I Used Claude to Plan My Entire Business Year (Here's What Happened)

In this episode, I will show you how I built our 2026 annual operating plan using Claude Projects as a persistent, context-rich strategic partner rather than a single chat thread. 

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Timestamps:
00:00 AI Runs Our 2026 Plan
00:24 Claude Projects Setup
02:28 Build The Business Brain
03:18 50 Question Interview
04:43 Current Reality Audit
09:06 Gap Analysis Goals
14:18 Fierce Blind Spots
18:29 Partner Alignment Hack
20:14 Annual Operating Plan
21:36 One Thing To Rocks
24:15 Prosper Plan Add On
24:48 Wrap Up And Next Steps

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Transcript

SPEAKER_00 0:00

This document is running our entire business in 2026, and it was all developed with Claude. Now, most businesses waste time every single year not developing a plan that aren't aligned with their goals, not built on what worked and what didn't work, not accounting for current team dynamics. I built this in a few focus sessions with Claude as my strategic thinking partner, and this process today is what I'm gonna show you. Okay, so the first thing I'm gonna talk to you guys about is that the architecture first is what makes all of this possible. So I'm gonna show you on my screen real quick what this means. Now, you'll see here, this is my project area. This is my strategic partner. I named it Tarvas, and you'll see here, here are all my threads as well as all my project files, instructions, and also the memory for this particular project. Now, this is very different from just a normal thread that you start. All right, so this is a huge distinction that most people don't realize because you're not just using regular Chat GBT or some generic AI chat, because what you're actually doing is building a project inside of an environment that is a persistent workspace where the AI actually retains context across every single conversation that you have inside of this area. So it knows your business, it knows your team, it knows your history, and it also knows your numbers if you choose to give it that. Now, inside of my Claude projects, I've configured it as my strategic co-pilot or my thought partner. And it has custom instructions that are defined to its specific role. It's going to push back on some of my bad ideas, it's going to ask discovery questions before proposing solutions. A lot of people have trouble with that, where it just starts giving you solutions that aren't necessarily tied to your specific business or not relevant. And usually what I find is that it can translate about 60% of what I come up with, and it helps me get to about 90% of execution ready spec, pretty much. Now, important because the data is really where the magic happens because these projects with those uploaded files that have your business model, team assessments, the past financials, the previous strategic plans that you've allocated for yourselves, your client data if you choose to upload that there. All of this is accumulated inside of that context and what makes those outputs useful rather than just generic. And the good news for me is that Tarvis had it from day one because I've been building this project for months before I even got to doing this annual planning. So if you haven't done that, I definitely recommend starting there before just jumping in. But I'm still going to give you the step by step if you want to go through that process. Just make sure you first have the right architecture in place. Now, inside of your Claude project, what you'll see here are all these files that I uploaded. I briefly skimmed through that before, but it's really important to know I use a lot of the capacity of this. I'm already up to 29% in this one. And I still do some hygiene and clean some of these out. So it just shows you how much I utilize this. But this is like building the brain, right? So imagine if your threads had the ability to kind of look inwardly and kind of access like an external hard drive and then pull that data into that thread. Like imagine times you've had these conversations inside of threads where you forget something and the thread doesn't remember it either, and then it's just lost forever. I've actually had clients tell me that they wish they were taking notes during their AI sessions because of this particular reason. So what I typically do, and this is outside of the context of what we're talking about today, but when you hit those like aha eureka moments, make sure you have it summarized and then add to one of your project files. It's a really easy process to do so. All right, so now that we have that set up or we're planning to get it set up, phase two is going to be going through and do your 50 question business interview protocol. Now, really, really important because before I tell you to do this, I hear, I'm sure you hear 50 questions and you like freak out and maybe turn this video off. But I did all this with talk to text. So I'm not sitting here answering, you know, typing 50 answers to all these questions. Most of this I actually did on walks in nature or while I was walking the dog or while I was doing something around the house. I just did talk to text when I had time to tackle these 50 questions. But it's really important, and this is why I don't want you to skip steps in this process because Claude was able to access these project files and then be able to interview me based off of that context, not just randomly opening up a thread and saying, interview me about my business to create my annual plan. Again, I'm just telling you things that I hear often, but most people that I talk to, they're just saying, write me a sales page, make it good, and don't make mistakes. You have to become a better pilot of AI if you want to get the full benefit from utilizing it. So, in other words, the way I like to say it is that AI didn't write my strategy. It extracted my brain, it took from my files and it helped me organize it in a way that made sense. And it probably was better from an organizational standpoint than I would have done myself. And it saved me over previous years, candidly, probably 20 to 30 hours minimum, and maybe more in some situations, if we had a big complex year that we were planning. All right. So in your 50 question protocol, questions one through 20 are going to be the current reality audit. Now, I have all this built into our AI platform that we utilize called Spark Hub. If you're interested in just using that instead of trying to figure this out on your own, let me know. There's actually a number you can text in the description. You can grab that and just text us and we can help you get access to that. It's for our clients only, but this allows you to go through this entire process and not have to go through this right now on your own and try to manually figure this out, right? But phase one is that first, let's figure out the current reality of what's happening. This is the foundation of what we're trying to accomplish here. So it's the current reality of where your business is at right now, and it's going to make you kind of address some things honestly that maybe you've been ignoring. So some examples of that is it'll ask me, what are my revenue streams? And what percentage of that revenue comes from each product or service? These are things that most business owners unfortunately don't know. Another example of a question would be for each team member, what are their top two strengths and their biggest gaps? Analyzing and addressing your team in a way that's both rational, logical, but it's going to set them up to win and take hopefully a lot of headaches off of your plate, right? Uh another example would be what's your actual weekly time allocation? How many times, how much time rather, do you spend on tier one work versus like regular operation stuff? Meaning tier one is like your highest return or your highest unique ability type items versus just regular operation type stuff. Really important, right? Which of the current offers in your product suite would you kill or would you eliminate if you had to do so tomorrow, or if it was up to you and revenue excluded? Sometimes difficult questions to ask, difficult answers to come to, but also important that we're moving in a direction, even if it's not immediately that you're building a transition plan. And then a last example of what would fit into one through 20 would be something like what process in your business breaks the most often. So we do this every year. We have what we call our issue solution map. And from that we say, what is broken? What is an issue? What's a problem? What are solutions? And how difficult are those going to be to solve? And then we take those on in stride when we have time. Or in many cases, sometimes business owners have like a virtual assistant, specifically people like us that are coaches or service providers and have online businesses. A lot of their people are working virtual in other countries in some cases. And sometimes when they don't have big tasks for them to do, they're just not doing anything. And so if you have your issue solution map, you can have them actually working on solutions in their fill time and you can just assign that whenever you don't have something to sit down and dedicate to them because you're busy doing your tier one stuff, which is what you should be doing. Now, for us, this process allowed us to really confirm what we already had speculated. There were several offers where we thought, man, it just seems like the time we put in versus the money we make, that just seems like where we really need to focus. And it actually was able to confirm that with data and numbers and the historical data from years and years and years. And it did it like that, which is super, super helpful. I don't have time for that. I'm not a CPA. I'm not a I'm not a big guy when it comes to stuff like that with digging into numbers. Some people are, I'm not. And so the ability to have that done quickly and confirm what we had already speculated, even at an anecdote level, was just crazy profound and worth doing the exercise if I only did that alone. It also asked me, like I said, to analyze each one of our team members and analyze their strengths and weaknesses or some potential blind spots and gaps. Now, it doesn't mean you're just going to go fire the whole team. That's not our intention at all. We're very pleased with the people that work for us. But as any good coach, and that's what you are, you're a leader in your business, you need to coach your people. Coaches put people in positions to succeed. You don't play somebody out of position or expect them to do something that's outside of their talent or capabilities. And so for us, the same way we put ourselves in positions to win, we also want to analyze our team and do that the same. And that's exactly what this is going to allow you to do, but with intention. Now, really important for phase one, it's not giving you answers in this phase, but it's really making you think more clearly about your business as a whole. And it's going to ask you some of those deep questions that you might not ever ask yourself, or even if somebody you have as a coach, I speak truth with love as a coach. That's just what I do because I know the opportunity costs. If you don't, I've had coaches that don't. And three years later, they're like, yeah, I thought that. I'm like, why don't you tell me three years ago? So I'm different in that. I tell truth and love, but AI is going to tell you the truth, specifically if you train it to do so, about things that maybe you've never asked yourself or even a coach you've worked with hasn't told you. All right, phase two is questions 21 through 35. And this is the gap analysis. So, what this is gonna help you do is gonna help you identify what's actually in the way in preventing the things you want to happen from happening. Really important, things we don't think about often. But like, what are the barriers that are causing you to not achieve the goals that you've set out for yourself if you've done goals at all? It's okay if you don't. I know a lot of people that don't, they just kind of keep doing what they're doing all the time because that's what our nine to five brain previously and our schooling taught us to do. So I get that this is a totally different way to approach even just living your life. But these are things that are sometimes remove this and everything else works better, right? And that's what we want to figure out and accomplish. And so questions 21 through 35, the way I structured it, accomplished just that. So these are gonna include questions like where do you want this business to be in 12 months? Revenue, team size, what's your personal role? What are you doing in the business? How do you want to be showing up? Sometimes business owners got into a business because of something they love to do, but then they don't actually do that thing very often because they got sucked into doing other things, right? Like, can I get an amen to that? Uh, another question could be um, or is in our protocol, uh, if you could only work on three initiatives this year, this is a big one for me, and I'll tell you why in a second. But what would those three things be? Now, for me, I'm an idea guy, and I constantly show up in meetings every week with like, what if we did this, guys? Like, what if we did this? Or I got an idea, like just on the fly, and so I've limited myself to two big ideas a year, and I've already used both of them, so I gonna have to beg the team to give me a third one. But if I can only work on three things this year, it makes me focus on what those three most important things are. And this is just a normal thing that a typical right-brained, creative type dreamer like myself, which is probably like you as well, if you're a business owner watching this video, you're probably the same way. So this forces you to have those constraints and make you focus on the things that actually are going to matter and make the biggest difference. Now, the cool thing about that, and that probably feels limiting to you. What I would tell you is this I mentioned something earlier. We've already finished most of our quarter one rocks, and that has given me, with what we did in quarter one, and I'll talk about that in a second, the ability to actually have more playtime for me, which is tier one work, than I could have ever dreamed about having. So sometimes when you dial in on the things with focus, you actually get them done faster and you operate in a better cadence as a team that you have more bandwidth for everybody to kind of do the things they love more because you have more time for the fun stuff in the business. That's super important to know because I know some people feel limited with constraints because they didn't get into business to be told what to do or to constrain themselves. And I totally understand that. Okay, next is what's the single biggest constraint between where you are and where you want to be? Like, what's the thing that's stopping all the things? And that's gonna take some time for you to think through and we determine what ours was, and I'll talk about it here in a second. But really, really powerful exercise. What are you currently doing that you should stop doing entirely? Now, how many by show of hands running business have been doing something that you're like, what like why am I doing this? Like, not making money from it, no one's engaging with it. I'm just doing it because somebody exampled that or modeled that to me as an example, and now I'm following them. We don't know, but we just find ourselves just doing things, and this is gonna really press you on. What are things you should stop doing to make way for the things you should be doing? Okay, another example is if your business state exactly as it is today for five more years, how would you feel? Now, this was a tough one for me because I'm an ambitious person and I love growth, and so this makes you really, really dial in and figure out man, I don't want that. So I'll accept the constraints. Does that make sense? You kind of like backdoor yourself on that one. It's like reverse psychology. I don't want to be stuck for five years. So, how would I feel if that happened? Okay, great, let's not do that. I'm willing to accept the constraints. In my case, limiting my ideas and focusing on the things that matter and saying, I'm good as long as we win because I don't want to be stuck where I'm at now. Not that that's a bad place. I'm happy with where we are, but would I want to be there exactly in five years and not see any growth? Not at all. And that would not make me feel good as a person that's I'm a benefits-driven person. I would not be excited if we're in the same place in five years. So this is gonna make you think about okay, but what's the trade-off? You don't like restrictions? Okay, but what's the trade-off? So it is a helpful exercise. So the bottom line is for me and for us, is that Claude really forced us to focus on things that mattered that had the biggest downstream impact. And that gave me the opportunity to put everyone in their best and ideal situations and giving us the best chance to achieve our goals this year. And then we created more bandwidth for me to be able to do the big picture dreaming stuff that I like to do as a result of our newfound efficiency. And that's what I mean by a strategic thinking partner. It didn't hand me a plan. Like I'm still the pilot, but it did help me think through my own plan more rigorously than I probably would have done if I just sat down and did this by myself. So, really important to know about AI because again, AI is a powerful tool, but you still need to be a trained pilot. I always say this you would never get on an airplane with like a guy that just stayed at a Holiday and Express last night, if you remember that joke. But if you saw that that pilot's just some guy off the street, you're not hopping on that plane. And some of us, that's how we're using AI, is we're not training ourselves, but yet expecting to land at a destination. And that's just not a realistic expectation. Okay, phase three and the final phase here is questions 36 through 50. Uh, and this one's tough. This is fears, blind spots, and some honest assessment. So this one's tough. And I do think that most people under normal circumstances would probably skip it, but I think it's also the most impactful. And that could look like this. So, an example, what scares you the most about this year ahead? For my business, I will say straight up, people adopting AI, information has been commoditized. And traditionally, we ran an info product slash membership and course business. We've had to completely adapt everything we've done. And what scares me a lot is that I'm not keeping up with the trend fast enough, specifically with AI. I'm not adapting our offers fast enough. It's a total reinvention, and maybe you feel that way as well. So for me, addressing that head-on and then building a plan around it, just getting it out of my head versus something that I just sit on and I'm not actually doing anything to reconcile that, it just puts me in a negative headspace. So putting it out there, addressing it, and building a plan, it just makes me feel like I'm taking the necessary actions. And then honestly, the rest is in God's hands at that point. And I trust that he's gonna lead us to where we need to be. Another question would be what conversations are you avoiding that you know needs to happen? Now, this could be with a spouse, this could be with a business partner, this could be with a team member. If there's anything that's lingering, the last thing you want is for things to fester. I have clients that I talk to all the time where they get to the end of the year and they're like, I'm really disappointed in so-and-so. And I'm like, you're telling me this at the end of the year, we could have addressed this seven months ago. This sort of thing happens and we let those things fester. The problem is this festering leads to bigger resentments, and then it just becomes goes from sour to toxic and becomes an environment where nobody's happy and nobody's doing their best work. Another question could be uh, what happens if nothing changes if you execute nothing from this plan? Again, this is kind of more reverse psychology. And if you execute nothing from this plan, what would happen? You can choose to add that or not if you want to double state that one, but it basically accomplishes a lot of what we accomplished already before. And really important, this is gonna feel a little bit woo-woo, but the next one, what does success actually feel like to you? Not the number, but how do you feel about it? Now, let me tie why this actually matters, right? We're all human beings, and so we can come into this and say that feels woo-woo, whatever. I'm not doing that. But I will say this life and business can beat you down, especially when you're going through tough seasons, which you're gonna come as a business owner. And so I think it's really important for you to remember the feeling of why you got into this to begin with. You probably had dreams and aspirations of what your business would be. And I think sometimes we lose sight of that in the muck and in the trenches of what we're doing. And so I think it's important for you to remember what it felt like when you got started, because that usually is going to lead to you taking action and hopefully getting to the point where you want to actualize some of the goals this year because you want that feeling. We're emotionally driven people that we will validate things with logic. And so I think if you can stack those two things together, the emotion of what you want to feel and then the logical actions that follow that, I just think it's a power stack that I wouldn't avoid if I were you. And I'm the type of person that typically avoids those things. And then the last example I'll give you guys here is where are you most likely to self-sabotage, right? Am I gonna fall back into big picture Chris mode, right? Uh am I going to avoid staying detailed throughout the year and not keeping track of things and just kind of trying to remember everything? Like these are things that I fall victim to. And so if that's the type of person you are, what we want to do is figure out what those are and then use your thought partner to help you build a strategy and approach to stop that from happening. Maybe it's equipping a team member. We're using the ClickUp AI agents now, so they'll give us reminders. I'm I'm forgetful. My brain's in a hundred places at once. That's just the way my brain operates. If I position it right, it's a powerful asset to me. If I don't, it feels like a curse. And so it's really important that you recognize the areas where you're gonna either self-sabotage or recognize your own blind spots in the business to just make things work for you. The biggest thing I tell clients is be your best ally, not your worst enemy. And sometimes we don't recognize areas we're gonna self-sabotage or areas that we need to have resources built around us. And then we find, well, I wonder why things didn't work the way they should, the way I wanted them to. Well, you didn't set yourself up to succeed the same way you need to be setting yourself, your other people in your company up to succeed as well. So, really important step that I think a lot of people skip. Now, really important if you do have a business partner at this point, now that you've gone through your 50 questions, is I went through my 50 questions and then I had Claude basically say, I have follow-up questions for Kim based on what you said to see if Claude found confluence between what Kim and I said, which was like a pressure cooker that I wasn't expecting. But if you have a business partner, I definitely recommend this. So basically we packaged all those questions up. I gave it a context handoff and I gave that day, that fork data over to Kim's Claude account, which we call Rosalina. And then Rosalina had her go through the follow-up questions and then send those back to my Claude account, which is called Tarvis for our specific business. So this is where it got really powerful. Again, specifically have business partners. Getting out of a business partnership is harder than getting out of a marriage. And I'm not saying the intention is to get out of the partnership by doing this exercise. What I'm telling you is you don't want to end up there if it is all avoidable, right? So doing exercises like this, making sure that you're both on the same page, making sure you're both agreeing on where the company needs to go and the direction that you're taking with your year, it's gonna prevent you from being in June and realizing I've been working on this and she's working on that, or you're just doing things because this is what you've always done. So this is where it got really powerful for us because it could immediately see where we aligned and where we diverge, and it flagged those misalignments and that allowed us to address it directly. That's something that, again, maybe we've gone months or years and not done that. And this forced us to do that in a very intentional way. And it kind of acted kind of like a moderator back and forth. Not that we needed it, like you know, we were not, we were at odds or whatever. That wasn't the case, but it allowed it to moderate like an interviewer to really dig deep into those specific questions and ask things that maybe wouldn't be asking each other because we're so busy running our lives and our businesses. So that's a really powerful thing, and it's a pro tip for those that have business partners for sure. Okay, so now that you finished your interviews, you're gonna move in towards creating that operating plan. So at this point, Claude had hundreds of pages of raw data from my answers, from Kim's answers, from where we agree, where we did, where we didn't agree, and then we arrived at an agreement on those items, and then we moved towards synthesizing that and putting that into our 2026 annual operating plan. So I'm gonna show you that and scroll through that as I'm talking here, just what that actually looks like from that output. But that was where it got really, really powerful. So you've got things like your revenue architecture. So, like your revenue goals, your stretch goals, your dream goals, the realistic math behind each one, how many clients you need to get and at what price point. So it's not just a random number, it's something that actually has meaning behind it. It's measurable. You can take action on it, see how realistic your stretch goal really is. Super, super important because a lot of people just put a vague number. I'm like, how much do you want to make this year? They're like six figures. I'm like, okay, well, how are we gonna get there? And so what we ab what we're able to do is intentionally put focus behind the efforts that are gonna get you there most seamlessly with the most ease, and then remove the blockades that are gonna prevent that from happening. And that's the reason why you did the interviews first. Now we're gonna go through and put those into actual action plans that you're gonna massage and then deploy to the rest of your team. So these weren't aspirational for us because Claude helped us build them into actual plans around conversion rates, current pricing, and a realistic capacity for every team member. We also built it around the one thing, which is a concept from Gary Keller that we talk about all the time. But let me explain kind of what that means because some people get confused with this. But basically, the one thing is the thing that leads to the many things. So for us, it was getting our internal protocol called Loungy Built, which is our AI operating system inside of ClickUp with their new 4.0 and their AI agents. This offloaded so much time for Kim, which allowed Kim to focus on marketing, which allowed us to focus on more of our YouTube content machine, which then allows us to enhance our leads, which we close at a higher rate than most, which we close at over 90% and we retain it over 90%, which is then enabling her to focus on ads. So the one thing for us was getting Kim out of operator mode, letting her truly just be the marketer. And that has literally already within a month of building that initial plan, has already created sizable bandwidth where she will literally tell you that she's spending about a third of the time in the business than what she used to. So for us, that was a huge one thing, and it played a massive role in our operations for this year. Okay, and then from there, so just to recap, right? We're going from let's have our interviews, let's figure out what our annual plan looks like, let's figure out the one thing that enables that and makes that most possible. And then we're gonna break that into quarterly rocks. Now, I'm gonna do a video on how we did this quarterly rock process in a future video, probably in the next week or two. So make sure you check that out and make sure you subscribe for that episode. But basically what we're doing is we're saying, here's all the things. How do we break that into chunks? And how do we make those chunks the most important things we should be focused on in an order that makes the most sense? Now, this is built on uh one of my friends and mentors, Gino Wickman, on his concept in the book Traction. You can read that if you haven't read that already. But a lot of people have trouble extracting their annual plans and putting that into the quarterly rocks, or they don't understand the concept. So for me, having Claude trained on that, my Tarvis trained on that, it was able to kind of pull the things that we determined from the annual plan and map those out for me. And another future episode, I'm gonna show you how I actually connected my Claude account directly into ClickUp and gave it MCP access to allow it to actually build those out in ClickUp for me and assign dates as well as people that are involved with those specific tasks. So basically all of our initiatives and all of our quarterly rocks are already built for me. And all I had to do was just initiate, hit execute, and it was done for me, which was crazy powerful. And that's something that used to take me hours to do just to sit down and actually finish that process. So again, you can see the cadence and the way we did ours was foundation to acceleration to scale to optimize. They're quarterly themes. So quarter one was foundation, quarter two is acceleration, quarter three, scale, quarter four optimize. I like operating in themes, but again, I'm gonna cover that in the quarterly rock video. So if that's something you're interested in, make sure you check that out. Now, the last consideration uh in this process is we have something we call the Prosper Plan, something Kim does every single year for our clients. It is wildly popular. It's why we do it every year. People in our community beg for it and our clients beg for it. That's not something you're gonna have access to, but if there is any kind of additional protocol you want to add on to what I've mentioned, you can always add that to it. And so for us, that's the Prosper Plan. Uh, if you are a member of our community or you're planning on being a member of our community or in our one of our coaching programs, you'll have access to that. It's already weaved into what I built inside of this entire process that you have access to that literally takes you through this whole thing. All right. So if you are a coach or a service provider running an online business and this video was really valuable to you, and you haven't used a tool like Claude before for strategic planning, I hope you got a lot out of this video. But here's the deal I cannot stress this enough. Don't rely on your own brain to try to plan things out or skip planning altogether. It's you need to build a system like this. And this was the easiest planning year that we've ever had. I enjoyed it the most. I'm not a guy that enjoys doing this kind of stuff. I like living in big picture land. This is not the most fun thing for me. But we've already nailed all of our quarter one rocks because of this focused attention we gave to this. So, as I mentioned, we do have some future episodes coming up, and I'm gonna build on this one, like how we built those quarterly rocks, how we gave MCP access to Claude to help me build through clickup, how we activated all of our team members and assigned those tasks or initiatives. So I think if you like this video or you got a lot out of it, make sure you subscribe, hit the bell for notifications, and like the video so you see future videos like this for when those get released. And if you are interested in more one-on-one help from us, we have a couple of different opportunities for you. You can join one of our coaching programs that I've talked about. That's gonna help you build this kind of strategic plan, both around your operations in your online business or your marketing plan or even your AI integration that we can help you with. Or if you just need a one off for now, you can also check out we're offering AI integration calls as well. And you can sign up for those down below in the description, as well as information on more of that coaching. You can text us and see if that's the right fit for your business. Hope you guys enjoy this one and we'll see you in the next one.