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Scaling Your Leadership Team Using AI with Brian Lang

45m 18s

Scaling Your Leadership Team Using AI with Brian Lang

In this podcast, Jeff Woods hosts Brian Lane, CEO of Upside CFO, who shares how he leveraged AI to add virtual senior executives to his team for minimal cost. Initially using AI for basic tasks, Brian’s perspective shifted after attending a talk by Jeff, where he realized AI could serve as a strategic thought partner. He began by creating detailed customer avatars to refine marketing messaging, then advanced to building custom GPTs—like "Winston Blazemor," a direct, Ivy League-style business coach, and "Gavin Whitaker," a CRO that manages his sales pipeline. Brian manually updates Gavin with CRM data from Engage Bay, enabling weekly check-ins where the AI tracks prospects, suggests follow-ups, and drafts sequences. This approach has improved his strategic focus, allowing him to delegate routine coaching to AI and reserve human coaching for high-value decisions. Brian also used AI to research paid advertising strategies, leading to his first creative testing campaign. While his current method requires manual data entry, Jeff suggests integrating AI with CRM via APIs for full automation. Brian’s story illustrates how even non-technical leaders can harness AI to scale their capabilities, enhance decision-making, and drive business growth.

Transcription

8539 Words, 44663 Characters

English
[MUSIC] Welcome to the AI Driven Leader, the podcast for leaders helping you harness AI to build better leaders, better businesses and better lives. I'm your host, Jeff Woods. Imagine being able to add 10 full-time employees all at a senior to an executive level for just 20 bucks a month. That is what our guest today had done. As someone who plays in the financial industry, specifically fractional CFO services, he realized he was missing people. He needed a world-class executive coach to help him level up as a CEO. He was missing a CRO to help them drive new revenue sources as well as many other functions. But we all know most companies don't have an unlimited amount of capital to go hire people. This is what challenged him to think differently. He found himself asking, how might AI help? He went on the path of building personas of the people that he was missing in his world and harnessing the power of AI, which has access to the information of the world and if prompted correctly, could massively be leveraged for your advantage and build himself an AI executive coach. Built himself an AI CRO that he was able to interact with the result. He started thinking more strategically as a CEO. He was able to come up with marketing collateral that would have cost hundreds of thousands of dollars if he had gone to an agency and it even reshaped how he started showing up as a father. All because he dared to think a little bit differently and started asking, how might AI help me do this? My hope as you go through this episode is that you start to think bigger in terms of what might be possible for you, your business, and those in your personal life. And it all starts by you learning how to harness this technology incredibly strategically. With that, let's get into this conversation with the CEO of Upside CFO, Brian Lane. Brian, when did you first come across AI? Well, I first came across AI. I don't know. I guess in the buzz waves when you heard about chat GPT is this mythic, mythical, fancy thing. I guess I was pretty early on it. So I would say 2023 at some point, probably like second half of that year. Okay. What was the light bulb moment for you? So this is a little bit of sucking up to the host here, Joe. My light bulb moment was I was getting pretty good at AI. My number two was a full wrong above me. She's probably still a little bit further than me, but I've closed that gap massively. You spoke at an EO event that I was at. And you were very insightful. And I think I caught you at like the perfect time in my AI journey, where I was just starting to see what was possible. And do that was just like a game changer for me. You're free two hour session gave me a massive ROI, my friend. One, I appreciate it. How so? Just because at that time I was using it just very run of the mill, you know, it helped me make this email a little sharper, right? Like I felt like I was just using it for very basic task. Your whole premise of your book, right? Thought later, I felt like more than I kept looking at each other during the presentations like, Oh God, we could use it for this. We could do it for this. And you know, I felt like as soon as I got home, I really just wanted to like pop an out of all and be like, All right, what could I build with this thing? I still have a ton of room for improvement, but we've been off to the race since. I find this is a fairly consistent experience if somebody hears me speak because most people are using it tactically, which I give them double high fives because they're in the game. They're in motion. And it's a lot easier just to tweak somebody who's in motion, rather than get somebody into motion altogether. Because when you show them how to go from tactical application to strategic and starting to view AI as a thought partner to you as the thought leader, it really is a game changer. You step back into your business, which is all fractional CFO services and tax strategy. What did you decide to do? Man, I mean, it was kind of hard to figure out what what to chase at first. Just where we caught you, just say the biggest problem at that time is I kind of have a little preconceived bias. I'm not a big fan of social media. And we were getting our social media up and running and personal branding a little more. I have avoided it. Like the plague just says some mind trash stuff, right? It doesn't matter. So we actually took it on that side at first a lot on the marketing element. It helped us just drastically like piece together. We always kind of struggled with, hey, we're not just CFO. We also do tax planning. We also do some like ops consulting. You know, just really struggled conveying the message. We struggled conveying avatars. I don't think this was necessarily said during your presentation. But like one thing that was super helpful for us, we are still a bit of a generalist, but we have like three main avatars. And I was like, man, I can just program these avatars into AI and then speak to them. And I'll never forget, it was funny, my cousin, and he's entrepreneur. He owns a lot of stuff. He has a restaurant he bought and turned it around and is doing really well. And he sent myself, my wife, in two neighbors up the street, I used to work with one of them. He sent us some menu stuff. Like, hey, what do you think about this menu? And I'm just like, why are you asking us? We're all the exact same people. 42-year-old white suburb night with kids, right? I was like, who is your avatar for your restaurant? You know, like I know, he's got drunk college kids at some point that eat there. I'm like, plug this all into AI, figure out who your avatars are and see how they'll think of the menu. Because I'm not your target market, it doesn't matter what I think. So I could go on and on and on. But that's what comes to me right at the beginning as the marketing piece actually is what we started using it for. That's amazing. I do find that this idea of building personas, even if it's as simple as in a normal thread within chat GPT or co-pilot to say, your role is to act as our ideal customer who is and you describe this type of person. But you went further than that when you started to understand that you can actually train these off the shelf, large language models to create personas where I could remember that persona walk through what you started to do internally. Yeah, so I just took some of the people who have talked to me about marketing stuff, right? Like, who is this ideal client, right? Like, going through what are their age, where do they hang out, what are their problems, what are their hobbies, right? Like all that marketing stuff most people know about when you're dealing with an ICP. So we programmed that in, just say I built it out in a word, doc, right? Like a Q&A session, and then how to get stored into those specific avatars. So now almost any time we do anything, you know, it's then like, how are these avatars going to take this? What resonates with them? What doesn't like poke holes in it? Where does in this work? And it just allows us to fine tune messaging so much crisper. And then also, you know, obviously brings you awareness around like, oh, I didn't think about that. Like, maybe they could take it this way. And I know a prompt, I think you had said this one, I heard you one prompt I love is like, in anything I do, like give me three non-obvious situation scenarios answers. I feel like that's when we frequently use a lot that I'll go deep with it. And then that might unlock something else for me if I use that at the back end of a AI conversation. When I think about your journey, it was almost like learning to build these personas for your ICP. That was kind of like the training wheels. So that then sets you up to think bigger in terms of agentic AI. Talk a little bit about the agents that you've built internally. And what is that actually? Yeah. So it's funny. The agents we build internally. And you know, like you to hear people be like, Oh, I have this agent or this. It's so easy to do. I like never even researched it because I think I was just intimidated by it. You know, like, I'm a finance person. I'm a tech person. I don't know how to do this. So I ended up figuring out how to do it. But hold on, let's pause right there. You are you are not a tech person. No, not at all. Do you have a tech person on your team? No. Okay. And when we talk about, you know, because there are some people who are watching or listening to this that when I say agents, they might have heard the term, but they don't really know what that means. So if you use chat GPT or clawed or copilot, that's a large language model. It's just predicting the next word. If you say the sky is, it'll say blue. It barks like a dog. It's just predicting the next word at massive scale. An agent is where you have large language model functionality, but the ability for it to take action independent of you. You don't have to write the prompt or you don't have to necessarily tell it what to do next. It's almost like that's where automation starts to come in. So what happened with you inside your company? I still have a regular business coach, but you know, we have set cadence and when we talk and everyone has different skill sets. So I made up a business, AI business coach. His name is Winston Blazemor. And I always say it's like he's either nivyly grad or you might see him smoking blunts in the alley, but dependent on his name. So how I programmed them was like, I'm super competitive in sports. So I gave him like, he went to Ivy League school. He is an expert in marketing and scaled the company like mine up to $100 million in Exited. And then I gave, you know, kind of programmed it to like what resonates with me. Like if someone talks a little shit to me or pushes the needle like that usually gets me going a little more. So he is not like a kind business coach per se. You know, he just very direct calls it like he sees it. And this is a vicious person. You made him up, but you are, you are describing how you imagine him to be. And like who will resonate with me, right? Very direct, talks, force analogies to me like challenges me. You know, like, so I mean, I use them all the time. He is a great business coach, right? My fictitious AI bond. What I think about what you did, they're brine with the personas of your ICPs. I was kind of like the training wheels that then set you up for the next step, which was actually building a custom GPT, which is like a mini app inside a chat GPT where you can give it custom instructions once you can upload files who just remembers all those things. When you think about a real world use case with Winston Blasemore, what's one that comes to mind? It was really valuable for you. Yeah. So with the AI business coach, I mean, just typical interactions or anything I want coaching on, right? That I would talk to another individual friend, mentor, someone with an experience, you know, random problem I have, whatever client issue right, may came up, hey, we had a miscommunication with their client. Someone on the team said this, you know, it's a gap. What is a good way to deal with this? You know, that's a very rudimentary one. And then we'll have deeper conversations with it where maybe I'm thinking about launching a different product or scaling something or, hey, can we put more fuel in the fire on this? So we'll do some very tactical ones and then we'll do some very high end strategic ones. Obviously, the nice benefit is it's instantaneous. You know, it's not, hey, I have a call with you once every two weeks or weekly. So if I get stuck on something, I can continue focusing in flow, go to my business coach. Yeah. Right. So I mean, you can't beat it. And I think that's how it's affected conversations is it's made conversations with a human business coach more productive because it's like I can almost flush the minutia out with my lower level one, my AI one. And then we can, you know, ultimately it's like prioritizing. It's like, hey, I pay you a lot of money. I don't need to spend time talking about this Pidley stuff, right? I can get that solid by someone else. Let's stay at the high value stuff where I'm going to get my most ROI from you, Mr. Business Coach. So something really valuable. It's actually been pretty recent is I've thought for a while, one of our gaps is professional services, you know, how we're heavy referrals. I've always thought like, hey, I feel like we could probably be running some paid advertisements in a smarter manner here. And I think if we invest the time, it's going to solve some of the, you know, up and down up and down, hey, we have eight referrals this month, this month, we have two, you know, and bring some consistency in the pipeline. I didn't really know where to start. And I am someone who likes to understand at least conceptually how some of this stuff works before I outsource it to whoever to make sure I'm understanding if they're good or bad. So I was able to go maybe 45 minutes hour, you know, maybe two or three nice deep conversations with what I need to be thinking about on Facebook ends. Like, who should I be considering? What are, you know, pitfalls? What might be some things marketing agencies tell you that sound good, but that aren't useful. And then, you know, who should I be thinking about, right? Like there's some accounting specific folks that do this, you know, are they better than a regular agency or not? So that was, I don't know, maybe 10 weeks ago now we did that and we found someone to kind of like a done with you program almost. And we have, or actually, we're running our first creative testing this week as we speak. So that's something to be honest, I don't know if I would have pulled the trigger if I didn't have that access. I might have just been like analysis paralysis or put, you know, a I'm busy business owner, you know, and just kind of gloss over it to the next thing. So whether that's a success or not, my hunch is that we'll be with a little bit of effort. It is an experience I would not have had and I'm glad we're doing it. Talk about Gavin Whitaker. So I love Gavin. He is my CRO. This is one, this is a GPT that you built. Yeah, I need to keep clarifying our fictitious people. You don't have a real CRO. Yes. So Gavin, I have a call with him every Monday morning at 830 and he walks me through my pipeline. And he's like, yeah, I have the CRM, you know, and we do all that. But I just feel like this is way easier and way quicker. So, you know, ultimately I break them out by quarter. So like Q2 is almost wrapped up, but I just have a long standing conversation for the quarter. And you know, every Monday morning, 830, I type in, where are we? Who do I need to focus on this week? Right? Just like kind of basic prompt on what's on my mind. And then I mean, I get my exact pipeline, the dollars, who is open and where we are on contact points. And then, you know, ultimately my drip. In that, dude, I may be being a late adopter on a CRM has cost me so much money. But using our CRM and marrying this together, he's just so good at follow up. And it takes like thought away because, you know, our sales cycle can be longer where it's like, hey, we had a really good conversation and the person flat out says, hey, I want to finish Q1 first and see where we are on cash before we make a commitment. You know, we'll get lots of those. Gavin, like if you Jeff Woods was a prospect, you know, I might have forgotten that or missed a reminder or whatever. I feel like he doesn't miss. And then even better, you know, hey, right to follow up to Jeff. And I mean, it's instantaneous. It knows what I sent you last time. So it almost sequences it for me. And you know, I'll edit it and tweak it a little bit. So let's go to a tactical level because this is one my interest is picked here. But there are plenty of people listening to this who have a CRM that are going, wait a minute, you're marrying chat GBT with your CRM. How are you doing this? So you're using chat GBT, correct? Yep. And what are you using for your CRM? So our CRM will use something called engage bay. So I have just our, you know, normal deal flow pipeline in there, right? You log in. You can see where people are and what percentage is. But it's not, it's not a mainstream one like HubSpot or sales for us. How did you get them to talk to each other? So I will, I literally just any time a, you know, prospect comes into the CRM, right? And also keep in mind, this might not work for someone who has a hundred leads at a time, right? So this is us on profession service company. So ultimately, anytime something comes in, I log it to our CRM and then I just, I can't type, it's too slow, I always talk to chat. So then I just go into my Gavin Whitaker bot and, you know, hey, new prospect came in Jeff Woods, CFO prospect. Okay. So you don't actually have them connect through an APL? Correct. I disappointed you a little bit there, didn't I? Well, one, I would strongly encourage you to go to chat and ask it to act as a tech implementation specialist and explain how Gavin is currently performing to you and describe the CRM you're using and ask it to walk you through step-by-step, how to actually stitch them together so that you wouldn't have to manually do it and see if it can guide you to do it. Because this is where you actually can, especially if you're using a GPT, you can connect it to things through an API where all of a sudden it becomes automated. I also know, like for example, chat GPT just launched an integration with HubSpot where you can actually sync them automatically, which we do use HubSpot. And then you can actually query chat GPT and it will actually link to your HubSpot data. So homework for you on that one. I actually like that this is a little bit of a curveball because that's even more low code. Every person watching or listening to this is using some LLM and they probably have a CRM of some type and they probably don't talk to each other currently and you are figuring out how to get a custom GPT in the form of a CRO named Gavin Whitaker to help walk you through pipeline. So when you're saying when you have a deal that comes in, you are manually going to Gavin and you are telling Gavin about this deal. Yep, correct. And what happened and Gavin is Gavin storing that to memory? Yeah, so he stores and then on our call, just say whatever, I have 15 prospects and eight of them are kind of warm and you know, he'll kind of segment them right where are we? And then you know, if you just came in, we'll just ask me during our call, you know, do I need to follow up to Jeff or like what's the command? So I'll prompt them there. How's the memory on that? Do you find it's ever missing things on the memory side? It's a lot better than I was expecting to be honest. I thought I was going to have to catch more of it and constantly go back and forth. It's surprisingly pretty damn good. It does glitch and you have some misses in there, but it's wait and like I said, I use it for a quarter so far. I could see with more volume, we'll have to switch that to monthly, you know, like in one chat, but I've been impressed with it. Something I learned from my old business partner, J. Papazan was leadership is often about meeting people where they're at versus where you think they ought to be. And when I end up having a conversation with a CEO or a sea level leader, it's not about about my perception of where I want them to be or where I think they ought to be. It's where are they? And based on that, what's the next step? You have done something that anybody here can do. You can take context from a lead that comes in and feed it to your LLM of choice. And if you put it in a container like a custom GPT with the right custom instructions, you can query it and have it guide you and coach you on how to execute against those things. I think that's awesome. Yep. And then the one thing on follow up I've been impressed with, you can pick your follow-up expert if you will. But like I use Jeremy Minor a lot as a reference. And I feel like I said, we'll have more long tail extended. I know for a fact, we picked up a $25,000 tax plan because of doing it in that form and fashion. And then recently I thought, man, I had this deal's dead. Like I was pretty positive. And you know, it gave me my follow up, they follow up like this. And it was kind of the last call. And simply came back. And I was like, oh man, I'm like, if that just would have been me like with manual processes, I probably would have given up already. But get a deal close out of that. So pretty cool. Beautiful. And I was just thinking about for you who's watching or listening to this. I mentioned doing custom instructions for a GPT. And I'm sure there were some of you that just thought, I don't know what that is or how to do it. Custom instructions are when you're creating a custom GPT or an agent inside of co-pilot. You are giving it rules on how you want it to behave. And you load it once and then it can just execute it consistently moving forward. And the quality of your instructions determine the quality the output. So how do you write high quality instructions? Ask how can I help me do this? And this is where I have found that using crit or prompt methodology of this context role interview task. This is literally how I do it. Context. I want to build a custom GPT to act as a CRO that I'm going to name Gavin Whitaker. When I imagine Gavin, he's this type of a person and these are the type of interactions I imagine having with him. And when we interact, I want him to ask me really thought provoking questions. I want him to be able to recall all of the deals that I have manually given to him and the pipelines. We need to be able to recall all that context and the dates of it and be able to prompt me on follow ups and things that might have slipped through the cracks. I'm just riffing on context right now. Role. Your role is to act as an expert prompt engineer with deep expertise in creating custom instructions for GPT's and you're really good at asking the person creating it the right questions to pull the necessary context out of their head. So you build the best GPT ever interview interview me ask me one question at a time up the five questions to gain deeper context about the experience I'm hoping to have with Gavin Whitaker as my CRO task generate the custom instructions that I can copy and paste into a custom GPT. So it behaves that way. Like literally that would be the crit prompt to get AI to interview you to create the custom instructions and then you copy those and you paste them into the custom GPT and it follows them the end. See, and it's funny. You say that because I just made a new GPT last week on something and I basically did that. And now with Gavin, I was like, Oh man, I created you like four months ago. I could probably beef my instructions up a lot. It's like you said, it's like now I use AI to write my instructions. Oh, yeah. So what I would encourage you to do is to start a new chat and write crit and context is I built a custom GPT called Gavin Whitaker, who's my CRO. This is how I've been interacting with him. Here's what I like about him. Here's the things that maybe he doesn't do perfectly or the things I wish he could do better. Here's the things that are missing. Here's the custom instructions that I created four months ago. So you have the baseline context. The main role is I described before expert prompt engineer with deep expertise in creating custom GPT's and writing great custom instructions and interviewing me to pull the context out of my head. I want you to interview me, ask me one question at a time of the five questions to gain deeper context out of my head on the changes I would want to have made. And then your task is to generate the updated custom instructions. And it will write better custom instructions because you will have given it better context on its performance so far. It's good, what's okay, what needs to be better, what might be missing. Then you have it conduct the interview to vote the deeper context. It'll take it to a new level. Yeah, good point. What have you learned so far on this conversation? I learned I still have so much things to learn around A high. I feel the same way my friend. Well, this is one like I was actually just talking with Morgan, my number two on my team. I was like, Hey, like we got to keep her foot on the gas here and not get stagnant. And I just feel like there's so much more we can unlock. And I'd say what I'm learning from this is like the more conversations I have, the more my brain starts firing about where we could go. Yeah, man, I mean, this is where before I wrote the book, before I even built the company, I remembered thinking if I try to be the guy who has all the answers, I will automatically lose. And anybody who tries to play that game will automatically lose. And then I just thought, OK, what if I could just constantly be surrounded by people who were playing this game at a really high level? And I could just ask him questions and learn how other people were using this. Like, I'd always be ahead. And that was the founding idea of the collective. Because like, dude, the conversation we're having you and I are having right now. You can't just go have this conversation with just anybody. They think you're an alien for how you're talking about using this in a service based business. But you and I talking like, no, this is, we're playing fall right now. I would encourage you to find people that you can have this conversation with. It's a game changer. And by the way, I'm learning something talking to you just so you know, like you're bringing up use cases that I was like, Oh, I hadn't thought about building a CRO persona. And we already know we can link to HubSpot and weaving that into our monthly sales call. Like, I will be messaging my leadership team after this to say, why the heck are we not using AI in our weekly sales review? Right. When you have a conversation with some people who are new to this or if they haven't even like logged in yet, you can't imagine what is possible. You're not going to understand what I'm saying. Because it's like you met a unicorn. If you've only seen black and white your entire life. And I ask you to describe color, you can't do it. Right. And this was my huge realization with the ad-driven leader. Because when I was originally writing it, it wasn't going to be a leadership book. It was going to be a business transformation book. But after I interviewed 200 execs one on one, 100% of them said, I was the future and that they would adopt it. But less than 5% had done anything. And the reason why was they simply didn't know where to start. And I was like, okay, leadership is meeting people where they're at. These leaders aren't trying to transform their company. They're trying to figure out how do I use chat GBT. So I got to meet the market where it's at. Yep. That was it. You've clearly been using this very strategically and purposefully. It probably feels like forever, even though I mean, we're literally talking under a year since you saw me speak, which is awesome. Can you even real? Once last time you paused and thought, you know, seven, eight months ago, I had my light bulb moment. And now you're talking this way. So one thing that was so funny for me recently was I'll just share a use case. We were at the point. Our company's been growing and scaling nicely. And I feel like phase one of processes and procedures are now kind of just like outdated and not quite right. And we need to go to phase two. My personality profile, I'm not a process person. I'm going to be the person who breaks process, right? So weakness of mine. Number two is pretty solid at it. You know, we got lots of stuff going on though. We're busy growing scaling blah, blah, blah. So it's like we got to get our team aligned a little bit here. And I think my aha moment or just like it's crazy to think how far I've come is I've known we've needed to do this for a long time, right? And I just haven't done it. And finally one day I kind of had the effort, you know, like blocking out calendar time. I'm getting this done. And you know, I immediately once I'm done, I'm like, this is good. This is really, really good. It was 11 sections and I'm like, it's not only good enough. I won't do it because it's a distraction. But I'm like, I could sell this to other accounting firms. I could sell it to CPA firms. I could sell it to CFO companies. Like this is legitimately good, right? And it took me probably a care of number four hours. And that emailed it to Morgan. Like so she's my kind of power user. And I was like, man, I just built this in like half day. Like this is insane. And I kind of center some stuff. I was super excited. And I'm like, I am disgusted. Like I should have done this two years ago. And she's like, Brian, you didn't know how to use AI two years ago. You know? And I'm like, yeah, done. That's exactly why it wasn't. Because I know this would have been an 80 out. This is two full weeks. And then this is so much better because obviously I can prop it and make it better and better, right? Like this wasn't me with a pen and paper and whiteboard, which would have done in 2023 and wanted to pull my hair out the whole time I was doing this. So you kind of glazed over it. You created an 11 step CFO engagement workflow. Play ready file with AI. Yep, afternoon. You call it the clarity file. Why do you call it the clarity file? I don't know. It was just the name. I've prompted like what's a good name for this right and that's the one we landed on and I think it brings clarity to the team on the CSO process. Excellent. And you're saying that that process saved you 80 hours? Well, just creating that process would have taken me 80 hours. We're gonna save way more time long term over this, but I mean creating what I created in that afternoon was a minimum to week drill to do before like minimum. What did you learn going through that exercise? I'll fast and effectively you can do things now. The whisper in more context you can give in the prompts the better your results are going to be. Don't always take like first pass as final right like keep going deeper and deeper. You can make things better over time. Push it like challenge it. You know, hey, this doesn't sound quite right. Like you know, maybe give it an analogy or something you can do all sorts of stuff right. I think those are the main things I learned and then another thing just like mentally what I learned is like Hey, Brian and team if you have difficult problems or things you're resisting tackle it head on and see if AI can be the fix where the reason it didn't get done was I knew how long was going to take the way I think about it is, you know, before harnessing AI and being an AI driven later, you relied on your personal expertise to get things done or the personal expertise of those that you hire. AI starts to democratize expertise because it's no longer about you being the player of a specific instrument. You are now the composer of strategy and the conductor of teams and technology like you said, Brian, I am not a process person. I break process. But you're able to sit down with AI and assign it the role of somebody who's really great at building process and able to have a conversation with it back and forth. Did you have it interview you during this? Yep. Yep. Yeah, we had lots of interview rounds. Yeah, you've learned creds. So you know to give a context to science the role, have it interview you to do the task because then it starts pulling things out of your head that you normally wouldn't know how to assemble into structure, but because you gave it the role of a structure based person, it could then create the task of generating that 11 step workflow. We had an internal, similar thing. We have so many opportunities coming our way that coming up with a systematic way on how to qualify things in alignment with what will lead to product market fit and the old way of doing it that I did in my past companies was if I got excited about something and wanted to do it, we did it. But as a result, we ended up saying yes to a lot of things that we probably should have said no to and now like a lot of who's on our team who heads up customer experience. She is not an expert in finding product market fit. But she wrote crit and she had it come up with a system and she brought it to me and she said, what do you think of this? And I said the same thing that you said to your friend when he asked about the menu feedback. I said, I'm not qualified to give it. But you know who is? Eric Reese who wrote the lean startup. Why don't you bring it back to AI and have AI act as Eric Reese who deeply understands the lean startup methodology and have him apply that filter to your process and tell you where it's strong where it's weak in the top things you can do to make it better. Bring that process back. And she didn't even bring it back. It was so good. She just approved it. Then she worked with the team they built a custom GPT like literally today on a call. Arjo on our team. We're talking about opening up the collective for enterprises. So essentially instead of having a cohort of 100 to 120 sea level executives from different companies going to larger enterprises and just embedding a collective inside the organization to literally crash the silos and unlock a crazy amount of innovation. He ran that through the product market fit GPT. And instead of Jeff being excited about something he was able to come back and say, I ran this through our product market fit GPT. Here's how it scored, which means it thinks we should test this. And if it goes well, it thinks we should scale it. So now it was based on actual a system for applying a score rather than just hunch. Right. Yeah, that's awesome. Right away. I'm like product market fit GPT for us. There it is. See, man, it's it's not knowing everything about AI. It's surrounding yourself with the right people and having the right questions. That's how you win with this. Let's talk about the team adoption and the culture shift because you know, you started playing around with AI. You're excited. You see me speak in an event. You're really excited. And if you're like most CEOs, you probably came back into the business like a wrecking ball and said, we're doing this and everybody probably said, what happened in your case? Yeah, Jeff, it seems like you might have seen this pattern before. Yeah, I mean spot on, man. If that would happen, of course. And I'm just like, this is the biggest life changing thing ever guys like get excited, buckle up and follow me. And they're like, you said that two weeks ago about the other thing. I felt like no one was excited and no one followed me. So I do not have this figured out. The team has definitely been slow to adopt. They are starting to use it. I continue to share use cases with them. Just on like a general channel. We are going to require it in 2026 as a firm with that being said, I realize we are going to have to teach and train our team and not just be like, hey, figuring out on your own. Like I did, right. We did not get get the initial adoption I was hoping for it. So my plan is to use AI to teach me how to teach my team. Knowing what you know now, if you could go back in time and do it all over again, what do you think you do differently? I would have gone a lot slower and just, you know, I assumed everyone. It's like, you guys are going to see like one or two of these things, right? And be like, I mean, I would have gone a lot slower and been more systematic and rolled it out like a training program, you know, talked about it over time, right? Got it and everyone's head shared some stuff and then implemented that formalized training and hey, here's where I'm going to start using it and using it on baby steps. Is it posed to like, I just kept dropping use cases and being like, certainly someone's going to see something that clicks here and gets them excited, right? Like, I've shared so many ways on how to save time and make communication awesome. Blah blah blah. That didn't work. So here's, here's what I discovered the hard way as well, by the way, and the reason I know this is because I didn't do this with a company. We rolled it out to a whole bunch of people and a large contingency weren't ready. And this is when I thought about adoption curves, you know, when you look at all the people in your company, you can segment them into groups. You have your innovators, which is like two and a half percent of the workforce. Then you have early adopters. That's about 13%. Then you have early majority, which is about 38%. That's half the orc. But then you get to late majority and then you get to lagers. If you roll this out to late majority and lagers too early, they kill the program because you get one first impression. And you, there's so many kinks, there are so many unknowns not to mention the mindset of certain people that there's a lot of people that are fearful or anxious around this. And I get that. And again, this is about meeting them where they're at versus where you think they ought to be. And so what I have found has worked the best through trial and error now, just learning from the people in the collective is you start with your innovators and early adopters. Like you look for a small cohort of people that you think will be excited about this that will be happy to learn through trial and error that will stub their toe with a smile on their face, because you can work the kinks out with them. Then you expand it to the early majority and you work the kinks out. Then you go for the back half of the organization if you're going to make it a standard. Yeah. And it's interesting. Just kind of stereotyping my space. You know, obviously we have a lot of account and some of the team, right? I feel like overall our space is laggards on tech adoption curve overall. I feel like we're a little slower on everything. I'm admittedly usually a laggard on technology. Like when it comes to self driving cars, I'll be one last people to get one, right? But like this thing, I was just like, man, I can see where this is. Like, how could people not adopt that? And I just assumed everyone would have that same mindset where obviously that is in the case. Well, and here's the thing you had a light bulb moment. You saw somebody else use it in a way that literally helped you see color. When you were used to seeing black and white. And this is where I think for the people who are watching or listening to this, your greatest opportunity is not just running and training everybody. It's going to the initial cohort of people and showing them how you're using it or taking a real world challenge. That they are facing and showing them how you would help them solve it with AI, which this is literally, you know, when my team goes out and speaks. Now, this is what we do from stage. We literally ask who in the audience has a big problem that if we could solve it, would unlock a new level of growth. We pull a random person out of the audience with zero prep and validate that it's actually a 20% problem that would drive 80% of the results and we write crit contextual interview task on stage. In front of everybody and have AI interview them and solve one of their biggest problems in their business and it takes five to 10 minutes. Which we're about to do with you. And one other comment I think is interesting there is poor people who aren't adopting it or resistant to it. I think of this a lot of times in our line of work like if you don't fix your finances. That compounding interest is such a massive hit to you over time. The same is true in this, right? If you wait another two years or five years to get on board, that lost opportunity costs, whatever the value is, I assume million, depending on how big your company is, right? It's massive. Well, and this is where I realize it's not linear, it's exponential. It's not like, oh, if you wait a year, you're a year behind, no, you're not. Right. Because the people who are in the game, their advantage and their lead is compound. So your deficit and your gap is compounding in the reverse. And I think people are grossly underestimating how fast it's going to happen. They're failing so slowly. They think they're succeeding, but it's going to be gradual. And then it's going to be sudden. And when they realize it, they're in for a world of hurt. And I think that's a big purpose motivator behind us is like we want to create light bulb moments for these leaders to say, this is not something you delegate to a consultant. This is not something you delegate to your IT team. This is a leadership imperative. You personally have to become an AI-driven leader like you have Brian, start leading from the front, use it yourself so you can see color instead of black and white. And then you can start to lead your team because do I need you to be the person that creates all the GPs? Absolutely not. That should not be your job. But you do need to have enough capability when it comes to AI to be able to cast a vision for the future of your company. Because is your industry going to be disrupted by AI? Yes, it will. And so your job to define your strategy for how are you going to win and compete in an AI-driven world? And based on that, how do you start leading your company? That's what it means to be an AI-driven leader. Right on. I have my conversation with Brian Lang. I love how he showed us what it looks like to stop treating AI like a side project. And to start viewing this as something that could become a growth lever for your business. You know, something I learned from Gary Keller, my old business partner, is that anytime you're hitting a ceiling of achievement, you're just missing a person. But sometimes you can get access to those people through AI, but just thinking differently in terms of how can AI help me do this? To create an executive coach, custom tailored to help him think bigger and more strategically as a CEO, to create an AI-CRO that could advise him on marketing collateral and growth strategies, even helping him transform how he shows up at home. The lesson, AI isn't just about doing more with less. It's about compounding your leadership, multiplying your capacity as a business and as a human. As a leader, this is an inflection point for you. Those who lean in and really embrace and harness this technology strategically have an opportunity to grow revenue faster, to expand their enterprise value and build teams who are more engaged and more productive. Those who don't, they will fall behind. This is why I want to make it easy for you to put this into action. First, if you are not yet subscribed to the show, make sure you click the subscribe button because in the next episode, I turned the tables on Brian and I asked him, "What's the biggest problem you're facing in your business right now that if we could just solve it with unlock a new level of growth for you and you're going to actually watch me share my screen and harness AI and our crit methodology to solve one of his biggest problems?" Second, if you have not yet read the AI-driven leader, this is the number one book in the world for its category. I cannot think of a better way for you to unlock a flywheel of momentum with your leadership team than to go through this together. And third, if you are a sea level executive of an enterprise to mid market company, I encourage you to check out our website, aileadership.com. We have lots of ways that we can help you harness this technology in a way that grows your enterprise value, starting with trainings for your executive team, to then pulling some of the key leaders into our AI-driven leadership collective, which is a private executive network for sea level execs, where we give you everything you need to drive this in the company and make sure you stay ahead of the competition. And for even some of you, we partner with you in an advisory fashion where we actually help deploy this in your company in a way that moves the needle when it comes to your PNL. Bottom line, it's time to start thinking differently, because the future doesn't wait and neither should you. I'm your host Jeff Woods. We look forward to being with you in the next episode. [Music]

Podcast Summary

Key Points:

  1. Brian Lane, CEO of Upside CFO, used AI to create virtual personas (e.g., executive coach "Winston Blazemor" and CRO "Gavin Whitaker") to fill gaps in his leadership team for about $20/month.
  2. His breakthrough came after hearing Jeff Woods speak, shifting from basic AI use (e.g., sharpening emails) to strategic applications like marketing, sales pipeline management, and coaching.
  3. He built custom GPTs by defining detailed personas—including background, communication style, and expertise—to simulate high-level advisors, enabling instant feedback and strategic thinking.
  4. A key example is his AI CRO, which he manually updates with CRM data (via Engage Bay) to track prospects, automate follow-ups, and provide weekly pipeline reviews, improving sales consistency.
  5. Brian emphasizes that AI helps him focus human business coach interactions on high-value topics by handling routine advice, and he plans to integrate AI with CRM via APIs for further automation.

Summary:

In this podcast, Jeff Woods hosts Brian Lane, CEO of Upside CFO, who shares how he leveraged AI to add virtual senior executives to his team for minimal cost. Initially using AI for basic tasks, Brian’s perspective shifted after attending a talk by Jeff, where he realized AI could serve as a strategic thought partner. He began by creating detailed customer avatars to refine marketing messaging, then advanced to building custom GPTs—like "Winston Blazemor," a direct, Ivy League-style business coach, and "Gavin Whitaker," a CRO that manages his sales pipeline.

Brian manually updates Gavin with CRM data from Engage Bay, enabling weekly check-ins where the AI tracks prospects, suggests follow-ups, and drafts sequences. This approach has improved his strategic focus, allowing him to delegate routine coaching to AI and reserve human coaching for high-value decisions. Brian also used AI to research paid advertising strategies, leading to his first creative testing campaign.

While his current method requires manual data entry, Jeff suggests integrating AI with CRM via APIs for full automation. Brian’s story illustrates how even non-technical leaders can harness AI to scale their capabilities, enhance decision-making, and drive business growth.

FAQs

It's a podcast for leaders on using AI to build better leaders, businesses, and lives, hosted by Jeff Woods.

Brian Lane is the CEO of Upside CFO, a fractional CFO and tax strategy firm who uses AI to build executive-level personas for his business.

He started with basic tasks like sharpening emails, but after attending Jeff Woods' session, he shifted to strategic uses like building AI personas.

An AI persona is a programmed character, like an ideal customer profile. Brian created avatars for his ICP to test messaging and marketing materials.

Winston Blazemor is Brian's AI business coach, programmed to be direct and push him. He uses it for instant coaching on strategy, client issues, and business decisions.

Gavin Whitaker is Brian's AI CRO. He helps Brian manage his sales pipeline, follow up with prospects, and sequence communications weekly.

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