AI Is a Survival Skill for Consultants

AI Is a Survival Skill for Consultants written by John Jantsch read more at Duct Tape Marketing

Episode Overview

John Jantsch welcomes Steve Cunningham, former agency owner, startup founder, and creator of the book summary platform ReadItForMe. Steve shares how generative AI nearly wiped out his business and forced a complete reinvention of how he approaches consulting and knowledge work.The conversation explores the rise of the AI-native full-stack consultant, the importance of context engineering, why deliverables must be built for both humans and AI, and how agencies must adopt factory-style workflows to survive. This episode is essential listening for consultants, agencies, and service professionals navigating rapid AI-driven change.

Guest Bio

Steve Cunningham is a former agency owner, startup founder, and AI-native business strategist. He built the successful book summary platform ReadItForMe, backed by a billionaire investor, and read a book a day for nearly ten years.

After generative AI disrupted his business model, Steve pivoted to helping consultants, agencies, and service professionals redesign how work gets done with AI. He is the founder of Simple and the author of The AI-Native Full-Stack Consultant.

Key Takeaways

• AI replaced entire categories of work: Tasks that once took hours can now be completed in minutes or seconds.
• AI-native is not the same as using AI tools: AI-native businesses redesign workflows, systems, and deliverables around AI.
• The full-stack consultant is emerging: With AI handling execution, consultants can deliver value across marketing, sales, operations, and strategy.
• Context engineering is the real advantage: High-quality, reusable context enables AI to perform at expert levels.
• Knowledge work is becoming a factory: Repeatable workflows, quality control, and standardized processes are now essential.
• Deliverables must serve humans and AI: HTML and structured formats outperform PowerPoint and Word in an AI-driven world.
• The cost of variations is nearly zero: Infinite testing and personalization are now practical and affordable.

Catch the full episode

Great Moments from the Episode

• 00:01 – 02:34: How AI nearly destroyed ReadItForMe
• 03:18 – 05:41: Defining the AI-native full-stack consultant
• 06:24 – 07:52: Why consultants must go beyond marketing silos
• 07:52 – 10:05: Context engineering explained
• 10:57 – 11:16: Hyper-personalization at scale
• 11:36 – 12:36: Why betting on one AI platform is risky
• 14:18 – 15:43: The decline of PowerPoint and Word
• 17:43 – 19:56: Guardrails, QA, and the factory mindset
• 19:26 – 20:14: The future of agencies and consulting

Memorable Quotes

“AI doesn’t need more prompts — it needs better context.”

“If you don’t turn your marketing agency into a factory by 2026, you’ll be out of business.”

“We need to build deliverables for humans and AI, not just humans.”

Resources & Links

• Free BlackBelt AI Training (Exclusive for Listeners):
  https://roiassociation.ai
• Book: The AI-Native Full-Stack Consultant

 

Duct Tape Transcript

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John Jantsch (00:01.371)

Welcome to another episode of the Duck Tape Marketing Podcast. This is John Jantsch. And my guest today is Steve Cunningham. He's a former agency owner, startup founder, and now AI native business strategist. He built a successful book summary platform called ReadIt.ForMe, backed by billionaire investor, read a book a day for 10 years. I feel like I do that sometimes. But when AI disrupted his industry, it nearly wiped him out. So now he coaches.

Steve (00:01.71)

I'm to you to sign up for the presentation. I'm ask you to for the I'm going ask to up for I'm going ask sign up for I'm you to I'm to ask you to I'm going you to sign up presentation. I'm going to sign the presentation. I'm going you to going I'm

John Jantsch (00:30.425)

solo consultants, agency owners, and service professionals to make more money faster and easier by becoming AI native through his company, Simple and his brand new book, the AI native full stack consultant. So Steve, welcome back to the show. I say welcome back. think this is your first time actually on the show, but, you and I tried to record and I was like in a hurricane and it didn't work out. so I'm glad you were able to come back.

Steve (00:31.822)

Thanks for having me, John.

Steve (00:56.622)

Good to be back for the first time.

John Jantsch (00:58.683)

So, I mentioned the AI destroyed your business. You want to talk a little bit about it or tell that story as I'm sure you have a number of times.

Steve (01:08.75)

Yeah. So read it for me was a business that I hoped would last the rest of my life. I loved that business. I like to joke if I could get in the time machine, travel back to 2022 and destroy all the AI, I would do it. That's how much I love that business. I got to read books from my favorite business authors like yourself. I live here in San Antonio, Texas by the Riverwalk. I would literally go outside.

John Jantsch (01:24.283)

Ha ha ha.

Steve (01:37.134)

I would take my, I would read on the phone. So I read Kindle on the phone and that was my job. Uh, so I loved it. And so when Chad GPT came out, um, you know, this is a content business, right? So it would take me about eight hours to read a book and summarize it, take notes and do all the, all the stuff from beginning to end. And when I realized that you could get a passable book summary, which is by asking for it and maybe, then with some good prompting.

get a finished product in much less way less time than it would take for me to read and summarize the book. I knew that we were in trouble. so it didn't happen overnight. We still have people reaching out wondering, can they bring Rita for me into their business? I, two and a half, three years later, it baffles me that people still have not figured out that they don't need us anymore for that. But

John Jantsch (02:31.579)

you

Steve (02:34.478)

Yeah. So the revenue went down, not overnight, slowly but surely. And so we realized that we had to do something about that and saw the writing on the wall transformed our operations with AI. Then lots of folks wanted to know how we were doing it and started showing them. And here we are two and a half years later and we're fully AI native and doing lots of fun and exciting things.

John Jantsch (03:01.231)

So I suspect, maybe I'm wrong, maybe I'm naive, but that most marketers today are consultants have figured out, know, yeah, I need to use this AI thing. You use the term AI native full stack consultant. How does that differ from someone who say just uses it in their workflows?

Steve (03:18.798)

Well, one of the things that has happened in the last few months is that the easiest way to put it is the AI has gotten really good. So there was this, we were on a short timeline for the podcast. We don't have time to dive into it deep, but there were studies done through OpenAI. So take that with a grain of salt, but it's called the GDPVAL. And what they did was they took...

bunch of subject matter experts. got a bucket of tasks across most knowledge work. And they said, give us your best blank. And there would be a task. And so they would do it. And then they would have the AI do the exact same task. And then they would give it to another subject matter expert. And they would say, which one of these is better? And so 2024, wins or ties by the AI was like a 10%. Now it's a caveat that the AI has all of the context it needs in order to do

the job. And most people don't get anywhere close to giving the AI all the best, all the contacts they need. So 10 % like people would say, yeah, it's not a 10%. Well, it's probably not a 10 % because you didn't give it all the context. anyways, move forward into 2025, middle of 2025, we're approaching 50 % wins or ties by the AI. So we're getting close. We call that the AI tipping point. As of a couple of months ago, the wins and ties by AI were

John Jantsch (04:17.56)

Yeah, right,

Steve (04:42.414)

70 % and since then you can feel if you're using AI, this is getting better and better and better. So what we mean by full stack consultant is if you understand what good looks like across any subject matter expert domain, you can get pretty close to doing an incredible job for your clients in all functional areas of a business. So a marketing agency can do

sales enablement, but they can also do some CFO work. They can do some strategy work. And that is what we mean by the full stack consultant. And the idea is that if you get very good at some new skills, which are not obvious to most people, like how to produce a really good, robust context library for your clients, you and the company can do amazing work. It can be done.

John Jantsch (05:15.385)

Mm-hmm.

Steve (05:41.166)

incredibly quickly and we're learning more and more every day about what that looks like. So today, this morning, I did about, and this sounds ridiculous when you hear it from the outside and I understand that it sounds ridiculous, but I did about, in about two hours with 30 minutes of my work and an hour and half of just waiting around for the AI to finish its work, about 260 hours of design, interface work, copywriting.

and development. I don't do any of those things in the past life. I have no skills in those things, but I know what to ask for. I know what I want and I know what good looks like and now I can get it. So it's an amazing time that we live in.

John Jantsch (06:14.232)

Mm-hmm. Yeah.

John Jantsch (06:24.731)

I want to go back to a point you made there because, I have jokingly, but seriously said, you know, marketing is everything. And what I really meant by that was in a lot of small businesses, I would go into, there were a lot of things I had to fix that weren't under the, you know, the heading of marketing a lot of times, because if marketing was going to work or we were going to grow the business, I had to get involved in this area over here. Sales was a typical one. Customer service is another one that, know, that you don't always hire a marketing agency for.

But I would get into it out of necessity. And I think what you're really pointing to is a great point, this idea of, you go into a business, it's not just a matter of offering a suite of like, what do you need? It's more like I can be more effective at doing my job that you hired me for if I can actually easily fix an area over here that I may not have true expertise in, or I couldn't spend the time because I wasn't being paid to fix their P &L, for example.

so I think that's a great point. Let me back up again, because I I circled, I wanted the word context. that, let's spend a little time talking about that. Cause I think AI has gotten better, but I also think prompters are getting better. and we're realizing, you know, we get better output with, context. how do you give a, how, how in your view is probably a really long answer. How in your view, do you give AI the proper context?

Steve (07:52.408)

So when most people talk about context and there's a term called context engineering, they're mostly talking about it in the terms of like a single task that's going on. What we mean by context engineering is how does the AI know everything about your business? that whenever you pull up a task to do that you actually, the AI can, it's really hard to explain without getting into the weeds, but here's my best shot.

John Jantsch (07:58.512)

Mm-hmm.

Steve (08:22.668)

So imagine that you have like the world's best employee on every single task that could be done in your business, but they have amnesia. Every single time you give them a new task, they know nothing. So you have to train them. And that sounds like a really painful thing to have to do. But if you build a context library and only has to be done once to start, you can train that, you can give that AI like,

10 years of training in about 10 seconds. So it forgets all the time, but it learns like years in seconds. So all you gotta do, like this is how I boot up my instance of how I'm AI in my world as the CEO of our company. I onboarded the AI, I go look at the, I literally create an onboarding file. I say, go look at the onboarding file and get yourself onboarded. And 10 seconds later, it knows exactly like,

John Jantsch (08:54.629)

Mm-hmm.

Steve (09:20.418)

from a meta perspective, how we're going to do our work today. And I'll say, go look at that folder and let's do this task, like redesign our interface for this page in our system. And knows exactly how I like to work. It knows exactly how I want design options. And as a marketer, you'll appreciate this. you can go in and you're doing, let's say you're doing ad variations. You go and ask for

You don't even have to be that specific. If it knows everything about your business, you just say, give me five ad variations on this one topic or this one offer we're making. Sends it back. You look at it. You're like, like that one the most. And I've had the AI give me like the rationale for like, is scored it and ranked it. Then I could give me five more variations on that one. And then five more on that one. And one of the things that's not obvious to people is that the cost of variations is almost zero.

John Jantsch (10:05.177)

Mm-hmm.

John Jantsch (10:10.768)

Right.

Steve (10:17.58)

So you can ask for an infinite number of variations of.

John Jantsch (10:17.594)

Yeah.

Yeah, I do that with subject lines for emails. mean, same thing. It's like, kind of like the idea of this one. Iterate on that 10 more times. Yeah.

Steve (10:27.31)

Yeah, but you can do it for really big things too. So it's not just like a single subject. You can do it for an entire interface, like an entire set of code. so like, because it works so fast and the cost of its work is so low, it transforms the way you approach the work. so customizing campaigns down to the individual level, not a problem anymore.

John Jantsch (10:31.193)

Yeah, yeah. Right.

Mm-hmm.

Steve (10:57.25)

Like I can find your LinkedIn profile, can scrape it and I can send you like an entire landing page that's speaking directly to you. And it cost me a penny to do. And so there are things that we can do that were quite literally impossible before that now makes sense.

John Jantsch (11:16.543)

This might be good time to talk platforms and technologies a little bit. Are you agnostic or have you really gone all in and maybe it's so complex that you can't really say it in one sentence, but is like, are you a Gemini person? Are you a Chad's EBT person or have you really building your own stuff?

Steve (11:36.942)

We're definitely not building our own stuff. We have a very particular point of view, which is we're serving companies and companies will eventually choose their LLM of choice. And that's what they're going to do all of their work on. So we are, we're not hitching our wagon to any one LLM. We also have the point of view that for the most part, most AI rappers go away. So an organization is going to build their own software.

John Jantsch (12:01.679)

Yeah, yeah, yeah.

Steve (12:06.894)

So that's our long-term bet. And so we're just using whatever one is most productive. I personally have the max subscription on Claude, OpenAI and Gemini. I'm mostly using Claude right now because Claude Cowork and Claude Code just came out. And so if you listen to this like a month later, maybe I'm on something else by then, but Claude Cowork has been that tool alone.

John Jantsch (12:28.558)

You

Steve (12:33.548)

has transformed our operations in two weeks. Like we literally operate day to day differently now because of that tool. So, whatever one's working the best when the next time we talk is the one we'll be on then.

John Jantsch (12:36.346)

Yes.

John Jantsch (12:45.349)

Yeah.

Yeah. You know, I contended for a long time that just what you said, it's, it's going to be plumbing. It's not going to be, Oh, I use this tool or that too. It's going to be, no, this already works with what I use. And I really feel like, doesn't that give Microsoft and Google because of their installed user base? mean, you know, I fire up Gmail and all of a sudden it's like, Oh, there's a new tool. Um, you know, I can opt into, you know, I mean, doesn't that give them an advantage? And also I think the other thing, the first version of AI tools.

Is there better kind of use them by themselves? Well, now all of sudden we got collaboration built in, which I think was a big missing part. And so it's like working the way people work already.

Steve (13:27.214)

Yeah, I think the like all other things being equal, Microsoft and Google have the biggest moat around it. However, for the longest time, Chad GPT was the best tool. And now Claude is by far the best tool. so I would have thought that if it was true that Microsoft and Google would be like for sure would win, it would have happened.

John Jantsch (13:34.372)

Mm-hmm.

John Jantsch (13:51.525)

Yeah, yeah, yeah, yeah.

Steve (13:52.224)

I know because they had not only they have the user base, they have all the documents and that's, that's what the AI needs for context. But as it turns out, the AI does not read and work with the file formats that we all produced over the last 20 years, which was PowerPoints and Word documents and all of those kinds of things. So there's, there's going to be a shift around that as well, which I think will loosen.

John Jantsch (14:08.995)

the

Steve (14:18.382)

the moat that they have because we're not going to be stuck on PowerPoint anymore. Like I, the, in the last couple of weeks, I've been on this kick of, and I think this is just true. I will never use keynote or PowerPoint ever again. Um, and I'm not using like another AI tool. just build HTML documents and it does exactly what I want. And I, that's my presentation style. Um, we do SOPs in our business. Everybody in our company builds HTML.

John Jantsch (14:32.155)

Mm.

Steve (14:46.132)

S O P S because you can just speak into a computer. HTML files open everywhere. And it's also a good language for the LLMs to understand because it's way easier to read than, than a PowerPoint. There's others. If you pay attention to how software engineers are using AI, you'll have a, you'll have a glimpse of the future. They're mostly using file formats that they're comfortable with and that are, that work well for.

John Jantsch (14:57.147)

yeah.

Steve (15:15.182)

development, like markdown files and things like that. So that's what you'll see them suggest. Like you have to use markdown files for these things. And, what our point of view around this, and I think this will just prove to be true is that we need to be building like artifacts or deliverables, whatever you want to call it for humans and AI, not just humans. Like humans only is like PowerPoint, like LLMs hate PowerPoint. I hate word document.

John Jantsch (15:17.722)

Yeah, yeah, yeah.

John Jantsch (15:43.201)

can't can't can't read them at all.

Steve (15:44.878)

There's so much code around it, right? So then you have the like markdown files and things that most humans they look at it. Like I can't, I can't, a picture is worth a thousand words. It's a real thing. Like we need to see visuals and workflows and all those things. And so HTML happens to do both of those incredibly well. So whether or not we're right on that, I don't know, but for now it's like transforming the way that we do work because we can now.

build things that both our humans understand, the LLMs understand, and also there's this magical thing that happens when a non-technical person speaks a website into existence, and just presses a button and it's live. So it's also a really good AI adoption tool, because it's cool, right? Like it's cool to like, you build something beautiful. So as a marketer, if you have a design system,

Most companies would never spend 30, 40, $50,000 on. You can speak one of those into existence. Like you can do it right now. Then everything that gets designed looks great in your company. And now everybody's sharing beautifully designed. SOP documents. Like that's, that's a weird thing to think about, but it's like, I like doing it. It looks nice. it explains what I explains my thoughts and my process. And so, yeah, I think, I think this year is going to be.

transformative in how we all do work and I don't think it's going to look the same by the end of the year.

John Jantsch (17:17.11)

So, and I know you have an answer for this, but this, I'm guessing listeners are out there going, okay, if I can just speak this stuff into existence, am I going to just start creating stuff without any kind of guardrails and without any human intervention? where's the, you know, the pushback you're getting from people that hate AI. So imagine the people that love AI, but don't want to be embarrassed.

Steve (17:43.31)

What do you mean by guardrails specifically?

John Jantsch (17:46.123)

just, just meaning like, if I can design all these things, who's going to actually go and make sure that they're, they're being done right. That they look good, that they say what they're supposed to say. Cause you know, some of, particularly some of the image, you know, generates today. I mean, there's, it's just like appalling. Some of the things that show up in, in some of those.

Steve (18:06.478)

Well, I think there's trying to figure out the 32nd way of answering this question. So the way we look at how work is done is by deliverables. you can look at it as a process, you can look at it as tasks, you can look at it as deliverables. But if you look at it as a deliverable, is that that's when the thing ends. And that's when the human has to look at it. It's when the deliverable is done.

John Jantsch (18:18.864)

Right.

Steve (18:31.182)

First of all, should have the AI do a QC process on itself. You can do that. And it actually does a really good job of QCing its own work. So that's the thing that most people don't understand. But then once it comes off the press, whatever metaphor you want to use, and a human looks at it and says, are we sending this out? And if you treat it, and this is a language that most knowledge workers don't like, it's a factory now. And so you don't QC every

energy drink can that comes off the line. But you look at some of them, right? And you know that if this one is this one's off, well, we got to look at the ones that just went out the door because maybe they have a defect as well. So it becomes more of a factory mindset, knowing that if you if you have a good manufacturing process and that this again, like marketing agencies will hate this like, but that is that it but

John Jantsch (19:02.97)

Right.

John Jantsch (19:22.297)

Yeah. Yeah. Even the word factory there, they're going to cringe at. Right.

Steve (19:26.894)

Like if you do not turn your marketing agency into a factory in 2026, you will be out of business. Like let's go have a, we'll do it next year and we'll see whether or not that's true. Like you have to, you'll have to learn good workflows. You need to learn good work instructions. You need to learn good QC process. And so, and once you do, you can start mass producing things that are top notch and

John Jantsch (19:37.403)

Yeah.

Steve (19:56.138)

knowledge work will be turned into a factory. And then what gets layered on top of that is a new skill set, which is not 100 % clear what that is yet, but we will invent new things to do that will just add value on top of that.

John Jantsch (20:14.085)

Fascinating, Steve. Appreciate you stopping by the Duct Tape Marketing Podcast. Where do you want to invite people to find out more about, I think it's simpleconsultants.ai and obviously about your book?

Steve (20:26.978)

Yeah, well, if you're up for it, I would love to give everybody in your audience free access to our BlackBelt training. We'll create a page specifically for your network. It'll be roiassociation.ai.

John Jantsch (20:47.931)

Awesome. And we'll put that in the show notes as well. So that was ROI.association, is that what you said?

Steve (20:54.824)

roiassociation.ai.

John Jantsch (20:56.973)

dot, dot A. Okay. Got it. Awesome. Well, as I said, we'll put that in the show notes as well. So Steve, again, appreciate you stopping by. This is awesome. And hopefully we'll run into you one of these days out there on the road.

Steve (21:11.662)

Absolutely. Thanks, John.

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Why Goals Fail and How to Change the Odds

Why Goals Fail and How to Change the Odds written by John Jantsch read more at Duct Tape Marketing

Catch the full episode:

 

Episode Overview

In this episode of the Duct Tape Marketing Podcast, host John Jantsch sits down with award-winning strategy consultant, speaker, and author Kyle Austin Young to explore his decision-making and goal-achievement framework called probability hacking. Kyle explains why traditional goal pursuits rooted in hustle, mindset, and positive thinking fall short and how identifying and solving for potential risks can dramatically shift your odds of success.

Guest Bio

Kyle Austin Young is a strategy consultant, speaker, and writer helping high achievers accomplish meaningful goals through his probability hacking framework. He’s been featured in top publications and is the author of Success Is a Numbers Game: Achieve Bigger Goals by Changing the Odds.

Key Takeaways

• Probability over Mindset: Success isn’t just about positivity—it’s about improving your odds.
• Probability Hacking Framework: Define goals, identify prerequisites, anticipate what could go wrong, and solve creatively.
• Success Diagrams: Visual tools to map out and de-risk goal pathways.
• Multiplying Probabilities: Understand true odds by combining variables—not averaging them.
• Resilience & Repetition: Trying multiple times can dramatically increase your likelihood of success.
• Mindset Shift: Think negative—not to be pessimistic, but to preemptively solve issues.

Notable Moments (Time‑Stamped)

• 00:01 – Introduction of Kyle Austin Young and today’s topic
• 00:59 – Odds vs. mindset in goal-setting
• 04:15 – Kyle’s story of landing a high-stakes job at age 21
• 07:04 – Breakdown of the success diagram framework
• 09:19 – Why averaging leads to false confidence
• 11:57 – Miracle on Ice and the math of multiple attempts
• 14:32 – Getting started with probability thinking
• 15:41 – The four paths to success explained
• 17:47 – Edison and the role of experimentation in resilience
• 19:54 – Where to find Kyle and his book

Quotes

“What’s going to have to go right? And what could go wrong? That’s where your opportunity to change the odds lives.” — Kyle Austin Young

“Success is really about identifying what could derail you and finding creative ways to make those outcomes less likely.” — Kyle Austin Young

Connect with Kyle Austin Young

• Book: Success Is a Numbers Game — available on Amazon, Barnes & Noble, and Penguin Random House
• Website: kyleaustinyoung.com
• LinkedIn: Kyle Austin Young

 

Duct Tape Transcript

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John Jantsch (00:01.218)

Hello and welcome to another episode of the Duct Tape Marketing Podcast. This is John Jantsch. My guest today is Kyle Austin Young. He's an award winning strategy consultant, speaker and writer who helps leaders, entrepreneurs and high achievers accomplish big, meaningful goals. His work centers on a unique decision-making and goal achievement framework that he calls probability hacking, a method designed to analyze and intentionally improve the odds of success in any pursuit. We're going to talk about his newest book.

Success is a numbers game. Achieve bigger goals by changing the odds. So Kyle, welcome to the show.

Kyle Austin Young (00:37.348)

Thank you for having me. Honored to be here.

John Jantsch (00:39.278)

So I'm going to start with the premise that I'm sure you, I won't be the first person to ask this question. I think a lot of times when people talk about goals, they think about hustle or mindset or heck even luck. You are saying it's more about odds. What's different in that shift?

Kyle Austin Young (00:59.15)

Yeah, let me give you sort of an example. Let's say that we've set the goal of training to run a marathon. Let's say that's something that we've decided we want to accomplish and we hire a running coach and she says, I can get you ready in time, but you're gonna have to do three things. I need you to eat, sleep, and train according to some specific regimens that I'm gonna create for you.

John Jantsch (01:02.872)

me

John Jantsch (01:14.829)

Mm-hmm.

Kyle Austin Young (01:16.334)

So let's say that we know that one of these prerequisites is we're to have to train according to some certain parameters. And so we identify some of the things that could go wrong, some of the things that might happen instead of what we want. And maybe we identify bad weather as something that could derail a training regimen. I'm currently preparing for a big wintery snowstorm. Let's say that we identify injury as a potential risk, or maybe we identify that our kids might have a crisis that could overwhelm our schedule. So the question that I like to ask people is,

tell me how wanting to run a marathon is an antidote to any of those threats to our success. How does wanting to run a marathon change the weather? How does wanting to run a marathon prevent injury? How does wanting to run a marathon keep a crisis from happening in our kids' lives? Certainly, we're going to need a measure of commitment and hustle in order to be successful. But ultimately, what we're going to really need is we need some creative solutions to the things that could keep us from getting what we want.

So I believe that we can understand probabilities similar to the way we've traditionally understood matter. It can't be created or destroyed, but it can be transferred and rearranged. The odds of success, the odds that we want for our goal are currently hiding in our potential bad outcomes. When we identify what those things are and what we can do about them, we can tilt the odds in our favor.

John Jantsch (02:30.488)

So it's all about quantum physics. Is that what you're saying? So when you talk about moving matter around, was the first thought I had. Sure.

Kyle Austin Young (02:33.54)

Very little physics in the book. I don't think I've ever taken a physics class.

Kyle Austin Young (02:40.418)

Well, I do think that there's a lot of truth in the idea that a lot of people want to conjure good odds out of thin air. This idea that maybe I can wish myself into a better position. And I don't think that's true. I think that a lot of times when we're pursuing a goal, we're encouraged to think positive. Don't worry about what could go wrong. If it's meant to happen, it'll happen. Just focus on the positive. I encourage people to do the exact opposite. I tell people to think negative. I tell people, for everything that has to go right in order for you to get what you want, identify the potential bad outcomes. Identify the things that could happen instead of what you want.

John Jantsch (02:55.8)

Thank

Kyle Austin Young (03:09.464)

and use your creativity to systematically de-risk your goals.

John Jantsch (03:13.826)

So in your bio, and I know in the book itself, you talk a lot about probability hacking. So let's talk about what that is or how you define

Kyle Austin Young (03:22.916)

Yeah, I define probability hacking as doing exactly what we just did. It starts with getting an idea of what's going to have to go right and then identifying what could go wrong and then looking for creative solutions. I'll tell a different example. You know, when I first graduated from college, I wasn't excited about the entry level positions that I was seeing. I wanted to try for something more ambitious. So I actually applied to become the product development director at a growing health organization. I was 21 years old. If hired, I was going to be managing people in their 50s, 60s, 70s, people with PhDs and master's degrees.

a crazy thing to do, but I got an interview and I wanted to make the most of it. So even at that time, I did what I essentially do now for a living. I created what I call a success diagram. I only needed to get a job offer at that point. That was the only step left, but I looked at what are the potential bad outcomes that could happen instead of me getting that job offer. And so I identified three. And so I'm giving this example. You kind of had the quantum physics concern because there's no numbers here. I'm just going to show you how we can do this at a story level. One of the risks I identified was they might not hire me because of how young I looked.

John Jantsch (04:15.054)

Bye.

Kyle Austin Young (04:21.54)

I might walk in and they take one look and say, he can't lead this team. So one of the very practical things I did to combat that is I just grew a beard. I still have the beard today. It was something that made me look about 10 years older than I was. And I knew that if I could do that, it would maybe take the edge off of that concern a little bit. A second bad outcome that I identified, a potential bad outcome rather, was there might be concerns over my lack of experience, which were valid. I didn't have a deep resume. I had just graduated from college. So what I did was I couldn't lie. I wasn't going to

John Jantsch (04:22.126)

Right.

Kyle Austin Young (04:49.54)

pretend that I had experience I didn't have, but I wanted to show the quality of my thinking. So I actually typed up a plan for how I was going to turn this department around. It was so thick, I had to have it spiral bound. It was a book. And every person I went to and interviewed with, I gave them a copy of it. And the goal was when they would ask me questions about my past, I would just redirect it to be a conversation about the future. What experience do you have with whatever the case might be, product development? Great question. Here's my plan for product development. Let's talk about the vision that I have for this role if I'm given the opportunity.

The third potential bad outcome I identified was maybe they would be concerned that I couldn't really get along with the existing team because there was just such a big generational gap. So I used a strategy that I'm still using today. It's worked really well for me. I asked one of the people in the organization if the product development team had read any books recently as a group. She listed a few titles, I think it was three or four, and I went out and read every single one of them. And what that did is it gave me the ability to have conversations with the team that no other applicant could have. I understood their goals, I understood their jargon, I could make inside jokes.

John Jantsch (05:25.538)

Mm-hmm.

Kyle Austin Young (05:48.56)

There was a group interview where it was me and a bunch of people 20, 30 years older than me with a lot more experience trying to decide who was going to ultimately win the opportunity to lead this department. And one of the books that they read was called The Wuffy Factor. I don't know if you remember that. was a book about how to, you remember the Wuffy? It was about how brands are in social capital. This was close to 15 years ago. And I remember being in that interview and I said, you know, I think this idea that we're discussing could help us get a lot of Wuffy.

John Jantsch (05:57.934)

Right.

I remember saying that, yeah, yeah.

Kyle Austin Young (06:11.632)

And I remember looking around and these other applicants, their eyes are bugging out of their heads. What on earth did he just say? You know, is he feeling, okay, what does he mean? We're going to get a lot of wealthy out of this. But the existing team members, they were all laughing and nodding along. They knew exactly what I was talking about. We were reading the same books. So when all was said and done, I got that job. At 21 years old, I became the product development director for a health organization. It dramatically accelerated my career, but it started with this idea of probability hacking. It started with getting clear on what I wanted and getting clear on what was going to have to go right. Then thinking negatively,

identifying the risks to my success and not resorting to desire as an antidote to uncertainty, but instead using my creativity to solve those problems.

John Jantsch (06:49.006)

So you gave very specific details and steps of what you did, but it sounded, it started to sound a bit like a framework, which I know you have in the book. So were those steps that you gave me a part of that framework? Do you want to outline what that framework is?

Kyle Austin Young (07:04.41)

Sure, I encourage people to start by creating what I call a success diagram. A success diagram is you write down what's the goal, what do I want to accomplish? I do that at the top right of the page. And then to the left, I just try to list out everything that's gonna have to go right in order for me to get what I want. So it might be run a marathon. And what I call critical points, the prerequisites to my success are eat according to the regimen my coach gives me, sleep according to the regimen she gives me, train according to the regimen she gives me. So now I have the path, I have the destination.

And then for each one of those things that has to go right, I try to identify the potential bad outcomes. These aren't just things that could go wrong, they're alternate outcomes to success. Things that would be so significant they would completely derail the goal if any of them were to come true. After I have those mapped out, I try to just assign a level of risk to each of them. Is this a low risk potential bad outcome, a medium risk, a high risk, so they know how to prioritize? And then probability hacking again is using our creativity to try to find solutions to that. If I'm concerned about

you know, inclement weather derailing my training routine, I might need a treadmill indoors or need to find some alternate exercises that can allow me to build my fitness on days when I can't go for a run. If I'm concerned about scheduling issues, something happening at my kid's school, then I might want to train first thing in the morning or I might want to buy an extra pair of running shoes to keep in the car so that I can train at a park if I need to, if my day gets derailed.

John Jantsch (08:20.034)

In a lot of ways, what I'm hearing you describe is, I mean, think there are a lot of people that have mapped out the plan to run the marathon. mean, you can buy books, entire books, will tell you exactly what to do on day one, day two. But what you're saying a lot of people miss is integrating the whole, you know, of life. And I think in a lot of ways, you're really just asking people to step back and you're calling it what could go wrong. But what you're really doing is saying, hey, you have to have a grasp of reality.

Kyle Austin Young (08:31.29)

Sure.

Kyle Austin Young (08:49.764)

I think you do have to have a grasp of reality. I think that when we consider these statistics that are floating around all the time, just how many people fail at their New Year's resolutions, how this vast majority of mergers and acquisitions fail to create lasting value for shareholders, how many new businesses will ultimately fail in the first few years after their existence, we start to recognize that it's because we haven't stopped to consider the things that could go wrong. And I'll demonstrate that with just a little bit of numbers. Let's use that marathon example. There's three things that have to go right. I need to eat, sleep, and train according to a certain regimen.

John Jantsch (08:51.307)

me

John Jantsch (08:57.139)

Mm-hmm. Right.

John Jantsch (09:13.763)

Mm-hmm.

Kyle Austin Young (09:19.14)

Well, let's take some imaginary numbers and try to estimate how likely we are to accomplish each of those three things. Maybe we think it's 70 % across the board. 70 % chance I'll stick with the diet, 70 % chance I'll sleep the way I'm supposed to, 70 % chance I'll train the way I'm supposed to. What a lot of people do is they fall into a trap called averaging. If they feel good about the individual prerequisites, they feel good about the goal as a whole. That's not actually logically sound, it's not mathematically sound. What we have to do is multiply those numbers together to find our overall odds of success.

John Jantsch (09:45.261)

Yes.

Kyle Austin Young (09:47.204)

And if we do that, we find that even though we feel really good about each of these things, 70 % across the board, our overall odds of being ready on race day are only 34%. And that I believe explains a lot of the dysfunction in our world. Why are people failing at goals and wondering, how did this not go the way that I expected it to? I felt good about each individual step. Well, you averaged in your head. You didn't take the time to understand what your overall odds were. And because of that, maybe you didn't pay as much attention to your opportunity to change your odds as you could have. Maybe you didn't get that grasp on reality exactly like what you said.

John Jantsch (10:14.926)

Thank

Kyle Austin Young (10:16.27)

and try to the odds in your favor.

John Jantsch (10:18.766)

Is there any, do you ever run the risk or do you find that people might, like if I sat down thought, oh, my odds of actually being prepared on race day is only in the 30 % range, is there any chance that I say, why bother?

Kyle Austin Young (10:32.538)

There could be, but if we're taking the time to think negative and identify the bad outcomes that are dragging those odds down, then we can use our creativity and see if we can't change those numbers, at least in how we understand them, to look like something that's more optimistic. You if we are using our creativity to address the risk of bad weather when we need to train, or address the risk of injury, or address the risk of our schedule being sabotaged, then we can ultimately run the numbers again. And maybe by the time we're done optimizing this plan,

John Jantsch (10:33.902)

Yeah

Kyle Austin Young (10:59.812)

we end up feeling like it's 90 % across the board. That's still not a 90 % chance of success, but I believe it's in the 70s. It's a lot better.

John Jantsch (11:05.166)

Yeah. So, so do you find that you have to help people reframe this idea of failure even?

Kyle Austin Young (11:14.426)

Give me an example of what you mean by that.

John Jantsch (11:16.844)

Well, I mean, in some ways you're, as I listened to you talk about the steps, you're, you're, you're not saying that's failures of possibility, but that it's part of the equation. and a lot of people, you know, would have, I think some people would, would struggle with that idea. I, I'm not saying what you're talking about doesn't make sense, but just the mindset that a lot of people have that might be hard to overcome.

Kyle Austin Young (11:41.37)

Sure.

Absolutely. Failure is going to be part of the equation. One of the things that I encourage people to consider in the book is the power of multiple attempts. If you're chasing a goal that's really unlikely, often one of the most reliable ways to ultimately succeed is to try more than one time. I tell the story of the miracle on ice in the first chapter of the book. I got to interview Jack O'Callaghan who played on that 1980 hockey team that beat the Soviet Union. And a lot of people consider that a miracle. It's been called the greatest sporting event of the 20th century, I believe, by Sports Illustrated.

John Jantsch (11:57.518)

Right.

Kyle Austin Young (12:14.028)

And as an individual event, it was really miraculous. But when you recognize that over the course of this Olympic rivalry, the United States played the Soviets nine times and won two, that's not that remarkable. Winning two times out of nine isn't unheard of. So was it surprising that they won the game they won? Sure. But the odds told us that we would expect them to win some games. And that's ultimately what they did. And what's interesting is when I interviewed Jack, he told me that in the locker room before they went out to take the ice for that game,

John Jantsch (12:23.842)

Mm-hmm. Right.

John Jantsch (12:35.18)

Yeah.

Kyle Austin Young (12:42.244)

Coach Herb Brooks gives this speech and there's a movie about it and the movie has some quotes that are really powerful. What Jack told me is he said he doesn't remember the exact words that were spoken. But he says he remembers that when he left the locker room, they're trudging down to take the ice. He says he remembers leaving with the idea that his coach believed if we played them 10 times, they might beat us nine times, but they're not going to beat us tonight. And so there was an expectation that failure was going to be a part of that, but they had an opportunity for tonight to be the exception. And ultimately it was.

John Jantsch (13:10.446)

I remember vividly watching that in my dorm room in college. does this, like a marathon I would call a long-term goal, particularly for somebody who hasn't run one, right? They should start early, right? Can this be applied to short-term decisions as well?

Kyle Austin Young (13:14.956)

Amazing. I missed it by a few years, but I'm jealous.

Kyle Austin Young (13:24.666)

Sure. Sure.

Kyle Austin Young (13:33.166)

absolutely. You know, in the context of me trying to get that job, I just did this as I headed into an interview. It was going to all take place in a day. When we have something that needs to go right, one of the best things we can do to help it go right is think about what could go wrong. Ultimately, that's what's dragging our probability down. If you think about flipping a coin, let's say you need it to land on heads, you have a 50 % chance of success. Why? Why don't you have a 100 % chance of success? Well, because it might land on tails, and there's a 50 % chance of that happening. Now, I don't know how to rig a coin to make it...

do what I want it to do. But in life, a lot of times we can rig it or we can re-rig it in our favor. We can try to take the risk out of the bad outcomes, bring those odds over to our side.

John Jantsch (14:11.448)

So if somebody hasn't thought this way, what's kind some of the first things you try to help people? And again, I don't know if you actually consult on this or teach courses on this as well, but what are some of the first things you try to do to get people to start putting this way of thinking? Because I think a lot of times these things are just mindset. So what do you get them to start thinking this way? What are some of the first things?

Kyle Austin Young (14:32.784)

Well, in the book, I tell people that I think there are four paths to success. One of them is some people just get lucky. I tell the story of Norma Jean Doherty. She's working at an aviation munitions factory in the war, and a photographer comes to take pictures for a military magazine to inspire the troops. He notices Norma Jean, thinks she's really beautiful, says, can I take some pictures for you for magazines that don't have anything to do with the military? And she said, sure. She ultimately finds a lot of success as a model and then goes on to star as an actress under the name Marilyn Monroe, has just this enormously successful career.

That is certainly a success story. Is it a success story we should reverse engineer though? If I meet a young woman who's coming to me for training or coaching rather, can you tell me what I can do to become a successful Hollywood star? Would I say, well, the first thing you need to do is get a job at an aviation munitions factory and hope that someday a military photographer stops by and notices how pretty you are and says, can I take some pictures of you? No, that probably wouldn't be a very reliable path to success. So some people succeed through luck. They succeed even though the odds are bad, simply because we expect unlikely events to happen sometimes.

Some people succeed, they don't beat the odds, but they play them. We think about entrepreneurs, there are some really famous examples of people who heard that nine out of 10 businesses fail, and that was actually what inspired them to start 10 businesses or 15 businesses, was the belief that they were going to experience those predicted failures, but they would also experience the predicted successes. Some people succeed because they have advantages, they have areas of tremendous strength in their lives, and so they try to lean into those goals.

John Jantsch (15:41.314)

you

Kyle Austin Young (15:54.084)

That can often be something that's really wise for us is asking the question, what are some goals that are pretty high probability goals for me right now that might bring bigger accomplishments within reach? One of the goals that I had for years was ultimately getting a book deal and hopefully getting a big advance and being able to publish that to a mass audience with a major publisher. At the time when I set that goal, it wasn't really realistic for me, but I was able to pursue smaller goals that changed my odds. One of them was writing for major publications.

John Jantsch (16:01.42)

Mm-hmm.

Kyle Austin Young (16:21.04)

As you mentioned, I've written for sites like HBR, Fast Company, Psychology Today. But one of my favorite things and one of the reasons I was so excited to have the opportunity to come on is it's an exciting full circle moment for me. When I first decided that I was going to try to write for some of these respected publications, get my voice out there and ultimately position myself for things like a book deal, the first site that took me was the Duct Tape Marketing Blog. It was in 2015. I remember I was in my grandmother's house at the time. They were having a garage sale. I was helping out when I got the response. I couldn't even tell you where I was sitting.

John Jantsch (16:31.63)

You

John Jantsch (16:42.292)

the

Kyle Austin Young (16:49.742)

and it was such an exciting thing. So it's an honor to be with you here today. So that's the third path of success is people making the most of areas where they have good odds. The fourth path is probability hacking, doing everything you can to tilt the odds in your favor.

John Jantsch (16:50.286)

you

John Jantsch (17:01.006)

So, you know, I was going to ask you about resilience. And then you kind of threw in that story about the entrepreneurs starting 10 businesses, but what, what connection do you think with the framework and just the whole mindset of resilience? What does it play?

Kyle Austin Young (17:17.774)

Well, it's incredibly important if you're going to especially be pursuing the path of repeated attempts. In the book, I tell the story of Thomas Edison. He's in a race to try to get valuable patents surrounding the incandescent lamp. If he can get them, it'll be something that's transformational for his career. And what this race came down to is he and these other people were all trying to find a practical filament. They needed something that could glow hot enough to emit light without catching on fire and without snuffing out really quickly to the point where it wasn't worth it. What Edison did that was different than these other people...

John Jantsch (17:23.0)

Yeah.

John Jantsch (17:29.709)

Mm-hmm.

Kyle Austin Young (17:47.376)

is he actually experimented with 6,000 different plant materials to find the one that worked best. He didn't try to divine the right answer. He didn't try to guess the right answer. The answer turned out to be, in his context, carbonized bamboo. And I don't know about you. That would not have been my first guess. If you said, what are we going to use as a filament? I would have said, I bet it's carbonized bamboo. That's not where I would have started. It's not where he started either. It took 6,000 attempts. But ultimately, he had a clear definition of success. He had a stopwatch, so to speak. And he was able to run more experiments than anyone else. And because of that,

John Jantsch (17:54.144)

Mm-hmm.

John Jantsch (18:04.718)

the

Kyle Austin Young (18:15.364)

he found these unlikely answers. so resilience is a big part of that. Some of it comes from, we need to be confident that there is going to be a best answer out there. And in his case, it wasn't, you know, it was comparative. He could be confident that one option out of the 6,000 would be the best out of the 6,000. And he liked his chance of creating a great product with a wider net when it came to ultimately trying to find the best filament than he did with somebody who's only trying two or three things.

John Jantsch (18:27.982)

Thanks.

John Jantsch (18:41.526)

Yeah, and there's obviously, I don't know that it's all true, but you hear these stories that people would ask him, gosh, aren't you tired of failing so much? He said, no, I just have one more thing out of the way that I know is not the answer.

Kyle Austin Young (18:55.116)

He has a quote attributed to him that's, to have a great idea, have a lot of them. And I think it's that exact same mentality. It's not about being the smartest person in the room necessarily. A lot of times it's being the most generative. It's being the person who's the most prolific and who ultimately uncovers that unlikely good idea.

John Jantsch (18:58.936)

Yeah, yeah. Yeah.

John Jantsch (19:12.396)

Yeah. And, and, you know, there's, there's certainly a mentality out there. People want to, you know, take the easy path, get rich quick, you know, be famous, all the things that, people aspire to. And I don't, you know, the, people that really get there, you know, they just show up and do the work every day for a long time. Sometimes.

Kyle Austin Young (19:29.614)

Well, it's one of the dangers of reverse engineering, like I mentioned, you know, the Marilyn Monroe story, we kind of chuckle at that, but I think we're doing similar things in our daily lives. We'll find somebody who started a successful organization and turns out he drives a blue convertible. So I should buy a blue convertible because clearly that's got to be playing a role in his success. What if he just got lucky? I'm not saying that they did, but we need to be really careful about what we reverse engineer because just because someone is seeing good results doesn't mean that they got there through good decisions.

John Jantsch (19:31.874)

Yeah, yeah.

Right? Yeah.

John Jantsch (19:46.924)

Yeah.

John Jantsch (19:54.646)

Yeah. Well, and I think a lot of times we miss the 10 years before, before they blew up, right? Yeah, exactly. Well, Kyle, I appreciate you stopping by the Duct Tape Marketing Podcast. Is there someplace you'd invite people to find out more about your work and to perhaps pick up success is a numbers game.

Kyle Austin Young (19:58.778)

Sure, yeah, that kind of quote that most overnight successes are 20 years in the making, sure.

Kyle Austin Young (20:14.0)

You can get a copy of the book pretty much anywhere, Amazon, Barnes & Noble, directly on the Penguin Random House website. Be honored if you did that. If you want to connect with me personally, I think we'll probably put my website in the show notes, just kyleaustinyoung.com. But what I'd prefer you do, honestly, this was something that was just kind of an unexpected blessing of this journey, is I heard someone who was encouraging people to find them on LinkedIn, and I thought, that's a strange thing to do. I'll throw that idea out too. And that was many interviews ago, but it's turned into one of just the best parts of this, is pretty much every day I wake up and someone has

John Jantsch (20:25.134)

Mm-hmm.

Kyle Austin Young (20:43.118)

sent me a message saying, I heard you here, I heard you there, can I ask you a question? It's led to some really engaging conversations that I've really enjoyed, some fun opportunities for collaboration for me. So feel free to find me, Kyle Austin Young on LinkedIn. I'd love to hear from you.

John Jantsch (20:45.1)

Okay.

John Jantsch (20:56.618)

Awesome. Well, again, appreciate you stopping by and hopefully we'll maybe we'll run into one of these days out there on the road.

Kyle Austin Young (21:02.16)

That'd be great. Thanks.

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Marketing Chaos Ends With a Real System

Marketing Chaos Ends With a Real System written by John Jantsch read more at Duct Tape Marketing

Catch the full episode:

Episode Overview

In this episode of the Duct Tape Marketing Podcast, host John Jantsch and Sara Nay, CEO of Duct Tape Marketing and author of Unchained: Breaking Free from Broken Marketing Models, discuss why traditional marketing feels chaotic and how installing a structured marketing operating system can drive clarity, consistency, accountability, and long‑term growth. Nay breaks down the seven core components of the system—from strategy and campaign design to AI integration, measurement, meeting rhythms, and optimization. They also explore the differences between this system-based approach and typical agency engagements, practical ways teams can implement these ideas, and how this structure increases business equity.

Guest Bio

Sara Nay is the Chief Executive Officer of Duct Tape Marketing, a leading authority in systematic marketing approaches for small and mid-sized businesses. She is also the author of Unchained: Breaking Free from Broken Marketing Models, a book focused on rethinking how businesses build and scale marketing with strategy, systems, and measurement. With deep experience in marketing operations and strategic growth, Sara helps organizations transform chaotic marketing into predictable, measurable engines of growth.

Key Takeaways

• Marketing Feels Like a Moving Target Because Tactics Proliferate
  Traditional marketing often jumps from tool to tool without strategy, creating confusion rather than results.
• A Marketing Operating System Provides Structure
  Like financial or business operating systems, a marketing OS installs strategy, processes, scorecards, and rhythms that make marketing predictable and accountable.
• Seven Core Components of the Marketing Operating System
  • Strategy First Core
  • Campaign Builder
  • Workstream Engine
  • AI Marketing Hub
  • Scorecard & Signals Dashboard
  • Momentum Meeting
  • Quarterly Optimization
• Strategy Before Tactics Is Non-Negotiable
  Creating a differentiated strategy rooted in ideal clients and core messaging informs everything that follows.
• AI Enhances People, It Doesn’t Replace Strategy
  AI tools are most effective when informed by strategy and integrated into documented processes.
• Measurement and Culture Shift Drive Accountability
  Dashboards and structured meetings cultivate team ownership and goal alignment.
• System Equals Equity
  Marketing systems not only improve performance but also increase the value of the business.

Time‑Stamped Great Moments

• 00:01 – Introduction to Today’s Topic
• 03:05 – Traditional Agencies vs. a Marketing Operating System
• 05:23 – Strategy First Core Explained
• 08:25 – Campaign Builder: From Strategy to Action
• 09:15 – Workstream Engine: Process, Roles, and SOPs
• 12:13 – AI Marketing Hub: Step Four
• 15:02 – Scorecard & Signals Dashboard
• 17:10 – Momentum Meetings: Rhythm and Accountability
• 20:04 – Quarterly Optimization: Bigger Picture Learning
• 22:32 – Engagement Models With Duct Tape Marketing
• 25:26 – How to Book a Call: Clear Next Step

Quotes Worth Sharing

“Marketing feels like a moving target because there are just more tactics now — strategy gets lost in the noise.”

“Strategy shouldn’t sit in a Google Drive folder; it should drive action and measurable outcomes.”

“If you don’t have a good process in place, it doesn’t matter if you use AI to replace a crappy process.”

“Momentum meetings aren’t about tasks completed — they’re about how those activities moved the needle toward goals.”

“A marketing operating system increases the value in your business and solves short‑term pains too.”

Call to Action

If this episode resonated with you and you want to explore building or optimizing a marketing operating system for your business, book a conversation with Sara here.

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Curious Leaders Build Stronger, Smarter Teams

Curious Leaders Build Stronger, Smarter Teams written by John Jantsch read more at Duct Tape Marketing

Catch the full episode:
 

Episode Overview

In this episode of the Duct Tape Marketing Podcast, John Jantsch interviews Dr. Debra Clary, a leadership strategist, narrative scientist, and author of The Curiosity Curve: A Leader’s Guide to Growth and Transformation Through Bold Questions. With more than 30 years of experience across Fortune 50 companies, Debra shares her insights into how cultivating curiosity can drive performance, culture, and innovation at every level of leadership.

About Dr. Debra Clary

Dr. Debra Clary is a narrative scientist, executive coach, and leadership strategist with decades of experience at top organizations including Coca-Cola, Jack Daniels, and Humana. She holds a doctorate in Leadership and Organization Development and is the author of The Curiosity Curve. She is the founder of the Curiosity Curve Assessment and a leading voice on curiosity-driven leadership. Visit her at DebraClary.com.

Key Takeaways

• Curiosity in leadership is measurable and can be developed over time.
• The most effective leaders ask bold, open-ended questions instead of providing answers.
• Curiosity drives engagement and productivity—especially among millennials.
• Leadership that promotes curiosity helps organizations adapt, innovate, and thrive.
• Culture change starts at the top—curious leaders model the behavior they want to see.

Great Moments & Timestamps

• 00:00 – Intro and Dr. Clary’s corporate leadership background
• 01:14 – How stand-up comedy shaped her speaking and leadership
• 03:01 – Why adults ask fewer questions than toddlers
• 04:06 – MIT research linking curiosity to team performance
• 07:05 – Restructuring meetings to foster curiosity
• 12:34 – Millennials’ disengagement and how curiosity solves it
• 14:21 – One question that changed a major executive decision
• 16:53 – What sparked her deep research into curiosity
• 19:11 – Practical curiosity-building habits for leaders

Notable Quotes

“Leadership is about playing the long game, not the short game.” – Dr. Debra Clary

“Curiosity is not just a mindset—it’s a muscle that can be measured, taught, and strengthened.” – Dr. Debra Clary

Resources & Links

• DebraClary.com
• The Curiosity Curve on Amazon

Duct Tape Transcript

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John Jantsch (00:00.866)

Hello and welcome to another episode of the duct tape marketing podcast. This is John Jantsch. My guest today is Dr. Debra Clary. She's a leadership strategist, narrative scientist, researcher, and executive coach with more than three decades of experience leading and transforming organizations, especially fortune 50 companies, including Frito-Lay, Coca-Cola, Jack Daniels, and Humana. She holds a doctorate in leadership and organization development from the George Washington university. And we're going to talk about her latest book.

the curiosity curve of leaders guide to growth and transformation through bold questions. So Deborah, welcome to the show.

Debra Clary (00:37.905)

Thank you, John, for having me.

John Jantsch (00:39.906)

I love to explore people's words and people's bios. So what does a narrative scientist do?

Debra Clary (00:46.461)

Storyteller. You like it?

John Jantsch (00:47.822)

Well, I do, but where's the science in that?

Debra Clary (00:55.916)

Well, there's science in telling a story. There's actually a formula on how you're able to connect with people.

John Jantsch (01:04.98)

So you've had a, I only read a bit of your bio, but did I see somewhere that you were an aspiring standup comedian?

Debra Clary (01:14.392)

I actually started right out of school being a standup comic and my father came to one of my shows and after the show he said, well, I want to talk to you about it. And I thought, well, he's going to say, look, you're in business school, why are you doing this? And he said to me, I love you, but you're not that funny.

John Jantsch (01:15.647)

You

John Jantsch (01:32.312)

Alright.

John Jantsch (01:38.183)

Debra Clary (01:39.421)

which was true. But it was great training ground for to be able to get on my feet and to talk to large audiences.

John Jantsch (01:47.862)

Yeah, I picked up on that because I there seemed to be a bit of a trend in the speaker world in the consultant world of doing like improv and stand up. And so I wonder if there's really a real tie to that actually being a great training skill instead of just something fun to do.

Debra Clary (01:58.637)

Yes.

Debra Clary (02:05.393)

Absolutely. You probably have heard of Second City out of Chicago, right? Well, Second City actually has a division that goes into organizations and teaches leaders how to think on your feet, how to build other people up. And when I was at my last role, we brought them in several times to help us.

John Jantsch (02:09.696)

Sure, sure.

John Jantsch (02:15.735)

yeah, I've seen that.

John Jantsch (02:24.91)

Yeah, think like half of Saturday Night Live's cast comes out Second City. Yeah. So let's get to the book. Curiosity is a word that actually got my attention because I've often said that that's my superpower is that what's really kept me in the game. I've been doing this for 30 years. So much has changed, all this new technology. And I always tell people, I'm just always curious about how stuff works.

Debra Clary (02:31.72)

Yeah, it's a great training ground.

John Jantsch (02:53.196)

You talk about it as more of a mindset rather than necessarily something we're just born with. Would that be fair to say?

Debra Clary (03:01.483)

Well, it's actually both in the sense that we come into the world knowing nothing other than we're hungry or we're cold. And as toddlers, we ask 298 questions a day. This is based on work by neuroscience out of London. But by the time we're adults, we might ask five questions a day. And that might be, where are we going to dinner? Are we eating out? Are we eating in? Those types of things. And the reason is that we are taught to be

in curious. We are taught that children are to be seen and not heard. You know, don't open Pandora's box, curiosity killed the cat, all of those things that we're taught to be in curious. And then we go into the university and we get a degree and then we come out and we're working in that field. And then we're being paid for that expertise. And by the way, we have time constraints. And so all of those things add into like what happened to us.

John Jantsch (03:55.725)

Yeah, right.

John Jantsch (03:59.756)

Yeah, yeah. Well, so if you're going to call it a skill, is it measurable?

Debra Clary (04:06.059)

Yes. So when we originally did our research, I had commissioned a team of researchers out of MIT to study one thing for me. And that was, what is the relatedness between leadership performance and curiosity? And they said, well, we're going to have to go deeper on that. I said, let's start with that hypothesis. And when they came back and said, there's a direct correlation between a leader's level of curiosity and the performance of their team.

Then we started going deeper and we learned that curiosity can be learned, it can be taught. And so we created the curiosity curve assessment. So we can actually measure the current state of an individual, a team or an organization's level of curiosity, because we know it can be improved.

John Jantsch (04:54.776)

So one of the things, especially with leaders, even worse the higher you go in leadership, is that there tends to be a mindset, not all, but with some of like, I have to have all the answers. That's why I'm here, right? They look to me to have all the answers, right or wrong. I think they take that approach. Is that one of the biggest hurdles to at least acting curious?

Debra Clary (05:20.895)

Yes. So it's an outdated model where leaders have to have all the answers. You know, most leaders arrive there because they've probably come out of those roles and they know, they know what to, you know, they become an expert in that, but now they're in a leadership role. And if we, when, somebody comes in and has a problem, we are prone to tell them what to do, right? That's efficient. And by the way, we need to have all the answers, but the

John Jantsch (05:46.478)

Right, yep.

Debra Clary (05:50.627)

best leaders are those that focus on the individual and not the problem. And so you're asking them a series of questions that leads them to understanding how they can solve it on their own. You're building their confidence and you're building their critical thinking skills. So leadership is about playing the long game, not the short game.

John Jantsch (06:09.836)

Yeah, I mean, the phrase that comes to mind to me is instead of just giving people to fish, right? You're going to teach them to fish by just stepping back and saying, I don't know, what would you do? I mean, can you start that simple?

Debra Clary (06:15.788)

Yeah, that's it.

Debra Clary (06:23.67)

Well, I probably would say something like, well, tell me what you've been thinking about, right? And get them to have a conversation. And then things like, are there other problems that are similar to this that you've solved and what worked in that situation, right? Is helping them dig deeper and understanding that they can solve it or together you can solve it. But I'm not going to give you the answer because I don't have all the answers.

John Jantsch (06:28.546)

Yeah, yeah.

John Jantsch (06:50.062)

Do you have or do you at least, obviously every business, every situation is maybe a little different, but particularly in kind of a like status type of meeting, do you have a formula for how you should restructure that?

Debra Clary (07:05.142)

Yeah, and I actually write about that in my book, John. And it's one about, you you set the agenda. And when you get your team together, you say, these are the things we're going to cover. Is there anything that's not on here that we want to make sure we cover? So you're leaving it open to what else needs to happen. The other thing is, you in those meetings, encourage people to ask questions and encourage people to challenge what's been said. Like get really comfortable with being challenged.

That's when you have a culture of curiosity.

John Jantsch (07:38.742)

I mean, does it kind of change, not just change the way that the meeting goes and the way that people act, but does it have the potential to actually change the entire culture at an organization?

Debra Clary (07:51.203)

Absolutely, absolutely. So culture and leadership is synonymous. So goes the leader, so goes the culture. And so the work that I do is mostly around the senior executives, know, the C-suite, because I recognize that when you make change at the top, then you can see greater change throughout the organization. So if you want a curious culture, the C-suite needs to be modeling it.

John Jantsch (08:04.91)

Mm-hmm.

John Jantsch (08:10.958)

Sure, right.

John Jantsch (08:17.57)

What are some of the misconceptions? I'm sure that curiosity to some people sounds like a pretty soft subject. So what are some of the things you have to really fight against when you say, this is really the secret?

Debra Clary (08:30.816)

Yeah, so when I started that way as being skeptical myself, I had the hypothesis that curiosity might be missing in the workplace, but it was a hypothesis. And as a scientist, I need data. So I brought the data together. when I'm talking with CEOs, someone has recommended me to a CEO and same thing like curiosity, come on. And then I say, I thought the same thing, you know, and having spent four decades navigating complex systems,

John Jantsch (08:34.936)

Okay. Yeah.

Debra Clary (08:59.446)

Yeah, I kind of have that doubt too, but now we have the data. And so I take them through the data and then you can start to see like their eyes are lighting up and they're like, they're starting to make connections. So for me, you know, I move forward with data.

John Jantsch (09:18.35)

So I find that curiosity takes empathy, takes self-awareness, takes compassion. And a lot, I'm sure you also have leaders like, don't have time for that.

Debra Clary (09:18.903)

Mm.

Debra Clary (09:32.298)

Absolutely. And I would add something to your list of attributes. There is one around forgiveness. You know, when I'm asking myself questions and it's, some might start off like, wow, you should have known differently or you should have done something different. And then I say forgiveness and I'll say, okay, what would I do now? Like what's my next move in order to either correct it or to build on something.

John Jantsch (09:33.038)

John Jantsch (09:54.68)

So, do you have a path for, because I suspect that it's going to be habit forming too, right? I mean, it has to just almost be a reflex in certain situations, start curious, right? So, is there a training path that, you know, in the next 30 days, if you do these things, you know, you'll become, it'll become more habit forming?

Debra Clary (10:17.217)

Yeah, absolutely. even curiosity is a muscle. We all have it, but we've stopped using it. Maybe like our abdomen, you know, our stomach muscles there, we've, we've stopped using them and you can get them back. so when I'm working with executive teams, I start with the curiosity assessment. I like to know where, what's our starting point, right? And so there are four factors that we measure on the curiosity curve. And when we get an understanding of

at the individual level, but at the team level, that's when we can make real progress. But it does start with the intention of we want a culture of curiosity because we know it drives performance. So we're anchoring around performance and the intention of creating this type of culture.

John Jantsch (11:06.488)

So are there a handful of bold questions that every leader should be asking their teams right now? I mean, are there any specific examples?

Debra Clary (11:17.945)

Yeah, you know, it certainly depends on the situation, but for a generic reason, I love questions that are like, what's not being said, right? What might we be missing here? Does anyone have a different point of view? You know, really creating an environment where people know I'm asking questions because your opinion matters. Your point of view matters to me.

John Jantsch (11:43.599)

Of course, the other end of that though is you have to be willing to accept that the opinion might actually be good, bad, or indifferent. You have to actually be open to not just encouraging people to make suggestions, but actually seriously considering them and maybe even taking action.

Debra Clary (11:51.115)

Absolutely.

Debra Clary (12:00.715)

Absolutely. In the best environments I've been in, when somebody brings up something, it might not be quite right, but then somebody builds on it and somebody else builds on it, just like an improv. And then you've now have the collective thinking of that team. That's the beauty of someone coming up with something and you might challenge it, you might build on it, but definitely you're creating the culture of curiosity.

John Jantsch (12:09.9)

Yeah, right.

John Jantsch (12:25.548)

Yeah, and we've probably all been in situations where leader, you know, is not open to those. so everybody just everybody just shuts up, right? It's like, bother? I've got a great idea, but why bother? Right.

Debra Clary (12:34.617)

That's right. Absolutely. Well, you might be familiar with last year, Gallup put out their engagement report in the history of measuring engagement. They've never seen it so low. And particularly the millennials who make up 35 % of the workforce and they're from the age of 29 to 40, they're 65 % disengaged.

John Jantsch (12:46.705)

wow.

Debra Clary (12:57.293)

Now, why is this a problem? Well, the obvious one is because they're not being productive. But the another one is this is the group of people that we would be developing to go into senior roles in the next decade. And they're signaling to us, we're not interested. So we brought together a group of millennials to do a focus group because we wanted to get underneath what's going on. And, you know, the scientists asked it in a better way than I'm going to do it. But I like, what's your source of unhappiness?

John Jantsch (13:25.518)

Mm-hmm.

Debra Clary (13:26.253)

what they said surprised us. They said, my leader doesn't know me and doesn't care to know me. And so the follow-up questions were like, they don't know you're like what you do personally, or like you have a dog or you like to run marathons. They go, no, no, they don't know what I can contribute to the problem, know, solving the problem. I have most of the information, but I'm least consulted. Now that can be solved by leaders shifting the way in which they interact with their teams.

John Jantsch (13:32.75)

Yeah.

John Jantsch (13:50.529)

Mm-hmm.

Debra Clary (13:56.258)

It's about asking questions of what do you think we should do? Do you have any experience that's parallel to solving this problem? I would love to hear what you have to say.

John Jantsch (13:56.364)

Yeah.

John Jantsch (14:07.34)

So I'm curious in your doing this work, has there been, of course, everybody wants the home run, right? Has there been like a single question that changed the outcome of an initiative that you've been a part

Debra Clary (14:21.461)

It was in an executive meeting and the organization, I was a part of this organization and they were moving into a new territory, a new discipline, if you will. So they were in an insurance company that now was going into actually delivering care. And the people that were in that room were used to the insurance company, a transactional company.

And we had one individual that was starting up this division who came from that discipline and they were, they were arguing about the way in which it could get done. And I realized they weren't even using the same definition for what it meant. So I pause and I said, everyone, let's take a second here. know, Brian, can you describe, define what your, what is the meaning of that word? And then I did for the other individual, they weren't even talking about the same thing.

Now it's just each of them were trying to present their case. So while, know, why we needed to invest in this or why we needed to pull back on this. And I realized we're not even trying to solve the same problem. That was an, that was an, an opener. And that, you know, that comes for me, just I'm listening to what they're saying and realizing they're not, they're not trying to solve the same problem.

John Jantsch (15:27.862)

You

John Jantsch (15:38.886)

Sometimes being the outsider is the only way you can actually hear that because you're like, don't know what you guys are talking about. So let's flip that around then. Can you share maybe a moment when a lack of curiosity was clearly causing setbacks?

Debra Clary (15:46.349)

Yeah, absolutely.

Debra Clary (15:58.654)

And we see that every day in organizations in the sense that, you know, leaders feel, mean, first off, have, you know, huge revenue goals to hear clear objectives to hit, and they have time constraints on that. And what I see playing in and out every day is that leaders just go to do directing and not exploring.

John Jantsch (16:00.568)

Gosh.

Debra Clary (16:25.195)

and because they think it's the most efficient way. And it probably is efficient in the short term, but not in the long term, right? And what happens is people begin to shut down and no longer offer opinions because it doesn't matter anyway.

John Jantsch (16:41.528)

So was there a moment for you, Mayer, that you could describe where you decided it's so clear curiosity is the missing piece? mean, was it the data that kind of flipped the switch for you?

Debra Clary (16:53.689)

Well, my hypothesis started in it was in a two week time period, three things happened to me that I think was like just a message coming to me to explore this. One was I was in Rome and I was sitting next to an Italian man and he said, you're American. I go, yeah. He said, I got the best American joke for you. What do you get when you ask an American a question? You get an answer.

John Jantsch (17:15.756)

Ha ha.

Debra Clary (17:20.173)

Right now I was a polite American. nodded, but I didn't get the joke. Right. Then I went back to work. sitting next to my CEO in the boardroom and he is watching and listening to someone present and he quietly says to me, do you think curiosity can be learned or is it innate? And at the end of that week, Gallup released their report around low engagement. And it was there that I just became.

John Jantsch (17:20.366)

You

Debra Clary (17:45.186)

you know, profoundly sad, but also clearer on, I think I want to go do more research on curiosity. And so I did a little bit of literature search, and then I realized there's not enough data for me to actually go out into the world and tell people this is the greatest thing. This is, this will solve all your problems. And that's where it came from. He is just in that short window of hearing what's missing in America or what's missing in organizations.

John Jantsch (18:13.144)

So I'm curious, is there a question that you maybe wake up and ask yourself every day that sort of starts your curiosity journey?

Debra Clary (18:23.437)

Well, I start off with this, just this notion of, you know, abundance flows to me, like great things are going to happen to me. I start off with that mindset because when I wake up, I'm typically negative. Something has hit me or something from yesterday and I have to say to myself, no, I have the mindset of, have this amazing opportunity to share with people the power of curiosity. And so that's how I start my day with the mindset of I may have an opportunity to impact others.

John Jantsch (18:54.114)

So talking to leaders, is there a practice again? Because I'm sure what happens to a lot of them is you get going, you got this meeting, you're just like the pace picks up all day long. Is there any kind of curiosity practice that every leader could adopt or should adopt that would really get them in the right frame of mind?

Debra Clary (19:11.245)

Yeah, it's about, I have a couple of suggestions. One is, know, listen more than you talk. So that means you're asking good questions and then you're the key is you're listening. The next thing is, is when somebody asks you a question, say, I don't know, or I might know, but I'd love to have a conversation about it in the sense of what you're inviting people in.

You're saying I'm vulnerable, I don't have all the answers, but together maybe we can explore this. And that's where I begin with my leadership and when I'm working with my teams and then the teams that are in organizations.

John Jantsch (19:51.116)

Awesome. And the curiosity curve assessment is, I assume, is found on your website. And anybody can take that? Yeah.

Debra Clary (19:57.422)

You can find it on my website, as well as you can find it in my book, which is found on amazon.com. It's called the curiosity curve.

John Jantsch (20:05.902)

Awesome. Well, I appreciate you taking a few moments to stop by. Is there any where else you'd invite people to connect with you or again, find out more about the resources you have to offer? I think it's just deborahclary.com. Is that right?

Debra Clary (20:18.925)

DebraClary.com and on my website I have multiple articles that have been published in the last year all around the topic of curiosity and how curiosity will save us.

John Jantsch (20:28.942)

Well, there's a banner for you. Again, Deborah, I appreciate you stopping by and hopefully we'll run into you one of these days out there on the road.

Debra Clary (20:36.929)

All right, thank you, John.

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