CRIT™: Building Your Leadership Playbook for Growth

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. And this is what challenged him to think differently. He found himself asking how might AI help? And he went on the path of building personas. In this episode, you are actually going to get to watch me share my screen and pull up AI and harness our crit framework to solve his problem. Crit stands for context, role, interview, task. This is a framework that you can apply today on any problem that you are having. You give AI lots of context. You assign it a role, meaning the expert you want it to become, then you turn the tables and you have AI interview you to pull deeper context out of your head so it can then help you solve your task. 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, would 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. 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. It's so easy for us to come up with use cases that are 80% tasks that only drive 20% of the value. I'm not interested in this. That's not how you deliver the maximum impact. I'm going to share my screen. We're going to do it. So for those of you that are watching, you're going to see it for those of you who are listening, I will narrate. So first thing I'm doing is I am literally just typing in context, role, interview, and task. And I've got those words and all caps because they're headers. It's like a delimiter. And I've got some spaces in between. So now I've got the structure there. Now let's fill it in. So first thing I'm going to do, I am doing this use case for a guy right now who's a CEO of a fractional CFO company that also does tax strategy. I will talk in first person like I'm him, but don't save this to my memory. And the reason I do this Brian is because I do these use cases so often, I asked my AI board one day for my weaknesses as a CEO. And it said for a guy who built a company based on one thing in the past, I'm wondering why you have 50 companies. And you're chasing too much stuff. Yeah, exactly make actually that's not a problem. Thank you, though. All right, Brian, what's a problem that you have right now that if we could just solve it or massively move the ball, it would make a material impact for you. A 20% priority that's going to drive 80% of the results. Start again on the context. What's the situation? Okay, so we have our core CFO services, you know, just think financial analysis for simplicity, budgeting and cash flow forecast, all the traditional stuff. And then we developed a system we called the working wealthy operating system. Working wealthy operating system. And for everybody who's listening and not watching everything that he is literally saying word forward, I am just typing. And Jeff, for you think, you know, like scaling up attraction, like a dummy down version of some of that stuff for your business book reader. So we've been implementing this internally and with a few clients. And it's getting a lot of traction. And I think it could be a legit product or tool. And then where we're kind of stuck, at least right now, this isn't out there anywhere. So I feel like we're almost honey trapping people. They come in to be a tax client or a CFO client. And then we kind of talk about this radium product, the working wealthy operating system, you know, basically at the bottom of the funnel. And no one's biting on it. So I think what I'm looking for is like, does this thing have legs where we put some time and resources to it, productize it, if you will, and focus on this and, you know, sell this as well with the CFO services. Or is this a distraction to our core offering in? Is it just a shiny object? Is it just a shiny object or a priority for our future growth? Yeah. Okay. Awesome. Role, who do you want AI to act as to guide you here? Your role is to act as what? A couple ideas would be someone who scaled professional services before and have added products. And then I also think for context, perhaps it'd be, you know, like Gina Wickman's the author of traction, I believe. Yeah, I don't know if that's a useful prompt in there or something like that, someone who's built this out before and understands what the build out of this looks like. Okay. You are also Gina Wickman, who started the traction methodology and know what it looks like to scale and operating system. Great. Now interview, interview me, ask me one question at a time up to three questions. And are you noticing how I have spelling mistakes everywhere and I'm not correcting them? It doesn't matter. It's so funny when I do this. And so there's always one person in the audience who like that will drive them absolutely wild. And I'm like, that it doesn't matter. Hey, I know what I'm saying. Anyways, don't worry about your spelling being complete. Just move forward. All right, task. What do you want to do here, Brian? Um, I think that the main thing is share some experience or guidance around does this fit in with CFO services. And then I'd also, if the answer was yes, this isn't a distraction or shiny object. I'd like to have a rough roadmap of how we would it, you know, get started, I guess. So now, basically, now that you said that what's going through my mind is I'm asking, where do I need to tune the prompt to make it a little bit more sufficient. So interview me, ask me one question at a time up to three questions to gain deeper context. Task, your task is to give me feedback on if you think this fits within CFO services, make an argument for why yes and make an argument for why no, then based on the context you capture on me, make a recommendation. On what you think I should do and why so because we're only giving it three questions, Brian, I'm going to ask you what context do you think it's going to have to ask for that we haven't given it yet that we can proactively give it so we don't waste a question on it capturing it. What if we not told it that we should tell it. I think I could see it being like, do you have the resources to scale this if it's a viable option rider are you going to great what's your answer to that. Yes, just say resources and capital are available. We have capital available to scale this operating system if it were a priority. Great, so I'm just adding this into the context section, all right, let's rock and roll with that and see what it comes up with. All right, thanks to the context, here's my first question, what core problem does the working wealthy operating system solve that your CFO or tax services alone do not think beyond tactical tasks what pain or transformation does this OS unlock the clients wouldn't get from your standard offering. So this unlocks pairing priorities and multiple steps to your annual goals. So ultimately just like an example I always give is hey you talked to most small business owners what your goal I want to grow revenue from 10 million. to $12 million this year. We think that's doable, you know, whatever the 20% growth. And that's like the goal. You know, they haven't listed 37 steps to get there. And then how do we prioritize those? Some are gonna be a priority. Some are gonna be a C. So ultimately aligning those together where CFO service is just clearly around finance. Okay. So that's more about overall enterprise prioritization. Correct? - Correct. Okay, so I'm typing that. This is about enterprise prioritization, not just CFO services. All right, cool. When you've walked clients through the operating system, what's been their reaction? Specifically, have they seen clarity results or said things like, "I never thought this way before. I'm looking for evidence of perceived value or transformation?" - Yeah, so I think the main, what you said on prioritization, the main thing it's giving people is they have a clear path on what to focus on. Where before the business owner, I feel like they chase lots of stuff. Like if I had a four hour gap in my schedule this afternoon randomly, what would I work on? The purpose of this is to align where you're always working on your A level priorities first. Is it supposed to just busy work, which I feel like lots of business owners are guilty of? And then the other piece everyone's been really impressed with is we've built out weekly scorecards around this, just like high level metrics. It could be marketing and it could be caching and now, a mix of finance and operational. And people have been very impressed with that where they can visually see what is going on with the org where they might have not had that before. What's going on in the org? All right, cool. All right, that's strong signal. One last question, who inside the client company actually uses the operating system? Is it just the owner's CEO, or is it rolled down to leadership team, operators or finance? Knowing this will clarify if it's a strategic tool or a solo leadership aid. - So our businesses usually have CEO and then very small leadership team. It would be for those individuals. Most of our clients are about 3 million to 20 to 30 million in revenue as a frame of reference. - The lightful. Okay, let's see what it says. Now, remember, you're the thought leader. This is the thought partner. - Yep. - My hunch is it's going to say stuff that's probably directionally correct and valuable and I can also tell you there's a ton of context that that's missing here. I would be asking you, what's the competitive advantage you want to be building in the long term? Walk me through what your long term goal is for the company. What are the things that you do that are your greatest strength, that are your source of a sustainable, defensible competitive advantage? 'Cause my guess is this is going to make an argument for you doing it. I will tell you, I think this is a fundamentally different business model. And you're getting outside of finance and into the world of enterprise prioritization and growth. That's a different capability. It's a different skill set. It's a completely different offering. - I could see that. - Now, let's see what AI says. Yes, the working wealthy operating system fits within CFO services. If you reposition it as a strategic layer that guides how financial clarity translates into execution, see there you go. But only if you lead with it. Right now it's invisible buried inside other services. That's the problem. Why it does fit? CFOs aren't just score keepers. They should be strategic partners. Your OS helps clients align financial targets like revenue or cash flow with real operational priorities. That's CFO at its best, turning numbers into action. It solves a core SMB pain, focus and execution. Most $3 million to $30 million CEOs lack strategic prioritization and invisibility. Your OS solves that. If your CFO service is the diagnosis, the OS is like the prescription. It enables recurring high value touch points. Weekly scorecards and OS reviews give you built in client rhythm, deeper embed and more sticking as something that CFO services struggle to maintain. Here's why it doesn't fit. It's a strategy product, not a financial one. Boom, see? Your brand is we help with taxes and books. Talking about enterprise prioritization feels like a bait and switch. Clients don't get what they didn't ask for. It's not obvious where the value lives. If it's pitched as a surprise bonus after they buy tax help, it feels like a shiny object, even if it's valuable. That erodes clarity and trust. Three, it can split your focus. If you try to sell both services equally without a clear front door, you confuse the market and dilute both offers. So here's the recommendation. Make the operating system the tip of the spear. Position your firm as strategic finance partners who install the working wealthy OS to align your leadership team, drive execution and hit financial goals. Then offer CFO tax services as the engine that support the OS. This solves the, what do I do now, pain of most CEOs? It converts strategy into numbers and back again. It elevates your offer above other generic CFO services. If you don't do this, the OS will remain an internal tool that creates unspoken value but never drives growth. And you'll always feel stuck wondering, should we go all in on this or not? What are your thoughts? - I think that's pretty good. I'd say spot on and you know, some of just belief I've had or internal debate is, hey, do we productize this or the other pieces? Do we still have our operating system and just build it into our CFO services? And that's one of the things that makes this better. You know, we're not necessarily selling it but it's just part of how we work as a CFO company where we implement it. And that helps us instead of an 18 month or two year lifecycle, maybe we have a four or five because we do that. So, I think you've got to ask the question, who do you want to become? That's why I like, immediately, I wasn't going to lead you here because I wanted to see what AI would naturally do. It's easy to say yes to something that looks shiny in the short term but if you don't have clarity on where you want to go in the long term, it's really tough to know if you're on track or not. Like if I say, you want to make progress, we're going to cover 100 miles. That sounds great. Except you want to go from New York to LA and I'm taking you from New York to Florida. - Yeah. - I don't want to become an operational expert. - So this is where the dialogue would then continue. I would encourage you to write, crit, and I'll copy this whole thread and email it to you so you can literally just copy and paste the whole thing and say, "Here's a used case I did on somebody else's "jadgbt, study it so that you have the context "now I'm going to continue the conversation "because you can say context. "I don't want to become an operational company "but what I really care about is this. "I would ask it to act as your AI board "that has a variety of personas "from the visionary who's great at casting the vision "for the future and defining a future sustainable "competitive advantage to the challenger "who's great at looking at shiny objects "and quickly being able to distill signal from noise "and priority from distraction. "And any other person is that you would want it to have "and I would have it interview you "and ask you say your job is to conduct an interview "not to please me but to challenge me. "To ask me the tough questions. "Interview me, ask me one question at a time "to really help me think through the clarity "that I am seeking. "And then your task is to help me articulate "a longer term vision for my company. "And once we articulate that, hold this opportunity "up to it and tell me if you think "it's a priority or a distraction. "My guess is Brian, you're gonna come out "of this saying is a distraction. "I think those prompts are a lot better "than where I've gone myself. "So I have a feeling that's my hunch too, I like it. "I'm definitely gonna run it through there. "Yeah, and I wanna be really clear. "I've become much more purposeful in my words. "I'll say my hunch is, my assumption is, my bet is, "my hypothesis is, I've learned to speak less definitively. "And more acknowledging where my stance is "and being open-minded to, I'm seeing one perspective, "and there are a lot more that AI can help me see. "And it helps me see them, "and then I'm able to make a better decision. "Here, let's do this. "Share, entire screened. "I'm curious to see what it's gonna say here. "So I'm going back to it. "So thanks for this at the end of the day. "We don't want to be an operations company. "We want to stay focused on finance. "Let's assume the OS was a distraction. "What are the non-obvious things I value "that the OS includes that are universal "and could be applied to what we currently do? "Because you're just like the OS "because that's the way the value is being packaged. "But instead of focusing on the package, "let's focus on the source value. "You follow me? "Yep, that's, yeah, very good problem." So 20% that drives 80%, the OS gives you leverage frameworks, decision-making clarity, prioritization logic, execution rhythms that elevate financial offerings into truth. strategic finance. You can make those into your existing CFO services without selling the OS as a separate product. Non-obvious OS elements you likely undervalue but should reuse. Number two, weekly focus plus scorecard habit. Value instills cadence and accountability without needing ops infrastructure. How to apply, integrate a weekly financial focus, your branded version into client calls include three to five simple metrics like cash, margin, pipeline collections that reflect a priorities make it visible. Now that's interesting. Three, visual clarity. Oh, and by the way, if you're doing their bookkeeping and whatnot, this is where you could totally build AI in. Where every week you could have it send the client an email with these three to five metrics. Almost like instead of an automated marketing email. Right, that's something I was like, we got to build out some sort of API that can talk to quick books that emails the client because the client's never going to log in to quick books, right? So it's like, how do I get it right in front of them? Yeah. So anytime you're hitting a ceiling of achievement, Brian, you're missing a person. You are missing a person who understands the tech enough to be able to stitch this together because I'm telling you this can be done. Okay. Roger says you can do it by the way. Yeah. Yeah. He would be able to do it just so you know, he has the capability. Three, visual clarity of what's working. Value reduces CEO noise and stress by giving them clarity, not just data, how to apply turn your deliverables and a dashboards with specific traffic light indicators, green, yellow, red, to key metrics, pair them with narrative interpretation, not just financials. Yes. By the way, I've already built this. I built a custom GPT where every month when I get my financials, I just feed it to the custom GPT. It immediately interviews me, asks me one question at a time up to five questions to gain deeper context about the business. And then it tells me the top five non-obvious insights I should know about my business that I probably don't know about my business. Love it. You could easily weave this into when the books get delivered, the insights get delivered as well. Yeah. For sure. For strategic alignment questioning, value, the OS helps them ask, am I working on the right thing? You can reframe that financially, how to apply it and every forecast meeting lead with if we only hit three numbers this quarter, what would they be and what would they fund? And then five annual planning structure, the OS creates discipline around future focus thinking, how to apply it, offer a financial deep dive, each Q4 where you help reverse engineer financial goals into quarterly focus areas and then stay in your lane by letting them solve how to execute it. Bottom line, you don't need to sell the OS, but you should absolutely extract and weaponize its principles inside your CFO service to increase perceived strategic value, elevate your positioning, reduce churn by proving clarity and cadence. That way you stay a finance firm but feel like a financial strategist, not a financial technician. I think dot three in that last sentence is like spot on on what I had in my head through this. Reduce churn and provide improving clarity and cadence. Yep, 100%. What have you learned today, my friend? Oh, what did I learn? I learned all sorts of stuff. First of all, I want to say I wasn't expecting, I thought this was going to be dialogue, I wasn't expecting to learn a lot of this. So this was a great takeaway. Obvious takeaways for me are continue to have these conversations as much as I can. Like just talking to you again, I feel like I'm having more light bulbs, right? Like I need to talk to my friends and peers that are using this. I'm for sure like with something I learned is how I can do that API. I've had this in my head and I haven't messed around with it. And I'm just like, damn, this would be such huge value add if I can get the systems to talk and email or clients. So that was really nice. I got re-acquainted with your crit framework, CRIT. I kind of forgot about that admittedly. I do some of that naturally, but not always the exact same. And then like I said, I think my main one is just from talking to someone who's really good at this. I've mentioned before, maybe pre-call one of my concerns is like, while in better than lots of business owners, I just don't want to fall behind the curve on this. I think it's so important, right? Like how do I always stay out or near the top and people learning? And I mean, just this was a great reminder of how much I still have to learn on this stuff. You rock, Jeff. Thank you, man. There you have it. 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. 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. If you have not yet read the AI driven leader, it 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.