You'll leave knowing the #1 mistake costing you clients and exactly how to fix it.
From Click to Client Podcast · Episode 87
Why a three-day challenge now converts better than a course or a webinar, and how to build one that delivers the outcome it promised.
Episode 87
Courses Are Dead. What Clients Want Instead with Jess Webber
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There is probably a course sitting in your inbox right now that you opened once. It was not a bad course. It just could not compete with everything else asking for your attention, and nobody was there to walk you through it.
In this episode, I am talking with Jess Webber, a clarity architect and curriculum designer who has built and rebuilt challenge and membership models for coaches and consultants. Her argument is that how-tos have lost their value now that AI will hand you a framework in seconds. What people will pay for is proximity to someone who has already gotten the result they want.
We get into the framework behind a challenge that works, why the selling never belongs inside the thing people paid for, the three pillars any group program needs before you build it, and the conversion math that tells you exactly how many people you need in the room.
How do you run a three-day challenge that converts?
How long should a business challenge be?
Are online courses dead?
How many people do you need in a challenge to get clients?
"Now we're in this new era of people paying for proximity to people who have done the thing."
— Jess Webber
Jess Webber is a keynote speaker, clarity architect, and curriculum designer who helps entrepreneurs and coaches turn their scattered expertise into frameworks people can actually follow. She's the host of the Big Ideas Made Simple podcast and the curriculum architect behind I Love Coaching Co., where she's built and refined challenge and membership models used to convert cold audiences into paying clients. With a background in education and franchise operations, Jess specializes in taking someone's brilliant, overwhelming IP and building the clearest, fastest path from where they are to where they want to be.
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Kris Jones is the founder of Red Door Stories, a Certified StoryBrand Guide, and a messaging strategist who helps service providers, coaches, and consultants clarify their marketing message so they can attract consistent clients. Her core belief: simplicity is a strategic advantage. Less noise, clearer message, more traction.
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Kris: [00:00:00] Jess Webber, I am so delighted to have you here on the show. I've been really looking forward to this. For those of you who don't know about Jess, you really should, and you're gonna get to know her today. I am a big believer in coaching, because we are all inside our own damn bottle trying to read the label that can only be read from outside. And I don't care who you are or what business you own, you are stuck in your own bottle, and the only way to really read that label is to get coaching. So I coach my clients all the time, but I also have coaches, and Jess is one of my coaches. Jess and, Adam Roach, she, the two of them work together. So- I, I've been working with Jess pretty consistently, and it has been so, number one, fun. Number two, it's been so eye-opening. Jess has a lot of different superpowers, and I'm gonna let her explain them to you. But before I do that, I will say That Jess is masterful at looking at someone's IP and organizing it in a way that makes perfect sense, and that's one of the big things that she does for her clients. She has a podcast called Big Ideas Made Simple. Is that right?
Jess: [00:01:31] Yep.
Kris: [00:01:31] Yeah. That is right. And I think that, like, that really encompasses what she does. She'll take your big ideas and simplify them in a way that they can actually be digested, and that's really fun for the person, learning about your IP to go through it in a way that feels really good and not overwhelming. So Jess, welcome to the show.
Jess: [00:01:56] Thank you so much, and for such a kind introduction. Oh. I'm excited to be here as well. You're one of my favorite people that I've met through this, like, coaching endeavor, and I just, I have so much fun talking to you, so you know, any day with Kris is a good day in my book.
Kris: [00:02:13] We do have a good time. So we have a, we have an hour-long call once a month, and we always like to allow another hour just for yapping. Yeah A little cushion on the other, either end of that. So, Jess, I'm really happy to have you here, and I, I would love to hear in your words, like, how do you describe what you do and the problem that you solve for your clients?
Jess: [00:02:36] Mm-hmm. I love that you ask this, because it's something that's constantly evolving, as I spend more time explaining it to people and figuring out what language resonates. But I landed on the language of Big Ideas Made Simple because it was the shortest, simplest, clearest thing that I could say that kind of was a nice umbrella for everything that I've found myself dabbling in. Because I am, a multi-passionate, multifaceted human that has different interests and loves and, entrepreneurial endeavors, and it was like, what do I... how do I encompass all of this? And so I built Big Ideas Made Simple as a coaching, consulting, speaking, podcasting container to help people create a clear path through information to an outcome. And so I've taken my background and all of my experience first in education, where I did have a master's in curriculum and instruction, and then my years in franchises and real estate operations, where I ran a billion-dollar brokerage and managed 500 agents, and, and kind of married all of that into this new thing of helping people really figure out what is their vision, what is their end goal, what do they currently have, and bridging that gap between the two. And so you mentioned my business partner, Adam. When I first met him, he, he gave me the label of an architect. And I said, "Oh, that's a fun way to describe what I do," because I, I sit here and I'm like, "Hey, what is the big thing that you want done? So Kris, what do you want for your business? Great. What are the parts and pieces that you currently have now? Is there anybody else in your world? Okay, let's, let's write the, the plan, the strategy. Let's architect the framework you need to get from where you are to where you wanna be." And so I, I just, I love doing that, and like you said, superpower all the way.
Kris: [00:04:26] Totally. You do. You really make the path clear, both for your clients, but really for the people consuming that information
Jess: [00:04:37] Yeah. It's, it's been really interesting because I've worked with a lot of clients in different industries, and most people think, "Oh, if you haven't been in that industry, how can you help?" And I think that is where my skill set comes in, because I can consume vast quantities of information and quickly understand does it relate to the defined outcome or not, and have that filter. Where somebody who's stuck inside the jar is drowning in their own IP, right? They've got so much intellectual property and so many assets that they don't know how to see the forest through the trees. And so I can come in and say, "Okay, if you say this is the outcome," I can look at this and say, "Does it match or does it not?" Mm. And anything that matches can go into that framework, and anything that doesn't can become a bonus asset. Because I'm not saying get rid of everything, it's just let's create the clearest, fastest path so that anybody interacting with your stuff actually gets value out of it, and they can attribute their success back to your framework. Because w- if you have 10,000 hours of video in a platform, nobody knows what to do with that. And therefore, they think it's a waste of time, money, and energy, and they don't, become ambassadors of your program. Right. And so I really just, I enjoy helping people figure out how to kind of showcase their brilliance and their expertise in a way that other people can digest it, and then go out and tell the world about it.
Kris: [00:06:05] Yeah. It's kind of like, uh, w- when you're editing a movie, you have 10 hours of footage, and you have to painstakingly remove all the clutter and keep only what is, the gold and- Yeah ... only what's additive to the actual story, and eli- Mm-hmm ... eliminate the rest. But to your point, you don't have to throw it out. You package it over here in a bonus or, you know, repurpose that for a blog post or maybe- Mm-hmm ... it's better for social media. Like, it's not all thrown away, but it's just not part of your core- Yeah ... uh, framework or deliverable.
Jess: [00:06:46] I love that you mention, like, editing movies, 'cause I know there were, were a bunch of books behind me if you're watching on YouTube, but I actually am a big movie junkie, too. And the key thing there is sequencing as well, and understanding the journey of the client or the person trying to get to the end goal. And I think that's where a lot of people really struggle- Not only because they've been in it and they've got, you know, kind of, um, curse of knowledge, but also because they might have not done it in the fastest and clearest order that they turn around and teach it to. They might have stumbled through it, hit a few pitfalls, all the things, and if they feed all of their experience into AI, it doesn't always know, like, how to d- sequence it for somebody else. It's going off of the person who's used the AI platform. And so that's where having a human who has this skill set becomes really valuable, because I've used it to help people build challenges. I've helped people launch group coaching programs, and then like you mentioned, my business partner, Adam, I wrote his entire curriculum and then eventually became partnered with him to teach said curriculum because he was like, "You know this better than anybody else." And now I have the nickname of The Professor in his ecosystem. I love it. I got my honorary doctorate rather than, uh, finishing that degree.
Kris: [00:08:10] You did get your doctorate with him. And he is an extraordinary coach, and you two together m- are such a power team. on one of our first calls, I said, "Adam, I, I like you so much, but I love Jess." "I, I love Jess." So this is... And here we are. I'm,
Jess: [00:08:30] I'm flattered, honored, and- ... I'm glad that you see it. No.
Kris: [00:08:36] So you brought up, the idea of a challenge, and I wanna- Mm-hmm ... delve into that. That's something that you and I have talked about doing for my business. It's something that we're gonna do together at some point. I wanna time it right with the launch of the book, which is now coming out in April. So probably a month prior to that we're gonna do- Mm-hmm ... our challenge. And my challenge is gonna be, as it stands right now, the soundbite strategy challenge, how to create the five phrases that you need to get more clients and to become memorable and allow people to be able to understand what you do so simply that they can share it effortlessly. And that's really how we become known for the work that we do. So Jess and I are talking about doing this project, and I've been through challenges, but I've never gone through it with the mentality of like, how would I recreate this, or how would I do my own challenge? So- Tell us about how a really good challenge works, and how, if you were to design your perfect challenge-
Jess: [00:09:50] Mm-hmm
Kris: [00:09:50] number one, why do people wanna do challenges? And number two, how do you make a challenge killer?
Jess: [00:09:58] Oh, thank you for asking this question, because I've been very, spicy about this recently. I literally, this week, episode 31 of my podcast was how to gauge whether or not to spend money on a membership or a challenge, because I just went through a half dozen different memberships, challenges that were so painfully bad that I ended up rewriting them and sending the pitches to the people 'cause I was like, "Can I please help you?" And, and so the, the premise behind a challenge is it's a replacement in today's world for a master class or a webinar or something like that. And the, the key here is that a challenge showcases a small subsection of what you do in a larger offer. And so this is great for people who are coaches, for, content creators or even, like, agencies if they're like, "Hey, you... This is a little bit of a, like a do it yourself in a contained timeframe, and then at the end we can, we can tell you how you can have more if you found value in this small thing." And so the, the thing that I tell people when we enter into the context of the challenge is it's gonna feel like you're not giving anything away as the expert. It's gonna be so hard for you because you feel like you're not giving enough for the dollar amount value. But the key here is that the, the secret inside of it is not about how much content you deliver. It's about creating an emotional journey for somebody where they do get the outcome that the challenge is promising by the end of the number of set days. So whether your challenge is, is three days, five days, seven days, I really don't like them longer than that, then whatever you're promising to deliver, they get that at the end, and they've gone through this journey with you, and they feel so good about it that when you're like, "Hey, if you found value in this, if you got the outcome, here's the next step, and I'd love to invite you to it." Mm-hmm. And so the reason I had those challenges that I felt like were icky was they had great names. They, they were very clear, like, "Hey, you get this in this number of days." And every single one of them did not deliver that outcome.
Kris: [00:12:15] Wow.
Jess: [00:12:17] It was crazy to me.
Kris: [00:12:18] Wow. S- give, give us an example. I mean, without- So one of them was a five- without, like, without dogging on-
Jess: [00:12:24] Yeah, yeah, yeah ... whoever the... Yeah I don't, I'm not trying to, like, be negative- Yeah ... about the human, 'cause I love the human.
Kris: [00:12:28] Right.
Jess: [00:12:28] But the human was offering, um, results of a specific nature, so it was like a double your whatever kind of thing in five days. I was so excited about this, 'cause I love this human, I've worked with this human before. I was like, "Ooh, five days is way better than, you know, the, the year container. That's way more costly." Yeah. "I wanna see what this is all about." And I even didn't do the first challenge. So this was a challenge that they'd done several times, and I was like, "It's got all the kinks worked out, it's gonna be amazing."
Kris: [00:12:57] Yeah.
Jess: [00:12:57] So I get on there, and day one is heavy content, heavy IP, and no explanation besides a 15-minute YouTube video that you were supposed to watch as a pre-rec. But there was no glossary of terms, there was no, "Hey, you should have this outlined before we start." So there was a lot of frustration and overwhelm of like, "I don't know this lingo. I don't know this jargon. I have no idea what's going on. I feel behind." Day two was a lot more of that, and there was homework with it. So you had to go learn the thing before you could understand the thing to then deliver the homework. Day three was a pitch for a product to help support you in what you learned in day one and day two, and that was it the whole time. The whole hour of the call was a pitch- Mm ... for a product. They gave you a free trial of it, but it was still a paid product- Mm ... outside of the scope of the challenge. Day four and day five was the pitch to the upsell.
Kris: [00:13:58] Wow.
Jess: [00:13:59] Two days of upsell. So three days of sales, two days of heavy jargon in a five-day container. The math doesn't math there, my friend. And it hurt, because like I said, I love this human.
Kris: [00:14:12] Yeah.
Jess: [00:14:13] A- and so, I mean, you know me well enough to, to appreciate this, Kris, but I had, you know, bronchitis a few weeks ago and I was on a steroid to deal with the cough. Well, every time I take one, I cannot sleep to save my life. And I was so worked up over that challenge not delivering what I wanted it to, and I had friends that I had put in the challenge and was like, "You should come do it with me," and everything. Yep. That at 3:00 AM when I wasn't asleep, because I just couldn't sleep, I rewrote the challenge using that f- creator's IP and the transcripts from the calls from day one and day two, and I turned it into a five-day challenge with a workbook at 3:00 AM on my phone.
Kris: [00:14:55] I love that. S- that is, that is so
Jess: [00:14:58] you. And then I sent it to her. Yeah. And I was like, "Hey, I love you, but here's what this ch- like, this is your IP. I'm not trying to take credit for it."
Kris: [00:15:04] Right. "
Jess: [00:15:04] All I want you to do is understand that what you promised was not delivered, and here's how I believe that you can take somebody on a journey to actually get the outcome."
Kris: [00:15:14] What, uh, w- how did she respond?
Jess: [00:15:17] Well, her person who's like her second in command was like- Yeah ... "Thanks, I think we've already got it on lock." I was like, "No you don't, I promise." So I actually saw her at an event last week in person, and I was like, "Hey, I know you don't read emails, but I need you to go back and read your emails and go look at this workbook, and, like, let's have a conversation." Yeah. And so I still haven't heard from them yet- Yeah ... but I'm like, they're- they've got a new challenge scheduled for like three weeks from now, and I'm like, "Can we please talk before you do this challenge?"
Kris: [00:15:44] Yes. Oh my gosh. They have, they have like, uh, gold sitting right in the box.
Jess: [00:15:50] They have no idea how- Yeah like, how much I could change the trajectory of their upsell even. Not only is it- Totally ... 'cause, like, their landing page was so good for this challenge. And the, the title of the challenge was perfect, because every challenge should promise a clearly defined outcome. You get this in this many days. Like, this is exactly what you get at the end of your commitment.
Kris: [00:16:13] Right.
Jess: [00:16:13] And so, like, theirs was gold. And when they talked about what you would get in the context of five days, like the bullet points sounded great. Mm. But they gave all of that in day one and day two. Mm-hmm. And so the emotional journey, like, I had a hard stop on day three, and I had no desire to continue to want to work with them when all they did was try to sell me on other products and services in the thing I paid for.
Kris: [00:16:40] Right. I mean, the trust, the trust is broken, right? It was a paid- Yeah ... it was a paid challenge, right? And
Jess: [00:16:47] then- Yes, it was a paid challenge. Yeah. And so the framework that works really well for people, and I would ch- tell you this just like anybody else-
Kris: [00:16:54] Mm-hmm ...
Jess: [00:16:55] is you have to start with an emotional story to start the emotional journey. So why does this matter coming from you? So like you, Kris, if you were doing your Soundbites Challenge, you would start with a story about why you needed Soundbites. How did they impact your life and your business so that you build trust with people from the very beginning.
Kris: [00:17:15] Right. And what did it
Jess: [00:17:16] feel like
Kris: [00:17:16] for me- And then- What did it feel like for me not to have Soundbites?
Jess: [00:17:19] Exactly. Right? Yeah, because there's a, there's an opportunity cost. There's also an opportunity lost cost, and you need to help people connect with everyone, whichever one of those two things resonates with them. And so storytelling is an amazing way to do that. Mm-hmm. And so if you can start with a story, then the rest of the challenge you can anchor back to that story. So it gives you that really solid trust-building emotional journey foundation. And then for the majority of the time, so like I'll, I'll use percentages, let's say. You, you don't spend a ton of time on the story, like 10% maybe, and then like 80, 85% of the time you're taking them through the journey of the steps. Like, you are creating the process for them and walking it through, and you are direct instruction teaching, but you can also have micro Q&As and things like that along the way that like breadcrumb to the invitation you're gonna make at the end. Mm-hmm. And then you make sure at the end that you capture their emotion again. So what did they think they were getting to what they actually got? What did they have false beliefs around that now they have true n- truths around, right? And so the end, like- percentage is really just making sure that you've walked them through the journey and they feel like they got what they paid for. Mm-hmm. And that's when you have the opportunity after the emotion and the resolution to say, "Hey, if there was value in this for you, if you stay on the call just a couple extra minutes, I'd love to invite you to what I, what else I do." And you do not make it part of the actual challenge.
Kris: [00:19:03] Right.
Jess: [00:19:03] Right. Because people are paying for something. They're paying for an outcome. You better darn sure make sure you give them an outcome.
Kris: [00:19:09] Right. Right. Right. And it's okay to-
Jess: [00:19:11] Sorry, I talked a lot there
Kris: [00:19:12] No, no, it's great.
Jess: [00:19:13] I, I told you I was spicy.
Kris: [00:19:15] It's, it's okay to sell, but you don't want that selling to be part of the challenge. You want it to just be at the end. I love the way you call it an invitation. Mm-hmm. It, it's... No one wants to be sold to, but they would love to be invited to whatever that next step is. Yeah. And that's such a different way to present it. When you were sharing, the image that came to mind for me was my... I have an eight-year-old son named Jude. We both have young boys. Mm-hmm. Um, and on the first day of kindergarten, they took a picture of each kid. Mm-hmm. And it was, like, kinda like almost a life-size kind of cutout of this kid. And then at the very last day of kindergarten- They did it again and just showed how much they've grown. And it said on the first, image it said, "I couldn't read." And then at the end of the year it said, "I can read." And we got to take those home and, Jude got to hang this on his wall of, like, looking at himself as a early kindergartner that couldn't read, and then the transformation that happened. And so I think such a big part of what you're talking about is also, like, celebrating that transformation and- Yep reiterating that transformation- Mm-hmm ... and acknowledging the transformation and putting a bow on it, just like you do at the end of a movie, then move on to the invitation.
Jess: [00:20:54] Exactly. one of the best challenges that I've seen done that I attended to study and learn from was Graham Cochrane's, and he's changed the name a couple of times, but I think he calls it, like, the 10K Challenge or something like that, 'cause he's like, "You can sell anything," you know? And here... You just have to frame it a certain way. And I wanted to rewrite part of his challenge, so I'm not saying it's perfect 'cause I still naturally do that. But he was the one that taught me that invitation language, and he shared it as if, you know, you are at a restaurant and they're like, "Well, would you like a side? Oh, would, would you like dessert? Would you like an appetizer?" You're much more inclined to say yes than be like somebody throwing the menu in your face and saying, "You have to buy this. You have to buy this." Yeah. And I was like, "That is so powerful when..." Because people buy through emotion. And so if you are not creating an emotional journey or, like you said, the transformation for them and reminding them that the transformation happened with... So, like, the visual of Jude is awesome. Then they're not going to be as tied to it and excited about the offer in an invitation format at the end. Right. And something that he does that I've also seen done in probably half the other challenges I've attended is they will take, small snippets or cuts from the previous day's group, um, recording and trim out some of the transformations and ahas that people had that remind... And then they play it right at the beginning before they start the next day's content. So it's like- 30, 60, 90 seconds. I mean, it's not a lot. Yeah. Some I've seen go as long as five minutes, and that's too much. But, you know, it's one of those things where it's like, oh, so-and-so said this yesterday about, like, they had this belief that changed, or they had this idea that changed, or they had this win. And by putting that at the beginning, it gets people in that emotional state faster so that the depth is there. And depending on how many days you do, I mean, that can really move somebody and move the needle from a, like, you were unknown to them to liking you, to trusting you, to wanting to buy it from you or work with you. Right. And, and so, you know, Adam and I have run challenges for his company, which is called I Love Coaching Co. Um, and we joke, I was like, "I need you to define what co means," because w- it's a community. It's not a company that, like, you're a coach of. I was like, but it could be cohort, collaborative. Like, co could be anything. Yeah. Yeah.
Kris: [00:23:30] Yeah.
Jess: [00:23:31] But anyways, ... his, his challenge is the same kind of concept. And it's so funny how many people we've been able to convert from a very low-ticket challenge to a high-ticket membership- Mm-hmm ... by taking them on an emotional journey and delivering everything that we promised. Because people go from not knowing you to trusting you in f- ours is, three days now. It used to be five days. But... And they're like, "Yeah, if you did everything you said you were gonna do and I got this result in three days, then when you ask me for something else, I believe that that's gonna be a thing."
Kris: [00:24:09] You've pro- "
Jess: [00:24:10] I believe that you can do that for me." You've
Kris: [00:24:11] proven-
Jess: [00:24:12] Yeah ...
Kris: [00:24:12] you've proven that you're, you've been able to solve a micro problem for them in three days. Yes. And if you can solve a micro problem for me in three days, I can only imagine the bigger problems that you can solve for me in six months. Exactly. Yeah.
Jess: [00:24:27] Exactly. Mm-hmm. And that's why this works so well for coaches and consultants and anybody who's in that kind of creator space, because, I mean, we're, we're in a weird era now, and I've said this on several other podcasts too. I believe that we're past the information age. You can get infor- information for free anywhere. We're past the era of buying how-tos, because you can ask AI for it. Again, Google it, whatever. And now we're in this new era of people paying for proximity to people who have done the thing, and they're paying for how yous. And so a challenge is a micro how you.
Kris: [00:25:05] Mm. Mm.
Jess: [00:25:06] It's, "Oh, I want to achieve this thing. I wanna have this result. I want this outcome. This person says they've done it, and now, in three days, they're gonna teach me how to do it? Cool." And so people are more willing now to buy into a challenge or something where there's proximity, they can get questions answered, because they're learning a specific path to an outcome, not just buying a PDF or buying a course that doesn't give that human feedback or the ability to, figure out what the story is for them that might be slightly different from the original presenter.
Kris: [00:25:45] That
Jess: [00:25:45] makes so much sense. And so I just, I think that's a really powerful thing for anybody who's in this space of understanding that- I, I don't wanna say courses are completely dead, but I think courses are much more dead than they were three years ago because of the advent of AI, and people are now desperate for proximity to real people. They- They want authentic humans ...
Kris: [00:26:08] I think enough people have bought enough courses and not gone through them, or not finished them, or started them and bailed, and they realize now more than ever that they need their hand held. Mm-hmm. And they, they, to your point, just crave the guidance. Yeah. Like, the actual human guidance, someone's brain, who knows how- Mm-hmm on their unique situation, because everyone's different. Mm. There's no cookie cutter solution that's gonna fit everybody. Like, there's just nuance- Mm-hmm ... for every, every coach, consultant, business owner, every- everybody. and so that proximity, I think, is incredibly valuable.
Jess: [00:26:54] Yeah. It is. Yeah. Well, and, and it's valuable whether you're doing a, a small, contained thing, like a challenge, masterclass, training, whatever you're calling it, or a larger thing, which is your membership, your community, your group coaching, whatever you're calling that. I mean, that's, it's the same thing at scale, that people would rather spend five, 10, 20,000 on something where they're getting proximity to humans. one that's already done it, so like a founder, but also others who are going along the same journey that they're going along towards the same outcome so that they don't feel alone in it.
Kris: [00:27:33] Mm-hmm.
Jess: [00:27:33] And, and I am very passionate about what it looks like to have a good quality group coaching or membership, and the three pillars that you need inside of that, because I've s- I've watched some of the foremost leaders in certain thought leadership spaces build things that flopped, that were very high ticket. and it hurts to watch, because I'm like, "I respected you. I might've, might've even potentially put you on a pedestal, and I probably shouldn't have done that. But, like, I respected you. I spent a ton of money to be in this room, and all you gave me was a book report and a Slack channel." And I'm like, "That's not what I wanted."
Kris: [00:28:15] Mm-mm. What, so what are the three pillars?
Jess: [00:28:18] So the three pillars in my world, I think of it like a three-legged stool, and the seat is the, that defined outcome, that payoff that you're promising people.
Kris: [00:28:25] Mm-hmm.
Jess: [00:28:25] And each leg is important to actually have that seat be balanced. So we talked about proximity, right? And this is not an ego play. This is, s- uh, ability to get feedback from somebody who's already gone through the process and done the thing. So proximity is not about celebrity. It's about success in the outcome space.
Kris: [00:28:48] Mm-hmm.
Jess: [00:28:48] The second one is that, that process. What are the steps that you took in, like, a three to five step process to get there? Nobody wants 52 weeks of something. I had somebody try to sell me on a high-ticket coaching when they told me it was a coffee and connection call, and I was like, "Oh, that was a bait and switch." And they were trying to sell me on a binder of 52 weeks of homework as part of it, along with daily one-hour calls to get the homework done in, and I was like, "I would pay to not be in that, thank you." Like, how much can I pay to get off this call right now? But, like, seriously. So they, people want a clear, simple, clean process, which is where my love language is. And then thirdly, they want peers. They want proximity to other humans that are trying to get that same outcome so they're not doing it alone. Because you can go read a book alone, you can go play with your AI alone. If you're paying for something, you're paying to be in the room with other people so that you can connect and learn from them and not do this in a silo or inside a bottle, as we were talking about earlier.
Kris: [00:29:55] There's so much power in the community part, the peer part. Yeah. Because I think people, people want their hand held. Mm-hmm. And They think they want one-on-one, but they really, they really need that peer community, 'cause So much encouragement, guidance, insight, support- Yes ... comes from people literally navigating the journey with you. Yes, you get that proximity too, so you get the best- Yeah of both worlds. But you do absolutely need all three of those, um-
Jess: [00:30:30] Well, and- ...
Kris: [00:30:31] stool legs ...
Jess: [00:30:32] yeah, yeah. It, it's such an interesting thing, 'cause y- typically, like, in I Love Coaching, so we teach people how to build coaching businesses from their unique experience and expertise. Mm-hmm. And so we provide the framework and the coaching on building a business, and then you get to go build whatever you want, which is a beautiful thing. And so in the framework, we teach people how to start with one-on-one coaching a- before they try to step into group coaching because I've watched too many people try to build it around their proximity, but they don't have a leg of process because they've never coached before. Right. Or they haven't streamlined their coaching into one outcome. Mm-hmm. And they, they throw people who are not connected to each other into a group, and then the group becomes dead silent because there's nothing uniting them. They're not all working towards the same thing.
Kris: [00:31:23] Right.
Jess: [00:31:23] And so for me, I am very, very determined to help people understand that people need people, people want people, but you do not just build a group arbitrarily, because it needs all three of those legs to, to grow and thrive, not just survive. And so- that's, that's where a lot of my personal coaching and consulting comes in outside of things, you know, related to I Love Coaching and, and the Big Ideas Made Simple, is I will help people build a challenge, build a community, launch it, all that, to make sure that they have all three of those legs in, in place so that they don't feel like they're having to carry the entire stool on their back while holding the proximity leg.
Kris: [00:32:06] That, that's a powerful visual right there.
Jess: [00:32:08] Yeah. I, I think in pictures, so...
Kris: [00:32:13] Okay. So the perfect challenge. Yes. The perfect challenge. I think a three-day is the perfect length. Mm-hmm. I think people- I
Jess: [00:32:22] like it ...
Kris: [00:32:23] I, I just think three feels good for people. It depends- It does ... on what you're trying to accomplish. But if you can do it in three days, that's way more valuable than having to do it in five days to people.
Jess: [00:32:34] Yeah. Yeah.
Kris: [00:32:35] Right?
Jess: [00:32:36] I like three days a lot. I would, I would typically cap it at five. The reason I said seven is maybe you have it run over a seven-day window, but it's not meeting all seven days.
Kris: [00:32:47] I get it, yeah.
Jess: [00:32:49] And, and so, um, typically I really love three to four meeting days.
Kris: [00:32:54] Mm-hmm.
Jess: [00:32:55] And, and so you can do it with three days of content and then a bonus Q&A or a VIP day or something like that.
Kris: [00:33:03] Yeah.
Jess: [00:33:04] and that works beautifully. Or a lot of challenges that I've done is if you offer VIP extra coaching, which is literally no prep, you just answer questions, you can do it where, like, the Q&A is before or after the live training, and you just use a different, like, Zoom link or whatever- Right you're using platform-wise there. Yep. Yeah. So that way people understand, hey, you're gonna get the defined outcome in the main session, the general admission ticket. Mm-hmm. The VIP stuff, the extra stuff, that's, that's an upsell, but that proximity should help you get there even faster. So yeah. Right. I- ideally three days of teaching.
Kris: [00:33:46] Yeah.
Jess: [00:33:46] And, and in less than a seven-day window.
Kris: [00:33:49] Of course. I like it. Yeah. Yeah, the, the challenge that you and I had designed was three days. Mm-hmm. And then on the third day after the teaching- Yep ... we're gonna have Donald Miller come in and do hot seat coaching. Yes. Which is the VIP upsell offer. Mm-hmm. Like, getting his eyes on your business, and I'll be, I will be there too. But that's a, a way to keep it to three days. I could have, and I, I still might, make the VIP portion of it day four. Yeah. But I really like, I like the idea of having that third day. You've got that momentum- Yeah ... and getting that VIP experience after that.
Jess: [00:34:32] I think out of all the ones I've- been in, and I think I'm, I'm high double digits now. Like, I collect, I collect things, Kris. I, I think I like the ones where the VIP stuff is on the same day as the training, 'cause I can time block and my head is in it, like you said. Right. So there's no, like, task switching for me or, like, mental train shifting, and that's really powerful. And so, the way that you designed yours is great because yours is unique with the Donald Miller play in. But if it's just you delivering, like Adam and I do for I Love Coaching, we actually do VIP every day. And so that's an option as well. Mm-hmm. And that when you... So the average challenge is a $97 challenge with the VIP upsell being $297. Like, that is almost the standard in the industry as of this recording at least. I
Kris: [00:35:26] love it. Okay.
Jess: [00:35:27] And, and so- Keep going ... you know, 97 gets you, for most people that's three hours, right? If you're doing an hour, three days a week.
Kris: [00:35:36] Yep.
Jess: [00:35:36] And that's about the same as a master class or a webinar. So it's, it's really the same thing, but it's broken up. Like, if you think about the length of time when you're teaching a, a webinar or a master class, all you have to do is take that time block and turn it sideways, and that becomes the arc of your challenge. Right. So it's really the same concept. Start with a story, teach the steps in a, in a bite size emotional journey where people get quick wins along the way. Mm-hmm. And then recap it and make sure that you get, you know, what you paid for at the end. And yeah, the, the, the VIP- And
Kris: [00:36:12] then, and then your- Keep going ... your, your VIP portion is at the end of the call every day, like a Q&A or?
Jess: [00:36:18] It can be beginning of the call. Okay. It can be end of the call. How do you do it? It can be extra call. How do you do it? It really doesn't matter, but I- The ones, more of them are on the same day, so that way people are thinking about it. So like yours being on the end of day three is perfect for that.
Kris: [00:36:33] Right.
Jess: [00:36:33] And VIP is only Q&A, so it's only paying for proximity to the person hosting.
Kris: [00:36:39] Got
Jess: [00:36:39] it. It is no extra content, unless you're delivering, like, an answer to a question that then becomes valuable to the people listening. Right.
Kris: [00:36:47] But it's your- So- ... the expert's eyes on your-
Jess: [00:36:51] Uh-huh ...
Kris: [00:36:51] situation, and that's- Yeah ... the VIP. I love it. It's so simple.
Jess: [00:36:56] It is. Well, the... We heard a line, Adam and I, somewhere, I forget who I can attribute it to, but they said, "People pay to pay attention. People pay a lot to pay a lot of attention." So the higher the ticket, the more likely people are invested in getting the outcome that they're paying for.
Kris: [00:37:15] Right.
Jess: [00:37:15] And so I like this framing of, hey, general admission is gonna get exactly what they paid for. They're getting this framework, this model, this whatever. The VIP, they're paying for extra proximity and extra feedback in their world, and that, that's where they're paying more, but they get more attention. Mm-hmm. And so they give more attention at the same time. And what we found math-wise super interesting for anybody doing the upsell thing is typically we find that on average a challenge has about 20% VIPs. And then you can convert about 20% of those into your upsell if you do that invitation the right way. There are some that go way higher and do more, but Pareto's principle of the 80/20 rule works really well math-wise- Wow ... for the average of challenges into upsells.
Kris: [00:38:09] Wow. And then the, the people who pay IV- VIP are way more likely to become clients. Is that what you're-
Jess: [00:38:16] Correct ...
Kris: [00:38:16] saying? Wow.
Jess: [00:38:17] Because they've already paid more, and they- Right ... and then they get more value, and there's more proximity, so the trust is gained faster. Your authority has grown larger in their eyes, so therefore they are more likely to pay attention. So if you're a math person, and numbers and percents don't scare you, and fractions don't scare you 20% of 20% means that somebody who is buying the VIP and then your upsell is 16 times more valuable than the person who bought a general admission ticket.
Kris: [00:38:50] Mm. '
Jess: [00:38:51] Cause 20% is, you know, one-fifth, and then you kinda do the math of 20%- Right ... of 20%, and so- Right ... that makes them 16 times more, more valuable. And I think that piece and that mindset of, oh, not all attendees are equal.
Kris: [00:39:07] Yeah.
Jess: [00:39:08] And, and so understanding also, like, your ratio of conversion and where you're getting people from and what your goals are on the other side of a challenge can also really help you. 'Cause for me, it's not about having 10,000 people in a challenge if my goal is a certain number of upsells on the other side. It's how many do I need in VIP, 'cause if that's roughly 20%, and then how many do I want, I can go and reverse engineer that. And that, to me, is a freeing thing for people who are big thinkers and high achievers and have big vision, but then they're, like, overwhelmed by the, the almost, like, the selling or the recruiting of a challenge. Yeah. It's like, no, if you want five people on the other side, multiply that by five. You need 25 VIPs, multiply that by five. That means you do 125 in the challenge.
Kris: [00:39:58] It
Jess: [00:39:58] just removes- That's a doable number ...
Kris: [00:40:00] it's a doable number, and it removes all the drama and all the emotion from it. It's d- Uh-huh. Math- It's a number, numbers game. Yeah.
Jess: [00:40:07] Okay. So my, my first career, I told you I was a teacher. I actually taught history and math, which are, like, the two most considered boring subjects or least emotional subjects, but I think they made people the most emotional bec- when they didn't understand them.
Kris: [00:40:22] Right,
Jess: [00:40:24] the most frustrating. And so I laugh now because I think in, you know, percents and fractions and all this stuff, and I use math to help me remove emotion from things when I'm feeling it. Yeah. And people look at me like I'm nuts, and I was like, "No, math does not make me emotional. It makes the path clear and easy." Right. Literally the path is in the math, my friends.
Kris: [00:40:43] I love that. So how frequently do you recommend doing a challenge, and how frequently do you do your challenges?
Jess: [00:40:51] Oh, that's a good question. I would say don't do it so redundantly that you burn out, like, your email list, if you've got an email list or an audience on socials. So I see it work really well either, like, every other month or quarterly, and then you can filter in other events in between if you want. Or that way it becomes kind of a cadence where people know it's coming, and they get a little FOMO if they miss out and they hear great things. Yeah. But it's not so far away that they can't buy into the next one and know the next one is coming.
Kris: [00:41:27] Right.
Jess: [00:41:27] And so I, I really like quarterly. And then what I do with I Love Coaching is we have live events in Charleston at the headquarters, in other months. Or we'll do a webinar solving a specific problem that isn't related to the challenge, but is related to a different facet of coaching. Mm-hmm. And invite people, and that's a paid class that's usually 90 to 120 minutes. So they're getting about the same thing for the same price, but we don't do a VIP upsell on those,
Kris: [00:41:55] so. Got it. Cool.
Jess: [00:41:57] Yeah.
Kris: [00:41:57] So yeah, you can and sprinkle in other engagements and ways to connect- Yeah ... with your people. But I, I love the idea of a, a quarterly challenge.
Jess: [00:42:08] Mm-hmm.
Kris: [00:42:08] A three-day challenge as a way of just continually, and relatively, not totally effortless, but once you get it down to a well, well-oiled machine, it just becomes rinse, repeat. It does. But what a wonderful way to bring new potential clients into your world, bring new followers, and if they don't become clients, th- that they can share you with the people that they know that might be a right fit for you.
Jess: [00:42:38] Yeah. And there's a lot of books out there, I think I've read 'em all on, like, launches and building groups and cohorts and programs, and I love a challenge as an easy way to extend an invitation to a group of people who are more ready buyers without feeling like you have to do a hard sales launch. Mm-hmm. And so I think that's a really powerful thing of you are changing your own psychology. instead of I have to go sell this, uh, so many seats to this thing- Right ... you can say, "Hey, I want this many people. I want in these seats. Let me go do an invitation to a warm audience." And that is so powerful.
Kris: [00:43:20] And an engaged, engaged- and warm audience. I d- Yes ... when we think about the, the last 10 years, I think the downloadable PDF is played. Nobody wants that. Nobody wants a DIY course anymore. Right. People are... The formula of a masterclass or webinar is also played, and people are, are m- tired of being sold to. Mm-hmm. And I feel like the challenge is n- much more relevant, much more current, much more ethical, honestly- It is ... than, th- than the way we've done things in the past.
Jess: [00:44:03] Well, you, you hit the nail on the head, of people are being- tired of being sold to. And I think anything that's labeled a webinar is automatically now filtered through people's ears as a sales pitch. Yeah. And they're like, "I will only sign up for a webinar if... And then I will, like, log in, leave my camera off, and wait till they give us the discount code or offer for the thing that I was actually planning on buying at the end or two-thirds of the way through," like the pitch usually goes. And so I, I love... I, I still think there's space for masterclasses, workshops, and challenges, because they are delivering something specific. And, and so, yes, webinars are dead, courses are dead, PDFs are dead in my world if they are not specifically giving somebody an outcome. Mm-hmm. And so, and I love that you said it, it's more ethical, because I, I agree. I'm like, I don't feel like I'm selling anything. I'm giving whatever somebody paid for every single time.
Kris: [00:45:01] Right. And rather than just, like, delivering this, vast amount of information and hoping and praying that they digest it, the challenge allows it to work with the human brain and be more bite-sized and feel- Yeah more supportive and just much more engaging. It's such a wonderful way to market.
Jess: [00:45:23] I look at it as if your membership, your offer that you have, the big thing, the core offer on the other side of this, is like a whole book's worth of knowledge. A challenge w- you know, master class, whatever, is like the first chapter of that book. So you can give away context, and you can give away the framing of everything they would get. And you're delivering something in a container, so you get to put your best foot forward to keep encouraging people to, you know, keep reading essentially. So we call it the first chapter framework inside of I Love Coaching, because it's really truly that of, you give away s- enough, but it's still attached to everything you're doing. It's not something totally random or different.
Kris: [00:46:08] Right.
Jess: [00:46:08] And so you're, you're whetting their whistle and, and getting them excited about reading the rest of the book.
Kris: [00:46:15] Mm-hmm.
Jess: [00:46:16] And, and so for me, I just, I think that there's more opportunity for more people to do this. And I'll tell you, it's not hard. And like I love you said, you can rinse and repeat it. It is. Like, it's so great. Adam and I have run this, the I Love Coaching challenge for, like, a year and a half now, so we've done it a number of times. I tweaked and iterated along the way to make sure it was more valuable. And like I said, we shortened it from five to three days. But at the same time, he and I can show up and com- like very, very committedly and articulately say everything, because we know that that leads to this outcome, which then in- informs everybody of what they could get if they joined our annual membership and worked with us, whether in a group setting or one-on-one or both. And so when you can get to that space of, oh, I don't have to create something new. I have to take a little piece of my best stuff and give that, like, best foot forward, then it, again, builds more trust and authenticity in you, because it's not a performative thing where you're not delivering.
Kris: [00:47:20] Mic drop moment.
Jess: [00:47:25] I need to get like a styrofoam microphone so I can just like drop it on these calls. All I have is from my friend Adley Kinsmen, a rubber chicken. Can I drop that?
Kris: [00:47:35] You can, you can drop that. That's... Yeah, perfect. Mic drop. Tiny mic drop. Um-
Jess: [00:47:40] Tiny mic drop. I love this.
Kris: [00:47:42] Jess, it has been so much fun talking with you today. I honestly, I feel like we should do a monthly, Professor Jess comes- Oh, my gosh ... to the show and just infuse all your wisdom- I,
Jess: [00:47:55] I mean- ... into our conversation ... I'm always happy to come back, Kris. All you have to do is tell me when and what I'm talking about, and I will be here- I- Yeah ... so appreciate the opportunity to have this conversation, 'cause like I said, I got, I got opinions for days.
Kris: [00:48:09] You do. We, y- we need to hear more of you, so thank you. Where can, where can we find you?
Jess: [00:48:15] Yeah. I'm on all major platforms as The Jess Weber, double S, double B. Not because I'm full of BS, I promise. and, and so you can find me on all social media platforms. My podcast is Big Ideas Made Simple, and that's on all platforms as well. So I would love to connect with anybody. If there's value or you heard something or you got a question or you wanna go, you know, verbally spar, let's go.
Kris: [00:48:40] Awesome. All right. Thanks so much, Jess.
Jess: [00:48:43] Thank you, Kris.

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