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A
I kind of like that approach, but that approach is scary for a change agent. Right. Because what if I'm bringing up something they haven't thought of?
B
Right. Yeah, that's like. That's exactly. I work with leaders and they go, well, we don't want to focus on the job losses. It was like, people know.
A
Welcome to Embracing Digital Transformation, where we explore how people process policy and technology drive effective changes. This is Dr. Darren, Chief Enterprise architect, educator, author, and most importantly, your host on this episode, Transforming Change Through Stories, with master storyteller and fellow podcaster, Gabrielle Dolan. Gabrielle, welcome to the show.
B
Hi. Thanks, Darren. I'm very excited to be with you.
A
Yeah, we had a great conversation last week or the week before last.
B
Yep.
A
And I said, hey, this would be great to have Gabrielle on the show, but before we dive into. Into what we're talking about today, everyone on my show knows. Everyone that's listened to my show knows that I only have superheroes on the show, and every superhero has a background story. So, Gabrielle, what's your background story?
B
Ah, God, where do we start? But yes, look, I'm. I could go back to. I'm one of eight children. That's a good one. That's a good one. That's a good one. I often people go, you know, I got. I learned the skill of storytelling, being one of eight children and sharing stories to get my parents attention. But no, I. And I. And. And what I loved about your podcast is I spent my first, you know, careers was in. It was around digital change, so working through the ranks and becoming. I started as a mainframe computer operator back in the 80s. Yeah, that's showing it. Showing my age right there, because I'm not. Don't even think they have mainframes anymore. But then, yeah, move from those roles into L and D roles and change management roles and decided, I don't know, about. About 21 years ago that I think storytelling is something people need to learn. So I left the corporate world and started teaching people storytelling. And probably one other little fun fact is I actually failed English in my final year of school. Not. Not because I think I was just lazy. I think I was just really lazy. And so the fact that I published eight books, I think the only person more surprised than me is my year 11 English teacher. That said, Gabriel lacks basic grammar and, you know, if she applied herself more, she might, you know, get better results. So I was like, okay, fine.
A
You know, it's funny, Gabrielle, because we have something in common there. My. My ninth grade year, I failed English. And my teacher wrote on the report card, he will amount to nothing. So the first time that I had an article that was published on the front page of a magazine, I signed it and I sent it to her. And then I've published three books myself.
B
That's very cool.
A
I've written several hundred articles now.
B
I. A couple of years ago, Darren, I was asked to go back to my school to do the graduation speech. And afterwards this woman came up to me and she, she introduced herself and she said, I'm the English teacher here and I've worked at this school for 15 years and that is by far the best graduation speech. She goes, and if you were in my class, I would have passed you. And I was like, can I get, like, can I get somehow, you know, when you get an honorary doctorate, can I get like some honorary pass in English?
A
That's awesome. That's awesome. So let's talk about digital transformation and the role that storytelling has in it. Because I actually think this is incredible kind of spin on things. Because when I talk about digital transformation, I always say people process, policy and technology. Always. I mean, that's what it is. And the people part is probably one of the hardest parts. And what better way to get your ideas across to people than through storytelling? Because people can relate and they remember which is some of the hardest parts of digital transformation is getting people to change their perspective.
B
Yeah, well, I actually think it's the hardest part of digital transformation, so. And because you could have the best technology and the best processes and the best systems, but if your people aren't adopting them and resisting them, then it's going to amount to a nothing. So, yeah, it was, it was in my final years. So, you know, this is going back about 25 years ago when my final couple of years in. I used to work for National Australia bank, so one of Australia's largest banks, and they were going through some major digital transformation then. But, you know, again, not sounding old, we didn't call it digital transformation then, we just called technology change. It was like. And one of the, it was like one of the very first implementations of SAP. Can you remember, like an implementation of SAP was a massive transformation back in the day. And I was so, like I said, I'd started in technology, so I knew the technology side of things. But the last, the last few years, it was in the people, the change management. So educating people why we need to change. And what I, what I started to notice is that I would go out to the business units and you talk about why we needed to change, and you'd sort of, you'd hit resistance all the time because people don't want to change. What I found is that when I shared a story about why we needed to change, it, it wasn't a silver bullet. Don't get me wrong, it wasn't a silver bullet. But what I found is, is more and more times people would go, yeah, I guess I never, I never thought about it that way. Or I can understand that. Or it just, it lowered their defenses. And sometimes when you're trying to get people to embrace digital change, you've got to get them to let go of what they're currently thinking so they can actually entertain and listen to the messages around change. And that's when I found story helped with that. So I sort of started to experiment more with it. And, and the more I did it, the more successful it became.
A
I like how you described how it breaks down those barriers that people put up, right? Oh, another, another technology, another change, and instead you break down those defenses so now you can actually talk person to person without the technology there. Right. And saying, hey, that's, that's actually really brilliant.
B
Yeah. And I think also too, Darren, when it comes to people embracing digital change, it's like, what's stopping them? So this, actually, even when I work with leaders now and they're wanting storytelling, share stories about the change, and you can share all the stories you like about how great the change is going to be. And I remember, I remember this one woman, she was sort of saying that, and I go, what do you think is going to stop them from adopting this? And. And she thought about it for a while, and I think one of her colleagues said that they don't think there's anything broken with the old system. So can you, can you imagine if you're going to push, this is a great system, it's going to make your job easier and blah, blah, blah. But everyone's thinking, there is nothing wrong with the current system. They're not going to be listening to your messages. So I sort of said, instead of your story being around how great the new system's going to be, you need a story to communicate that sometimes we're very, you know, like, sometimes we think there's nothing wrong with. And there's maybe isn't anything wrong with the new system now, but we need to, you know, change it. But like, and to me, it's like you share a personal story around that. Like, you know, it's like, and we've all had times where we Go, well, what, what I'm currently doing is working and might be working for you now, but it's probably not going to be working for you, you know, in a year's time or whatever. So it's identifying the real problem of why they're not embracing the digital transformation in the first place. And a story will help you.
A
So, so I, I like what you said there. We have to find out their motivator. Yeah. In, in both the positive and the negative motivators. Right. We've got to dig deep into are they afraid of losing their job? Maybe they're going to retire in two years and they don't want to have to learn anything new.
B
Yeah.
A
Or maybe, maybe they just have a lot of other change going on in their lives that now work wants me to change things I can't handle. So I, I like how you do that first and then you tailor the story to help them. Maybe even show a little bit of
B
empathy in the story is that it's definitely showing empathy. And I think also too, you know, Darren, look, I've been involved in digital transformation for probably 30 plus years and you know, there's often talk about most of it fails. And I think because we don't acknowledge the negative stuff, we sort of try to, we try to focus on the positive and just squash it. But it was like, you know, people, people resist change, they don't like change. They got so much change going on. You know, can I just come to work? And they feel like it's constantly changing. So and, and, and sometimes they will potentially lose something. I mean, you know, let's not, let's not ignore the fact that a lot of digital transformation will result in job losses for a start in a lot of the cases. And why aren't we talking about that? So I think we got to acknowledge that and show that, yes, we know this is a reality, but you know, then, then focus on the positives and not squash all those negatives.
A
I, I kind of like that approach, but that approach is scary for a change agent. Right. Because what if I'm bringing up something they haven't thought of?
B
Right. Yeah, that, yes. It's like that's, it's, that's exactly. I work with leaders and they go, we don't, we don't want to focus on the job losses. It was like, people know and you can use all different words like we're going to be restructuring or. Right. Sizing or whatever that just equals I potentially will lose my job. And how do you not, how do you Just acknowledge that, that that's going to happen. I remember I worked with this leader, and he, he very much didn't want to hide the fact that was going to be job losses. He goes, there will be job losses, and I'm not going to shy away from that, and I need to accept. And I spoke to him more about, well, what do you. And he goes, but I really, really want people to know that, that we will do the best to find them other jobs, and we'll work through them and we'll respect them. And, and again, everyone's probably heard that in the past, but do they truly believe it? And so I, I said to him, you need a story around that so people understand that you truly, truly believe this, because you can say that, you can say you'll be treated well throughout the process, but people don't. And, and he had a story. He goes, I've actually got a story. And the story that he had was in a previous job, like a previous company. His manager came up to him and said, at the end of the day, he goes, we need to get rid of 50 people. And he gave him a blank piece of paper. He goes, by tomorrow morning, I want 50 names on this paper. And he goes, and if you can't find 50 names, make sure your name's on it. And he said, he remembered going home feeling so, like, disgusted with the process. And, and he said, I made a promise to myself then that if I was ever in a position where that needed to happen, I would treat people as people and not as numbers. And I said, you've just got to share that story. And it's. Through that story, even though I'm sitting here going, yeah, I might lose my job, I now truly believe that he, that I'll be treated with respect. But it's only through the story that you get. He got credibility around that message as opposed to just saying, you know, everyone's going to be treated with respect.
A
So I, I like that because it, it humanizes us. Right? Both. Both the deliverer of, of bad news and also as the receiver, like, you know, this really stinks. Yeah, right. I mean, it, it does. It does. When you're, when you're going through. Through that. All right, so let's say I am. I'm working through a digital transformation, and there are not going to be any job losses in my company. All right?
B
We're like, oh, good. All right, great. Yeah.
A
But there's going to be a lot of reskilling and a lot of, A lot of training and it's going to be bumpy and hard for the next three or four months. All right, how, how do I develop a story? So what, what are the key elements in, in storytelling that I need to bring out as. To help with, with what we talk about, about this emotional empathy and, and, and getting people to buy in. Right, That's.
B
Yeah, yeah. So that's, that, that's a great, that's a great question and great example, Darren, because a lot of people, yeah, predominantly I, I, you know, I work with organizations who are going through change or rolling out new values, and they want to communicate it through stories, which is brilliant. And the first place I say is like, what are all the messages you need to communicate? So, for example, if you're rolling out new values, it's like, well, each of them is a different message. You know, there's a value around, well, integrity. What does that mean? Or curry, you know, courage, or whatever it is. The ones around change is I help them identify, okay, what all the messages around change. But one of the messages that should be. And that you've just said there'll be messages around, but there's going to be. Reskilling is going to be required and that's going to be frustrating at times. So it could be a message around, you know, reskilling is frustrating and we, we know about that. It's going to, it's going to take, this is going to actually going to take a long time. And so we're going to need a bit of persistence and resilience to actually get through this. So it's identifying those stories. I, maybe would it be helpful if I gave you an example of a client story like that and then we can, and then we could break it down like, what the elements of why that's a good story. So. I remember distinctly doing some work with a leader, executive leadership team, and they wanted to learn storytelling to communicate why they were going through the change, which is great. And one of the execs, his name was Anthony, and his, his area, his department was going to bear the brunt of the changes. So they were sort of going to be the most disrupted by the change. And so he wanted the additional message of, yeah, this, this is not going to be easy. This is going to take a long time. We, we're going to need a bit of, you know, persistence and resilience to sort of get through this. So that was his additional message now. And I sort of helped him to say, well, you know, what's the story you could share about that? So Before I share the story, what I, what I often say to people is the most powerful stories you can share are the personal stories and attach it to a work message. So when I say it's just something that didn't happen at work, and they can be, they're the most underutilized stories, but they're the most powerful stories. Now, some of your work related stories can also be really powerful. So the story I shared before about the exec being told, you know, right. 50 people, that's a, that's a work story. But it was still a quite a personal story for him. Right. So I, I was working with his Anthony, this exec going, okay, so we, we've got to try to think of a story about persistence and resilience. Now I'm going to share the story that he shared.
A
Okay.
B
It's a really simple story, but then maybe we'll talk about why this is a really powerful story and the elements of it. The story he shared was earlier this year, my daughter Julia started school, and she came home from school really, really excited on the first day saying, dad, dad, guess what? They got monkey bars at school. And I noticed on her hands that she had blisters from the monkey bars. And I said to Julia, don't go on the monkey bars tomorrow because it's going to make your blisters worse. And she went, but, Dad, I really want to make it to the other side. She came home from school the next day, her blisters had burst. She'd been on the monkey bars again. Again. I said, don't go on the monkey bars because it's going to make your blisters worse. And this went on for about two weeks until she came home and said, guess what I did today, Dad? I made it to the other side. And I'm sharing this with you because it reminds me of the change we are about to embark on. We are going through something a hell of a lot more significant than climbing monkey bars. But imagine what we could achieve for our customers if we have the determination to make it to the upside.
A
Wow, what a great story.
B
Yeah. So. So a couple of, A couple of things. I can, I can talk about this. Yeah. Why that story is so powerful. First of all, it's so simple. Like, it's, it's about his kid climbing monkey bars, but it's so relatable. And those simple stories are really, really relatable. Now he's preempted someone saying, oh, yeah, but we're, we're doing something much bigger than climbing monkey Bars. He's preempted that by saying, we are doing something a lot more significant than that. So he's preempted that. The other thing. Have you noticed all the stories I've shared are really short, really, really short and succinct? So my guidance to people is aim for about 60 seconds with your stories. Like, they. They could be 30 seconds, they could be super short, and they could be 90 seconds. But if you're going to. If you're getting close to two minutes, your stories are too long. And especially if they're personal ones, people will start thinking, get to the point. And the moment anyone starts thinking, get to the point, you're losing them. So there's a real discipline about being super succinct. You'll also notice that when I'm sharing a story, I'm not using the word story. A lot of people go, let me tell you a story. The reason I'm telling you this story, the moral of the story. And they're just using the word story all the time.
A
So it makes it unpersonal, right?
B
Yes, it's sort of like. But also too, as our human brain. Our human brain is hardwired to listen to stories. We actually listen to stories differently as human beings. And especially in a work situation where it can be a little bit dry. And if someone says, well, that actually reminds me, when I went on an African safari last year, it's sort of like, hello, I'm listening to you differently because the brain has registered. You're about to hear a story. So my advice to people when they're sharing a story is start with time and place. So, you know, literally, I went on an African safari last year, or when I was a kid, I grew up on a farm. What that indicates is you're about to hear a story. One of the worst ways to start a story is, let me tell you a story, because please don't. So that's a. That's a. That's a. That's a. You know, keep them short and sharp. One minute, maybe 90 seconds. Start with time and place. You don't want it. And the way you end a story, it's sort of got to get the point across because. So in that story I just shared, it was like, imagine what we could achieve for our customers if we had the determination to get to the outside side. Can you see how that's quite respectful? Like, it's not. It's not like, the moral of the story is you need to have the determination to get to the other side.
A
Yeah, either I'm not an effective communicator, or you're too dumb to understand my story.
B
Yeah, exactly. And that's. That's one of the biggest mistakes people make is they start to go really directive with the story, and then. Then the person's going, yeah, like, I'm not an idiot. Like, and then. And then the story doesn't work. So it's. There's a. That's where the real skill is in how you take that personal story, connect it to the business message so people get it. They get the message, and they connect with it without you going, the moral of the story is,
A
Now this total. This totally makes sense. And why. Why can't we just naturally do this?
B
I think. I think as humans, we naturally tell stories. So a lot of people go, I don't tell stories. I go, well, you do. It's just how effectively you tell them in business. And. And look, I. I often say to people, it's a skill. It's literally sharing stories effectively in business. It's a skill. And if it wasn't a skill and it was really simple, everyone would be doing it, and everyone would be doing it well, and. And they're not. And we've seen so many. I wouldn't have a job. I can tell you right now, I wouldn't have a job. If storytelling in business was simple and easy, and I sort of get on one hand, it's like, well, how hard can it be just telling stories? But there's a real skill to that. And, you know, and what I hope is what I give people is, first of all, I hope. I feel like I give them permission. And what I mean by that is, there's still a lot of people in business that would say to me, you know, I've just never, ever thought of sharing a personal story in business. I've thought, it's not professional or whatever. So I give them permission, and then if I give them the skill how to do it, it's given them the capability to do it, which then would lead to the confidence to actually give it a go.
A
Okay, so here's. Here's a serious question.
B
Yes, all your questions have been serious, Tara.
A
Oh, can I make up a story?
B
Oh.
A
Or should it be a personal story?
B
That's a very serious question. And the answer to that is, well, let me. Let me answer that, because a lot of people ask me that. A lot of people go, oh, you know, if you make up a story and it gets the point across, that's okay. Little white lie. So Imagine if you were in the audience and you work for Anthony that did the monkey bar story and he shared that story with you as a
A
leader and he doesn't have a daughter
B
and he doesn't have, or he just said, or you said, God, I really loved your story about the monkey bars. I, you know, I, I remember, you know, my daughter doing the same thing. And he went, oh, I just, I just made that up. So where's his credibility?
A
Yeah, it's gone.
B
It's gone, it's gone. And, and the point is now you, it, it, that's very hard to get back because can you, can you sense this is, it's more than a little white lie. It's more than a lie. What it feels like is a betrayal of trust. What it feels like is emotional manipulation. And I fell for it. And it's like the credibility's gone. And so I think people, I say to people, I get that you've probably made up stories in the past because you think your own stories aren't big enough, but the reality is once you know how once, it's so much easier to find your own stories and, and stick to them and don't exaggerate them. And so, yeah, if you, if you're sharing made up stories, you're running a real risk to your credibility. And also you'd want to be a bloody great actor if you're making up stories.
A
Well, you brought up another thing, because I've been totally guilty of this, exaggerating the story just a little bit. Right.
B
To make the site. You know the saying, don't let the truth get in the way of a good story.
A
Yeah, yeah. I mean, but what you're saying is that's, that's dangerous to trod.
B
Yeah, right. It is. And not. And the reason we've exaggerated stories is because we think that the version of the story that we've got is not good. Like it's not big enough. It's like no one would be in. I'll just add it, I add a little bit of mayo here and there. And the point is those day to day stories, like the average stories, almost to the point you think, why would anyone be interested in this? Like, why would anyone be interested in a story about my daughter climbing monkey bars? But the reality is they are the most relatable stories and it's what people connect with and then they connect with you. And so all the research shows that if you share a story, people not only connect with the story, but they connect with you as the storyteller.
A
So, so if you're in genuine, then yeah, yeah. Then you don't have a genuine relationship.
B
Yeah, absolutely.
A
Which you and I both know as a change agent, those relationships are what gets you through the tough times of the digital transformation.
B
Absolutely, absolutely. So the story, I say this, stories, what we just spoke about them before, they can actually fast track relationship. So if you're meeting people for the first time, whether it's a new person to your team or a new stakeholder or a new client or potential client, it can fast track the relationship, but they also strengthen existing relationships. So again, as a leader and you've got a team or a project team, when you're sharing personal stories to communicate the message, every time you're doing that, it's strengthening the relationship. And as you just said, a digital transformation isn't a one week project. It can sometime go for years. And how you strengthen the relationship with those people you're working with and strengthen and maintain that is critical. And like the added benefit of sharing those personal stories is that's what will happen.
A
How, how dangerous is it to use. Because when you were talking about digital transformation takes time. How dangerous is it to use stories that happen during that digital transformation as a story to continually build a bond and a relationship with your team? Or are they going to see that as manipulation? Because I hate to say it, storytelling is a little bit of manipulating, right? Kind of. Or is it not? Or am I thinking.
B
So. No, I, so I, it's what, it's what you think is manipulation or influence. And so I think, and I genuinely think if you come from, from storytelling from a very authentic place around, around two things. One is you've got to believe in the message. So for example, if you're good, if you're delivering a message about this change but you think it's not a good change, like you don't. Then that can start to feel like manipulation. But if you truly believe in the change, truly believe in it and, and your story is true, then to me that's inspir, like inspiring influence and inspiration, not manipulation. I just to give you another example, I was working with a team a couple of years ago and they were, they, they wanted, it was just upskilling their leaders around storytelling around all these changes that were happening. But one of the changes that was happening is they were moving to an open plan office. And one of the, one of the. Yeah, like I, I couldn't, this was a few years ago and I was thinking what you just like most people are going back the Other way. But anyway, y.
A
Exactly.
B
She said to me, she came up in the break and she goes, what? One of the messages around the open plan, she goes, I can't tell a story about why going to open plan is so great. She goes, because I have been a very vocal, like, against it because they were like lawyers, the legal. The legal team. And she's going, I have been so vocal against this. It's going to cause so much disruption to my team. I can't go out with a story about how great it's going to be. And I. And I looked at her, I went, no. Like, no one's telling. Why are you even thinking that? And I go, tell me what you really think about, you know, open plat. And she said, I understand why they're doing it and I appreciate that there are benefits. I get that it is actually just going to be a massive challenge and transition for our team to get there. And I go, right, that's your message. That's your story. Okay, so now the message is around. Oh, not all great. And then I started telling her, have you had times in your life where you've really resisted? And, you know, and how I help people get stories is ask some questions. And as soon as I did it, she went, oh, my God, I've got this story where my husband, we used to live in Perth and he wanted us to move to Sydney. And I just resisted, resisted, resisted for so long. And then we've moved and I look back now and it's the best decision I've ever made in my life. And I was like, fine, there's your story.
A
There it is.
B
There's your story. So the story is acknowledging. I get this is going to be hard. And, you know, but, yeah, so, yeah,
A
I really like what you said because you're. The storytelling that you're talking about is really about your authentic self. People can see through. People can see through you making stuff up.
B
Absolutely, Absolutely.
A
Oh, this is. This has been fabulous, Gabrielle. We're out of time, which I'm really excited.
B
Oh, my God, it's gone. So.
A
I know. I mean, we can talk on stories all day long and share. Share some stories. If people want to find out more and learn more from you and your books and things. Where do they go? Is there one place they can go to to find out more?
B
Yeah, Look, I'm on LinkedIn, so absolutely connect on LinkedIn and my website's just Gabrielle Dolan dot com. But yeah, my latest book, the Story Intelligence book, I feel like is. Is the 20 years of my life in this book. So if you want one resource that I that's going to help you understand why storytelling is powerful. How to find the stories, how to share them, where to share them, how to use AI to help you find and refine stories but not lose your voice. I truly, truly believe that in a world of AI generated content, our stories are needed so much more than ever. So yeah, so that's where you can find me.
A
Well, hey Gabrielle, again, thanks for coming on the show. This has been incredible.
B
Thanks Darren for the opportunity.
A
Thanks for listening to Embracing Digital Transformation. If you enjoyed today's conversation, give us five stars on your favorite podcasting app or on YouTube. It really helps others discover the show. If you want to go deeper, join our exclusive community@patreon.com embracingdigital where we share bonus content and you can always connect with other change makers like yourself. You can always find more resources at Embracing. Until next time, keep embracing the Digital Transformation.
Host: Dr. Darren Pulsipher
Guest: Gabrielle Dolan, Master Storyteller & Author
Date: February 26, 2026
In this episode, Dr. Darren Pulsipher welcomes master storyteller Gabrielle Dolan to explore the powerful intersection of storytelling and digital transformation. They discuss why people—not just technology and processes—are at the heart of any transformation, and how authentic stories can help leaders break down resistance, foster empathy, and build lasting engagement through challenging change initiatives.
“I learned the skill of storytelling, being one of eight children and sharing stories to get my parents’ attention… What I noticed, when I shared a story about why we needed to change, it wasn’t a silver bullet, but it would lower people’s defenses and help them see things differently.”
“You could have the best technology and the best processes and the best systems, but if your people aren’t adopting them and are resisting, it’s going to amount to nothing.”
“…We don’t acknowledge the negative stuff, we try to focus on the positive and just squash it. But it was like, people know… let’s not ignore the fact that a lot of digital transformation will result in job losses in a lot of the cases. Why aren’t we talking about that?”
“Our human brain is hardwired to listen to stories… if someone says, ‘That reminds me when I went on an African safari,’ it’s like, hello, I’m listening differently…”
“If you’re sharing made up stories, you’re running a real risk to your credibility... it feels like emotional manipulation and it’s hard to get back.”
“As a change agent, those relationships are what gets you through the tough times of digital transformation.”
This episode reveals that authentic storytelling is a leader’s secret weapon in overcoming resistance, fostering empathy, and sustaining momentum through turbulent digital change. The best stories are simple, personal, honest, and brief—never fabricated or overly instructive. In an age when AI threatens to depersonalize communication, human stories are more vital than ever for meaningful connection and transformation.