Ep 98: The Art of Storytelling – Experience From a Microsoft AI Ambassador

  • 11 Sep, 2023
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Join the discussion: Ask Doug and Jordan questions about AI and storytelling

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In today’s fast-paced digital world, capturing the attention of your target audience has become increasingly challenging. As a business owner or decision maker, you understand the importance of effective communication to drive customer engagement and ultimately achieve business growth. This is where the art of storytelling, combined with the power of AI, can make all the difference.

Crafting Personalized Pitches:

Gone are the days of generic and one-size-fits-all pitches. The podcast emphasizes the importance of tailoring your message to the specific audience and environment. Utilizing AI-powered tools, you can gather insights on your target audience, enabling you to create personalized and compelling narratives that resonate on a deeper level.

The Art of Connection:

The most impactful pitches are not mere sales spiels; they are stories that connect with the desires of your audience. By understanding their needs, aspirations, and pain points, you can create narratives that evoke emotions and foster a genuine connection. Learn from the best storytellers like Steve Jobs, who captivated audiences with his ability to weave technical details into compelling narratives.

Balancing AI Assistance:

AI tools, such as ChatGPT, can provide invaluable assistance in crafting effective stories. They allow you to refine your narrative by suggesting content based on data and trends. However, it is crucial not to solely rely on AI-generated content. The podcast emphasizes the importance of editing and adding your own voice to ensure authenticity and maintain your unique brand identity.

The Science behind Storytelling:

Understanding the science behind storytelling can elevate your marketing efforts. The speaker discusses the concept of a story arc and the hero’s journey, which are powerful frameworks for engaging and captivating your audience. By starting your stories where the audience lives, leveraging relatable experiences and language, you can create an immersive and memorable experience for your customers.


In today’s competitive business landscape, telling a compelling and relatable story can significantly impact your success. AI-infused storytelling empowers you to connect with your audience on a personal level, capturing their attention and compelling them to take action.By crafting personalized pitches, leveraging AI tools wisely, and understanding the art and science of storytelling, you can create narratives that resonate with your audience, drive customer engagement, and ultimately lead to business growth. Embrace the power of AI-infused storytelling and give your business a competitive edge in the digital era.

Topics Covered

Topic: The Art of Storytelling with AI
– Importance of storytelling in capturing the audience’s attention and making a message resonate
– Steve Jobs as the best technical storyteller
– James Whitaker and Mary Rodriguez as examples of individuals who excel at storytelling
– The speaker’s best pitches are tailored to specific audiences and environments
– Using ChatGPT to assist in crafting effective stories
– The importance of editing and adding the speaker’s own voice to the content

Topic: Elements of Effective Storytelling
– The use of a story arc and the hero’s journey
– Starting a story where the audience lives, using personalized and relatable experiences and language
– Stories should inform and persuade, particularly in the context of marketing products
– The focus on imagining a better life with a product, rather than relying on features and benefits

Topic: The Future of Work and Storytelling
– The speaker’s perspective on the future of work and storytelling, given their experience with technical innovation and understanding of consumer behavior
– The influence of AI on the future of work and storytelling

Topic: The Guest’s Background and Mission
– Doug Thompson’s background as a technical sales nerd with experience at Microsoft and Tanium
– Doug Thompson’s mission to help technical sales nerds and anyone trying to sell or relate to others by teaching them storytelling skills.

Podcast Transcript

Jordan Wilson [00:00:18]:

One skill that I think no one is talking about ever since we’ve been riding this huge generative AI wave is storytelling, the ability to tell a captivating tale that brings viewers, readers, and potential customers along for the journey. So That’s what we’re gonna be talking about today on everyday AI. This is your daily live stream podcast and free daily newsletter helping everyday people like you and me not just learn what’s going on in the world of AI, but how we can all actually leverage it how we can leverage it to grow our our businesses, our career, and everything else. My name is Jordan Wilson. Thank you so much for joining me. I’m excited. Hey. As a former journalist, I’m excited to have a dedicated episode on storytelling and a great guest, to to come along with us on today’s episode. So if you’re joining this live, Let me know where you’re joining us from. If you’re on the podcast, make sure to check out those show notes. We always have related episodes and other links to help you come and join us on this journey.

Daily AI news


Alright. So before we get into that topic today, let’s go over what’s going on in the world of AI news, what we do every single day. So number 1, Meta has reentered the large language model race, so recent reports show that Meta is training a new AI model specifically to go after GPT 4, which right now is kind of the leader of the pack and the generative AI large language learning models. So Meta is investing in a lot of chips and new data centers and everything that a company needs to create you know, a a leader in the large language model space. So keep an eye on that and more in the newsletter as well.

So, next big story of the day, Google pledged $20,000,000 for a responsible AI fund. So this is from an Axios report that details Google’s philanthropic arm. They invested into the digital futures project about a $20,000,000 round, to go out to companies that they felt were doing positive things in the world of AI. And to make sure that, you know, AI doesn’t kind of go into those dangerous pitfalls. So a group of nonprofits and executive or in academic institutions were named the 1st recipients.

Alright. And last but not least, AI is outperforming humans and building software, that might not be a surprise for many, but a new study showed that AI agents could develop software in less than 7 minutes and for about $1 in costs. Yeah, That’s right. 7 minutes, $1 crazy. Right? So, researchers from Brown University and a few Chinese universities, Tastin AI powered agent, kind of experiment to create 70 different programs, in this, study, and they found that on average, It took the AI agents about 7 minutes to develop each of those programs and only costs about a dollar. Wow. Right? You you know, when when we talk about the future of work, you you you have to keep AI agents, in mind.

Intro to Doug Thompson and background

But Today, we’re not here to talk about AI agents or the future of work, or maybe we’ll talk a little bit about the future of work, but we are talking about storytelling and about AI as well. So I’m extremely excited to have today’s guest, onto the show. Please help me. Welcome. Doug Thompson. He is owner of the Duck Thompson dotcom. Doug, thank you for joining us. Appreciate you coming on the show.

Doug Thompson [00:03:51]:

Hey. Thanks a lot for having me. Yeah. It’s a easy name to remember. You know, I hate trying to remember what my website is. So I just look at that.

Jordan Wilson [00:03:58]:

Yeah. Just just Doug Thompson. Doug, your your experience is all over the place. And I I I feel I would do an injustice if I try to quickly recap it on my own, but could you just, you know, quickly tell our readers a little bit about your background? Because it’s impressive. So I’m gonna let you, you brag on yourself here first.

Doug Thompson [00:04:17]:

Oh, well, gee, that’s I never give me a microphone to brag brag about myself. So, anyway, I am, I am a a technical sales nerd by by trade, by nature, by most of my career. I spent 20 years at Microsoft before I came to my current employer Tanium. And, you know, this sort of interesting being a new employee at sixty years old. So it’s I’m I’m I’m I’m like methuselah from the, if you look at it from the technology age, started back in the Windows 3. I mean, I’m very used to have floppy disks to put things in, so I’m kinda sort of a nerd self taught. Just always sort of curious about things. Exit. And then I am a storyteller. I’d learned that somewhere along the way. We can get in if you want. I’m actually gonna write a chapter for a book coming up here soon. About that sort of event where I discovered, hey. I am a storyteller. I I did it unintentionally, but, it it’s it’s you know, just been fun journey. And it actually sort of led me into the I know you talk about your favorite role as my AI ambassador role, which we can talk about a little bit. And it sort of led me to that. So I’m I’m on a mission now to help all my technical, sales nerds, nerds, just anybody that is out there. You’re trying to sell something or relate to another person. You know, heck, even tell your story And I’m here to help you do that because it’s storytelling can be taught, but they don’t do it in school. They and they don’t really have any of the things that I had to do when I was in school to sort of develop those skills. You know, the texting by phone now has sort of just ripped that storytelling piece out of us because everything sort of shortened.

Finding the balance between AI and storytelling

Jordan Wilson [00:05:53]:

Yeah. It’s so true. And let’s actually start there, Doug, because like I said at the top of the show, I’m a former recovering journalist, I guess. And you know, it’s I I think right now, and and maybe it’s it is because of AI. Because so many people are pumping out just mediocre content at extreme rates. And I feel as consumers now, we are being, just buried in a lot of just just copy and messaging. That’s just not very good because of how easy it is to create not very good content using AI. So so with that, Doug, like, what kind of recommendations and and and kind of given your, you know, background and and recent history and really, helping others tell stories How can people still find that good balance between, you know, using AI, but still telling a compelling story?

Doug Thompson [00:06:45]:

Yeah. I you know, the big things that I see happen is you you read a story and then there’s 2 things. 1, it doesn’t really jive with the audience. That they’re doing and doesn’t really resonate well. It’s just sort of a generic story. Imagine a cartoon with no color and no special characters or anything like that. You know, you watch Mickey Mouse, and you expect certain things to happen. Right? And and, you know, you get these things now that come out of a paper or something that’s used to trust. And they just don’t have any flavor. They’re just bland, and and they’re not even sometimes you question the the the factualness of it. You know, that that that some can be suspect, but he we’re we’re wired to hear stories and learn from stories, but it’s a very human thing. It’s a very experiential thing. And I talked about that my TED Talk that I did, sort of, where stories developing were wired to learn from them. And they need to be personalized. They need to do something. So I use ChatGPT GPT and as we to discuss in my my podcast that you were on, which drops next week. The Doug Thompson podcast is hard to figure these things out. You know, I I just my branding is just so so bad. But we talked about that is, you know, when you start I started a story. I I I was talking to some a guest on my podcast the other day. He’s a dog trainer. And and I said, well, you’ll obviously, you tell nonverbal stories to to dogs to train them. And they said, actually, what the verse very first name is gonna meet a dog at their house where they are, where they live, get experience with it. And that’s really where you need to start your story is where your audience lives. What’s your experiences? What’s the words that they use? What is their life like so that is you’re trying to tell a story that that a a story is meant to inform, but also in the Salesforce to convert. Right? To show them the value of your product. And if you can’t verbalize it articulated in their language, then they’re just gonna okay. This is just another pitch or something. You know, it’s you need to do that. Right? And you gave me some good tips on how to sort of best use ChatGPT. To help do that. But it takes work. You just can’t have a spit the very first draft that it spits out is horrible. Yeah. I mean, I have to go back and And he said, okay. No. Do a little bit of this, a little bit of the massaging and stuff in it because I have to put my voice in. It has to be in my voice. And I think, you know, as you as a journalist there that you sort of recognize when you could probably recognize, okay, they didn’t even try on this one, you know, or or or somebody ghost wrote it for them that didn’t have their their flavor and stuff. So that’s the key thing of that. And then simply the art of storytelling where you have the arc and there’s struggle and there’s other things in the hero heroes journey. So those are the two things that I I work with. Again, the very first one is starting where the audience lives and making it familiar to them. Right? You can’t you can’t write a generic story.

Jordan Wilson [00:09:29]:

Yeah. Speaking speaking of making it familiar with the audience. Thank you. Thank you for the audience joining and and tuning us, tuning in right now. So, you you know, Bronwyn saying, you know, she she prefers a a book and a pen and then adding it to the computer. Great great tip there. And just as a reminder, you know, yeah, here also remembers the floppy disc era. If you have a question for Doug on either his background in Microsoft, which we’re gonna get into in a second, or just, you know, ways to, improve your storytelling with or without AI. Go ahead and drop that comment in now so we can get to it. But But it’s

Doug Thompson [00:10:00]:

I wanna just talk about that book and pen here real quick because there is scientific study that as you’re writing things down, like taking notes in the class, there’s studies back when I was back at Microsoft and the education team that typing, you don’t remember. You don’t connect with a lot of stuff. Or if you’re writing, you have to sort of summarize things in your head. To make the connection and and write that down. So it has a more personal feeling to it, and I think it does resonate. Unfortunately, I can’t remember. I can’t read what the hell I wrote. So that doesn’t help me very much.

Should we use AI in storytelling?

Jordan Wilson [00:10:29]:

Oh, man. That’s a good point. So so I’ll ask I’ll ask this, Doug, because, being a a huge AI advocate and enthusiast myself. You you know, I’m always encouraging, you know, listeners for the everyday AI show, and just other people I meet, like, hey. You should start to tap into the world of AI, because I believe it is the future. You know, all the big companies are you know, even changing how search engines work and and making it more conversational with with the chatbot style. Right? So what’s what’s your advice, for people to still, or or or do you even encourage people to use AI in their telling, or should they they just go the old school way, like, Brown, who’s saying pen and paper? Like, how can we still tell great stories?

Doug Thompson [00:11:14]:

No. I mean, it’s I think you I mean, even if you take it further to jobs of the future of jobs today, and I’ll go back to when I was an AI ambassador. So so when we’re coming around with with AI. This is I don’t know if chat GPT was ever even sort of a a figment somebody’s imagination back then. Again, I’m talking 5, 6 years ago

AI [00:11:34]:

Jordan Wilson [00:11:34]:


AI [00:11:34]:

Doug Thompson [00:11:34]:

that we were doing this. And the AI Ambassador role came out because Microsoft was starting to do a lot of stuff with artificial intelligence, machine learning, and we had to sort of articulate the message of what we were planning to do at the time. And, you know, they were looking for storytellers because, again, AI was just sort of this big big scary. You know, the AI to that point was Arnold Schwarzenegger. I’ll be back. Right? I mean, that’s where it was. And our job here was to relate that I if if you need, it’s best done as a copilot, I’ll use the brand that they’re using now.

Jordan Wilson [00:12:08]:

Got it.

Doug Thompson [00:12:08]:

Somebody do help the human be better. So take off some of the task and stuff that takes a lot of time or analyze so much damn data that the human would take decades decades to do — Mhmm.

AI [00:12:18]:

Jordan Wilson [00:12:18]:


Doug Thompson [00:12:18]:

help make them make better decisions. So it was really there to sort aid that and sort of articulate that message out. And and that’s why they they had us go along. It was really cool. It wasn’t really defined. We went through different iterations before I left, but I got to talk people and really sort of get a lay of their fear that it’s not all evil. Anything can be used for evil.

Jordan Wilson [00:12:37]:

For sure.

Doug Thompson [00:12:38]:

But if but if you don’t sort of embrace it, if you don’t do this and you’re somewhat of a competitive disadvantage. So in the storytelling, yeah, you can use it especially if you’re like me who has sort of I I try to write and edit it the same time a lot of times so I get no words out because because that’s not just I can’t get anything out. So I said, here here’s an idea. Put something out there. Let’s see. And I end up rewriting mostly. I mean, I may use about 30% of what was is put out, but it helps get me out of my where I’m stuck. So, yeah, definitely definitely use it. But know how use it well. Right? And and you give a lot of great tips on how to do that.

Doug’s experience as an AI ambassador for Microsoft

Jordan Wilson [00:13:15]:

Yeah. Yeah. Thanks. And that’s, yeah, it’s some it’s something we teach people all the time. You know, we have a little course prime prompt polish, the PPP method, where we we we walk people through that and how you can still retain, you know, that human voice or those important details of the story and kind of balance with AI. But I do I do wanna hit rewind here, Doug, because this one We’ve talked about it. I’m so fascinated. Yeah. You know, my my, my wife always jokes around and tells me, hey. You you know, you’re either very early to something or, you know, you were born too late. But I I have to talk about you being a Microsoft AI ambassador. You know, for those, you know, 2 years, talk about timing, right, October, right, October 2018 to December 2020. You were an AI, ambassador for Microsoft. Right? And then months later or right around that time, actually, kind of, you know, kind of all this GPT just started to to hit the shells. So talk a little bit about what your experience was like as an AI ambassador and also being early to the party, it must have been very difficult to advocate for something that now I think would be very easy to to advocate for and to and to be an ambassador for.

Doug Thompson [00:14:26]:

Yeah. I mean, it it was great because I got to talk to a lot of I normally wouldn’t get to talk to, you know, going to talk to events and things. And it was sort of nice being on the inside understanding from from that perspective at the time, what what the plan was. You know, and and one of the one of the things we one of the fundamental questions we had to do, if we were trying to somebody We found a use case for a customer or something that an account team did that they wanna use AI for. We would have to go through this review process.

Jordan Wilson [00:14:54]:


Doug Thompson [00:14:54]:

And one of the things, you know, like ethics and stuff that comes in, one of the things was just because we can do it, should we do it? Right? Because because you look at something here where you could automate something or do something where it could decimate in the only employer in town of a developing country. Is that the right thing to do just because you can? Yeah. You know, so the so that was some of the discussion with philosophical discussions and stuff that we’d get to have and that, you know, we We were sort of help help taking crowdsourcing, if you will. What could you what do you think you could use AI for? What do you think would be a good use for that? And we got to do some. So there’s really just it’s like sometimes you’re in this area where you don’t there’s no rules. There’s no rule book and you’re trying to figure out your way and what’s a good path forward. You’re you’re stuck in sort of this in a sailing, you know, example. You’re sort of stuck at the start of the race. You really you’ve got some science of where the wind may be blowing us up, but the wind changes.

Jordan Wilson [00:15:48]:


Doug Thompson [00:15:49]:

You know, based off what’s going on, that will let, you know, the end of the road, we wanna be here, but my road there is, like, over here over there. It’s not if you’re watch sailing, it’s not a straight path. Yeah. So lot lot of learning and a lot of listening. So and I think that’s helped them end up where they are today.

Microsoft Copilot and the future of work

Jordan Wilson [00:16:05]:

Sure. And and I think where where they are today and and where we all are, I think and, you know, we talked about this a little bit before the show. I I had a an episode a week or 2 ago, about Microsoft Copilot. So from someone that that worked there for for 20 years, you you know, my my hot take, Doug, is is that Microsoft Co pilot is going to be, a much is going to have a much greater impact than even chat GPT has had over the last, you know, year, probably, I would say, 5 x 10 x. What’s what’s your thoughts on that? And and just quick, you know, if if if you are new, Microsoft Copilot is essentially think of, you know, generative AI, but on your operating system, you know, so if you’re using you know, Microsoft 365 and the newest version of their operating system, having that generative AI follow you around in a good way, I think, you know, from all your different programs. So so, Doug, talk a little bit about what you think Microsoft, you know, 365 Copilot means specifically for the future of work.

Doug Thompson [00:17:08]:

Well, I I go back, you know, when I was there, you may remember Clippy.

Jordan Wilson [00:17:14]:

Oh, yeah. Oh, yeah.

Doug Thompson [00:17:16]:

So that was the early attempt based off the technology we had at the time to be helpful. To to go on and help you do AI. I see you’re doing the, you know, Saturday Night Live did a great skit on the on the Clippy thing. Go watch that YouTube. I’ll watch that every now and then just to laugh. But, you know, it it got a bad rap, but it it somewhat ahead of its time.

Jordan Wilson [00:17:34]:


Doug Thompson [00:17:35]:

But be it because, really, because the back end wasn’t there to make it extremely useful. Right? So it was sort of we did the same thing with tablet. So when I was started out, I was in the OEM division. We did Windows XP, and then we had the tablet PC edition. So you had pen and paper. That was always Bill Gates’s big thing. So pen and on a on a thing but the hardware and software re the hardware really wasn’t there to support it because they weighed £8 and had a 40 minute battery life. You know, it was just not until until you came out with the iPad and stuff that it didn’t that form factor really didn’t come to life. But so I think Clippy was the same thing. Now now you’ve got the back end to do it, and it can be more useful instead of saying, hey. It looks like you’re doing, you know, it is simply saying is, you know, you can tell it what to do. It’d be it’s a little bit more of, like a virtual assistant, truly, that that responds when you ask it to do not be so pushy that pops up everywhere and just annoys the hell out of you. So it’s,

Jordan Wilson [00:18:30]:


Doug Thompson [00:18:30]:

know, it’s there. It’s, that’s the you go back to the early thing. It it’s rough when you’re you’ve got a great idea, but there’s not the back end to support it. I think this is great timing, and it makes a lot of sense because office and everybody, so many people use that and and and going back to the PowerPoint, if you go back to the head, this sort of presentation and coach. Right? They had they built that feature in to say, hey. Look. You got way too damn many words on this. Yeah. I have to apologize because we allow you to do bad slides.

Jordan Wilson [00:18:58]:

You know,

Doug Thompson [00:18:58]:

there’s there’s a reason when I was there that the death by PowerPoint has it true because people would abuse it. How much stuff can I cram on here? Yeah. So in using things, knowing what what makes a good presentation stuff, it helps you not shoot yourself in a foot. So so I think this is the this is the good improved clip. I don’t think it’ll go away. Yeah. Although there are con privacy concerns and stuff that you have about that too.

The challenges of “expensive” AI tools

Jordan Wilson [00:19:21]:

Oh, absolutely. And and just just as a reminder, if you are tuning in now. We have Doug Thompson joining the everyday AI show talking about storytelling, AI, but also, you know, his background, at Microsoft. So one question here. I wanna bring up Jackie’s comment here. So talking, you know, saying co pilot is expensive to incorporate been told by many inter enterprise companies that. I’d like to get your take on that, Doug, and I have a hot take as well because I believe that, you know, Microsoft co pilot is about I think it’s $30 a month, to to kind of, incorporate, per user. So, yeah, if if enterprise companies have, you know, 100 or 1000 of employees. It definitely is a a a big cost to incur. So, again, not not asking you to put your Microsoft, you know, sales cap on, but I have a hot take on this, but I wanna know what you think, Doug, about this, you know, because it is, you know, I think we’ve been trained to expect very cheap You know, because the $20 a month for ChatGPT, and a lot of these tools are even free to use. So what’s what’s your take, on this price of or on this piece of the the price of generative AI for enterprise companies.

Doug Thompson [00:20:30]:

Yeah. I mean, I I would have to think again. Yeah. I haven’t been in in that that realm for a long time, but I know just some current environment that everybody’s looking to trim IT expenses, which — Mhmm. It’s a battle. Is is it a strategic asset for you, or is it a nuisance you have to have. I mean, they they do it from a security standpoint as well as they they try to go in and and cut budgets here. Well, we don’t need that. Right? We’ve got and they can’t but they can’t hire people to do it because there there’s not enough of the people to the security, but I I I think that you know, for everybody in there, a janitor doesn’t necessarily need that access. Right? But it but if you have knowledge workers who are truly trying to do this, then you have to evaluate how much time are they spending trying to do it manually. You know, and and, you know, it’s not the object is In a, from a society standpoint, the object’s not to eliminate humans is to make them more productive at what they do. Mhmm. There’s a lot of job openings, although they, you know, they’ve had layoffs too that come up. So it’s sort of a mixed a mixed thing. I think you covered it on there that there is a risk that this will replace some people. Mhmm. But the every transition that you’ve had in history, you know, there’s nobody making iceboxes in more, although Getty does a pretty good job with

Jordan Wilson [00:21:44]:

the cool. That’s true. Right?

Doug Thompson [00:21:45]:

Right. So you have to go ahead and sort of evolve and but you do it judiciously. It’s not just not for everybody there. So the cost is based off of, you know, how you are going to use it, the number of employees and stuff. I don’t know what the licensing is for that. It probably goes into the enterprise suite somehow. Yeah. But, you know, it’s it’s always a value thing. What do you see the value there? If not, and you’re not gonna use it. You know, when I was at Microsoft, we had so many people there that would buy a suite of stuff and not use half of they go out and buy a third party thing to go do it because they liked it better than whatever, and it’s just not a smart way to to spend money if you’re just gonna do it and not use it. Right? Here. Yeah. We’re gonna shelfware as we would call it.

Jordan Wilson [00:22:27]:

Yeah. Oh, yeah. Gosh. Don’t don’t remind me about my shelfware right now. I’ll I’ll say this. And I’m I’m echoing, Douglas’s comment here saying 30 bucks a month for software that multiplies your productivity is actually a savings. I’m in that pain because, you know, I had a guest on a couple months ago, Corey Warfield, and I’ll I’ll I’ll make sure to drop the link to this later, but you know, he essentially said that the the companies that aren’t using generative AI top to bottom are putting themselves at risk to go out of business, you know, in 18 months. And I I agree with that. You you know, I say this, for, even for enterprise company, even for enterprise customers, if they’re not willing to to pay that $30 a month, that just means in my head that they’re putting themselves at risk to lose to lose their market share by far because, you know, I think for these tools that are 20, 30, 50, I mean, even a $100 a month, you you you make that up, you you know, within a couple clicks of using it, of using it correctly. I do wanna get I I wanna transition a little bit here, Doug, because we have some great, some great comments that I wanna get to. So, again, thank you, everyone, for getting in your comments for Doug. So let’s get this one here. So, Doctor Harvey Casper asking any tips regarding storytelling, top suggestion on which AI tools to use, and any out of the, out of the box recommendations. So, yeah, do you have any, specific, you know, AI kind of tools or softwares that you think can help in storytelling?

How to tell a story

Doug Thompson [00:23:53]:

Yeah, again, ChatGPT GPT used the right way prompted and stuff can definitely help with doing that. There are I haven’t tried a lot on I have seen some out there that sort of you’re almost like a coach to to help you do that. Mhmm. Yeah. You know, maybe for for me, for the elementary type stuff, it may be okay for somebody if you wanna get to say, like, I don’t know, 5th grade, 6th grade level of doing it or or maybe my again, I know I haven’t used them. But, those are the things, but the storytelling piece of that is is think about when you’re, again, starting with what the message you wanna convey, but think about how you talk to your friends. Mhmm. Not necessarily your coworkers. What what I find, especially with very smart people, like like, our doctor friend here probably is that when they’re talking to their peers, it’s a totally different conversation they have because every they everybody has the same basis, base level of knowledge.

Jordan Wilson [00:24:47]:


Doug Thompson [00:24:47]:

Right? And so you take shortcuts. You talk about things that are sort of with the 3 letter acronyms or whatever, you know, whatever you use. And where the normal person or your audience and stuff does not use that. They don’t understand, and they will just tune you out. So that’s why I think about, you know, but you talk to your friends that don’t understand or your your some of your family that doesn’t that, you know, how do you talk to them and explain it? Because that’s the language you may think to do. If you’re not talking to, again, your peers, go talk to them about that. And if it’s a scientific paper and you got a bunch of sheldens out in the audience, stuff, and, you know, that’s fine. Nurt it nerd out because that’s what they expect. But if you’re talking to about, like, that’s the thing I do when I’m going to talk technology to somebody I may talk into a chief marketing officer or something who doesn’t really care about technology at all. I got a problem. Can you help me do that? And that’s the language, again, getting back to starting your story where your audience is. That’s the language that I get rid of. I I have this. I’ve been on this mission for probably close to decade to in tech explaining. Right? So if you take that, you combine mansplaining with technology, and that’s what a lot of very smart people do as they tech by, you know, death by features function speed. Mhmm. No. Nobody cares about that. Don’t use it. How does this help me? Right? Yeah. Focus on that. Who’s your audience? What do they need? and start there.

The power of storytelling in pitches

Jordan Wilson [00:26:08]:

Yeah. That’s that’s great advice. And, think so many times, Doug, especially when we see, you know, so many new, AI softwares and tools. I think we rush to try to use the next versus just just focusing on on what you said is is who am I talking to? What are their problems and and really just starting there? I’m I’m I’m actually curious, Woosie, thank you for this question because, I’m sure in in in Doug’s, lifetime, he’s heard a lot of great stories. So Woozy’s question right here is asking you what’s your most most memorable story that you’ve heard in a sales pitch demo. So kinda what’s that that most impressive or memorable story that that you’ve heard kind of in the business world, Doug.

Doug Thompson [00:26:49]:

Wow. That’s yeah. I’m glad you didn’t ask what would my best one was because because honestly, I I the pitch out and I’ll answer his question. Just a minute, but but the the pitch that I use is different every time. I, the best ones that I’ve had, somebody’s come up to me after, said that you finally said something in our studio. I said, good. Could you tell me what I said? Cause I honestly don’t remember. Because because I get it’s it’s a little bit of an improv type thing is is, again, I’m taking what environment they’re in. Questions that come up, but I I talk to people ahead of time. You know, I do some little LinkedIn stalking on who I’m talking to today. And so I’m trying to get this picture here of what I wanna do. Then I tailor the core message. You may be there’s 4 5 or 6 different things. To that. So the best messages that I’ve the best things that I’ve had is that Steve Jobs was the best technical storyteller that I’ve ever seen. The way that he could he could get us to, you know, I didn’t know I needed 10,000 songs in my pocket till he told me about it. Right? So so those are the best pictures and all that I ever seen that they’re not really a pitch. They are a story that connects with something that I lately want or I don’t even know that I want. It would be cool, then then it makes me go take an action to go do that. So those are the best ones. If you want examples against Steve Jobs, I do this. A a guy that did a really good job was a mentor of mine was James Whitaker. He worked for Microsoft and Googled and back at Microsoft. Now he’s out brewing beer and telling stories or stuff. Something like that. Mary Rodriguez is a good technical. She’s got kinda book called Brand Storytelling. Mhmm.

Jordan Wilson [00:28:19]:


Doug Thompson [00:28:20]:

were both mentors of mine, but Steve Jobs, by and far, if you want sort of see a technical story done well. That’s it. And the best sales pitch is not a pitch at all. It is something that a story that connects that makes me go wanna go take an action in part with my hard earned money to go do something.

The future of storytelling with AI

Jordan Wilson [00:28:35]:

Yeah. And and even even to add on to that and, I think it’s actually easier now to playing after hearing you say it, Doug, is is, I think effective stories are not necessarily, you know, selling, you you know, you you have all these different copywriting, you know, very famous you know, copywriting techniques, you know, ADA features and benefits. And I I think what you just said right there, Doug, is, amazing is the best stories aren’t you know, taking those traditional, quote, unquote, copywriting routes. They’re they’re helping you imagine how much better your life would be with something, but not talking about it through, you know, the features and benefits or, you know, attention and and and all these other, you know, traditional writing techniques, which is, extremely interesting. So one one other thing, Doug, I I wanna ask, what is, you you know, because from your perspective, You’ve seen a lot. You’ve you you’ve seen a lot of of of technical innovation. You you you kind of understand where consumers are from from working on the front end and now helping them on the back end. Where do you see just, the future of of work going and and maybe even the future of of storytelling? Because I think it changes every day. And, you know, I think consumer behavior is changing. So where do you see kind of the future of of storytelling, going, especially with AI?

Doug Thompson [00:29:52]:

Yeah. I mean, well, unfortunately, the tension span of humans keeps going down and down and down. So the art of storytelling is to be How concise can I do then? And it really sort of becomes sort of this here’s this hook. And then maybe one chance to back it up to get interest, maybe 2 very short ones, but it needs to happen less than 2 minutes. Mhmm. And that’s really, I mean, when you’re given a presentation, you’ve one of the things I you got about 2 minutes for people to decide, yay, or nay. Am I leaving the back of the room? Are I gonna give this person some time. So so you really have to have that hook that goes through that. So that won’t change. You know, and and and I use storytelling because there always be things for good books things like that. Right? So the longer form stuff will be there. That that really doesn’t change that much other than self publishing and you you how do you know that it’s not ChanteeBT that wrote the whole thing? You know, I I think that the authors that still put their secret sauce a step 8 that I call. There’s a bunch of different things I have that is the your secret sauce into that. That makes that connection with people and all that. I saw somebody mentioned signing Simon sent earlier. You know, starting with wise, a great thing to do, but he he has some great thoughts. He’s set Seth Golden has a lot of great thoughts and stuff to go in that. Did you know they didn’t come from ChatGPT? Right? So you can connect with that. But from the pitch perspective and all that or selling or these other, but I’ve gotta do this. Then I I think you you have to just learn to be very concise. And I’ve had mixed results with ChatGPT gbt being very concise and totally missing the point. Yeah. Okay. You got me 5 you got me a 100 words. What the hell do you mean? We lost the essence of what was going on. Right? And and you’ve explained it to me. It’s it’s the it’s the model and stuff that they use as predictive type thing. It it should get better over time, but right now, it’s sort of a challenge, right, and so you have to sort of evolve. I totally lost the first part of that question. She got me on storytelling on it, but the the future of work here, I think.

Jordan Wilson [00:31:44]:

Yeah. Yeah. Let’s talk about that quick. Yeah.

Doug Thompson [00:31:47]:

You know, I I started out. My first degree was in industrial electronics and electricity, and I had assembly code language was the thing that I had because At the time, the oil boom was one of the oil booms was going, and I lived in Southeast Texas. And there were five jobs for every person. Most of them were offshore, and this was back in the early eighties were $50,000 a year. It was a lot. That was that was a good pay.

Jordan Wilson [00:32:09]:


Doug Thompson [00:32:10]:

And by the time I graduated, we had a bust. And there were five people for every job. So I had to go learn to do something else. I’ve worked on copy. I was a copier technician for for a while. And but I, again, curiosity came, but I always had that curious thing about, okay, what’s this technology do? How does it work? I was a kid that would take things apart and try to put things back together without the extra pieces. Right? I was assist the way you have to have that curiosity. You have to if if you’re not if you just simply ignore what is out there under French. And I think you told me you had, like, a Gazillion. You talked about shelf where you tried ate everything that came out, just to see what it was and see if there’s some potential and stuff there. That’s what you have to do. You have to have that curious mindset to go on and do that. Or You can’t trust just because I’ve always done it, and I’m good at this, you know, turning a a knob or do something like that. Not always gonna be there. There will be some automation. There will be some things that happen. So so learning to use AI and learning to do these other things, that puts you step above everybody else that has no interest in doing it because it’s hard. Right? I I, you know, I don’t I don’t like it. Right? There that’s sort of the things it’s it’s adaptor die almost. I mean, that’s sorry. That’s the sad thing about it.

Jordan Wilson [00:33:23]:

Yeah. What a what a note to end on, right, adapt or die. You

Doug Thompson [00:33:28]:

you know, adapt or suffer, haven’t.

Jordan Wilson [00:33:30]:

Yeah. I know. Right. So we’ve we’ve we’ve been over you know, your background, we talked about your time at Microsoft, how to tell better stories. But as we wrap up here, what is the one kind of takeaway that you hope people, you know, listening, whether it’s, you know, improving their storytelling through AI or just you know, maybe not using AI, but what’s what’s your one, you know, takeaway piece of advice for everyone listening out there, to just tell more impactful stories, whether using AI or not.

Doug Thompson [00:34:00]:

If I boiled it down to one phrase, the story is not about you. It’s about the listener. It’s about what they can get out of it. You’re taking them on a journey. They’re investing their time with you. They want something out of that. That’s the best story. It’s the one that’s not about me. I’m simply the vehicle of which that story is told.

Jordan Wilson [00:34:18]:

Absolutely. It’s it reminds me, you know, when people ask for copywriting, tips. My number one thing is as well. No one cares about you. I think I think that’s important important to keep in mind. Right? So so, Doug, thank, yeah, thank you so much for joining us. We colored a lot as a reminder, make sure to check out today’s newsletter. We’re gonna be sharing a lot more, from Doug hopefully sharing some some great resources and other things from his website. And, also, if you haven’t already, please make sure that you do go to your everyday ai dot com. Sign up for that free daily newsletter. We’ll be where we will be breaking down, today’s episode in great detail. So don’t worry if you missed it all or tuned in late. We got you. Doug, thanks again so much for joining us, and I hope to see everyone else back for another day of everyday. AI. Thanks y’all. Thanks.

AI [00:35:06]:

And that’s a wrap for today’s edition of everyday AI. Thanks for joining us. If you enjoyed this episode, please subscribe and leave us a rating. It helps keep us going. For a little more AI magic, visit your everyday ai dot com and sign up to our daily newsletter so you don’t get left behind. Go break some barriers, and we’ll see you next time.

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