
Loading summary
Bill Gallagher
Abdicating your judgment, wisdom, your advisors to AI is a horrible idea.
Chris Staigle
You might say, oh yeah, that's good. And not really necessarily think it through, but just take the output from the model and say that's pretty good.
Bill Gallagher
Treating AI today as a decision tool, probably not great as a thinking partner, as a research tool. Like lots of great ways to use.
Chris Staigle
It, not specific to a technology. But do you see any pattern shifts that are going to occur in knowledge work in US industry in 2026 because.
Bill Gallagher
Of these tool how to make AI normal, get comfortable with change and lean into this time.
Chris Staigle
Even if the technology could replace people, the missing piece is going to be the execution of that technology.
Bill Gallagher
Maybe you're worried about it's going to replace you or your work. Fine, replace yourself. Because if you replace yourself with a tool like AI, you'll end up with a new job. You're now an AI implementer.
Chris Staigle
Bill Gallagher is a global business coach and host of the Scaling Up Business podcast. With four decades as a CEO and a power user of AI, he helps ambitious leaders scale fast without burning out or handing the reins to the robots. Welcome to Using AI at Work. I'm your host Chris Staigle. Each week we'll be learning how today's business owners, entrepreneurs and ambitious professionals are getting more done with smart use of tomorrow's tech. Let's get started. 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 chiefaiofficer.com and see how we're helping companies of all sizes finally get results from AI. Greetings esteemed listeners listeners, this is Chris and welcome back to another episode of Using AI at Work. And we're going to be taking a kind of a broader perspective of AI in the workplace today with our guest Bill Gallagher, who is the CEO of Scaling Coach. I met Bill through a blossoming relationship with the Scaling up organization. If you're familiar with their work, I think their original Book was called the Rockefeller Habits. It's now called Scaling Up. But Bill does way more than just as a scaling up coach. He actually hosts their podcast. They're up to almost 700 episodes, I think, getting close. So they've been doing that since 2016. So he's had a lot of conversation, a lot of consideration, a lot of investigation into the dysfunctions inside of businesses, the constraints inside of businesses, what's keeping them from growing. And obviously with generative AI playing such a big part in the question that all businesses are having today, those perspective is going to be extremely valuable for our listeners, whether you're a solopreneur or you're leading a, you know, an enterprise company at an executive level with a background as a CEO, tech and with a family connection with generative AI, which we might talk about today, his perspective on things is way more than just like, oh, I'm seeing what's happening in the marketplace. This is something that is, this is a discussion that's happening at the dinner table when his kids are home, I would imagine. So with that, Bill, before we get started with this, what would be. And I'm going to borrow from Greg Eisenberg, who I spent the weekend with. He's got a fantastic podcast, but he opens his podcast with this question by the end of this episode, what are people going to learn? And I know that that's kind of a curveball and this first time I've asked it. But if, if the ideal outcome from this episode and our conversation together, what would you want the listeners to, to understand, to, to walk away with?
Bill Gallagher
Well, I guess two things really. I'd like people to have an idea or a. It's like something new for themselves personally. But then because the kind of people that you have listening, watching this show, I think that we want them to have things they can take to their teams as well. Right. We want to have some access to making your teams more competitive and getting through.
Chris Staigle
I like it.
Bill Gallagher
The natural sort of adoption curve that people are seeing right now.
Chris Staigle
So I think as we get into the conversation, we might want to set the context of the scaling up framework with people, strategy, execution and cash. And can you just take a moment for those who maybe they've heard of it, but they haven't really had much exposure to it. The like just the paradigm of scaling up.
Bill Gallagher
Well, so scaling up is a best of business growth framework that was originated by Verne Harnish, who's been my friend and mentor for decades. Verne, you mentioned mastering the Rockefeller habits. He was Teaching a program for entrepreneurs at MIT years ago. And he read this book about the life and times of John D. Rockefeller. And he introduced, furred, intuited, discovered in there some habits that were useful in any time, not just in olden times, but in modern times and into the future. Like enduring things that we now enable with technology, but like basics around alignment and focus and prioritization and rhythms and like all that. So all of that is distilled into the first book and then expanded into these four decision areas. People, strategy, execution, cash. And strategy is about getting a simple, differentiated strategy that's actually driving growth. So growth is needed to have a good strategy simple enough to communicate and use and differentiated, not just like every other company. What is it about you that's unique and different? So how do we figure that out? Is part of our work, and that's greatly enabled and accelerated with AI today. And then people is getting the right people on the bus, working together well, recruiting, retaining, developing your people, the whole people, and not just the people on your team, but the people your customers and suppliers and like that kind of thing too. And then so all the people you interact with and then execution, like, what are the basics? And to be honest, I see this with some of the AI companies today, where they want to sort of say, nothing of the basics applies to us. We're going to do everything differently. And that clearly spanks you at some point. So how do we dial in and then not work so hard, like, keep things running well and smoothly and that kind of thing, and not drown in meetings or drama? So that's about consistent, repeatable, scalable things. And again, there's a whole bunch of places and ways that AI touches that to make your execution easier and better than ever before. And then cash is, you know, is the kind of thing that people lie about more than anything else or they avoid looking at because they don't understand or that kind of thing. And again, AI has a great opportunity to simplify and help us gain access. You know, people in finance and banking, that kind of thing, love to throw around terms and intimidate others with their knowledge and use of jargon, but they can't even agree on what to call things. Just like a lot of the world of business. So is it opex? Is it gna? Is it. All those things mean the same thing, right? Like, so they throw around terms and they try to intimidate you. And if you don't come from a finance background, then it can be uncomfortable, and so you look away or whatever. AI can Cut through that BS and help you to be smart about your cash. And then, and then even before AI, our simple tools around, what do we actually need to focus on here so that we have a business that's worth more, that isn't like running to the bank all the time. So those are kind of core things around. And then taken broadly, people, strategy, execution, cash scaling up is a best of open framework. So unlike some others who put a trademark on every single thing and put their spin and make it really rigid or whatever, we're like, look, let's keep evolving it. So I was just having a conversation with Vern who's as we talked today back in Sitja, Spain outside of Barcelona, Barcelona over the weekend. And he was grappling with something, wanted some feedback on that. And then I had something that I needed to share and that kind of thing. But we're talking about the evolution of our tool framework that is not static, like okay, how do we expand this one? How do we revise that one? Who wrote a book now that changes the way we think about things.
Chris Staigle
Interesting. And I know that the relationship that chief AI officer is having with scaling up is just going to further accelerate the integration of AI thought into how these things are structured. So I'm going to start with something we'll call it a hot take. I guess. I was on the phone with senior senior leadership at a a well known business framework, business operating environment. Right. And we were talking about AI. This was just last week, we were talking about AI. And his position was that AI in the planning phase was not good. That it.
Bill Gallagher
I'm called BS on that one.
Chris Staigle
So I was a little like, well maybe we're not using the same tools. Turns out he's an avid user of multiple models. He was very capable. But his position was that the kind of the soul of the conversation of the important things related to culture and core values and things like that, that you might find a situation as listeners if you're using this in your planning. His position was that you might say, oh yeah, that's good. And not really necessarily think it through, but just take the output from the model and say that's pretty good.
Bill Gallagher
Abdicating your judgment, wisdom, your advisors to AI is a horrible idea. Horrible idea. And here's a simple experiment. Come up with some cockamamie fakacta idea for a business and then ask AI how to make it work and it'll tell you, wow, that's a novel take on things. I think putting a cannabis truck next to a middle school is a Great idea. You know, there's some things to worry about, but let's make it work. You know, it probably won't do that one, but like really close to absurd nonsense. It's sycophantic in nature, it wants to please you. And you could ask the same thing a couple times with slightly different prompts and you'll get, get really different answers. So treating AI today in the current things with that with primarily thinking about LLMs, not small specialized models and that kind of thing as a decision tool, probably not great as a thinking partner, as a research tool, as a process. Like lots of great ways to use it in your planning and strategy work. But abdicate it, like, tell me what to do, bad idea.
Chris Staigle
So. And I know that scaling up like they do a lot of work with Jeff woods and his positioning on, on using it as a thought partner, everything so totally concur there. I'll tell you though, from the experience that I've had with, with working with, because we come in not necessarily on the people, strategy, execution, cash side like you guys do. We come in on the strictly. Okay, we're assuming you've got that framework in place or a framework, how do we introduce generative AI into, you know, elements of that? Right? So what we're seeing is the executives, they've probably got one tool that they're using and it's either going to be copilot or chat GPT and they haven't had a voice, tell them like no abdication, right? Use it as a thought partner, but don't say, okay, write this for me. And now make our, you know, make our core values or make our strategy. Are you seeing kind of the same thing, at least with initial engagements and conversations that that's where the executives are or are they past that in the people that you're working with?
Bill Gallagher
Well, look, let me just walk you through some examples instead of talking about it theoretically. So somebody is thinking about working with me, right? Or curious about what it looks like. First thing that I do today is I send them to a questionnaire. Now we used to have some different questionnaires or highly guided structured assessment. I have a beta kind of an assessment today that's entirely AI driven. It's. And it's not fully automated yet because we're still iterating on what it looks like. So we ask you a bunch of questions. The questions we ask you, I would ask them verbally, I would ask them in writing, lots of different ways. I've asked them in the past. Today we're collecting with just a web form, right? You empty your brain. Then I have those things processed with a specific prompt and a set of questions like, okay, based on these answers, what do we think about this, this and that? And go look at these competitors and go do this thing. And then I look at, and then I massage it a little bit. So there's still a fair amount of manual today. There is a template, there's a sequence of prompts, not a single one. And then some manual review. And then when I feel good about it, we send it along to you. Then we have a conversation about what does this say, what were you thinking? And that kind of thing. We talk about the different pathways to growth and what you might consider, maybe you haven't even thought of some of them. And we explore and we look at your competitive positioning, we look at the risks and strengths relative to growth and things you might want to consider. We consider areas we might focus on first. So all that happens with less than 20 questions. And then a really rich conversation emerges. It's not about getting the answers, it's about speeding and expanding the reference. In that rich conversation that then happens between a potential coach and a potential, whether you work with me or not, or you just take that thinking and go on, that's like step one. Then I start. So you know, we start, I don't know, a few clients all the time and we're so. And then in the beginning, especially with, at our private client level, I'll interview all the senior team and I'll interview the senior team. I'll talk with them in depth, open ended, exploratory. I take handwritten notes, which is my brain filter what I'm noticing. But then I also record the conversation in most cases. And then I feedback both of those things from the whole team and I say, okay, what do we need to do? What's working here? What's not working here? What's the split between the CEO's view and the rest of the senior team's view? Where are they divided? There's almost always a split there. Now let's look at the competitive environment. Let's consider what areas we might focus on and why. So I'm using it as a thinking partner in an ongoing conversation. Then about that I'm like, okay, now give me a write up to share back with the senior team to reflect back to the things that I heard. So now I get a particular, maybe a more sanitized version because I don't want necessarily it to just dump on the split between the CEO and The senior team, I want to manage that, finesse that in the background. I don't want that. So there's a whole. You're starting to see a sequence now. I'm going to have my first off site with the team. We've interviewed them, we've chosen a sequence of things we're going to work on. I will then say, okay, everybody answer these questions. We always did that like 20 years ago we would say, here's some pre work for the senior team off site, go do some thinking. And they might answer a survey, they might send emails, they might do handwriting, they might just bring. It could be done different ways by different coaches. I always gave people like either an email or a web form and I would collect it back and then I would pre read it. And sometimes we would summarize it, anonymize it. We used to have to do all that with an assistant fairly manually. And then I would have to read through a lot of things. Took a lot of time. Today I can say, hey, AI, summarize this, give me some thoughts about it. Okay, now create a version to share with the team. I can send to the team a day or two before the off site. The team now is already getting the shared view. They start to get aligned. They did their pre thinking themselves individually. Now they see kind of we haven't even met yet or begun discussion yet. Now we meet, we start to expose some of those things. I'll have AI create a set of slides for me based on the summary and then I'll throw that up and then let's talk about this. What do you see? What's missing? What do you see of your voice? What surprises you here? So we can have a thoughtful conversation about all that. And then we get through to, well, what should we do? Right? So then we start to brainstorm in the room. And sometimes that'll be discussion based, it'll be pretty obvious. Other times we'll go to sticky notes or whiteboards or that kind of thing. And we'll build models and prioritization. I'll send people to take a walk and discuss in pairs. So we'll use any number of things to get like really great thinking going. And then we often will take a picture of handwriting notes and through the whole meeting we're capturing an AI transcript and a summary of the meeting using Zoom or Otter or some other tool. And then we will go and we'll say, okay, summarize this for me and give me this back. Now the ideas usually emerge and we might even explore some Things. Well, how does that look like? Or let's boil this down. I did a session recently where we were trying to work on core values with a senior leader and he's like, you know, we created these core values. We've now had them for three years. We did them with you in the beginning. I feel good about them. I think they are. And yet there's something cringey about these for me. I'm like, oh, tell me more about that. He's like, I'm afraid to ever sort of talk about them because I just feel like they're awkward and artificial. Like, oh, I'm hearing that the language of the core values that you wrote with your business background doesn't resonate with your more blue collar team. And he's like, bingo. I said, great, let's just go. So we drop his core values, which are technically correct, describing things, but not in the language that fits his team. Right. And so I said, okay, break this down for me for a company in this industry so that we could talk at every level, at line level, all the way up to the. The boardroom. And then it gave us back a draft, but it wasn't done. We were like, ooh, that's kind of good. All right. I like this one. I don't like that one. This word is giving me. So now we're having iterative conversation. It's not an answer. It's a thinking partner that speeds up. Now, could he and I have worked through the language on each of those, rephrasing it? Yes. He would struggle to do it on his own, but working bias and background.
Chris Staigle
And all that, yeah, sure.
Bill Gallagher
And just like being stuck one perspective, right?
Chris Staigle
Yeah.
Bill Gallagher
Partner with an outside coach, it's going to get better. With some peers, it's going to be better. AI can bring all of that and up level all that. Now if you have a coach or a peer and a CEO and the AI tool, boom, we accelerate that stuff and then in a matter of minutes, we produce something that's awesome. Them. It's still not done. We say, okay, now go socialize this with the team and say, hey, team, we did a. I know the values. We don't talk about it too much because I never like, whatever. We did this new version. What do you think? And then socialize it and then hear what people say. First time he did it, they were like, that's awesome. But there was like one word that was a little like, what do you mean by that? And. And then there was another word that was sort of like mixed for Some people in one situation, he took it as like a opening to go back and refine further. And the other one, he used it as a teaching moment. Like, everybody needs to know this word. It needs to resonate with you. We're going to lean into this one and build on it. So none of that AI is advocating. We're not advocating or letting AI be decisive, but it's accelerating the whole process, right?
Chris Staigle
So if I was going to feed this back to somebody, like one of my peers and everything, and say, hey.
Bill Gallagher
Listen, wait, wait, wait. One more.
Chris Staigle
Sure.
Bill Gallagher
Then we're come to the end of the meeting. What are our next steps? What are the action items? Who needs to do what by when? And we'll create a list of things that needs to then get calendared into people's calendars. So we follow up. Because people say lots of things they mean to do, they're capable of doing, and they just effin forget to do them. Like, it just disappears because we're busy and distractible. This case, we're like, okay, good, I like that list. Now put that into my calendar for me at the next available time. At least once a week, 30 minutes, right? We'll do a thing like that. So it'll take the action items out of the meeting and it'll sequence them over the next 13 weeks, throwing them into calendar either at a set time. In some cases, it's like, put them Mondays at 11am or that kind of thing. And a recurring thing, it'll give you a new task every week. Or in other cases, it'll throw it into the next available time, favoring early. It can use more judgment and we can say either if we're connected. So if you have like Gemini maybe, or I'm not clear how copilot might do with this, but it could actually put it in the calendar for you. Or you could say, hey, just give me a ICS file with all those tasks. And then I just drop that thing. Boom, now it's in my calendar. So we've created a thinking partner through the thing. A summary, a conference report, insights, action items, and we've even calendared them. That is planning with AI Assist.
Chris Staigle
So I think any executive that's been to an off site, they'll say like, none of that was, oh, I've never heard of that before. But the missing piece from the way it used to be done to the way it's done now is that by leveraging AI, none of that gets missed. Like, it's not like, well, we don't have enough Time to do it all. Or we got some great ideas but we didn't capture everything or we ran out of time. So we weren't able to fully flesh out the, like the action plan for everybody. So, and, and this was what you just explained was a combination of both the strategic and like really digging in and going back and forth and back and forth. And oh, we need human input here. And here's some synthetic output. Let's see, what would the humans think about that?
Bill Gallagher
That.
Chris Staigle
But also you introduced some of the, like the tactical usage, like plugging it into the calendar. So if, if you're a listener and, and you guys were using AI in your annual planning, maybe back before the turn of the year or even now, one of the things I bet some of you did was, wow, this didn't take very long. We just put everything into AI. And there you go. You missed the part that Bill's talking about, which is looking around the table off site with the rest of your peers and saying, what do you guys think about that? Like, does that land with you? Rather than just going push, hey, look.
Bill Gallagher
Don'T just accept, look. AI's first output often looks good, sounds good, but it also, if you scratch the surface of it, you know, it's kind of bs, it's kind of fluff, it's kind of filler, or maybe it made some things up or maybe there's another way to think about it. So I think surrendering your wisdom, your judgment, your creativity to it, not a good idea. But having it be an accelerator, a partner through the whole thing, powerful.
Chris Staigle
So Bill, if somebody said, what's a standard company that you work with? Who would that like, what would their industry size, age, all that kind of stuff.
Bill Gallagher
The defining characteristic for, there's three main things that are true for the companies I work with. But the biggest thing is some hunger for growth, right? There's some ambition for some unusual growth.
Chris Staigle
Growth.
Bill Gallagher
It's not just like I want to grow 5, 10% a year. They're like, I want to double triple 10x 20x this thing. I want to be number one in the world. I want to own my state. I want to, like there's something more like that. So the driver and the ambition for the people that work with me, you could run a business lots of different ways and maybe you have a multi generational thing. You just don't want to get eaten up by AI. You want to stay relevant, that you might not work with me and that kind of thing because it's not about growth very often. Those companies also are thinking about some kind of a transition. Like they want to sell the company and retire, put some money into their retirement. They want to exit, they want to sell it to the team, they want their kids to take over. There's some kind of an exit anticipated, even if it not clearly yet, but like at some point off in the future. So. And then coachability is a tough one. It's really critical for my work. But. And it's not like we all think we're coachable and yet mostly we're not. Right? And I think, like, as a coach, I can point to evidence where I'm exceptionally coachable on a comparative basis, and yet my wife and my mom could both tell you about areas in time when I'm exceedingly uncoachable. So even if I skew higher overall, there are, There are definitely places. And listen, when I think back to my history as a CEO before being a coach across multiple companies, when things were going wrong, I really wanted to find anyone else to blame but myself. When things are going wrong, my first instinct, like most of yours, is not to look in the mirror, not to go, how did I fuck this up and what am I missing and how did I set this up? It's like, like, which SOB can I fire?
Chris Staigle
Yeah, they should have known. Yeah.
Bill Gallagher
Yeah. So I think that's a really common kind of a thing to phenomenon. So I'm looking for coachability and I'm testing. Are you willing to try things and are you willing to look in the mirror? And I re. I frequently get people who think they are, but it's going to take a lot of artful approach on my part to get them to actually do it. Because we're all. We all have egos. And if you're a leader of a company or the owner, founder, CEO, you probably even have a bigger ego. Right. And so it's more sense.
Chris Staigle
So the coachability. And I used to, when I lived in la, I used to go to this restaurant, it had this big mural and it was two kind of like stick figures sitting at a table. And one had the name, one had like the label growth, and the other one had the label comfort. And they were sitting at the same table and growth was standing up and pushing away from the table and saying, I don't think this is going to work. Yeah, right. Because growth and comfort don't live in the same house.
Bill Gallagher
Right.
Chris Staigle
So you're dealing with these individuals who have ambitions for growth. They need to be coachable. But as, as we know, like those definitions Are malleable, let's say. But now you're introducing something that is. Is kind of sweeping the business landscape. There's not a lot of really true experts on it.
Bill Gallagher
Yeah. How is.
Chris Staigle
How is AI, I don't know, exacerbating the. The. I don't know, the skepticism, the. The fear, the. The resistance to growth. Like, what are you seeing with the executives?
Bill Gallagher
Well, people are worried about their own incompetence, whether they're up to the challenge. People are worried about failing. And sometimes when you're really worried about things, you avoid even looking at it.
Chris Staigle
Right.
Bill Gallagher
Like, I know people that are behind in their bills and having money problems, and they don't open the mail that's there.
Chris Staigle
Yep.
Bill Gallagher
It's funny. I have a stack of mail over here. Be careful. Things I need to. There's nothing I know pressing, but they're all things that I can't just throw away. So. So look, that's a real thing. We know people are afraid to look at it. They hope, and yet they're just bombarded with it on the daily. So I think you point out something great, and I've thought about it a lot over the years. Right. I have worked with people who love having breakthroughs, Depending on the kind of work that I'm doing and that kind of thing. People are like, I really need a breakthrough in this area. I want a breakthrough. Oh, it was a great breakthrough.
Chris Staigle
Wow.
Bill Gallagher
We really had a breakthrough around our marketing or this kind of thing. Right, Right. So everybody loves breakthrough, just like everybody loves the idea of growth. A breakthrough is an interesting word, though. Breakthrough implies a barrier.
Chris Staigle
Yes.
Bill Gallagher
So you want to have a breakthrough in something. Start running at walls. Right. Nobody wants to go run at a wall.
Chris Staigle
No.
Bill Gallagher
Come on, you know, unbuckle your seat belt and floor it. Now head right for that wall. Nobody wants to do that. We know running at a wall is going to be painful. Running at the wall is going to be uncomfortable. And the first couple times, you might hurt yourself pretty good. Eventually, if you don't die, you'll break through. Right. But we're actually more interested in not suffering than we are dying. Like, at some point, we all face our mortality. If you've been around people who are grappling with a serious disease and facing their mortality more often, they don't want to suffer more often, they don't want to be in pain. And they. They want to live. They want to live well. They know that they won't live forever. We, none of us are getting out alive so far. So we Mostly avoid that. You're right, there is a tension there. And some of us, just by our nature, our drive, we're restless and we get out of bed and we're thinking about things and we can't just leave it well enough alone. We will open up a can of worms and start to deal with the consequences. But a lot of times we'll be like, oh, I don't want to look at that one. I don't want to let that person go. I don't want to scratch that thing because who knows what it's like the Pandora's box. I'm going to open something up and then I can't get it back in there. Right, right.
Chris Staigle
So in that vein then, what are some of the. Now we've already talked about. I think that was fantastic. The, the distinction between abdication and support and using the models don't just say, hey guys, we're done. We got our chat. GPT did our annual plan. What are maybe some other areas that, that you would encourage executives who are, they're probably using Chad, GPT or co Pilot. They're doing something right, but they're not like a stat that I saw all.
Bill Gallagher
The way through it every step. Look, I'm using multiple AI models. My son works for Anthropic. My son, the early versions of Midjourney were built on the front deck of my house before it was a thing. So he was the principal AI scientist for Midjourney and he did a little work for Cursor. Now he is working on one of the problems as an AI scientist at Anthropic. For the Claude tool. I'm using Claude, OpenAI, Gemini, other things every day, almost every hour. And sometimes I'll open one thing I'll use Claude for a lot. I love the way Claude's language and reasoning works. I don't love the way it's difficulty looking back and sort of learning me broader that might get fixed. I like the research ability and the math capabilities of OpenAI and Gemini is getting better and better all the time. But it's really integrated with, with the whole Google suite. So if you're a G Suite user, oh my God, it can be fantastic. So I'm using all. I might open one and I might say I might give some particular business or even a personal challenge, hey, I'm trying to figure out to get to this country using this thing and this thing, like where could I go nonstop? Like how could I do that? And I'm thinking about, I need a venue that looks like this and analyze this for me. And then I go over to the other one and I'm like, I need to find all of the academic papers that relate to the research topic for my PhD and I'm doing like my literature research. Competitive review, all that stuff. Often with OpenAI because of its research ability, or if I'm going to run a math, hey, I want to run this company's numbers against this target. I'm looking to get to evaluation of this, help me create some scenarios. OpenAI is great. Yeah. So a lot of different kinds of things, but I might have those going on because I'm a scatterbrain entrepreneur, right. I got three things going across.
Chris Staigle
Power user.
Bill Gallagher
Yeah, yeah, yeah. Awesome. Especially like morning, middle and end of the day.
Chris Staigle
Yeah, I'm with you, man. And I think that if you're listening to this and that's not how you're operating. First off, don't feel like, I don't know that it's too late. Although the window is shutting for sure. But I can tell you a stat that I saw back in December.
Bill Gallagher
This is the beginning. Look, this is more like. This is less like the beginning of the Internet, okay. This is more like the beginning of the personal computer world. Right?
Chris Staigle
Okay, tell me more.
Bill Gallagher
Well, the first practical computer that I had was a CPM system, right? And there's a whole different. Nobody even remembers that anymore. And we did command line stuff on that. It was all command line, right? And we're looking at green letters on a black background and we had. And if we wanted to connect into some other system, we used acoustic couplers and 300 baud modems where you hand thing down.
Chris Staigle
And so.
Bill Gallagher
And then in the beginning of that, like I remember my uncle's law firm, they. They're like, ah, we're getting computers now and they got the PET Commodore Mach and they had cassette drives and things like that. And you know that people were like, I'm going to put this in my room and put my recipes on it and that kind of thing. And today I'm like, okay, I have these three ingredients. AI, tell me, what can I make with this? I feel like there's some kind of a braised chicken thing I could do here. Great. You have a Dutch oven, you know.
Chris Staigle
Well, you know, man, it's interesting you mentioned command line. And here we are again with Clis, with Claude and things like that. It's like.
Bill Gallagher
I don't use it enough. My son's like, oh, stop being a wimp. You know, open your terminal and use Claude. Code there and it's better for you. And I, I do have it, but I don't use it that much because I, I, maybe because I'm 61 now, but there was a time, I mean, look, I learned, I learned Cobalt Fortran, basic. I mean, I even wrote some stuff with Hex, right. Like a long time ago. Do I want to do that? No, I kind of left that pretty early on because I realized there were people better at it than me. But understanding both and being able to. Yeah, but you don't need to. And to do, like, cowork. I know a lot of people know about this, but you can open on your desktop and you can give it some access to your computer. You can let it just run stuff and go take off.
Chris Staigle
Right.
Bill Gallagher
So I've been experimenting with some prompts around a daily news brief for myself, Right. So, you know, I, I don't like necessarily the way the news is written and, and I don't love to go around a lot, but I, but I want to be informed and entertained and stimulated. So I've been trying to rewrite my own thing there, right. And I have it building over there as a, as a recurring kind of a thing. There are certain situations I'm monitoring. There are some commodities I hold positions in. I'm monitoring very close, thinking about, do I want to get out of this or do I want to hang around? Yeah, yeah. Like, so there's a whole range of. Or look, we got a contract in a proposal to invest in a company. Should I do this? Like, what are the terms of this contract, aside from just the fundamentals of this thing? Help me look at this contract. We did a multimillion dollar deal. I don't know. It was a little couple months ago and, and it was the weekend. I don't know where my attorney was. He was like, off camping or whatever. He certainly didn't answer my text. But I had to get some shit done before Monday morning because there was an event. And so we went through, and we didn't just say, fix this contract, rewrite this contract, or whatever. We said, what are the worst things that could happen?
Chris Staigle
Interesting.
Bill Gallagher
How would we change this? So we're not just asking for a work product. We're having an ongoing conversation given this situation. Here's the background, here's the thing. Ask me some questions. All right, now let's do some scenarios. Okay? And what we change, do we really need to worry about that? So two of us are talking about the deal, and AI is our third partner, acting as a Consulting attorney in the whole thing. And we're going through and we're iterating. In the end, we decided pretty much to just take the contract as was, that the risks were fine and weren't worth the time with one little exception. Option. But yeah.
Chris Staigle
So this is interesting for, for those of you that are listening and you're like, whoa, I never thought about that. That's probably pretty common. The, the thing that I hear a lot or would love to use it more, I just don't know where. Right, yeah. So, like, obviously Bill is. Yeah, Bill's a power user. Like, he's, he's using it, as he mentioned, multiple models, multiple times, all day long. So for you, if you're listening to this, what I would suggest is if you're not sure, go to the models and say, hey, I got a contract I'd like some help with, you know, from AI, But I don't know what to ask.
Bill Gallagher
Right, right. And that should I think about what are the possible situations here, who I am here. Let me give you another, like a meaty one. We didn't go here, but I think it's good. Before we get too long in this show, this is a really a great one. Process work is core to any business, and there are across any industry and category. There are process consultants who will spend months, sometimes years working on your processes to refine them, improve them, automate them, that kind of thing. Right. Things that would take at least a month or longer in the past, I can now do in an hour. And here's what it looks like. So we bring a team together, either an operating team or a senior team. We say, what's a key process that we need to work on? And they'll lay it out. Okay, great. So like a process consultant would do it in the past. We start to diagram it. A quick way to level that up is everybody do your own version of it. We all go stick them up on the wall and then we start to merge them until we have one common view. Now we have the current process mapped. Then as a team, we flag the issues. Now I'm talking about sticky notes and handwriting.
Chris Staigle
Old school.
Bill Gallagher
I now have some flip chart paper or a whiteboard, and I'm moving sticky notes around until I have a diagram of process and I've identified the areas, the gaps, the mistakes and the delays. So of what our best thinking is of either of some team in the room. Now I take a picture of it. I take a picture of that thing and I upload that to my favorite AI. Tool. And I say, okay, transcribe this and clean it up. Create a summary of what we've done so far of our current process. Then write me an sop, a standard operating procedure in a consistent traditional SOP language and then create a checklist for me so that I conform to this process consistently that can be used and operationalized. So now I have just the write up, the raw thing cleaned up from handwriting notes. I have a standardized sop, I have a checklist. And tell me the differences between this process and best practices in this industry. What are we missing and what should we go to work on? Give me five recommendations or give me 10 improvements or get like whatever, prioritize it for me. Tell me what do you see? Now I get all that done in the space of an hour and now it's still not like it's not perfect or it doesn't matter. Go use it now. Go spend the next month not trying to get to this point, but actually testing it, refining it in practice. So now that lives as like a Google Doc or some kind of shared doc. We print out and laminate the checklist. We start using in a department we see, okay, that's worded wrong, that's not actually what we do. And then we start refining it. And you think about it, go use the aviation checklist as a great comparable, right? So an aviation checklist, if anybody of you pilots, you'll know and understand this well. But like it starts one way and then over time they're like, oh, an airplane or two crashed and they're like, oh, well, we need more drainage things. And then you end up with a Cessna 172 Skyhawk that has like 17 fuel drains all over the wings and body because they are some places with some sediment and water and things like that accumulate. So it starts to refine and iterate and improve over time. But then you end up with something that's highly reliable and better and better and better. So it just keeps getting better because now it's like a living document that we keep improving on. But I didn't spend three months working.
Chris Staigle
On this thing or $150,000 on the process documentation team to come in and take three months doing it.
Bill Gallagher
Here's what we're not talking about here. We're not talking about in any of this, in this conversation about wiring in AI to your core decision making and customer process. I'm not talking about handing over your customer service or thinking, I'm not talking about firing people. I'm just talking about supercharging all of the thinking and work in the business at every department. Somebody's like, well, who should be involved in AI in our company, everybody, every day should be thinking about where to use it. Love it. That's your challenge. Play with it. It's growing and changing. It'll keep growing. There will be places it may get smart. I happen to know that Jack and the senior team are like, are we going to be out of jobs? They are all thinking about maybe this thing gets so smart that it trains itself at some point. And we aren't really. They don't even as the senior AI scientist for or, you know, one of the leading companies in the world, they don't think of themselves as immune from the possible future of it. But you know, who knows? Like, personally, I, I wouldn't worry as much about that. I think we will find things to do as human beings.
Chris Staigle
Yeah. And you know, it's interesting. Back to some research I did in December. I think I heard it maybe on the artificial intelligence podcast by Paul Reutezer. It's great show. If you haven't listened to it listeners, go catch add that one to your list. They were talking about how some research that MIT had done maybe across 900 different careers in the U.S. primarily knowledge workers, and they said that the current capability of the tools could replace about 12 to 14% of what, what's being done in the economy. And I thought, man, but that's not happening because just because the technology is there, it's sitting on the shelf for a lot of people, they don't know that it exists, they're hesitant to use it, they're slow adopters, they're going to get around to it or whatever. So even if the technology could do a lot, you know, like could replace people, the missing piece is going to be the execution of that technology, like the introduction of that technology. So for those of you who are still cautiously investigating AI, there's some time, however.
Bill Gallagher
Well, maybe you're worried about it's going to replace you or your work. Fine, replace yourself. Because if you replace yourself with a tool like AI, you'll end up with a new job. You're now an AI implementer.
Chris Staigle
Yes.
Bill Gallagher
100 somebody else, right?
Chris Staigle
100%.
Bill Gallagher
Yeah.
Chris Staigle
So I guess let's kind of like this year, you know, it's still early in the year. Do you have some predictions? Because, man, like in the course of a month, especially now, so many new developments can occur with the models and new tools can come out and do you see or anticipate any big Shifts in the business landscape, maybe not specific to a technology, but do you see any pattern shifts that are going to occur in knowledge work in US industry in 2026 because of these tools?
Bill Gallagher
Well, I have two big trends or a couple that I think are worth paying attention to. One is I think we can expect AI to become basic normal. The generative AI tools today that feel new are going to just become kind of standard. Use it to write your proposals, use it to manage things, use it to identify prospects, use it to identify parties like you want to find a company to buy, do your AI research, look for acquisition opportunities. Hey, what companies could we buy with owners who are in their 60s that fit this profile? Give me a list. Hey, who are the 10 companies that could bid on our company? Give me a list. Hey, who could I sell to for this area that has this need? How do I find these people? What's an approach? It'll give you stuff. So I think you can go again and again and again across a whole variety of things like that make it the normal in your business. And I think you can expect that it'll just become normal in background in some way. It'll keep developing and surprising with new tools and capabilities, but I think it just becomes baseline. What's then rising in value are all the personal human contacts and experiences. So if people are just generating AI slop content and your customer service is filled with silly AI, find ways to bring the humanity and to elevate the actual human touch and human interactions for when you are. So I think that becomes better. Use it to bring real people together for real things and then know in the background one of the things that's like chaos. People are getting comfortable with chaos. So instead of getting triggered by tariff threats or international conflicts, we're getting it like, okay, yeah, there's a conflict happening there and there's a threat and we don't know what's going to happen with that. Like, getting comfortable with chaos feels like it's part of the next period. So figure out how to make AI normal, get comfortable with change and lean into this time and how to elevate in real life experiences for people. I think those are a few like, oh, and then one more like big call out. This doesn't apply for everyone, but if you look around you, what's becoming exceptional is like basics everywhere around, from governments to like basic utilities, things like that are breaking from neglect, from any number of reasons, things are breaking down and we end up being surprised. Hey, I went to a city the other day and everything wasn't broken there. Wow, that's awesome. Yeah, yeah, just, just actually worked. It just wasn't like filled with homelessness and broken roads and crap like. Yeah, so getting competent is now. So just go do the job to figure out where you're losing competence, where things are eroding, where things are breaking in your world. And look, everything's breaking right. In a universe, entropy. In a universe filled with entropy, everything's always breaking. So you're going to work at things at fixing, repairing, building, tuning until you die, sell the company, retire, whatever. So just lean into it like.
Chris Staigle
Well, I think what's very encouraging for the listeners is guys, if you, if you notice all of those kind of trends that were just forecasted, none of them require you being an expert at AI today. Now the introduction of it and accepting it as part of just the day to day, certainly we did talk about that, but the rest of that stuff was more about the authenticity of the experience as compared to how do I squeeze the, you know, AI to get more stuff out of it. So, so I think that's very encouraging, especially coming from somebody who's got optics on so many businesses that are focused on hyper growth, focused on maximizing valuation at exit and all those types of things. So built. Fascinating conversation. I'm looking forward to more of these as chief AI officer and scaling up continue to integrate. But for those who want to find out more about. Maybe you got a fantastic podcast that you've been doing since 2016, scaling up with Bill Gallagher.
Bill Gallagher
Just go look for that.
Chris Staigle
Where should people go to just like plug in with what Bill's up to.
Bill Gallagher
So wherever you get like we're virtually everywhere. The Scaling up business podcast with me, Bill Gallagher, you'll find that. And then my personal website in the world of scaling up is scalingcoach.com scalingcoach.com and that's where my world and workshops and newsletter, things like that are. So you can go to the broader scaling up world or you can can come to me there. Either one.
Chris Staigle
Awesome dude. Thank you so much for taking the time. I know how busy you are and I know that you're at the apex of the scaling up world. So to get a few minutes with you has been fantastic and it's really helped me kind of see like what's the, what's the conversation going on in the scaling up businesses and coaching world. And that was very helpful for me. So I guess any closing remarks or anything before we call this one?
Bill Gallagher
Look, I know we're gonna, we're gonna have you on our show. We're gonna, I'm gonna thank you, give some thoughts on elevating your, your curriculum, tool set, that kind of thing. So I'll be around with you more in the next little bit.
Chris Staigle
Thanks and everybody, so we'll be back with another episode next week with some more fascinating conversation related to using AI at work and all of the the fun and fear that comes with that. So with that, Bill, thanks again and everybody, we'll see you on the next episode. Thanks for tuning in into 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.com. follow us on Twitter Twitter at the handle Using AI at Work and visit www.usingaiatwork.com for free resources to help you harness AI in your role.
Title: Using AI at Work to Lead Through Change Without Losing Trust with Bill Gallagher
Host: Chris Daigle
Guest: Bill Gallagher, Global Business Coach and Host of the Scaling Up Business podcast
Date: February 2, 2026
In this insightful episode, Chris Daigle sits down with Bill Gallagher, an experienced CEO, business coach, and AI power user, to discuss how business leaders can effectively leverage AI at work—leading teams through rapid change without undermining trust. They explore real-world applications of AI in business strategy, planning, and process optimization, as well as the mindset shifts and leadership skills required for successful and ethical AI adoption.
| Timestamp | Speaker | Quote | |-----------|----------------|-----------------------------------------------------------------------------------------------------------------------------------------------| | 00:00 | Bill Gallagher | “Abdicating your judgment, wisdom, your advisors to AI is a horrible idea.” | | 10:27 | Bill Gallagher | “Treating AI today as a decision tool, probably not great as a thinking partner, as a research tool. Like lots of great ways to use.” | | 19:38 | Bill Gallagher | “AI can bring all of that and up level all that. Now if you have a coach or a peer and a CEO and the AI tool, boom, we accelerate that stuff.” | | 23:39 | Bill Gallagher | “Don’t just accept, look. AI’s first output often looks good, sounds good, but it also, if you scratch the surface of it, you know, it’s kind of bs...” | | 28:03 | Bill Gallagher | “People are worried about their own incompetence, whether they're up to the challenge. People are worried about failing.” | | 31:23 | Bill Gallagher | “I'm using Claude, OpenAI, Gemini, other things every day, almost every hour...” | | 38:27 | Bill Gallagher | “Process work...that would take at least a month or longer in the past, I can now do in an hour.” | | 45:14 | Bill Gallagher | “I think we can expect AI to become basic normal... What's then rising in value are all the personal human contacts and experiences.” | | 44:26 | Bill Gallagher | “Maybe you're worried about it's going to replace you or your work. Fine, replace yourself. Because if you replace yourself with a tool like AI, you'll end up with a new job...” |
Connect with Bill Gallagher:
This episode gives listeners both the mindset and the practical playbook for AI leadership—how to use technology as an accelerator, keep human judgment central, and build organizations ready for continued change.