Optimizing with AI: A Thought Partner, Not a Search Engine

Welcome to the Optimizing Beyond podcast. I'm Josh Negron, and this show's all about sharing lessons, ideas, and strategies that sharpen your thinking, strengthen your habits, and push you to grow beyond comfort zones. Let's dive in. Welcome back to the show, and today I want to talk about AI. We can't talk about optimization without talking about AI. It is something that is definitely helping people optimize and really scale their efforts in themselves, in their abilities, and do some incredible things. I myself, it's something that I use every day, and I'll be honest, it's been a long time since I've had this much excitement around using a product every day and finding different use cases and ways to expand my thinking, challenge my thoughts, and also build and scale systems. So today I'd like to go over the main principles of the book AI-Driven Leader by Jeff Woods, and then go over the top ways that I use AI. When I prompted ChatGPT and Claude, what are the most common things that I ask you to do and the things we collaborate on? Those answers were pretty interesting and we'll go through them together. I've not actually read them, so that'll be pretty fun. So let's get started. Now, Jeff has the biggest thing in his book that he talks about, the change of thinking of not how can I do this, but how can AI help me do this? This is a definite change in thinking because sometimes you get assigned a task or sometimes you have a responsibility, or maybe it's something that you do only every month or every quarter or worse off every year. Those kinds of things are hard to remember and to automate. And so when you come back to these semi-regular tasks or maybe something you've never done before that you don't have a lot of awareness of. Then AI can be a really helpful thought partner. That's the number one thing this book really, really focuses on, on using AI as a thought partner instead of just asking it really general questions, because the less it knows, the less useful it can be in a way. So Jeff does a great job of talking about shifting the language about trying to create some kind of flywheel of awareness. So Sometimes that means you might spend a little extra time prompting, but it's designed to help you spot opportunities that AI can provide high-level thinking instead of leaving you where you're at. Easiest way to put this is, have you ever been stuck in a project, a task, or maybe even in high school or college that you were procrastinating because you didn't fully know how to complete the assignment? So you were just kind of stuck. So I find that AI is really useful in that way. So for example, I'll just let it know like, this is what This is what I'm supposed to do and I'm not really sure. This is what I'm stuck on and kind of give it some details like that. And then I'll have it start to get me unstuck and it's really, really helpful. And that feeds into the second technique that Jeff talks about in his book. And I think this is the number one thing that I use in almost all my prompts unless I don't think it's very broad and I don't need to. And that is the reverse interview technique. Now this is when you give it a prompt and then you ask it to ask you questions. Interview me with questions one at a time. I like to do one at a time instead of all at once, because then it just poops out 10 questions or whatever. And then sometimes you're answering multiple questions, or at least multiple dimensions of questions that one answer would've answered. So I find it's way more effective for both of you, because if you answer number 2 a certain way, it likely wouldn't have asked you maybe question 7 or question 10. So I'll give it the context of whatever I'm trying to say, you know, give it the role, like I want you to act as whatever, this is what I'm trying to do, and then say, ask me 10 questions one at a time so that you can best do your job. And I find that that's a really easy way to prompt, and then it'll just start asking you those questions one at a time to give it the necessary context and information that's in here that it doesn't have. And so this makes it feel very similar to how you would train a new employee that has no idea of the context of anything. And so, uh, it can ask some really relevant questions to things that might seem obvious to you, but those answers that you give it can be the difference between AI's response being absolute trash, useless, and a waste of your time to something that can really have a massive impact on what you're doing. The next thing Jeff talks about is focusing on areas of high impact. Like if you have your to-do list, Or whatever you're responsible for and identify what items are going to have the biggest impact. Maybe the things that are the toughest to do or that are going to have the biggest impact on your business or in your life. Tackle those first. So the whole idea of the Pareto principle, what are the 20% of things that are going to have 80% of the impact? Identify those, those cases, those goals, those things that you're trying to tackle. Maybe you're putting them off because they're too ambitious. You don't have time or those kinds of things. This is, this is good things that AI can help you tackle. That's not to say that you can't use AI to help respond to emails and those kinds of things. Sometimes saving 5 to 10 minutes every day with things like that are useful. There's definitely use cases for that. But in this book, he is really trying to aim advice to leaders to maximize their leadership and their abilities. And so naturally focusing on the 20% that can have 80% of the impact is, is massive. So don't hear me wrong, you can obviously use AI for Really classic mundane things. Like if you're a Gmail user and you have Gemini, Gemini in that context is gonna understand a lot about your voice and how you respond to things. So you can easily use it to respond to emails quicker, get through the, the email triage, and then get onto more useful tasks. So there's definitely some application for things that you can, you can do low impact tasks with AI and what can you automate in that way. But I love Jeff's point in focusing on the 20% that affects 80%. Because that, that's his advice in how a leader can scale. The next one is hiring or specifying a skeptical board member persona in your AI. The idea is that it's difficult to see your own blind spots when you're deep inside your business or in your life. And so Jeff talks about, you can't read the label from inside the box, is one of his quotes. And so he suggests using AI to act as a challenger or a skeptical board member. You have to specifically prompt AI to be this way, and even then it's still might be a little too much of an ego stroker. ChatGPT, I feel like, is the worst at this. It, you know, you can tell it to be direct and not stroke your ego, and it'll still be like, man, that is such a great question. You're like, oh my gosh, stop. But some of the prompts that you can give it is to say something like, act as an aggressive, growth-minded board member and challenge my assumptions and tell me where this plan might fail. And you can really expand this. I have a mentor who has taught her mastermind group to employ an entire board of people. So I've done this with my ChatGPT account and my Gemini account, and I've told it, hey, I want you to identify 4 to 5 board members and each of them taking different specific roles in the same way a board would for a company. And so there are different identities for those board members, like a visionary, an operations person. I have a philosopher, which it identified as Jordan Peterson. My operator is Jocko Willink. Steve Jobs is my visionary. And you can use these kinds of people that maybe you resonate with or whose personalities you think might be useful to challenge you. You can train a particular chat or you can create a project in ChatGPT or in Gemini, you can create a gem, so on and so forth. Projects exist in Claude too. If you're into Claude, Anthropic is doing some incredible work right now in expanding their tool to be highly capable. And then you can expound upon this so you don't constantly have to say this prompt of like, act as a, as a board member to challenge my thoughts and those kinds of things. You can do a dedicated chat, you can do a project where you can grow things and give it in more increasing context. You don't have to keep repeating yourself. This is something that's been very enjoyable in getting challenged and, and seeing things that you're not seeing, because oftentimes unless you bring it to someone else, you're likely not gonna get that perspective. So AI is a really good dry run for some of these kinds of things and vetting your ideas and really helping you maybe get past the stump point or in brainstorming. It's one of my favorite uses of AI, brainstorming. Just get my mind going. Like, what are some things that, based on what you know, what are some things that I can do here and can do there? Help me brainstorm, help me plan, act as a thought partner. That's, that's Jeff's biggest thing. And then just some quick bullet points and some additional things he talks about in his book is using AI as a thought partner. You're the thought leader. It's the thought partner. So you should never abdicate your responsibility and expect AI to lead the creative or decision-making process. It lacks the deep context and perspective and human judgment that should still lay with you. You're bringing things to the table. You're guiding it to allow it to do the heavy lifting of processing data, challenging your biases, and generating alternatives, but you're still acting as the thought leader, and that's when it becomes really powerful. His prompting framework, he calls it the CRIT framework, the C-R-I-T. That is context, role, interview, and task. Context is any information that it needs to know that's relevant to what you're asking. The role is, you know, act as an analyst, act as a news reporter, act as an expert CPA, whatever you might be talking about. And then interview, that's the ask me 10 questions one at a time. And then the task is, this is what I'd like to accomplish. These 4 things can really help it along in guiding you through that process. And then I love the last thing he says in his book about AI will enhance your people, not replace them. And so I love that he put this in the book 'cause there's a lot of people that are afraid for their jobs or afraid that their leaders aren't gonna value them or their positions anymore. This is where I think using AI is an important thing for anyone in any job. Because at the end of the day, you could be replaced. But right now in today's climate, the odds are you'll be replaced by someone who does what you do only with AI, because AI can help an individual scale what they're capable of. And if you're somebody who's been very skeptical, not wanting to use it for whatever reasons that you may have, then that could end up being a long-term liability for you because you haven't developed the skill. And flex the muscle of using AI and leveraging it to your advantage, and then to the advantage of those that hire you or work with you or work for you. The last thing he talks about is to stick with it because there is a journey of adoption that he describes that I think is pretty funny and true. And even as AI continues to advance, I feel like this journey keeps repeating itself to certain extents. And so he describes it 3 things. Light bulb moment. This is when you see what AI can do for the first time and you have this like wonder moment. Like we all know what that's like. We all know the first moment that AI did something absolutely incredible and it was like, whoa, you know, like write me a meal plan and make sure to eliminate gluten and dairy and blah, blah, blah. And then also give me the groceries I need to order and then give me the macros for each meal. And then it's all there in seconds. You're like, man, I would've had to pay a nutritionist. Like, this is crazy. So that light bulb moment. The second one is reality check. This is when AI falls on its face and the answer is total garbage and you're like, man, I wasted hopefully only 5 minutes, but maybe 10, 15, 20 minutes on all this exchange back and forth, and I haven't gotten any closer to getting my project done or getting any valuable information at all. This is where you're frustrated with the results because they're not good. And then the third one is building momentum. This is learning to communicate better with the AI and seeing consistent wins over time. Now I said I feel like this repeats because sometimes the AIs will come out with a new feature or a new connection or a new way to do things and you're like, man, maybe I can do this now. And sometimes you set it up, it can take some time and you're like, nah, that was a waste of time. But other times you're like, you set something up, you give it the context, you teach it how to do it, and then boom, it just works and it's awesome. And then it makes its first mistake. Right. You can't just let it run and be like, yeah, it's good to go forever. I had it look at an invoice and put things on a spreadsheet for me. 9 times out of 10, good to go. But then it misread a decimal, moved it in another place, and the invoice total was way off. And I was like, yeah, still got to double-check the work. So I love that description of the— this is the journey of adoption. Usually people start to give up when they hit That second reality, when that reality check hits them, they're like, man, I knew this was dumb. I knew this wasn't gonna work. I, this just sucks. So you gotta keep pushing through and using the tool. So like I said, I asked ChatGPT, Gemini, and Claude to tell me what are the top things that I use you for? What are the most common things? And these are just funny use cases here. The first one being using it for operations and processes and systems. That makes sense since I'm a director of operations at a, at a car dealership. And so this is your most frequent professional use case. You use AI to bridge the gap between the way it's always been done and building new high-efficiency processes and procedures, restructuring departments, CRM workflows, SOPs, HR situations, and training. So this makes total sense. I absolutely use this on, on the regular in analyzing data. That's a huge thing that I'm doing now because in having all your data in place is not something that's very easy to do at the moment. Every company has their own data that they build, that they keep in their own silos. You have to pull data from multiple vendors and try to put it in one place. It's all formatted differently. And so to get all that in one place and then try to get useful information from that is definitely a huge challenge. But I feel like we're in a situation where we can use AI and leverage it to analyze that more than ever before. The second one here is entrepreneurial infrastructure. This is building the backbone for your different companies and investment ventures. Yes, absolutely true. So this is building systems for accomplishing large tasks like quoting insurance for real estate portfolios, tracking properties and details, different analysis of investment strategies side by side, analyzing mortgages and different ways to pay them and how fast and how slow. Now that's easy to do in AI these days. Yeah, just playing around with different, different ways to build those systems in my, in my side businesses as well. The third one is health and performance optimization. No surprise there. Why wouldn't I do that? Especially when you can connect ChatGPT, Claude to your health data. I think Perplexity just released that a couple weeks as well. So you can connect it to your Apple Health. I also am a Whoop user and it has its own AI that has gotten increasingly capable. I've been very impressed, especially in the last month. I traveled to Phoenix and came back and it helped me with some jet lag things from a diet, water, and sleep perspective. It was really, really helpful. And so I use it to give it context into my food logging because I do log my food daily. And so I have my health data, I have my supplements and my nutrition data, and I can do a lot with that data and have some conversations like, hey, these were my, these were all my labs. All my labs are charted out on a giant spreadsheet since 2020, I believe, maybe 2019. And I can have some really great conversations like, hey, this has been increasing over time. What's a way that I can change my diet or what's a supplement that I can take? I always try to do changes with diet first before taking a supplement. That's a whole other conversation. And then, in the CrossFit space, I have conversations a lot now with the Whoop AI of like, hey, this is kind of how I'm feeling. What should I do today in the class? This is the kind of weightlifting movement we're doing today. It's been really, really cool in just just trying to optimize movement, weight, nutrition, supplementation. I've actually stopped a lot of supplements because I've changed how I've eaten, and I said, hey, how can I get this in my diet and analyze it afterwards? And it's been cool to see how the diet has affected my labs as well as supplements. So that's no surprise, but huge way that I use that, and I absolutely love it. Number 4, good thing I read this book, right? Strategic thought partner and decision frameworks. Thanks, Jeff. So this is high-level thinking before taking action. So this is giving it scenarios and doing analysis— analyses? Yeah, that's probably a better way to put that. Doing calculations, risk assessments. So instead of asking, what should I do? I ask for basically like trade-off discussion, pros and cons. I have it, I give it the scenarios and I said, give me the pros and cons because writing a pro and cons list has never been something that that I've been a fan of, but I love seeing it. So if the AI can do the heavy lifting here, it is huge. I love that. So if I'm ever debating between 2 things, even if it's 2 products, I use it for research all the time. I'm like, hey, I'm considering these 2 things. What's the differences? What are the similarities? And what should I, you know, what are things that I should consider? What am I not considering? Number 5 is multi-channel context and brand strategy. Well, that's no surprise. So I use it for this channel, Optimizing Beyond. I use it for Cars and Coffee. We have a group that we do. We host Joplin Cars and Coffee in our local area. And so using it for that and some of my other businesses and my personal social media as well. I use it to get ideas and things that I can say. It has the context of a lot of my previous things. And so I use that to have discussions like, hey, how have I talked about this before? What are ways that I can talk about it maybe in a different way? Even if I repeat the topic, how can I talk about it from a different dimension? So I like kind of playing around and exploring what I've already done, what I've already talked about. It's helpful on the podcast as well. Like how many times have I talked about marriage? I'm really passionate about marriage, so I'm gonna talk about a lot. Number 6 is high-stakes communication and tone matching. Now, this is, this is an easy one. You know, have you ever rehearsed something, a hard conversation in the mirror? This is kind of that, just with the AI. And so there'll be times where I'll just hash out an email in, in, in as passionate as I want to. And then I'm like, hey, calm it down a little bit. Other times I'll just spew out in like an audio recording the exact email that I'm trying to say. I can give it context of the previous, you know, email chains or whatever. And then I'm like, hey, Write me an email to reply. And I just like, I just vibe out. And then it writes the email for me. I'm like, write it in my voice. And it's getting pretty awesome. There's a lot of times more and more lately that I don't have to really edit. But in these more delicate conversations where you're maybe giving bad news or having hard conversations in, like, especially in an email or text context, this can be super helpful in being clear, but also maybe having, having some tact as well. And sometimes even when you're frustrated with a support team, like, how can you put accountability back in their boat by also being respectful. You know, what do they say? You get more bees from honey than you do vinegar. Yeah, that kind of idea. So that's, that's, that's very helpful. Number 7, this one's actually really fun. My wife crushes this as well. And this is consumer and travel optimization. I talked about it slightly earlier about, you know, comparing product research and products and things like that. But also like, how do you keep track of like loyalty programs. If you're a credit card person where you leverage points and you pay off the credit cards every month, don't tell Dave Ramsey, and you're just trying to track all these things. And then also travel itineraries. AI is so good at this where you're like, hey, we're going to be in this city on this date, in this city on that date. What are the top 10 places we should consider? What are the best restaurants that are nearby? Whatever. Or you can just tell it, hey, plan me a trip in Washington, DC. I'm going to be at this hotel, whatever, whatever. It has been absolutely incredible and not a letdown. We've been increasing the use of AI in our travels, and I'm— I will tell you right now, it— in Washington, DC recently, it was pretty good. Number 8, game changer for me. I'm a techie guy. I love smart homes. I love technology. But sometimes that means that I don't always know how to fix something when it's not working. So for troubleshooting specifically, I can give it the make and model of what I'm dealing with and then tell it like, hey, this is what it's doing. I've had some smart home products that have been really troublesome, especially in the last 3 to 4 months. And so just giving it all that information, I've done some electrical things that haven't been functioning well. And so I'm like, hey, what am I doing wrong? I had the power turned off, don't worry. And it's been super, super helpful. You can sometimes even download the manual and have it in there. And then it'll just say, hey, have you tried this? Have you tried that? And there are times where there's something I haven't thought about. And so, and I'll give it the things that I have done. I'm like, hey, I've already restarted it. I've already done this, that, and the other. I've done this in the manual. What am I missing? And it's been super helpful in getting things fixed quickly. A little bit different than a Google search that where I'm looking for the information. Instead, it's bringing me ideas and we can kind of collaborate. And it's been really, really good. Number 9 has been tough, but also kind of fun. So I've gotten into vibe coding in the last 3-ish months when I have some free time. And it's been interesting. I've been working with multiple AIs to kind of develop my vibe coding experience and abilities. I even used Lovable to create a couple apps. It's been interesting. This is where I've experienced those 3 stages where it's like, oh my gosh, this is awesome, I built something, and then it's not really working right, it's broken. And then when you try to fix it, sometimes it feels like you're just duct taping code on, you know. And what I found is it's definitely more useful if you have a conversation with a chat AI first about what you're thinking about, what you'd wanna do, have it brainstorm with you and develop like more of a full idea instead of going to the coding app and brainstorming in there. I know Lovable has a plan mode and I actually really, really like it, but to develop what they call PRD documents, like that is product requirement documents and other supportive documents that the chat AI can help you develop so that when you go to the coding app, it knows more of a full picture of what you're building. So you're not building like a small little thing and then decide you want to add 7 tiny things, and then it's all just kind of this junky slap together. Yeah, so the bigger it gets, the more opportunities, in my opinion, it has to break. That's why I don't think really good developers will be replaced anytime soon, because what they're doing now is they're helping corral vibe coding for people who don't know what they're doing and going, hey, let me, let me write the framework for you and then you can code to your heart's content. I've seen that work and it's been incredible in some of my buddies' businesses. And then number 10 is personal growth, mindset, and personality dynamics. No surprise there. I always look to see what I can learn from a situation. I always challenge myself, like, how could I have done this better? How could I have approached this differently? Even if somebody is in the wrong and completely mishandles a situation, That still won't stop me from asking, you know, how could I have done this differently? How could I have optimized this interaction and maybe helped them in a different way? And so at the end of the day, we talk about you can only control yourself. And so out of that comes what is the way of personal growth here? And then other times, you know, you screw up and, you know, I think it's helpful sometimes to analyze those things. Looking at it is something that most people don't want to do. And so I think the more you can get comfortable getting uncomfortable in looking at when you make mistakes, when you have failures, and when you screw up, that's not comfortable for anybody. I don't think that's an automatic thing for anyone. I think if you can learn to do that, AI can be another tool to help you look at that closer, make sure you are able to see past those blind spots and then really, really advance past those. In mindset, it's sometimes it's like if you feel stuck about a certain thing, there's been specific things. I don't use it as a therapist. I don't know if that's particularly Again, that's an entirely different topic. Kevin Wiseman and I discussed that in our podcast episode and some concerns that we have about that. But using it to collaborate and think through certain things has been very helpful for me. And then personality dynamics is actually pretty fun. You can load your own personality assessment in an AI to give it some context and then describe any scenario that maybe you're challenged with or that you're trying to get through. And it can really help you lean into those things and get through those things. And then other times you can give it 2 different people's personality dynamics. So, and then, you know, how can I help them resolve this conflict? Or yours and someone else's, and like, hey, how do I approach this person? How can I speak their language? I've talked about how that's been something that's been useful to me in the past as well. And then it says that my overarching theme is looking for ways to use AI to create systems. And the way that I would describe this is when I use AI to do a task, I always ask myself the follow-up question. Is there a way that I can build this chat into something bigger so that it's repeatable? If it's a small thing, I have a general inquiries channel and I treat that like you would Google, like for general questions that I'm not going to ask again. I was tired of having all of these chats that were just meaningless that I asked one question, got my answer, and it was done. And so I have a general inquiries and it's pinned to the top of all of them. And when I, depending on which one I go to for whatever, I just ask it the question. Maybe there's a little bit of back and forth and then it's done for a hot minute until I need to ask something else random. So that's been huge. On other things, I always ask myself, hey, is this something that I can systematize, which is a completely different approach and sometimes takes additional work in AI. So is there a particular chat that I need to set up, give it certain context so I can come back to it on a regular basis? Is this a repeatable task that this chat can help me with? Is it a project or a gem that I need to create, give it reports or give it certain files or documents that could help it help me with certain tasks? Those are the kind of questions that I ask. And when I do that, that takes a 3 to 5 minute task that is gonna have to be repeated in 3 to 5 minutes in the future to something that takes me maybe 15 to 30 minutes depending on what we're talking about, but doesn't need to consume hardly any time in the future. So that's just interesting. Yeah. There's so many different use cases. It's hard to be specific. Notebook LM has been another thing that I've used a lot of where you can just upload, I mean, I think up to 300 files and then you can use Gemini to chat with Notebook LM, which that's when it really started being very useful and powerful because I can give it a ton of context and have those conversations. So what's the biggest takeaway here? The biggest takeaway is I use it every day and that's my biggest encouragement to people. Glenn Lundy, in the episode when I had him on the show, said that if you do something for 17 minutes a day, you will be better at the end of a year than 95% of everyone else, which is pretty cool. Now remember, that's 7 billion people on the planet. You'll be better than 95% of them. A lot of them don't even use AI. But I think that's super, super critical. The more you use it, even if it's some— for something stupid, for product research, for something you're looking to buy, or Or a coupon code for something you're wanting to buy. Easy, simple things, crafting an email, starting small, getting past the friction of those kinds of things. Because if you constantly use it for huge ambitious things and it falls on its face 30% of the time, every time you're pulling that trigger and investing all that time, it's gonna get challenging to continue. So use it for a variety of different tasks every day. I don't know what its best use case is gonna be for you because it depends on, on you and what you need to accomplish in in a day. However, it is super helpful in so many ways. It just depends on the context, the use case, and those kinds of things. So my biggest encouragement, my biggest takeaway from all of this is to use it every day. It's better to use it daily to get better at using it than to obsess about what's the perfect prompt, what's the, what's the best tool, like jumping to different tools. I use all of them daily because I want to continue to see how they're different. And as these companies keep evolving, I think that'll help me be a better power user. And then when the dust settles and we see which companies make it, don't make it, and how they advance, then I will be able to feel comfortable in any of them. And I love that. And so that's my biggest encouragement. Use them daily. Get really good at getting past what Jeff calls the reality check moment when AI falls on its face and doesn't do a good job. When you can do that on a daily, daily basis, like we say, daily anything changes everything. If you can do that, I think that you can wield AI to be useful and to multiply your efforts and your capabilities far into the future, wherever you're at, whether it's meaningful for you and those next to you or to just you in simplifying and helping your life out and making your life easier. Both have tremendous value and I think they can be very useful. So thanks for listening to Optimizing Beyond. As always, remember, growth happens when you take action. So subscribe, share this with a friend, and most importantly, put what you learned into practice because as we know, daily anything changes everything.