because previously someone would join and I'd be like, hey, I'm here to help, we're here to help. Where are you at? And they'd tell me and then I'd be asleep or whatever. I'd come back the next day and be like, cool, I have a follow up question and it would be very clunky. Whereas now people will join. I will literally. Often it sounds like I sleep a lot. I keep saying I'm sleeping but everyone sleeps every day. Hopefully. But people always sign up when I'm asleep. It must be a time zone thing. So I'll wake up, I'll be like, cool, there's a new member and I'll go to give them a personal welcome and see a message being like, hey, you've just started the defined stage training pathway. Hey, you've just completed this stage. And they've been working through it themselves before I've even interacted with them. And so people are kind of self onboarding and then I'm able to give the knowledge that would have taken hours of conversing and me explaining things to them. They can just go through it at their own time and then start engaging in the community and have that flywheel going as well. So that's been amazing. As a result, member success has genuinely gone up a lot. We've had some people doing amazing launches and getting incredible results and I can see where they've worked through the pathways. So one of our members, Ruth, she just had a, a sold out launch And I interviewed her and she literally did it step by step. She was like, I'm going to talk you through exactly what I did with the pathway. And other people were like, oh, so if we just follow it, it really works. And so that was really cool. Engagement is up significantly. And so I found there's been two big levers for that. Most of our engagement now comes either from people doing the pathways and then seeking help and sharing wins, or participating in the monthly sprints, but where they're sharing progress and accountability and so on. So those two things are just feeding the main feed all the time with really timely engagement. Retention has been improving since the pathways rolled out, so churn's been going down, which is awesome. And the completion rate I mentioned before the static course was like 20% is more like 50% with the training pathway, so it's been significantly more completed and used. And the final thing is I get visibility now, so I feel like I have so much more of a grip on where my members are at and who's doing what and if they get stuck and so on. So it's like some pretty compelling wins compared to the frustrating old way that I used to do it.
- [56:08]
Chris
If you want to join me and Tom in the lab, visit creatorscience.com lab or the link in the show Notes. If you're listening on Spotify, leave a comment and let me know what you thought about this episode. I love reading comments on Spotify. If you're not on Spotify. If you're on Apple podcasts, leave us a rating or review. I see all of these. I read them. I love them. They fuel me. And it's been a couple weeks since we've had one, so if you haven't left an Apple podcast rating or review, help us break the streak. You can learn more about Tom by visiting his website@learn.community or find him on social media as TomRoss. There are links to both in the show notes. Thank you for listening. I'll talk to you next week. Man, you're just ahead of me on the kid journey, though. I'm going to be coming to you in October and be like, okay, month one with two kids. What do I need to know?
- [57:03]
Tom Ross
Well, at least we didn't do the podcast then, because we would have been zombies.
- [57:10]
Chris
Close your eyes, exhale, feel your body relax and let go of whatever you're carrying today. Well, I'm letting go of the worry that I wouldn't get my new contacts
- [57:21]
Tom Ross
in time for this class.
- [57:22]
Chris
I got them delivered free from 1-800-contacts.
- [57:24]
Tom Ross
Oh, my gosh. They're so fast.
- [57:26]
Chris
And breathe. Oh, sorry. I almost couldn't breathe when I saw the discount they gave me on my first order. Oh, sorry. Namaste.
- [57:35]
Tom Ross
Visit 1-800contacts.com today to save on your first order, 1-800-contacts.