Shannon Flanagan Podcast Transcript
Shannon Flanagan joins host Brian Thomas on The Digital Executive Podcast.
Brian Thomas: Welcome to The Digital Executive. Today’s guest is Shannon Flanagan. Shannon Flanagan has been retailing it since she was 18 years old. She is now the founder, CEO of Retail Connections, doing business as Retail Women in Tech, a movement uniting women and allies regardless of title, function, sector, and age to get more women in the rooms where decisions are made.
She is a recognized top retail expert on AI, leadership, and workforce transformation. Drawing on a career across retail, consulting, and technology, she writes and speaks about building organizations where technology expands human potential. Well, good afternoon, Shannon. Welcome to the show.
Shannon Flanagan: Hello, Brian. Nice to meet you.
Brian Thomas: Absolutely, my friend. I appreciate it. I’ve been excited, looking forward to this podcast. You’re in Berkeley, California. I’m in Kansas City. So I appreciate you- Oh,
Shannon Flanagan: I was born in Kansas City
Brian Thomas: Oh, yeah. That’s where-
Shannon Flanagan: But I grew up in St. Louis.
Brian Thomas: That’s amazing. Yeah, that’s just a stone’s throw away.
So I appreciate you making the time. I know time zones and calendars is hard as you know with sometimes in PR as well. So Shannon, if you don’t mind, I’m jumping into your first question. You’ve said you caught the retail bug at 18, folding jeans and never looked back. Going on to merchandising and buying, consulting at Accenture, business roles at Gap, Lands’ End, Macy’s, and eventually a full tech general manager role before founding Retail Women in Tech.
At the age of 25, you discovered your why: to create the conditions for people to love what they do every single day. How did you… How did that early sense of purpose shape a career that spanned so many sides of the industry, and what finally led you to strike out on your own?
Shannon Flanagan: Well, I think it’s important to come back to that moment that happened.
So it was, It, it originated b- around a couple of things. One, I found corporate America soulless and was trying to find meaning in the work that I was doing. I was also really interested in neuroscience, and at that time, this is when all the -ologies were starting to come together. There was a lot– Now, now it seems kinda commonplace, right?
This is twenty-five years ago around what it means to be satisfied, content, happy. But more practically, my client was Gap Inc., and we were imple-implementing, like, new technologies, processes, structure, and nobody was adopting it. So I dug deep into organizational design and leadership and change management, and really recognized that at the end of the day, I, I…
And I always knew that my, you know, it’s kind of my Achilles’ heel, that I believe in the potential of people. But it came back, though, to we can create conditions for people to love what they do every day, and when they do, there is a ripple effect. And when they do and maybe we think about from a nonprofit perspective, which now I run a charity organization, but we, we don’t really think about the, the power and impact of happiness in the day-to-day work that people can have in, in, in corporate America.
And if they’re happy, they’re gonna go home and be happier with their family, their kids. They’re gonna pay it back to their communities. So I really did think about this ripple effect and virtuous cycle at a very young age. And that has been my through line throughout my career. And we can go on to the, like, striking out on my own, but I, I wanted to pause and give you a second on that question.
Brian Thomas: No, it’s totally fine. Yeah, no, you can, you can talk about striking out on your own if you like.
Shannon Flanagan: So striking out on my own, there’s, there’s two facets to it. I’ve written a book called Choose Don’t Chase Your Career, and it… you can dive deep into the stories that I have there around how, how I got where I am.
But I decided to go out on my own, facing every limiting self-belief in spades multiple times. But then the, the biggest decision for me was actually not going out on my own, which I thought it was. The biggest decision was going all in on starting a nonprofit and writing a book, and putting aside all of the definitions of success that I believe the majority of us, in particular women, but also men, assign to titles, status, and money.
And I chose to prioritize fulfillment. And financial fear was a huge part of my ethos that I had to work through, but I got to my… when I came back to my why, which is to create the conditions for people to love what they do every day, I knew that the way that I could do that was through building this nonprofit and writing this first book, amongst many that I plan to write as well.
And the belief is that, for me, is that we, we should love what we do every day. Now, that doesn’t mean that it’s easy. I will tell you, making the choice to go out on my own has been the hardest thing I’ve ever done. I am working the hardest I ever have. I am the s- most stressed I’ve ever been. I am the poorest I’ve ever been, and I am the most fulfilled
Brian Thomas: That’s awesome. And really, we’ve heard this, follow your bliss. You’ve heard different things like that. If you love what you do, you won’t work a day in your life, and totally get that, so I appreciate you sharing the backstory. It’s very helpful for our audiences. That’s kind of usually how the first question starts out on the podcast.
But talking about corporate America, you’re absolutely right. I liked how you said it was soulless. But you were curious why as you moved through your career, why new systems weren’t being adopted successfully, and you dug in. I thought that was, that was interesting with your curiosity, and it comes back to people, the glue that holds everything together.
And if people aren’t happy, as you said, things don’t come together. So again, appreciate the backstory. Shannon, Retail Women in Tech, and I’m gonna call it RWIT here, is a global community you create to… you built to create life-changing connections for women and allies passionate about retail and technology.
You’ve been candid that starting it was risky, living in an expensive area, supporting three teenagers, willing to burn through retirement to build a nonprofit. What made you believe this community needed to exist badly enough to take that kind of personal risk?
Shannon Flanagan: So one, it wasn’t even my idea. That’s a whole story in and of itself.
But the reason why I’ve dedicated my life to it, and it was a decision I made a little over a year ago is because there… And it was the cause of the, the community being started in the first place. But a handful of reasons why I’m willing to do this and do it every day is, one, there is so much incredible talent untapped.
And that’s not just true in retail, that’s true in other industries. We are so defined by the silos that we have grown up in, and that thwarts not only industry growth, but individual growth. And I also believe that too many women’s organizations, not all, and we’ve evaluated a bunch of them, are really a focused on the community and not the outcomes.
And for me, the reason why I’m willing to take this risk is because I know we as a society have to have women in the rooms where more decisions, where the decisions are being made especially in the world of AI. Like we are, we are effed as a society if we’re not there. So for me to take the, the risk, this isn’t a, this isn’t…
It is, yes, maybe a personal risk, but this is a commitment that we all need to be making in the world that we are moving into. And there is something about the, the qualities that women traditionally have or have been assigned to as soft skills are now going to be the competitive skills in the world.
And so we’ve got to foster the spaces. And when we foster these spaces, so many of the women’s communities focus on those that are senior And the word exclusive is a word they love. To us, it’s an ick word. We really represent those that regardless of age, title, function, sector, status, gender, that we’re all coming together to say the best outcomes for our society, let alone our industry, is more perspectives in the room.
And we need more women there sitting in the rooms, making the decisions, and helping to frame what’s coming next. And we as women have been evolutionarily designed to be actually pretty primed for what’s going on in the world as it… in, in the world of AI as we, as we optimize the difference between what AI can do and humans can do
Brian Thomas: Thank you. Appreciate that. Lot there to unpack, but I, I really do appreciate your insights. You, of course, you started out talking about that personal commitment and risk you took to step into this nonprofit. I thought that was awesome. And then you said too many people or, or women sometimes focused on the, the circle or the community versus the outcome.
I thought that was interesting. And then, of course, it is important that the people we’re doing business with, right, were, are represented in those companies in leadership roles, and that’s what your, your whole mission is here, is to get that representation, so I appreciate that. Shannon, your take on change management is refreshingly simple.
Love this stuff. You’ve said the easiest and best strategy is just to talk to your people and have everybody engaged. As retailers race to adopt AI, why do so many transformation efforts still fail on the human side? And what do leaders consistently get wrong about bringing their teams along?
Shannon Flanagan: So I do come back. I have a very simple change model that I learned about 20 years ago, which is potential minus interference equals performance. So we have inc- an incredible amount of potential, right, that’s sitting right in front of us. And I think as leaders, our focus is supposed to be around removing the barriers, so we can get to performance.
But there’s a paper we’re actually going to release in about a month that is talking specifically on this topic, which is the paradigm shift that I personally believe we need to have around how we’re thinking about transformation, in particular in AI. We are living in a world where we’re doing everything that we’ve done always the same before.
We are plug and playing it into projects, et cetera. This is all uncharted territory. Nobody knows what we’re doing and we’re all trying to figure it out. And the Maslow’s, like, he’s got a quote, I think it’s from him, something like, “If the only tool you have is a hammer, you tend to see every problem as a nail.”
And that is how we’re approaching AI. To me, the paradigm shift that we need to think about is that it’s not human in the loop. It should be technology in the loop. When we think about who we are as humans and our basic needs, we all need to feel… All, every human, right? Coming back to Maslow’s needs, but I’m gonna do it the way I think about it.
We all need to be, feel seen, we wanna be heard, respected, feel safe, trusted. That is as an employee, and that is also as a consumer And so we believe my organization and what I’m do- we’re doing with Women to Watch, is that we really need to shift the conversation around not ROI, not adoption, but to readiness.
We really need to reframe the trust as an infrastructure that we’re leading to hard with technology, we’re leading to more forward with business. We really need to reimagine the way things work and who is bringing the value. And AI is not, AI is doing a lot of amazing things, but it’s also exposing a lot of the weaknesses that we have and the way that we operate today.
So to me, it’s the biggest opportunity is that we, one, as a society need to recognize what we are amazing at as humans. But when we think about it from a change perspective, is to recognize that there’s a ton of fear in the system. And that fear could be you’re at a C-level, you’re an individual contributor.
And the fear is not just because of my job, it’s because it’s also what’s happening when we’ve got models going out and, invading other places, right? That we didn’t know about. So the orientation shift that is important for us as a society and as change leaders is to start with the humans first and design the, the, the processes, the technologies, the business around what human needs are.
Brian Thomas: Thank you. Appreciate that. I love this this takeaway, your take on change management. Potential minus interference equals performance. I thought that was interesting when it comes to projects as well. There needs to be a paradigm shift, as you said, as we try to implement a transformation, you know, especially with AI.
You dipped into, of course, Maslow’s hierarchy of needs. You talked a lot about people and the needs of people and what it takes to really build something great and engage people. And again, you mentioned also not about ROI, but readiness. So thank you. Shannon, the last question of the day, this is great.
You’ve– you’re recognized as a top voice on AI leadership and workforce transformation. As AI reshapes both how retail operates and what careers in the industry look like, where do you see retail tech and the retail workforce heading over the next five, maybe ten years? And what should women entering the field be doing right now to position themselves to lead it?
Shannon Flanagan: The biggest shift that we’re gonna have is what has defined success is changing. So the qualities, the skills, the capabilities that we have measured against, as an example, functional expertise. That as we transition to, I, I believe, new roles and new qualities around builders, operators, but more importantly, connectors.
And as a result of that, we are going to have to figure out new ways that we build talent, we judge talent, we measure talent. Because things like judgment, discernment, ethics, right, are going to replace functional expertise. So with that being said, the qualities that are required to win in the new world of AI are shifting, and they’re shifting dramatically, but we don’t actually have the infrastructure to manage to that.
So, and this comes back to this idea that the softer skills are not gonna be the competitive skills. I also think it’s a conversation around the fact that we have 32 senses as humans, but we really only rely on five of them. And for humans to succeed in the world of AI, let alone us as individuals or women, we need to be opening the aperture and tapping in to the things that make us uniquely different.
And for women, what that means is, one, we’re more like– we’re, we’re more likely to be uncomfortable or not confident to enter AI roles. And in my point of view, AI is not a technology, it’s a way of life. So it’s not about being a data scientist or whatever, it’s that we as women have the opportunity to bring the things that we have been evolutionarily designed to be great at.
It’s not that we’re– like, it’s not binary, right? Men can do all of these things as well. But to come in and really recognize the value and the voices that maybe we have suppressed historically, and bringing them in to the conversations as we design a operating model with AI at its core
Brian Thomas: That’s awesome. Appreciate that, and you’re absolutely right. Obviously men and women are built a little differently, but they all have something great to contribute in this whole ecosystem that you talked about. Bringing them into the conversation, making sure that they’re represented at the table for decision-making and, and, and just all kinds of stuff.
I think that’s amazing. You also said you- the shift that is gonna be defining is really what success looks like in the future. You talked about having operators, builders, but most importantly, having those connectors, those people. We’re still gonna need that human connection even more, I see, as, as we move into this age of AI.
But as you also mentioned, soft skills will be one of the most important skills to have in the, in the future as we move forward. So thank you. And Shannon, it was such a pleasure having you on today, and I look forward to speaking with you real soon.
Shannon Flanagan: Sounds great. Anytime.
Brian Thomas: Bye for now.
Shannon Flanagan Podcast Transcript. Listen to the audio on the guest’s Podcast Page.
