Why Do Inspired Clients Stay Stuck? Build workshops that drive real change w/ Jake Wysocki

In this episode of the Level Up Creators Podcast, host Amanda Northcutt interviews design‑thinking strategist and workshop‑facilitation expert Jake Wysocki. Jake recounts his unconventional career path—from mechanical engineering to product management, to corporate design‑thinking, to a family‑focused life‑design practice, and finally to a solo business helping coaches and consultants create high‑engagement workshops. The conversation pivots to why workshops matter more than webinars, emphasizing a human‑centric, "help them take a sip" mindset that guides participants to take their first actionable step rather than merely receiving information. Jake shares concrete frameworks for building world‑class workshops: (1) defining dual outcomes (client and business), (2) articulating a three‑adjective program identity, (3) using the 10‑50‑99 iterative development model, (4) conducting Hopes‑and‑Fears or Voice‑of‑Customer research, and (5) mapping the full customer journey (pre‑work, welcome videos, in‑person moments). He also outlines ritual structures for cohort programs (wins at the start, takeaways at the end) and provides "wow" examples such as AI‑augmented Pillars exercises and in‑person meet‑ups that boost human connection. Jake differentiates workshops from webinars by stressing hands‑on work, low‑lecture, and the "drill‑instead‑of‑hole" analogy. He advises on packaging (free vs paid), sales‑first design (sell the 10% outline), and the importance of fun, authenticity, and lowering the filter to create memorable experiences. The episode closes with Jake’s 45‑minute “Workshop Why” consult offer and a reminder of Amanda’s MRR Accelerator program.
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Hello, you're listening to the Level Up Creators Podcast. Amanda Northcutt here, founder and CEO. We build boutique coaching and consulting firms for subject matter experts so you can run a stable, predictable, multi-five-figure recurring revenue business. And we are so glad you're here. Welcome. Today, as usual, we have a guest, the incredible Jake Wysocki. Jake is known for designing high-engagement, high-outcome workshops and teaching, teaching the facilitation discipline that makes them work. And our conversation today is something really, really special because we're diving into how to craft world-class group workshops that deliver clarity, momentum, and measurable results. results for your clients, which, yes, you absolutely need. Um, Jake is a former design thinking strategist who trained hundreds in corporate workshop facilitation. He now partners with coaches and consultants through a done-with-you approach to architect workshops and cohort-based programs people love to run and attend. Beyond his expertise, he's obsessed with the psychology and product design behind the sessions that actually change behavior. Jake, welcome to the show.
Thanks for having me, Amanda. Happy to be here.
Yeah, I'm glad you're here. Let's just like kind of kick off right from the top. Can you give us kind of the Cliff Notes version of how you moved from design thinking strategist to helping coaches and consultants? Kind of, you decoupled yourself from the corporate world and are now doing your own thing. Like walk us through, how the heck did you get here?
Yeah, I'm going to say what probably everybody says, which is I have this crazy backstory and like, you'll never believe it, but I think everybody says that. So I'm going to say it anyway. I have this crazy backstory, never expected to end up here. I'll, I'll actually take a brief step back. And say, I actually have a mechanical engineering degree. So that kind of sets some of my mindset, systems, processes, stuff like that. Took a left turn into sales out of school. Then I quit my job, traveled for a year with my wife. And then I came back to the United States with the same company I was at just by chance in a product manager role. That's where I got introduced to, and I was actually running a software project basically. And that's where I got introduced to the design team at the company I was working for and design thinking. And I don't know if you know design thinking, but I'm going to assume you don't and your audience doesn't just for clarity here because I feel like it's a little bit buzzy and everybody's like, I've heard this before, but I don't know what it means. Tell me what it means. For me, to keep it super simple, it's a capital D designer, like someone who went to school for design and does design work all day, every day. It's their mindset and their toolkit, which is usually human-centric for a mindset and sticky notes, which is another way to say structured exercises. For like their toolkit, and so anyway, I started. I joined the team a few years later after I met them at the same company, and that's when I became this design thinking strategist you mentioned at the top. And I was teaching, coaching, and actually facilitating workshops within our big Fortune 200 company that I worked for. So how did I get to where I am today? Which is the real question you asked, which I kind of did the politician's approach and answered the question that I wanted to answer first anyway. But really, the simple answer is I felt like it. So I've been talking for a few years about. Like doing my own thing, kind of in this vague sense. And my wife one day said, so when are you going to do that? This was about, as of this recording, about 2 years ago, actually almost 2 years to the day, end of summer 2023. And she kind of pressed me on it. I didn't have any good answers. And we kept digging a little bit and she pressed me some more. And I said, I guess I don't know. Like, why not now was basically the answer. And so I put in my notice, gave them a few months' notice, and I left at the beginning of 2024. There's a few other beats in there real quick. I started with Life Design. Yeah. So, my wife and I have been doing— the original idea for me leaving was life design, helping other millennial parents live regret-free. And my wife and I have been doing these state of the unions, which is kind of like a zoom-out strategy session, if you will, for our marriage. And I'm like, all my friends, they're great. They seem to be doing fine. But man, they could just use a little bit of like some of these things that my wife and I do. There's going to be a ton of people who want to want help with this. And there might have been. And I was starting to get a little bit of traction. But along the way, somebody knew my background and asked me to help them with an in-person workshop that they were doing for their coaching clients. And I was like, yeah, I'd love to help you. I just helped them for free. I had like notes everywhere and I was like super energized, more energized than I'd been. And so to answer your question in a different way along my entrepreneurial journey, I also just kind of went with my gut just like I did to leave my job. And I said, you know what? It feels like I should be headed this direction. And that's actually around the time I met you in Dustin's accelerator was in the middle of my pivot basically. And that was about a year ago. And so that kind of leads me to where I am today, helping people build world-class workshops. So there was probably a longer answer than I should have given, but I like to talk. So there you go.
No, I think that's great. And that's very helpful context. It's good to know. And I feel like at the top of this podcast, every guest I speak to does talk about this crazy winding road, unexpected path to get where, you know, they've gotten. And all of us have chosen this road less traveled, if you will, of entrepreneurship. And it is a tough path and it is full of unexpected surprises. And by factors that we cannot control. In some cases, we can. Sometimes we make intentional decisions. Sometimes we fall into things. Sometimes we follow our intuition. Sometimes we take other people's advice for better or for worse. And so, it's always, I think, really insightful for people who are listening. Like, the idea is for our show to help be a couple of steps ahead, right? So that there's a path and a trail that's been blazed and we're like, we're shining the flashlight on where to go next and knowing that there's no one tried and true set path here and that it's okay to— take a left turn, like you said, or stumble and start over, or, you know, go 2 steps forward and 1 step back, or 1 step forward and 2 back. So I think that's really, really useful information. It's also very relatable. Like, this is a very human process and it's freaking hard. So I appreciate it.
Definitely.
Okay. I have to ask you about travel because I also traveled full-time with my family for a couple of years, many years ago. So where did you go? How did you— were you like in an RV? Did you guys Airbnb it? Tell me.
Okay. So, uh, I'm just going to earmark this and then you and I offline can talk even deeper unless we want to make this a, uh, travel the world podcast or something like that. Because my wife and I also want to take our kids and travel. We haven't done that yet, but that's on the horizon, hopefully in a few years. But anyway, that's for another conversation for me and you. To answer your original question though, we did Europe, Asia, and South America. And our favorite, because usually people ask and I like to share, Europe was Switzerland. We happened to hit the Alps like In springtime with the flowers blooming, and we were in this hostel up in the mountains. I don't like to use the word magical too much, but it was about as close to magical as I'll allow myself to use that word for. It was awesome. And then Japan overall was our favorite. We just loved Japan. So I'll go back there any day. In fact, I'm going to try to manifest this right now. We're hoping, we are planning to go to Japan with our kids for spring break in not this coming year, but the year after that and hit it during— Oh, that's awesome. cherry blossom season and stuff like that. Because we have 11 days because it butts up against Easter. So we're going to try to capitalize on that.
Nice. And how old are your kids right now?
Right now they are, um, just turned 8 and almost 5.
Oh, that's such a sweet age. Yeah. Our son was 5 and 6 when we traveled full-time. So that was—
All right.
Interesting. Uh, but it was like, you just gotta freaking do it, book the trip, schedule it and go. Otherwise, yeah, that's great. Y'all are planning ahead, but don't plan too far ahead. Do it now.
Okay. So, I love that. I'm going to turn the tables really quick and I'm going to take the host mic because I know everybody wants to know, where did you go? Just tell me briefly. I want to hear really briefly about your trip.
We really thoroughly covered the Western US, a lot of the Caribbean, and Western Europe. So, I have like this long crazy health journey. And so, that was limiting in terms of where we could go. So, I had access to practitioners and food that we were familiar with and that kind of stuff. So, that was Frustrating in some ways, but that's okay. We still had we had a pretty amazing time and ended up permanently relocating from Texas to Colorado. And we live right on the foothills of the Rocky Mountains now and absolutely love it. So that you know was kind of like the catalyst for a pretty seismic shift in our life, and it was pretty cool. I just needed to give myself permission to do something different and to go a different path than anyone in my family or anyone in our friend group was doing. But we just felt you know a really strong pull toward. travel and learning about different places and cultures and opportunities and ways of living, you know, like mission accomplished. I think travel is a very, very, very important part of life so that we're exposed to difference.
Yes, I love that. I think some of these themes will come in when we talk about world-class experiences and stuff too. But I want to ask so many more questions, but I'll give the mic back to you and you can take it wherever you want to go next.
Well, let's double-click there on world-class experiences because we're talking about Workshops, and you are specializing here in this area. So I want to hear a little bit more around your thought process on why workshops. You kind of like took the lid off on that a little bit, but I want to hear more about that and the role that workshops play in a coach's and consultant's playbook. Obviously, I've got a pretty strong like point of view on this, but with your background in design thinking and facilitation, I'm so interested to hear kind of how you've put all these skill sets, kind of the kitchen sink of skill sets into this one area of focus. So How did you get here and why is it so incredibly important to coaches and consultants that you're going all in, all your chips are on the table for this?
Yes. Okay. So I have a few things that come to mind. Let me try to hit them all here. The first thing is just why I liked workshops and design thinking, which those 2 things aren't necessarily synonymous, but they're often intertwined along with human-centered design, if those out there listening are familiar. All these things are in the same world. What I love about them is it mixes this thing I kind of mentioned at the very beginning with my process mindset, my system mindset. And I don't know if I heavily mentioned this, but I love the human element of things. I love things to be fun, to enjoy life like we kind of talked about with travel. And to bring those 2 together is what like design thinking is for me. And that's— so every workshop doesn't have to be that per se. Like that's not necessarily inherent to workshops, but that's what I want to emphasize in the workshops that I help design and deliver, right? And I think it's kind of natural for most workshops to have some element of that. Contrast that to, and I'm not knocking, I don't know your stance on webinars. I'm not knocking webinars per se, but I have this sort of soapbox, if you will, about webinars where I don't know if I'm going to make this stand exactly, but like never do a webinar, always do a workshop instead if you're going to do a webinar type thing. Now, sure, you can record a webinar and release that and it's scalable and stuff like that. But what I like about workshops is that you're actually doing work and that's what differentiates a web— Excuse me, a webinar from a workshop. And these 2 things get conflated, but that's why I like to differentiate them. Webinar is an online seminar where someone's talking at you and maybe they're asking you to do some things. But for me, a workshop is I'm actually going to take you by the hand and guide you through at least a few steps of this material. And I'm gonna— my goal is to talk at you as little as possible. I'm not gonna lecture at you. I'm gonna teach you by doing. And I personally think that's the best way to learn is by actually doing a thing. Like how many books, for those of you listening out there, how many books have you read and never done anything with? I know. I know I'm guilty of many, many, many books where I've never done anything. So have I learned it? Not really. Like maybe like some phrases or something. Maybe there's some value there, but it's not the same as actually doing something live. So the phrase I like to use, by the way, and listeners out there, you can kind of take this, this like tip or mindset or whatever you want to call it, like, and start applying this now. People always ask me like, well, great, people will show up. How do I actually get them to make a change or transform? And my short answer is because I have young kids, like we just talked about, you can't. You can't. You can't make anybody do anything they don't want to do. It's impossible. I can go brush my 5-year-old's teeth, but then by definition, like, I can take their hand, but it's not them brushing their teeth. It's me brushing their teeth for them. So then when I'm not there, they haven't changed. They haven't transformed at all, right? So the phrase I like to use is help them take a sip. And this comes from, you can lead a horse to water, but you can't make them drink. But how can you help them take a sip? And so that's why I love workshops, because you're helping them take that first step. And then hopefully they'll use that momentum to see, oh, I've started. Now I can keep going, or now I have better questions. There's a bunch of threads I wanna pull here, but those are the main things that come up when you ask that question.
I love that. So you've answered part of this question, but what differentiates a world-class workshop from a basic, not well planned or thought out or informed by adult learning theory and things like that? Like what are key differentiators?
Yeah. Okay. So for me, a world-class workshop, and this may be a little bit of a cheat and you can, you can poke me and say that's not good enough and we can go deeper. That's totally fine. Is honestly really caring about the people on the other It starts with that human-centric mindset. So this is the big thing with design thinking that a lot of people don't think about, I think, most of the time, is you think you know what people want and you don't actually listen. Even when you're talking to them, you don't actually listen. You're looking for confirmation of what you think they need. And so I'll give you an exercise that I love using for all of my engagements, or most of my engagements. I like to be clear, even though it's not very concise. Most of my engagements, I like to do hopes and fears. And some of my clients have actually used this at the beginning of their group coaching programs on the first day. And they've come back to me and they said, Jake, holy crap, everything needs to change. We need to change everything because there's things I didn't even expect. And like the weight of the world is now on my shoulders. They're talking about how my course is supposed to help their family from having to like go into poverty and all these things. Like, I'm not being hyperbolic. These are some of the phrases that came back to me. But it changed immediately how we were viewing the actual task at hand. And oh, now it's clear. Here's what I actually need to help people with. So I don't know if that's sort of a cheat, but that's honestly it, is listening to your actual clients and participants and what they need. And at some point, if you're doing the same thing over and over, you'll get to a point where it's probably pretty good most of the time, and you're just swaying a little bit in the wind, so to speak, instead of like turning 90 degrees one way or another, like my example I just gave. But that's what sets a world-class workshop apart. There's not like one thing, do this thing and it's world-class. It's really It depends on what you're trying to do, how you're trying to solve it. So it's a classic it depends answer, but that's how you get to the, this is the answer.
It's like, know who you're talking to, understand your value proposition, your positioning, and your ideal customer persona on a very, very deep level. Like, do you have your clients do voice of customer research, surveys, polls? Like, how do you help them nail that as they're planning the workshop so they don't get into the top of the live round and then hear, kind of have a lot of oh shit moments with like, I planned the wrong workshop for the wrong people.
Yes. Okay, good. So I'm glad we can swear because now it's just going to be like free-for-all. Not really. But so this actually, I'll use a meta example, actually. So I helped my, one of my clients design a workshop for, with research in mind. And I'll tell you one of the things that they actually said. So this guy was a YouTuber who had 500,000 subscribers, presumably been doing it, well, he's been doing this for a long time and presumably knew exactly what they wanted. He's like, I don't, he's building a community is what my client My clients helping their clients build community. So, very similar thing, by the way. But I love this phrase, so I'm stealing it from someone else instead of using my own example because I love it. And this YouTuber came back and he said, I didn't want to do it. I didn't want to do that research. I felt like I already knew everybody, but I trusted you enough to just go try it. And it was like gold was coming out of their mouths. This is the quote that was relayed to me. Gold was coming out of their mouths. And this guy was blown away at the things he did not know. So, to answer your question, yes, research is important. I don't necessarily enforce that in my clients from like a in middle of the process. I think that comes a lot from the sales process and also from like your iterations along the way. It kind of depends on the scope of the workshop. So we didn't talk about this either. Workshop can encompass a few different things, by the way, in my opinion. They're all here's the analogy I've been using lately. It's like Americanized Mexican food. All the ingredients are the same, but the packaging is all different. So like enchiladas, tacos, whatever whatever it may be, quesadillas. All these things have the same basic ingredients, but. They're just packaged differently. So workshops, I think, are similar. You have group coaching programs, which is a series of workshops. You have a 90-minute workshop, that's a workshop. You have an onsite retreat for like 2 days, that's a workshop, just packaged differently. It's the same ingredients. And so anyway, if you have a chance to iterate, so whether it's like the example I gave at the beginning with hopes and fears, you have a chance now to iterate and make that even better live during like a Specific go-through, or you can deliver over and over again with a 90-minute workshop and make it better over time. Plus you should be factoring in the things that you're doing with sales. And I have some thoughts on sales and I know I'm talking a lot, but I wanna share one more thing if I can. So with sales, the thing that I tell people all the time is you do not need to design your whole thing. In fact, please do not design your whole workshop before you try to sell it. People may never buy it. And so part of that research comes inherently to design the 10%. And I have a framework we can talk about, 10-50-99, but design the 10%. That's like the rough plan. Go sell that and then use that feedback, which is research, to then improve it. So to answer your question in a long way, yes, I definitely recommend research. And I gave you a few examples of how. There you go.
Okay, awesome. Thank you. Yeah, we're big on honoring iterations and starting with a hypothesis and going through validation rounds and iterating like How do you eat an elephant? One bite at a time, right? We don't ever try and bite off more than we can chew, or you can make a really bad decision. So work, work in small steps. Tell me, okay, you mentioned selling your workshops. So do you help people put together both free and paid workshops or just paid?
Yeah. So again, back to my Mexican American, American Mexican, Americanized Mexican food analogy, the things I help people build are agnostic to the packaging. So if it's free or paid, it doesn't really matter. That is the input that I use to help you design what you want. So this is actually a perfect segue into another thing that I help my clients with, and anybody out there can do the same thing. There are 3 main ingredients that I use before designing a workshop that I think anybody should think about. First is what are the outcomes? And there's 2 kinds of outcomes. These are 2 of the 3. One is what are the outcomes for your client? The most important, like what are you actually trying to help them do? What are the outcomes for you and your business? So that may be a free workshop, but I want leads or people to buy my next offer or whatever, or this is my flagship product and I want people to rave about it and refer it to other people, you know, whatever it may be. And those 2 things are sometimes in conflict, not completely, but at least on the face they can be in conflict. Like I need to scale my business and go from one-on-one to group coaching and I need to buy my time back. So you may be tempted to reduce how much you're putting in for those reasons if you just look at that outcome alone, but then you, you've temper it, if you will, with, I want a great experience for my clients and I want this and that. And those 2 things play off each other. The 3rd thing is the identity. And I love this. And I feel like most people don't talk about this. This is kind of like a brand identity, but it'd be a subset of your brand identity. It's your program identity or your workshop identity or whatever. Again, whatever container. And it boils down to, for me, 3 adjectives. So how do you want the client experience? Like, what do you want the client experience to feel like is ultimately what this explains. And I have a structured exercise, no surprise, design thinking mindset here, a structured exercise to get there, but the output is 3 different adjectives. And for example, it's like exclusive, guided, and unreasonable care or something like that. And that then informs, so then all 3 of these things combined inform and act as a lens on what actually goes in this workshop. How is it structured? How do I position it? Who's it for? All those things act like a lens. And that makes it a lot easier to design a great world-class workshop.
Yeah, those are great frameworks. Let's talk a little bit more about customer experience. I presume that customer experience is, well, we teach customer experience as like, we teach 'em the bowtie funnel for LTV maximization, all that kind of stuff. And we're thinking about every single step and how to pull someone through that bowtie funnel in a really fun and experiential, high-end way. So with us like zooming in on workshops specifically, How are you helping your clients create really, really memorable experiences within the container of a workshop, whether it's free or paid or an in-person event or something like that? What are some core elements that help your clients create the most kick-ass experiences possible?
Yeah. Okay. So trying to think of what the phrase is. I actually don't use this, but this is what immediately came to mind. It's like, first impressions last a lifetime or whatever. And The concept here that most people don't realize is your workshop doesn't start when whatever, 3:00 PM on Thursday starts. It starts when your client first becomes aware of your workshop, this or any kind of experience. And so the best way to have a great experience is to set them up for success and kind of set the tone early and then follow through with that. So it starts with how do you start like your engagement with them before they're even like trying to show up for the actual experience? Maybe you're sending a welcome video that depends on what stage you're at, but let's say you're, you're doing a new workshop, send a personalized video to each person. Like, don't do the Loom thing where you do a Loom and then it has a changed name. Just like record a new video. It can be like 2 minutes for 10 people. This isn't that much work. Send a video to them and they're going to feel seen and special and connected with you. And that'll make it easier every step of the way. So that's kind of like a tactical thing. But zooming out, it's like, again, the identity that I talked about, it's like, what does that experience feel like? And make sure that every step along the way, I sometimes might use a journey map. This is This is another design thinking tool. It's like, think of the major beats of a workflow or an experience or a process. And then you map out what you want them to be doing or what needs to be done. And there could be different categories. But one of those categories often is, how do I want them to feel? Or rather, how do I think they're feeling? And how do I make them feel the way I want them to feel? They might be nervous or wondering if they spent the money in the right place or whatever. And so how can I make sure that they know? Maybe if they're worried that they might not have made the right decision or they're curious, like, OK, this is a lot of money. Did I do the right thing? Like, how can I make sure they know as quick as possible, oh yeah, I made a great choice? And then that might change how you interact with them early on. So again, most of my answers are, it depends, but they're based in principles. So this principle would be, think about the whole experience. What do you want it to feel like? And try to put yourself in their shoes, that human-centric mindset, and think about what are they feeling right now and how can I make them feel the way I want them to feel for success, whatever that's defined as.
Cool. All right, let's try and make that a little bit more tangible. So what are some— can you think of maybe 2 or 3 examples of wow moments that have been really, really unique that either your clients have done or that you've experienced yourself within a workshop context?
Yeah, so I'm going to use a— I'm going to use this. If this is a cheat, you can cut this out or you can tell me to pick a different one, but I'm going to pick one that's really recent for me and my wife, going back to those State of the Union conversations. So it's a little bit different, but we found that— so one of the main activities that we do is called the Wheel of Life. We don't call it the Wheel of Life, but that's what most people know it as. We call it the Pillars Exercise. But it's basically you take your life and you look at it in, say, 8 different categories. You have marriage, family, friends, health, job, you know, whatever it may be. And then we rate how satisfied we are in each of those, and then we come together and talk about it. What we've been doing is we basically are talking out loud for an hour, trying to unpack this for ourselves and communicate it to the other person. And I said, what would this look like if we could come better prepared with more of our thoughts, more concisely phrased, which would be useful for this podcast too. I'm very long-winded. But how can we think for ourselves first, come with better insights, and then maximize that time together and really think, oh great, that meeting didn't need to be an email, for example. And so I built an AI tool to help talk through and think through. And now we can talk about AI later if you really want. I have pros. There's obviously pros and cons to AI. But one of the things I love about AI is it can help me make sense of what I think. Yeah. And then repackage it in a way that's easier to reproduce my thoughts into like someone else's brain. So we tried it and my wife was like, that was so fun. That was amazing. So this is why it came to mind immediately. It's again, a little bit of a cheat, but she loved it. She's like, this was such a great experience. We could just come show up. We could get straight to the point of sharing how we feel about each of these things and then talk about what's important and what we should do about it. So I haven't implemented this in any group programs yet, 'cause this was like, I don't know, 3 weeks ago as of this recording that we tried this and I haven't had a good opportunity to try it, but these are the kind of things I want to do. Which is the answer to the question of how can we maximize the human side of these gatherings? So, like, this goes back to don't talk at people like that email or that meeting could have been an email kind of thing, or that meeting could have been a video. Any of those moments, try to pull those out and then leverage that really valuable time of everyone being together. That's, I think, what makes a great, like, experience, like, resonate. So, to use a different example that is more business-focused because that other one was kind of a cheat but still relevant, I would actually say, and this may be super simple, but honestly, like emphasizing the human connections, like so many of us are remote all the time. So again, like we met, got to meet in person at Craft and Commerce this year. Anytime you can go above and beyond and have some way for people to meet in person is just like a, I've got to come up with a good analogy, but like a nuclear explosion of energy compared to like Zoom calls are great and they're very effective and they're very efficient. And they still can build relationships. There's nothing like meeting in person. So if you can, especially if you have a high-ticket program, find a way to get people together somehow, whether it's you happen to be in the same city and you want to meet someone in your program is like the super low-hanging fruit, or hey, we're doing the Level Up Creators Retreat. We're doing it. We're going to copy Jay Clouse and we're going to do it before Craft and Commerce. Come on out. You know, whatever it may be, that's the kind of thing that I think will really stick with people. So, those are 2 examples that come immediately to mind. You can poke deeper if you don't think I answered that well enough though. I give you permission.
No, I think that's helpful context. And like, we are trying to teach people how to think differently, right? And look through a different lens, to your point, different frameworks. We're big on mental models over here. And so, yeah, sometimes talking about how to think can be more helpful than super concrete examples. Tell me more about your 10-50-99 rule.
Yeah. Okay. So 10-50-99, I use this all over the place. Let me use— it kind of is a relative measure, but at the core, it's the level of doneness that you have something. So 10%, 50%, 99%. I'm going to explain the 2 extremes because the middle is kind of just like somewhere in the middle. So 10% is like the basic idea. It's the rough guide, the brief outline, the napkin napkin sketch, for example, that kind of thing. It's like the why often behind something. And then the 99 is what I call deliver-ready. So in a group program or a workshop, you're going to have maybe slides or some kind of workbook. It's those things done and ready to deliver. Now it's 99 because it should never be 100%. It can never be 100%. And mentally, 99 may even be too high, frankly, but I like the ring, so I use 99. And it signals that it'll never be done, but this is good enough and it's deliver-ready. And then 50 is somewhere in the middle. And I'll share with you, if you work with a team, by the way, and I know you have some teammates, Amanda, I learned this from a feedback model. So I think this is really useful from a feedback model. When I was in corporate, this may just be an example that may or may not be true, but hypothetically, if an employee was going to present something to the big boss at the division that he worked for and was looking for his manager's help, on a presentation and brought a 10% level of slides, just very basic, how frustrated do you think they're going to be if you're giving 99% level feedback? And vice versa is also true. I'm almost ready to deliver and you're asking me why I'm even talking about these topics. That's kind of where this 10-50-99 came from. And so I matched that with like my development process. So develop it in those stages. And yeah, so anyway, I lost the thread there a little bit. I apologize. But 10-50-99. is basically about do things in stages. And it's kind of that iterative stage where do a little bit, get a little bit of feedback, or let it sit and then come back to it and keep going. And I can, I can tell you how I apply it to group programs, because that's a little unique.
Yep. Let's do that.
With a group program, 10%, like I mentioned, is all you need to sell. So 10% would include like the promise, like what transformation you're offering to people, um, so that they actually care about it and want to buy it. They don't need to know how you're gonna get there. You don't need to know how you're gonna get there, except maybe like for a group program, it'd be, here's each of the 8 weeks in a very, very basic level. Here's the topic and the takeaway I want them to have. And it kind of explains the journey for you, but you don't even need to share this with people, by the way. That's my personal recommendation. That's all you need to sell. And then what I do with especially a group cohort program, 2 weeks before your first delivery, you've sold it, you know you're going live. Now, 2 weeks before you start the 50%, which for a group program, I label as like your detailed agenda. You know what you're going to do, you know what you're going to say, you don't have everything built, but you have an idea of how the agenda is going to go. You know that the timing feels reasonable and it's not like too much stuff packed in there. That's the 50%. That's like your delivery plan. And then one week before, or within the week before you actually go live, that's when you're buttoning up the details, you're finishing slides, you're building a workbook, and you're kind of iterating and just refining some of those instructions. While you're also doing the 50% for the next week. And so you're not doing everything at once. You're doing it in a rolling, just-in-time fashion. 50, 99, 50, 99, things like that. So that's how I use it.
Interesting.
Yeah.
Okay, cool. Tell me kind of the checklist, if you, or if this is like too much secret sauce, you can, you can just tell me, but like, what's a good gut check checklist for our listeners as they're planning a workshop? Like, what are the core elements of a killer
Yeah. Okay. So, not— I'm happy to share because again, the devil's in the details, but the principles here. So, let me talk about— let me first start— talk about group programs because I think this is easy to like grasp onto. Whenever you're designing a repeated system or process that people are attending, the same group of people's attending each week, have a ritual. So, you start the same way, you end the same way. Now, maybe the very first one, the very last one might be a little bit different, Just as an asterisk there. But you start with, for example, wins. A classic one that everybody can start with is wins. Wins are always great. It starts people on positive energy and usually connects the previous meeting or session to the current session. On the back end, you end with takeaways. And I'll come back to talking about why I love asking what your favorite takeaway was in a second. But that's another good ritual to end on each one. And then the very last session, you'd ask what your overall program takeaways. Bonus, those are great testimonials. You can use those actual phrases With permission, of course, for testimonials. And that's a great way to hear like what people are really getting out of your course, or rather your cohort program. The reason I love what's your favorite takeaway is it gives you and them a benefit. So one, they have to actually stop and think and synthesize a little bit about what they heard. And that actually makes you more valuable in their eyes. It's not a trick. It actually is cementing some of the things in their eyes about how valuable you were with your program. And It can reinforce that learning for them. It gives you feedback. And I mentioned this briefly, when you're designing that 10%, one of those things that I usually have my clients do is what's the takeaway that you're trying to design for? You can see if you actually accomplish that, which isn't a problem if you don't. Because sometimes what you learn is, oh wow, that thing that I just was like a throwaway comment, everybody loved that. Like, I thought that was easy. It's like the curse of knowledge or the curse of expertise or whatever, right?
Yep.
It's like those simple things that people just eat up and you're like, isn't that basic? That then becomes—
The expert's dilemma.
Yes, expert's dilemma. There you go. And, and so that's really useful feedback for you. Is it landing or is there something else that I should be leaning into? Or maybe I should bake that in officially into my plan for next time. So that's how you iterate. And then in between, that's where the variability comes. And I say, it depends on what you're trying to do. So if you are doing— my default is always, how can I get them to do things like we talked about at the top of the episode? So how can I quickly get them into something? I want to talk as little as possible and I want them just to start. So here's a really tactical example. Let's say you're teaching someone about offers. Start with the— don't even tell them. Say, we're starting with— let's start talking about offers. I want to hear in the chat, what do you think an offer is? And just start with something that gets them thinking about the topic. And then the bonus there is you get to see where they're at. Maybe everybody's like, oh, an offer is blah, blah, blah, blah, blah, whatever. Perfect Hormozi textbook offer definition or something like that. And everybody's already there. Either maybe you agree with that and you can say, great, seems like we're all here. Since we're here, we can dive into the work of doing this or whatever. Or, oh, okay, we have all different types of responses to that. Now I know how I need to adapt sort of how much I'm talking about this so I can help you give people what they actually need and meet them where they're at. So that's how I like to start. And generally, I try to keep the teaching as little as possible, and I just try to get them— here's like the thing that I think is going to be a newsletter soon for me. So this is hot off the press. Let me see if I can do this concisely. I think the best way to teach is by doing. Instead of front-loading all the education, try to get them to do something. And then ask you questions where they're getting stuck. And then that's where the teaching happens. So I know for me, whenever I'm trying to do something, and this happened to me earlier today, I'm like, hey, should I use Bitly or should I just do like a slug on my lead magnet or like whatever I was asking people? And then it actually sinks in because I'm trying to solve this problem right now and I don't have the answer. And now I'm searching for that just-in-time information. And if you're in a cohort, you have that just-in-time expert who can give you that information right there. And then that learning is sinking in. in real time, in a way that actually impacts real people. And even if not everybody's asking that, they're probably learning too. And a lot of people probably have that same question. So that's how I like to design it is what is the topic? Let me, let me work through what I want them to do. And then those questions and those teaching moments come up organically instead of me thinking I need to teach, teach, teach, teach, teach. I think too many people default to talking, talking, teaching, teaching.
Let's talk about that for a second. So we kind of kicked off our time today talking about like your experience with facilitation and you've, I think, created kind of this beautiful marriage with all of your design thinking and facilitation and all of your skills. Would you define facilitation as you see it from where you're sitting? It'd be super helpful.
That's a good question. I would say facilitation or good, effective facilitation is when you are able to help someone through a problem that they have and they've come out the other side better. I could probably tighten that up. But it's the act of facilitation is guiding people through the problems that they have, not just giving them information. So I think that's the differentiating factor for me.
That's great. I feel like it's almost agency, helping people recognize the agency that they have. And it's like, it is leading the horse to water, if you will, in a very skillful way, as opposed to just talking at people and thinking that they're showing up for you to talk at them and that that's the value of the session. But what they want is the outcome of your knowledge. Like you're talking about, like getting that sip, you know, at the end of the workshop, you've led the horse to water and they're taking a sip and you haven't just like word vomited or word diarrhea at them, but you have like actually given them a taste of agency and transformation in whatever your area of expertise is in. Is that fair? Is that all fair?
Yes. That actually brings me to one of my— I love analogies, and I actually haven't used too many during this talk, so I'll try to pepper some more in before the end and meet my quota. One of my favorite analogies is like, for those of you in the United States, we have Home Depots, right? And they're home improvement stores. I don't go to Home Depot to buy a drill because I want that drill. I want the hole that that drill gives me. And this is not a new concept, right? There's lots of other analogies like this, but I love this metaphor because they don't want your workshop. They don't want your knowledge. They want the thing that their knowledge is giving them, the solution to their problem, whatever that may be. And so if you think about it like that, it completely reverses the instinct of most people, which is, oh, I need to teach them all these wonderful things I know. No, you just need to take them by the hand, metaphorically speaking, through the process that you know will get them to the, to that, that, that solution that they need, right?
Yeah. People are smart. And like, you know, you're big on human connection and being human and recognizing humans. It's like, You're not a kindergarten teacher here. Like, these are smart, intelligent people that I'm sure your clients are working with, certainly that my clients are working with. And, uh, it's, it's, it's more about equipping and empowering than it is like— you're not preaching a sermon, you know? It's not like Sunday morning situation here. Yes. But it's like you're offering a very specific transformation to a very specific, probably niche audience. I mean, we're really big on like going narrow and deep because then you can have the greatest amount of impact and leverage if you're speaking to a hyper-specific audience that needs a hyper-specific solution or transformation. But I think that is, that's a great analogy that, yeah, you're not buying the drill, you're buying the outcome of the drill, whether it's the hole in the wall or putting the desk together or whatever the case may be. Yes. Hmm. Okay. Super interesting. I mean, gosh, this like topic of facilitation, I've never heard the word facilitation more than I have in 2025. I mean, it is, I think really, really rising in importance. And I think this is, this has obviously been a concept that's been around for a really long time, but in terms of how individual, like solo practitioner coaches and consultants are leveraging it to produce value outcomes and transformation for their clients is really, really, really on the rise. So, I think your market timing is right on the nose for your area of focus here. Okay, what else, what else do our clients need to know, or listeners need to know, in order to put on killer workshops?
Somehow, I don't think this has really come up. Maybe at the very, very beginning, but I'm gonna bring it back to fun. I think the thing, and this is easier for me to like soapbox about in the corporate world because corporate is often so like buttoned up, like almost literally where, side note, I got feedback one time that I'm using too many emojis or our team was using too many emojis in our slides or something. Like, thank you. You're welcome. So whenever you can have fun, I think people are doing better work when they're having more fun. So how can you infuse some fun into your workshop? Don't take your— here's the phrase I love to use. I don't take myself seriously, but I take my work seriously. Or maybe the opposite way, depends on the day. But like, don't take yourself too seriously. We're all human. We all make mistakes. We all have fun, or we should all have fun. We'll all benefit from having more fun. So how can you have more fun? And so what does that look like? Well, it's kind of like, you know it when you see it, I suppose. It kind of depends. Everybody has a different flavor. Some people like dad jokes. Some people like goofy slides. Some people like funny music. Some people just like to be super serious and once in a while break character. It kind of depends on you, but think about how to make it more human. And I think that'll be also more fun. Quick pro tip that I learned from Craft and Commerce last year from Tristan DiMontebello of Ultra Speaking. He said, if you want to be funnier, and this is a little bit different than fun, but those 2 things kind of go hand in hand. There's a Venn diagram. If you want to be funnier, lower your filter. So if you lower your filter a little bit, say those things that you're a little bit afraid to say, that will usually infuse a little more energy, a little more human, and a little more fun. So that'd be what I recommend. So just freaking say it. There you go. I don't know, something. I couldn't quite go all the way there, but yeah.
No, I think that's great. So tell me what role you feel like workshops play in a coach or consultant's kind of overall, we call it a product ladder, but their whole, their business, like what puzzle piece is this? What is the puzzle piece here? Part of the bigger picture?
I mean, so I have this hammer that like on a Home Depot home improvement Bend right now. I have this hammer called workshops and I love workshops. So my answer is almost, it should be most of what you do. Coaching to me is very similar to facilitation. There's probably some nuance there, but the ultimate same thing with coaching I think applies to workshops and facilitation, which is you're trying to help someone go from point A to point B. So the same fundamentals can apply. Maybe they're packaged different, but maybe I'm going to turn that back around on you. Do you think there's a difference between like coaching and workshop facilitation? Like, do you have something in mind that you want to challenge me on or question me on? Because I'd love to dig into that.
I mean, I feel like, I guess I don't know any coaches or consultants that only sell workshops. But I mean, you're saying we're using kind of workshop as a framework, and there's a specific checklist and cadence and rhythms and rituals to it that can be applied into Group coaching programs, I'm sure one-on-one coaching, maybe consulting, trainings. So, I think you're kind of building a framework that is applicable across a number of different sort of like product ladder items. So, the way that I think about workshops is we often use workshop as a beachhead, and we help our clients sell in like B2B. And so, it's often like a keynote, workshop, you know, one-two punch. Usually there's some kind of like bookends, like some pre-work and some post-work that leads into a much larger, like a multi-six-figure engagement with that organization. So the workshop is not the be-all end-all, but it's rather, again, the foot in the door. So I'm curious about how you view that and the role that you explain workshops to play to your clients.
I
don't think that made sense, but you get what I'm saying?
No, no, no, that makes total sense. And I have a bunch of ideas on this. So the thing that your explanation unlocked for me was, so workshops to me are usually group, like one-to-group, one-to-several, or one-to-many. They don't have to be. The same principles apply. I've just decided to focus mostly on group experiences. But the same, I take the same, I work with most of my clients one-on-one today. And I still take the same approach, especially when I am trying to get information from them or help them think through something or help them go from point A to point B. So I will take a workshop Format to my one-on-one engagement with them. So kind of like you're talking about, like a kickoff—that's a great time to use. Like let's say you are an agency even. You should start with a workshop where you're making sure that they actually understand what problem it is that you are being hired to solve, so that everybody understands. You can take you through exercises, which whatever there could be. There's hundreds of exercises we could talk about, but there could be a workflow where you now understand really clearly what the problem is that you're trying to solve and why and like who it's for and all these things that really go into that really good design. Kind of like those three things I mentioned earlier: the two outcomes and the The identity piece, that's like the initial kernel that then turns into the product. So I don't know if that actually answers your question, but for me, workshops come in anytime you need to work with anybody else to understand them better, to help them understand themselves, and to help them transform. If you're just creating work by yourself, obviously you don't need that, but maybe you're co-creating, could be a workshop. So again, everything's kind of a nail for me because I see this almost as a workshop is so flexible for me. It's really like Lego building blocks. Like I can, I can apply workshop principles, whether it's a tech— like I don't have a super strong definition of like, this is a workshop. That is not a workshop, except for webinars. Webinars are not workshops.
Fair enough. Yeah.
Besides that, it's those building blocks. It's the structured exercises or a purposeful flow that helps you get from one point to another. That's what I see workshops as. And that's why, that's why I've like de— sort of de-niched, and you may slap my hand for this, but I was going under world-class group coaching programs. But I realized a lot of my clients actually wanted help with in-person events or a 90-minute workshop to act as their attract offer, their attract offer. And these weren't group programs, but the same principles applied. And so it's kind of like building blocks that you can apply throughout your process.
Nice. That was a great summation. Thank you, Jake. That'll be, that'll be a good place to kind of put a pin in it. But we can't let you go without letting our listeners know where to find you online and learn more about what you do?
Yeah, this has been great. Thanks for having me. I'm actually really excited about this. This is the first time I'm offering this. I'm calling them Workshop Why sessions. So, we did, we kind of talked around this a little bit, but I'm a real big believer in It Starts with Why. I believe that's Simon Sinek's book, same concept. But in 45 minutes, I'll help you get clear on why your workshop matters. Why should somebody show up? Why do they even care? Why are you doing it in the first place? And that will be the kernel that turns into that world-class workshop. And And what it does for you is it helps everything become easier. It acts as one of those filters, like we mentioned, that everything can be judged by. So, you know, what should be in or out. So, it's free. It's 45 minutes. You can go to worldclassworkshops.co/why. That's like worldclassworkshops.co forward slash the word why, W-H-Y. And I'd love to see you there and help you out any way I can.
That's a hell of an offer. 45-minute consult with you, man. That's, that's great. And we'll make sure all those links are in the show notes and show description. But thank you so much for your time today. I really appreciate it. I appreciate your insights and your wisdom, and you dropped a lot of little like knowledge bombs and nuggets for everybody. So thank you so much, Jake. I appreciate it.
Yep. Thanks, Amanda. Thanks for having me.
Thanks. And to our listeners, we know your time is precious. Thank you for sharing yours with us. If you are a coach or consultant looking to build multi-five-figure MRR in a very predictable, scalable way, head over to mrraccelerator.com to learn more. Thank you so much. I'm Amanda Northcutt, and you can follow me on LinkedIn. We'll see you next time on the Level Up Creators Podcast.
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