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Jeff Woods
As a leader, your ability to think strategically is the difference between growing your business or going out of business.
Chris Daigle
The IT team, are they the right ones to be leading AI in the organization?
Jeff Woods
No. Flat out, I believe this is the CEO's job. And I want to be clear. There's a difference between being an AI expert and being an AI driven leader.
Chris Daigle
Do you find that there are CEOs out there that are like, hey guys, we do something about AI, Go figure
Jeff Woods
it out all the time. You, as an AI driven leader, are personally using the technology every day to elevate your own performance in the company because then you are qualified to cast a vision for the future. You can lead from example, not theory. How in the world can you cast a vision for how to create a competitive advantage through your products or services with AI? Or how to transform your operations and drive efficiency and cost? If you haven't transformed yourself, that's hypocrisy. It's not leadership. What if instead, as a leader, you empowered your people to ask, how might this make me irreplaceable?
Chris Daigle
Jeff woods is a leading voice in
Podcast Narrator
AI driven leadership who helps executives transform
Chris Daigle
AI from a collection of tools into
Podcast Narrator
a strategic system for faster alignment, smarter decisions, and stronger execution. Welcome to Using AI at Work.
Chris Daigle
I'm your host, Chris Daigle. Each week we'll be learning how today's
Podcast Narrator
business owners, entrepreneurs and ambitious professionals are getting more done with smart use of tomorrow's tech.
Chris Daigle
Let's get started.
Podcast Narrator
Right now, every business leader is asking the same question. What are we going to do about AI? If this is you, chiefaiofficer.com has the answer. We give you a simple path forward where we provide executive and team training so your people know exactly how to safely use generative AI in their day to day. We also manage the deployment and implementation to make sure tools actually get adopted and deliver results. And we'll also guide company wide transformation so AI becomes part of your operating system, not just another shiny object. The companies that act now will increase productivity, cut costs and grow faster than their competitors. Those that wait will get left behind. So if you want to make AI work in your business, visit chiefai officer.com and see how we're helping companies of all sizes finally get results from AI.
Chris Daigle
Hey everybody. Welcome to the latest episode of Using AI at Work. And this is. I'd consider this like an urgent episode. Our guest today, I was able to reach out to him yesterday because there's something very exciting happening in his life related to AI said, look man, can you get on the show tomorrow. And he said absolutely. So you're hearing this a couple days after we've recorded, but I'm dialing in from Chicago. I'm here speaking to a couple Vistage groups for the next couple days about a leadership perspective on AI. So our guest today, perfect topic fits in with everything that we're talking about. So who is the guest? Well, his name is Jeff woods and I met Jeff right before his book came out, the AI Driven Leader. If you are a. I don't know anybody who is serious about the leadership, the strategic perspective as well as tactical application of generative AI. If you haven't gotten his book, AI Driven Leader, don't worry about it because today Jeff's going to be talking about how the book has been updated. What was it two years ago that you released it? September of 2024.
Jeff Woods
September of 24 was the original release and the updated version released a few days ago.
Chris Daigle
Yeah. So awesome. So Jeff, thank you so much for taking the time. I know you're traveling and busy and. And the AI expert of choice for many groups. So thank you for being on Using AI at work and welcome to the show.
Jeff Woods
It's my pleasure, Chris. Thanks for having me.
Chris Daigle
Awesome. So I guess the obvious. Well, first, before we get into the obvious question, which is what's new in the book for those who maybe they are familiar or aren't familiar, what was the impetus? What was the catalyst for you to launch the book in the first place? The AI driven leader in September of 2024.
Jeff Woods
Sure. So I was a chief growth officer for a big public company out of India. We had about 100,000 employees. I saw ChatGPT two weeks after it hit the world. And Chris, I remember thinking, this is amazing. I think we should lean into this. And my original thoughts were what most leaders thought, which is I'll get to it later because I'm so busy or I'll delegate this. I have a huge org, I have a great IT department. They can do this or I can hire McKinsey, they can come do it for me. But then there was something in my soul that said, I think this is a skill that's worth mastering. I think you need to focus on mastering this. I'm not technical, but I just made a commitment to lean in and start using it once a day. Very quickly I realized I was using it for the things that didn't really matter. I was using it to write better emails. And I'm thinking I did not get to this level in a company because of the quality of my email writing and I'm going, I'm using this to major in the minors. What would it look like to major in the majors? And I had this realization, Chris, that as a leader, your ability to think strategically is the difference between growing your business or going out of business. One of my superpowers is asking leaders the right questions to unlock new levels of growth. And I'm going, I'm asking AI questions like it's Google. Could I turn the tables and get it to ask me questions as a thought partner.
Chris Daigle
Interesting.
Jeff Woods
That was a game changer. To compress the story. I presented how I was using it for strategy instead of tactics to the chairman. He put me in charge of AI for the whole company. I knew nothing about it, partnered with Google, learned a lot about it, started living at their headquarters, started driving it through the organization and realized most leaders were asking the wrong questions. They're asking how, what's the right use case? I think that's the wrong question because that is technology first, strategy second. It's a solution looking for a problem. What's timeless in driving enterprise value is strategy first, technology second. And I proved it. I mean, over a four year period, we moved the market cap from 750 million to $12 billion. So this thing worked. And that's when I realized it really has very little to do with tech. It has a lot to do with people. No one at the time was talking about people and leaders and who they'd have to become to keep humans and human interest at the center. So I burnt the ships, said I'm going to write a book about it. It has been number one in the world for the past 18 to 20 months.
Chris Daigle
Congrats.
Jeff Woods
We've now released the updated version. I mean we're over a quarter million copies moved.
Chris Daigle
Wow.
Jeff Woods
In a very short period of time, which is pretty, pretty rare.
Chris Daigle
Wow. Yeah. I talk to. We don't really teach the tactical stuff to the staff level at our company. We work with executives, helping them kind of get a perspective like you're talking about. And your book is the one book that universally I can go into a room and somebody's like, yeah, I'm using crit, which we'll talk about. Or I've got the book, or I've been to a class where they've talked about it. So it has definitely been the kind of like the obvious choice, I guess, for a leader who's doing exactly what you did, which is we got to figure something out. I'm going to take that responsibility. I'm Not a tech person. Where do I start? If they get a hold of your book, the examples and the ways. Yeah, like it's. They get it and they're able to start using it. Starting to be that leader. Now you mentioned a couple of things. You know, initially you said, hey, I got a tech team. Is the tech team, the IT team, are they the right ones to be leading AI in the organization?
Jeff Woods
No.
Chris Daigle
Flat out, no.
Jeff Woods
I believe this is the CEO's job. And it really hit me when, and I want to be clear. There's a difference between being an AI expert and being an AI driven leader. I do not need the executive team to become AI experts. You can leave that for your technology division. This is about leadership. This is about knowing just enough. Because you as an AI driven leader are personally using the technology every day to elevate your own performance in the company. Because then you are qualified to cast a vision for the future. You are qualified to define the strategy on how you are going to win. And you are qualified to start to demand that the workforce use this. Because leaders go first. You can lead from example, not theory. I just need you to be in the game using this to elevate you. And what happens, Chris, is leaders figured out very quickly that they've been living in black and white, trying to describe color. And this is why you see so many reports of millions of dollars being invested with no roi. And it's because a person who doesn't speak the language, it's like, I don't speak Japanese, but I got to go give a speech in Japanese. How in the world can you cast a vision for how to create a competitive advantage through your products or services with AI? Or how to transform your operations and drive efficiency and cost? If you haven't transformed yourself, that's hypocrisy. It's not leadership.
Chris Daigle
Do you find that there are CEOs out there that are like, hey guys, we need to do something about AI. Go figure it out all the time, all the time.
Jeff Woods
And what happens with that. And look, I believe leadership is often about meeting people where they're at versus where they ought to be. If those CEOs are making those mandates, I give them double high fives because at least they're doing something. They're in motion. I can give them a little tweak that will take enterprise value through the roof because they're already in motion. If they're not. If they're not in motion, we got to get them in motion. We can do that too. But I think the Realization is people do not think if they're not at the C level, they don't think at that level of strategy and vision, which is why they very quickly start going like, what's the use case? Where can I put this thing? They don't think at that strategic level. But if the, if you start at the executive team or once you get the executive team on board, they don't look at it as technology they have to use. They look at it as a resource to solve the company's biggest problems or to achieve their most ambitious goals. And that's usually what we end up doing if we come in with an executive team. My question for them is, what is the biggest problem you are facing in the company right now, period. If we can just solve unlocks a new level of growth. And I will pull up whatever LLM they are currently using, whether it's co pilot chat, Claude, Gemini, doesn't matter. And I will literally write a prompt following my crit framework, which we'll get into stands for context, role interview, task. And we will literally either solve the problem or massively move the ball in a matter of 20 minutes. That blows their minds.
Chris Daigle
When you ask them that question. What's the biggest issue? Do they always have something on the tip of their tongue or do they need help like getting to the bottom of what is the biggest issue?
Jeff Woods
Well, whether or not it's actually the biggest issue is not what's most important point.
Chris Daigle
Yeah, what?
Jeff Woods
It's a frame that causes them to filter out the junk, to filter out the 80% that only drives 20% of the results. It automatically takes them to the 20% that drives the 80. And you know, I was, I was in the boardroom for Nike and I did this with their executive team and I mean they threw like six or seven ideas out there and the CEO said, I want this one. And that's the one we workshopped. And it was fricking remarkable. It was so cool. But so it's, it's more about just saying, hey, most people are using this like Google or to write better emails. Still at a leadership level.
Chris Daigle
Yep.
Jeff Woods
And this gets them into a strategic level where they pick something that's massive, that's big, that's important for the company and they use the same tool but in a strategic way and achieve extraordinary results.
Chris Daigle
You know, man, like that's. I encounter that same thing. I'll talk to executives and they'll say, oh, I use AI all the time. And I'll, oh, that's awesome. What are you doing? Like Writing emails and summarizing documents. So that's been my experience as well. How do you is it, by the
Jeff Woods
way, one of those people double high five because they're using the tech now. Let's raise our standards for our relationship with the technology.
Chris Daigle
And that was going to be my next question.
Podcast Narrator
How do you.
Chris Daigle
Is it as simple as saying hey what's the biggest issue? And then moving into like a thought partner exercise with AI, how do you get them to go from that from email guy to strategist with AI Literally.
Jeff Woods
And I do this so many times. I ask for a problem and then I pull up whatever LLM they want me to use. Doesn't matter. They're all the same, they're all different. The difference is not the difference that makes a difference, it's how you use it. And I will write crit. I will put context role interview task into the context window with spaces, you know, shift enter between each so it's like a ladder and then we just fill in the blanks. Context was all the context describe the problem in vivid detail. And I use speech to text and I haven't talked for minutes to give it lots of context roll. Who do you wish AI could be right now to advise you? Talk about the type of experts you wish AI could be right now? Oh, you are a world class chief growth officer who's also an aggressive growth minded board member. You think strategically about the business that's going to put you out of business and you figure out how we can build it first. But you don't go to the 80% that only drives the 20, you go to the 20 that drives the 80. Interview is interview me. Ask me one question at a time. Up to three questions to gain deeper context. Then your task. My favorite task, give me the top three high impact, non obvious strategies I can deploy to solve this problem. You write that you guys should be like rewinding and running your a annual taker to pull this out. You do that, you have what I call the light bulb moment. You start to see color instead of black and white. It's a whole new world. And it's so simple that people literally get out of that session, cancel their next meeting and start writing crit like it's immediate application and then it just spreads virally throughout the company.
Chris Daigle
So for the listeners, I want you to understand like what Jeff just talked about context. You may say, well we've got a problem with this. He's turning on speech to text to dictate and letting that executive ramble. Right? Capture that context the next thing with the role. He's not saying, you're an expert at growth. Rewind it and listen to the nuance that he added to the actual role there. This is different than how you're prompting now, dear listener. For sure. I guarantee it. So this is fantastic. So.
Jeff Woods
And I want to, Chris. Because I'm putting myself in the mind of the person who's watching or listening to this.
Chris Daigle
Yes.
Jeff Woods
For those of you who just thought, I can't do that, or I don't know how to do that, how do you know? All I'm doing is I'm being creative. So if I ask you what's the problem you're facing in vivid detail, go. And when you think you've run out of air, ask yourself what else? And keep going. And when you think you've run out of air, ask what else? And keep going. Don't judge the quality of your thoughts. Don't worry if you're a hot mess. Just dump it into the context roll. You're tapping into the greatest intelligence network of all time and the greatest processing power. Any expert you want to advise, you can. I wish you were Elon Musk right now, but you weren't an asshole. And you think like Steve Jobs in terms of product design and vision. But I'm not interested in you being. Giving me advice on being a husband, a father, or a leader. And you're also, like, you're a simplifier. Like, I need you to make things simple. Almost like I'm an 8th grader. Like I'm literally just making things up right now out of my head. You can do the same thing. Try it. Try it. It's a skill.
Chris Daigle
You can't be wrong. Yeah. You cannot be wrong. That's one of the things that a saying that I've heard a lot. Repetition is the mother of skill. So if you're. If you're. I've never done crit before. Do it once and you'll learn something from that one time. It'll improve how you do it the second time and the third time.
Jeff Woods
And I'll give you some really simple homework that I say this with the evidence to back it up. If you do what I'm about to tell you to do, it will change your life.
Chris Daigle
Let's go.
Jeff Woods
It's a big statement. Big statement. I know, but hundreds of thousands of people have done this. I want you to get two sticky notes and a Sharpie. Come on, Jeff. You wrote a book on AI. Two sticky notes and a Sharpie.
Chris Daigle
Yeah.
Jeff Woods
Sticky Note number one, right? How can AI help me do this? I'm literally holding it up to the camera. I have these on my desk. How can I help me do this? Sticky note number two. Context, role, interview, task. Here's why. Put them on your desk. Put them on your computer. It's tough to read the label when you're inside the box. Every day you're doing things the old way, you're doing it the industrial way. It's hard to always remember that I can help you with pretty much anything. These are triggers in your natural environment. I was reviewing my financial statements one month, Chris. And while I was opening them, I looked down and I saw that first sticky note that said, how can AI help me do this? And I was like, huh? What would that prompt even look like? And then I saw context. Role, interview, task. I'm like, come on, Jeff. And I literally just opened up AI and put in context, held down shift, hit the enter key a few times. Role, shift, enter interview, Shift, enter task. Then I went up to the context section and said, context. Here's my financials for the last month and I drag and drop them in roll. You're a world class CFO who's really good at telling a CEO the things they don't know about their business that they should know about their business based on their financials. Because most leaders suck at reading financials. They just look at revenue and profit. Yeah, that's not optics to drive your business. Interview me. Ask me one question at a time. Up to five questions to gain deeper. Context, task. Tell me the top five things I'm not seeing that I should be seeing and what I should do in the next 30 days to improve the financial health of my company. That crit blew my mind, Chris. It called out that our dso, our days sales outstanding, meaning the time from closing the contract to receiving cash in the bank was 105 days. And it said for my type of business, industry standard would be 45 days, meaning we're acting like a bank giving our customers free loans and that we needed to crush our ar, our accounts receivable. I completely, I had no idea that that was happening. And it told me make this the top priority financially. In the next month, we crushed our accounts receivable by 90%.
Chris Daigle
Wow.
Jeff Woods
In the next 30 days, it completely transformed the financial health of my company from one crit. I did that for three months back to back to back to the point that I said this matters so much that now I will choose to turn this into an agent. I think a Lot of people are building AI agents for things that really don't make the biggest impact in the company. Because if you build it, building it's easy, but getting it to production where it really works hard, maintaining it harder. So now I have an AI CFO that checks my email every morning if there's financial reports that come from my finance team. It's highly sophisticated in tuned with skills and processes on how to run that analysis. Turns it into a beautiful PowerPoint doc that's on brand with our company. AI leadership sends it to slack in our finance channel where the right executives have now the right optics. So we're not looking retroactively at what we've done. We have vision for where we need to go.
Chris Daigle
It's beautiful. So anybody listening to this, that exercise Jeff just said, do that like as he mentioned, rewind. And for my team, please add that exercise into the show notes because that's easy, but powerful for sure.
Jeff Woods
Easy. So easy.
Chris Daigle
So the number one thing, I think that, that most people that sticks with people from the original book, obviously the, some of the stories, the anecdotes, the. Those really help people because I talk to executives like I would love to use it more, but we don't know where. And those stories help people a lot. But the other thing that stands out from that is crit. You've mentioned it several times. And why crit?
Jeff Woods
It happened organically. One of my superpowers is I'm a simplifier. I am able to take really complicated topics and boil it down to the 20% that communicates 80% of the value and saying it in such a simple way that people can remember it and repeat it. And I remembered thinking, you know, prompting with AI is like a relationship. For any of you who have ever been married ever or ever been in a romantic relationship with another human being, ever. You understand how important communication is with a human. We weren't taught how to communicate with others in school. It's a huge miss. And I found myself realizing people didn't know how to communicate with AI because make no mistake about it, this is a relationship with technology. The better your communication, the better your results. And so I started to boil down, what do I think are the 20% elements of effective AI communication that drives 80% of the results. And that's where I was like, you got to give it context because while it's been trained on the information of the world, it doesn't know you, your business, your problem, the way you do role. You got to be really articulate on who you want AI to be because it can literally simulate any type of expertise and give it direction. You're the thought leader, it's your thought partner. The interview is the game changer. Stop asking AI questions and start making it ask you questions to pull deeper context out of your head that you would have never thought to have shared. And then task is whatever you want it to do. What's that bullseye that it's got to hit? And when I started doing it myself, I got extraordinary results. I didn't realize I was onto something, Chris, until people. Originally I didn't even call it critical. I said context, role, interview, task. When customers started calling it crit, when customers started saying this changed my life. That's when I knew I was onto something.
Chris Daigle
Yeah, I'll tell you man, I walked into the Vistage meeting yesterday, they had their, their big sticky pad on the thing and on that was written crit, like just randomly. So it's, it's landed with people. And for those of you who haven't ever used it, please try it. But Jeff already mentioned it. The, the big distinction for that prompt framework is the interview. Hey, AI ask me up to blank number of questions one at a time so that, so that AI can get the additional little points that it needs to give you the best answer that I use that, that piece all the time.
Jeff Woods
And here's why it matters. Again, leadership is meeting people where they're at. I'm not going to assume that every leader on the planet is suddenly going to become world class at communicating. So let me meet them where they're at. Make it AI's job to get what it needs out of your head. You as thought leaders just have to give it the permission to do so. Because as humans we're pretty terrible at providing sufficient proactive context for our team, which now includes humans and technology, to do what they need to do. Make it AI shop. And by the way, this is how I lead my company. Even before AI, the things I'm at least self aware about is that things might be crystal clear in my head, but what comes out of my mouth can sometimes be as clear as mud. And I know I'm not always the best proactive communicator with my team. For years, Chris, I have created a standard that for you to own 100% of your job, you need to ask me the right questions to pull what you need out of my head so you can do your job. You can never say to me, jeff, you didn't tell me that. Then it's on you. You did not ask the right questions. This is before AI and why it's even more relevant now than ever is I think the way organizations are running are going to shift from top down to more bottom up. It's not hierarchical. Boss tells you to do this, which is very industrial revolution way of thinking.
Chris Daigle
Y.
Jeff Woods
It's. It's empowering people to have agency as. As the CEO or as the leader. You got to cast the vision for mission like, what are we going to do? What are our cultural standards? What's our goal? Like, you got to say, what mountain are we, are we going to take? But then it's giving people agency on how do they want to approach and tackle this? Because now they have this very powerful tool in artificial intelligence to do way more than ever before. You got to teach them to ask the right questions. I just do it with AI too.
Chris Daigle
So at least my understanding of your approach is that you. You exclusively work with the C suite or executive teams.
Jeff Woods
We start there.
Chris Daigle
Okay, you start there.
Jeff Woods
There. There are two problems we see in companies that we focus on solving. One is every executive team is now mandating the use of AI. But not every person on the executive team personally wields it daily to elevate their performance so they earn the right to lead the company. We solve that problem very fast, that then scales through the company. And then the other thing is, I've realized, if I think back to my time with Jindal, what drove the market cap by over 12 billion in four years was something very simple. There are very few things that can drive that kind of growth. It was creating clarity and alignment on company strategy and aligning the execution of the workforce with it. That's it. So literally, think of a river. On one side of the river is strategy. On the other side is execution. Most companies don't have a bridge between those two. They have a strategy. They have a company plan. But is the. But the plan is constantly changing. The job descriptions are not dynamically updating. People's calendars are filled with random meetings. They spend all their day in inbox meetings and people saying, hey, do you got a min? And if you ask a person, walk me through the top five 20% priorities you need to accomplish this week. So you're automatically on track for delivering the progress you need to deliver by end of month, quarter year in alignment with company plan. They can't answer that. We solve that with AI. So we literally build the AI infrastructure for companies that creates clarity and alignment between strategy and execution. People know what the plan is, and when the plan changes, they know how they have to shift what they do on a weekly basis so they always execute the things that matter most. That's all we do that moves the value of a company.
Chris Daigle
Yeah. And you know, if you know how to use AI as an individual, like that becomes so easy. So one of the things that I see is that when I go and speak to a group, the people that are in the room, usually nobody forced them to be there. They want like, they're excited to be. But if they go back to the office, not everybody at their strata of the business is equally excited. If somebody is listening to this podcast or listens to your podcast and they are the enthusiast and they want to be the champion, but they're not necessarily seeing the same excitement reflected by their peers. What advice would you give that person that wants to make sure that like, hey guys, this is serious. Let's get going.
Jeff Woods
It's normal. History repeats itself. View, study, change over time. There's what's called an adoption curve. 3.5% of the workforce are, are your innovators. Then you've got about 13 that's going to be your early adopters. Then you got about 34. That's going to be the early majority. Now you've covered roughly half the org. Then you have the late majority. Then you have the latter, the, the, the laggards. It's a bell curve. I knew going into this it was going to follow a certain trend and that's proven to be true. So we're still on the front half of that curve, Chris. So I don't expect everybody in the organization to be gung ho about this. You got to figure out where your org is. The key is how do you just worry about you. First, let's get you to become an AI driven leader. Let's get you used to identifying the 20% opportunities, communicating effectively with crit. And then when you get an answer from AI, not trusting it, but remaining the thought leader by challenging it, telling it what you like, telling it what you don't like, telling it the top changes, truly staying in that driver's seat, let's build that foundation with you first. When that happens, you will see vibrant color instead of black and white. Then you look at somebody on your team and it's so simple. People come into your office or call you and say, hey, you got a minute? And you say, sure. And they ask you a question on how to solve a problem or how to overcome an obstacle or how to do something. And if you're not Careful, you'll give them the answer, which is you doing their job. Yeah, because let's be clear, to do your job, you have to bring thinking leverage, not just execution leverage. When you give people answers, you literally train them that they do not have to think independently of you. Here's what I would suggest that you do. Ask them if they used AI to solve it first.
Chris Daigle
Boom.
Jeff Woods
If they say yes, ask them what prompt they wrote. If they say no, say, great, we're going to do this once. Pull up a chair and write. Open whatever AI tool you want. Write crit and just start to interview them. Hey. Describe the problem in vivid detail and click that record button and let them talk. Roll. Who do you wish AI could be right now to advise you what expertise? Be really creative. Just, just, just go. Just be creative. And then fill out the interview part. Interview me. Ask me one question at a time, up to three questions to gain deeper context. Fill out the task for them. Your task is to give me the top three high impact, non obvious strategies we could deploy to solve this problem. Hit enter and then AI will start to interview them and record their answers and blow their mind. Then pull out a pair of a pad of sticky notes, give them a sharpie and say on sticky note one, number one right now, right? How can AI help me do this? Great. Take that sticky note number two. Write, context, rule, interview, task. Go back to your desk. Put these on your desk. The standard now is that once a day, every day, you will write crit in a strategic way and enforce it. Hey, what was your crit today? Did it work? Did it not work? What are you learning? Like, make this part of your meetings. Like, you start to do this with people. A flywheel starts to spin.
Chris Daigle
Cultural adoption. Because they see. I see my neighbor doing that. Hey, what are you doing? Oh, the boss showed me this thing. What is that thing? And then they, everybody, I see this now. It starts to become like organic cultural reorganization around.
Jeff Woods
Or you're in a meeting with your team and you guys are debating something. You and I've done this, right? Guys, stop, hold on. And I've shared my screen and put crit into the context when I said yes. All right, guys, let's just throw it in there. What's the context of the situation? I started bringing it into meetings.
Chris Daigle
Yes.
Jeff Woods
And it blew people's minds.
Chris Daigle
Yes. So if you're an executive and you're the enthusiast and you're in a room of folks who are mildly interested or just outright not interested in AI, demonstrate. Say, hold on, guys. I Want to try something? Share your screen. Do exactly what Jeff just said. And it will be hard for somebody to maintain skepticism when they see a demonstration applied to exactly what everybody's talking about and seeing the output that CRIT can give them. Brilliant. That's great.
Jeff Woods
And then this is where leadership comes in. Like you're meeting people where they're at. Then it's about leadership is also holding standards. If that person comes back into your office with a question. Hey, did you write CRIT on this? No. Love ya. Get out of my office. If you're asking me to do your job, not gonna do it. Go write crit. Let me know if you need my help. And, and, and if they still refuse to do it. Now we're having a fundamentally different conversation.
Chris Daigle
Yeah.
Jeff Woods
About performance and their relevance if they refuse to adopt the technology, what have you.
Chris Daigle
I'd like to make sure that we have plenty of time to talk about the new book. And this kind of leads into that. What have you seen? Because you were very early working with companies, even before you launched your consultancy or advisory. What have you seen like the behavior or the zeitgeist or the macro of AI from then, a year and a half, two years ago when you launched the book to now?
Jeff Woods
Yeah. So I focus on what's the 20% that drives 80% of the results. So you need to know what I'm about to say is through a filter of. I automatically filter out 80% of the news, 80% of the model releases, 80% of the use cases because frankly they only drive 20% of the results. So they're not the priority. At a high level we've gone from every leader knew AI was the future, knew they would adopt it, but didn't know where to start to Every leader knows AI is the future. They think they've started.
Chris Daigle
Yeah.
Jeff Woods
And they have a false sense of confidence and they all still think they're falling behind. The reason I say they think they've started is I'm. This is not every company, but a lot of them. They're confusing access to the tool with genuine adoption of it.
Chris Daigle
Interesting. Okay.
Jeff Woods
There's a very difference between I gave everybody ChatGPT or Claude or Copilot versus we've actually trained people to use this to elevate their performance. And I can prove it. Very different ball game leaders overall still think a lot of this is it's job or they're, or maybe they're waking up to the fact that they need to own it, but they think owning it means telling other people to do it versus, like, genuinely looking in the mirror and saying, I need to model the behavior. I need to figure out how to elevate my own personal performance, so then I can advise people to do this same. And the tools are way better than they were before. Way better.
Chris Daigle
Yeah. You know, I. I guess this kind of goes back to. If you're writing emails. I. I've noticed that that frequency of use, a lot of times people associate that with proficiency. I use it all the time. Right. But they're not using it for the 8020 like you're talking about. And, you know, I was. I was about to say, well, what do you advise them to do to discover the 8020? Well, I guess ask AI critical. Yeah, what is my 8020 here? What? So now let's move into the book. What? First off, I. It's hard to create any type of static written material about AI because it can go stale a week from now, two weeks, especially if it's talking about the models and things like that. You were wise to choose the strategic approach because strategy doesn't pivot like that. Right. Like the tech does. So why. Why come out with a new book when AI Driven Leader is still selling and still changing lives?
Jeff Woods
The original, it was. I mean, it's been number one in the world for 18 months. It's held that spot consistently. One of the biggest publishers reached out and said, I want to take it global. So I ended up going with a publisher to now have it translated into all the languages in Barnes and Noble, in the airport bookstores. That also created the opportunity to ask, what changes do I want to make? What's interesting is that the main thesis has not changed. I wrote it to be timeless, not timely. That has held true. But the number of keynotes that we have done, the number of podcasts, the way I talk about it has shifted. And so it was the opportunity to make sure that the wording matched what I say. It was an opportunity to enhance the quality of the prompts throughout the book. It was a chance to ask, am I still telling the best stories? Because the stories are what really make the impact. And I have changed some pretty significant stories inside the book because they just. I couldn't have even imagined that to be possible when I originally wrote it. Then, now we deliver those types of results all the time. And so I wanted to put that in front of readers to give, to help them see color more vibrantly.
Chris Daigle
So. And again, folks, AI Driven Leader, the title didn't change. It's just an updated version and the book came out on. We're recording this on Thursday, July 9th. It came out this week on the 7th, correct?
Jeff Woods
Yes.
Chris Daigle
Okay, great. So, like, be the first one in your Vistage group or your YPO forum or your network to get the book
Jeff Woods
and to get that updated copy. Because if you just go to Amazon, it's still prioritizing the. The older one, because there's still some stock there. Go to my website, aileadership.com book. You'll then see you can get it on Amazon, Barnes and Noble, like all the various distributors. It will take you to the correct version.
Chris Daigle
And yes, there's audiobook version, which is what I got on Monday. So, yeah, and it's me. It's me.
Jeff Woods
I'll read you to sleep.
Chris Daigle
It's not an AI voice. It's not your AI clone voice.
Jeff Woods
Well, so I think this is an important lesson. I think we should use AI to do the things that are not distinctly human, that are not distinctly aligned with our greatest strengths. One of my superpowers is communication. I'm good behind a mic. I'm great on a stage. I'm a very effective communicator. Why would I rep. Why would I use AI to do that? There's no way AI could create a remarkable experience for an audiobook listener the way that I could. That's my job.
Chris Daigle
Yeah, I think that's a pretty good distinction for everybody. Just because you can doesn't necessarily mean that you. You should maybe play with it. But certainly we call it like the difference between synthetic output and authentic output. And for us, what we try to do is have synthetic feel or read as authentic as if the human did it. But 11 labs can't cut that. Can't replace Joe.
Jeff Woods
I'll share a real example. This is one of the examples of me top grading a story in the book because it's so mind blowing. Marianela is my former executive assistant. Four months into the role, she's crushing it. She's a 10 out of 10 on every KPI. And I'm going, okay, if she's already there, let's give her bigger shoes to fill. Let's give her a bigger opportunity. And I sat down with her and I told her how well she was doing and said, I'd like to give you a promotion, but I'm going to do this differently. Instead of me coming up with a job description, which is me assuming that I actually know how to utilize your strengths better than you do, and me fitting you just into a box and saying, follow this. That's very industrial revolution way of thinking. We're going to do something different. I want you to use AI. I want you to write a crit where AI will help you self discover what you think your greatest strengths are that you may or may not even be harnessing inside the business right now and compare it to the company goals. And I want you to cast a vision for how you think you can bring 10 times to a hundred times more value to the company. Any questions? She went, nope, Got it. Now let's be clear, Chris. Before working with me, she knew how to spell AI. That was it. She literally never used any AI tool. Before working with me, she read the AI driven leader. She learned how to write crit, which she got the exact same training all of you have gotten watching or listening to this episode. Your level playing field. She comes back the next week with her vision. She goes, okay, based on my greatest Strengths, here's the 20% things I'm currently doing that I need to double down on. They'll bring ten times more value. Here's things I'm not doing that I really think I should be doing. Like I think I should be running our advisory practice for Latin America. This is my executive assistant saying this. I think I should be building all our internal systems for culture and rhythm of the business to drive revenue. I would have never thought of this. And she goes, but if I'm going to focus on these things, here's all the things I'm going to have to stop now. I've segmented them into three groups. Here's the ones I actually just think we should stop doing. They don't bring value. We don't need to do them anymore. Here's the things I think I can use AI to augment or automate so they still get done, just not by a human. Here's the things that require a human. Based on that, here's a job description for my replacement. Here's what I believe their 20% priorities are. Here's their 90 day onboarding plan. Here's the compensation research. I recommend we pay them X. Do I have permission to post the job?
Chris Daigle
And I go hired.
Jeff Woods
Wow. And she goes, I appreciate that, Jeff. We're not done yet.
Chris Daigle
Oof.
Jeff Woods
What do you mean, Jeff? That was my vision for ten times more value. That's not what you asked. You asked for 10 times to a hundred times more value. I'm going, oh my gosh. And she goes, here's my realization. There's no way I can bring a hundred times more value unless I made you 100 times more valuable. So here's a crit I've architected where AI is going to interview you to identify how you can bring a hundred times more value. I go, I can't wait to do this. She goes, good, you'll do it now. I'll wait.
Chris Daigle
Wow.
Jeff Woods
She waits while AI interviews me, spits out a vision, but also spit out a full system of rules that would have to be embedded in the company to transform my time allocation. I tell her it's one of the most amazing prompts I've ever done, and she goes, that's good, but we still have a problem. I know you very well. You love to break the rules. I can put these in place. You're not going to follow them. I'm like, oh, my gosh, you're right. She goes, don't worry, I got you. Here's another crit I've architected where AI is going to interview you on how you will break all the rules. It will then create a defense process. So if you ever want to break a rule, you're going to have to go through AI first. She went from executive assistant, where her job description was email, calendar, and my 80%, to now executive multiplier. Her job description is literally make me 100 times more valuable. She has a system for this. Run our advisory practice for Latin America and run all our internal systems for culture and rhythm of the business to deliver the revenue number. There's no way I would have ever thought that big for her. And what I realize is, as a leader, how often are we putting a ceiling over what's possible for our people versus if we can just align them on the mission of the company, the cultural standards, the goals that we have, and then empower them to harness AI to self, discover what their greatest strengths are that make them who they are, that they may or may not be doing in the job because they just try to fit inside the box you gave them. Can you give them agency to cast a vision on how they can bring more value? Doesn't mean that she's in charge of whether or not that job description gets approved. She's bringing the thinking leverage to me. Then it's my job as the leader to apply discernment and judgment to either approve, refine, or reject.
Chris Daigle
It's a killer exercise. So for anybody listening, like, get your lieutenants around, have them listen to this and say, hey, that. Go do that.
Jeff Woods
Go do that.
Chris Daigle
Exactly. Hey.
Jeff Woods
So, Jeff, which, by the way, when you get the new version of the book, if you go to aileadership.com book. There's a place where you can submit your receipt. We actually give you access to a training that depending on how many books you buy, your team then gets to come to this training that we do for companies. We've already architected that prompt. It's called becoming an AI driven leader. We've already architected it to be highly sophisticated. You will get that exercise where you can do it for yourself or your whole team can do it. If you get books for the whole team that will automatically be delivered to you.
Chris Daigle
So let's talk about that because I did that, I'm queued up. That's July 15th. Is that when that is happening? Okay, yeah. So folks, I know that doesn't give you a lot of time. By the time this comes out it'll be Monday. But you've still got time. If you get the book now and, and do it to the site, submit your receipt, you'll get the email. Now you also have something for those who are buying it for like the leadership team. They have an invitation to attend. Is it an in person event in Austin in October?
Jeff Woods
Yeah. So we, we realized that the original product we launched the company with was called the Collective which was an executive network for C level execs coming together almost like a YPO or an EO for AI driven leaders. What we realized is that we were world class at accelerating an executive from nothing to extraordinarily high levels of performance and realized that that was actually the right product. So in October we are now doing a team accelerator in Austin, Texas. Two days. Day one is going deep on becoming an AI driven leader yourself. Day two is actually learning the skills and systems to build an AI driven organization. You will come out of that two day off site with your team actually having moved the ball and have raised your skill level to go and drive this inside the company.
Chris Daigle
Is there a limit to how many, I mean with the volume of books you're selling.
Jeff Woods
So that's a very specific tier where you get an individual ticket to that. But tickets are going to be on sale for that and you can buy a package for the team.
Chris Daigle
Okay.
Jeff Woods
Aileadership.com the website. October mid October, October 20th, it's that Monday, Tuesday I think it's like October
Chris Daigle
26th, 27th and well my team will have it in the show notes as well. So like the chance to work with Jeff, if you've read his book and you've heard this and maybe you've heard him on another podcast or whatever, but to get your Team, you may be like, pumped. Oh, wow. The Jeff woods episode. Your team may have never heard of Jeff or seen his book before, but after a couple days in the room with them and every example that he's just talked about, your team is now thinking that way. Imagine the impact like that you've got a different business after those two days together.
Jeff Woods
Like, that's incredible because I'll tell you, like Marianella, now, she's blowing my mind in terms of her application. I look at the team that she's managing. She's using Claude code where she's had each of them do a similar exercise and created an agent that becomes their own personal development coach every week. They have reviews, views about what's the 20% that drives the agent, how are they using AI to supercharge that they're prioritizing the 80 things. They want to start building agents to, to. To take off their plate. Like, I never told her to do this.
Chris Daigle
Yes.
Jeff Woods
I just taught her how to write crit and got out of her way. So this is what I mean with leading, with agency is that that type of stuff starts to happen in your company.
Chris Daigle
So another resource that I, I've really enjoyed. You have a podcast. Are you going to continue to do the podcast? Is there a new season coming? Okay, great.
Jeff Woods
Yeah. New season's dropping, like, very, very soon season. So podcast, same title. The AI Driven Leader season two, we are focusing on the idea of building an AI driven organization. So season one was telling the stories of real leaders, how they were becoming AI driven leaders. And then we did a two part where part one was their story. Part two was me doing a live crit where you could literally listen or watch me solve their biggest problem.
Chris Daigle
Yeah.
Jeff Woods
On the podcast.
Chris Daigle
Yeah.
Jeff Woods
Now this one, we're getting more into the leadership side of building an AI driven organization. So we're following a seasonal approach and those are going to be dropping here any day.
Chris Daigle
I'm looking forward to it. So, dear listeners of the Using AI at Work podcast, like, this is Jeff's book. If I was at home, I happened to be in a hotel because I'm on the road. If I was at home, I'd be able to grab his book and show it to you. It sits on my desk. It is the. I can have conversations with, with rooms full of executives and they're on different models and they're doing different things and different skill levels. But one common thing is that they've all either got the book or heard of the book or their friends have told them about the Book. This is the tome for executives to go from using AI like a drive up window, hey, I need an answer. And then leaving to like really the thought partner concept that Jeff has introduced. The like, it becomes intertwined in every consideration that you make in your business. And that is what is an AI driven leader? Not somebody who's writing email again. Double high five like Jeff said. Fantastic start. You're off the starter block. You're now in motion. But take it further. Get this book I like. I was pumped that we had a chance to get Jeff so quickly after the release of the new update onto the podcast. But man, you've got like a few days to be able to join that class. You'll see. I'll be there on July 15. I went through the process, got my book, added the receipt and everything, and I'm excited to hear what Jeff's doing. Like, there's not many people out there. I can't think of anybody who has had as much impact on as many decision makers and leaders and organizations when it comes to AI as Jeff and his book. So a must have. Even if you've got. I've got a copy. I still got the new copy because I want to know what's, what's new. Jeff, any closing remarks or anything like that for the listeners?
Jeff Woods
1. Thank you. Your words mean my pleasure. Impact is a core value for me, so it really does touch me deeply. So thank you. Before I wrote the book, I was super clear. I want to create a new category of leader. This is not about technology. This is not about profit or business growth. Yeah, there's so much fear around job loss and will AI replace me? And I think this is a leadership question. The questions you ask matter. If you ask, how can AI replace me? You can search and probably find answers to that. But is it the right question? What if instead, as a leader, you empowered your people to ask, how might this make me irreplaceable? How might we harness this not to remove headcount. How might we harness this to raise our standards for the impact we make with the headcount we have? For me, our mission is to create better leaders who build better businesses and create better lives. We do not work with companies that just want to slash headcount. We want to work with the companies who want to harness this technology and keep the human at the center so they have better leaders, better businesses and better lives. My ask of you is if that aligns with you, join the movement, join the future of leadership, which is AI driven leadership. And it starts with you. How can you become an AI driven leader?
Chris Daigle
Love it. Jeff again man, thank you so much. This is powerful. I'm excited to be a small part of helping get this message out because I'm a big believer in your positioning and your thoughts about this. So thanks and everybody again, July 15th. If you can make that, please get the book today. Join that class. You'll see me there. You'll get to hear Jeff really dive into this stuff way more than we could ever do on a podcast. So Jeff, safe travels. I know you've got a busy schedule and all that jazz changing the world when it comes to AI. So just again, thank you for being on the show, bud.
Jeff Woods
Thank you, Chris.
Chris Daigle
Thanks everybody. We'll see you on the next episode of Using AI Work comes out on next Monday.
Podcast Narrator
Thanks for tuning in to Using AI at Work. Don't forget to subscribe for more conversations about how to use AI at work and a special thank you to our sponsor, Chief AI Officer for empowering businesses with AI education and training. Visit their website for a free AI Readiness Assessment and AI Strategy Guide to help you get started using AI at work. That's www.chiefai officer. Follow us on Twitter at the handle usingaiatwork and visit www.usingaiatwork.com for free resources to help you harness AI in your role.
Title: AI-Driven Leadership: Using the CRIT Framework to Make Faster, Smarter Decisions with Geoff Woods
Host: Chris Daigle
Guest: Geoff Woods, Author of The AI Driven Leader
Date: July 13, 2026
This episode focuses on how business leaders can personally embrace generative AI, not just as a technical tool but as a fundamental driver of strategic leadership and organizational transformation. Geoff Woods, author of The AI Driven Leader, returns to share insights from the updated edition of his best-selling book and explains the widely adopted CRIT prompt framework (Context, Role, Interview, Task) for using AI as a thought partner. The conversation dives deep into empowering leaders to go beyond superficial AI adoption, fostering a culture of strategic AI engagement, and building organizations where AI amplifies—not replaces—human strengths.
AI Leadership Isn’t About Tech Expertise:
Hypocrisy vs. Leadership:
Quotes & Takeaways:
Genesis of the Book:
People Over Tech:
Market Impact:
What is CRIT?
How to Use CRIT:
Why CRIT Works:
Memorable Exercise:
From Access to Adoption:
Driving Top-Down Change:
Advice to Enthusiasts Facing Skepticism:
The AI Adoption Curve:
Why Update the Book?
Favorite Updated Story:
CRIT Homework (Sticky Note Exercise):
Organizational Practices:
Book & Training Availability:
On Leadership & Adoption:
On CRIT’s Impact:
On Empowering Others:
On Mindset Shift toward AI:
Geoff Woods challenges leaders to own AI transformation personally and to use prompt frameworks like CRIT to make AI a true strategic partner. The shift is not just operational but deeply cultural, moving from a passive user mindset to one that continually seeks leverage and value. By modeling this behavior, leaders cultivate not only stronger businesses, but more empowered people and enduring organizations.
Key Call to Action:
Resources:
For anyone seeking a non-technical, yet deeply strategic roadmap for AI-enabled leadership—this episode, and Woods’ CRIT framework, are essential listening and practice.