How do you inspire employee adoption without forcing it?

Ron (00:01): Welcome to season two of Frontline Fridays, brought to you by YOOBIC. I’m your host, Ron Thurston, and this season we’re digging into what it really takes to lead on the front lines of retail and hospitality. Together we’ll explore the biggest shifts in frontline work and how smart leaders are navigating them to drive results where it matters most. Each episode, you’ll hear from top executives, industry experts, and powerhouse operators to share practical tactics you can put to work immediately.

Ron (00:30): Today’s conversation is about something every leader faces: rolling out new systems, tools and ways of working. But this isn’t about change management. It’s about inspiring adoption. How do you get your teams not just to try something new, but to truly believe in it? My guest is Missy Poole, an executive leader and consultant who’s held senior roles at Apple, Ralph Lauren, Gap and West Elm.

Ron: Today she helps retailers design digital strategies that enhance employee and customer experiences through communication, training and connection. Missy has built high performing teams across luxury and large scale retail, and she continues to champion what she calls building trust with your customer through frontline tech adoption. We’ve been friends a long time and I’m excited to welcome her to the show. Missy, I am so excited to have you on this episode of Frontline Fridays.

Ron: For many reasons, but maybe most importantly, you are someone who has grown up in the field, has led the field, has been a frontline leader for your entire career. And our friendship goes back, we’ll just say, more than a couple of decades. And the best part of this show is being able to highlight people like you that have done the hardest work and have built incredible teams. So I just wanted to say welcome, and thank you.

Missy (01:50): Ron, well, gosh, I look at you and you just make me smile every time I see you and hear your voice. And I’m honored to be here, and so grateful for the work that you are doing to promote the work that everybody in retail does, and that retail is a career. You’ve been an inspiration my entire career. And I now can go to your podcast and to your books for advice and insights if I can’t reach you. So grateful to be here today, and thank you for highlighting the work that everybody we know in the retail world is doing.

How did Missy Poole build a career across Gap, Ralph Lauren and Apple?

Ron (02:34): I credit Gap Inc for much of my career. Some of the early mentorship, early learning and development that I had, the investment that people made in me very early in my career, all happened at Gap Inc. And sometimes it is right place, right time, right leadership team, right investments. And you and I had similar experiences, very early Gap. So give us some quick highlights of your career.

Missy (03:00): Yeah, Gap Inc for sure. It was the foundation where I learned from so many amazing leaders who inspired me, guided me and were by my side. In fact, there is one person that stands out specifically when I was making my decision to select which company I wanted to work with after college. This person, who would then become my boss, reached out to me at home. I was living at my parents’ home, on our landline. My mom answers the phone, and they get into a 30 minute conversation. I was away, and I came back that night, and my mom said to me, this is the person you need to work for, because she already demonstrated care, investment, and that she was going to focus on my development right from the beginning.

Missy (03:56): The way she made me feel is how I wanted to become as a leader throughout my career, and stay in the field and in the stores. And we had fun. Gap Inc, Banana Republic. The Gap division launched a new division for Gap called Forth and Towne. And that was a very cool experience, starting from the ground up. That was all about field development, getting people ready for the next level. I was there about 15 years.

Missy: After Gap, I followed our president from Banana Republic to West Elm. West Elm was converting from a catalog business to brick and mortar. So again, growing a business, getting people ready. And when he left, that was when I made the choice to go work for a brand that I had admired for so long, and that was Ralph Lauren.

Missy (04:40): I fought so hard to get a role at Ralph Lauren. I just loved everything that Ralph Lauren stood for and what it was about. It was based in New York City, and the dream that Mr. Lauren would create through his imagery and through his product. So thankfully I got to be selected to join the company as a regional director of the Southeast, and then opened up the women’s store on Madison Avenue, the flagship of the world for Ralph Lauren, and had such the honor to help Mr. Lauren become known as the premier women’s American luxury designer. And then I took over the East Coast, from Boston to Florida, bringing the brand to markets outside of New York City. Did that for about eight years.

Missy (05:20): And then I had the opportunity to work for Apple. And I believe, and Steve Jobs says this, you connect the dots looking backwards. Everything in my career led me to working in the field for Apple, and bringing Apple’s vision to life every single day in our stores. I did that for about eight years.

Ron (05:51): And recently moved into board work. Your power for even a bigger purpose.

Missy (06:00): I recently graduated from the corporate world.

Ron: We don’t retire, Missy. We come from the field. We don’t retire.

Missy (06:10): We don’t stop, exactly. So I graduated from the corporate world after 33 years. And now I have the fortunate opportunity to support in multiple ways: our future talent, board work, advisory work and mentorship.

Ron (06:30): When I tell my story about the fact that my career was not all just luxury, my career varied between technology, between luxury, between contemporary, and the power in that, which is what I really encourage students to do, and I’m sure you will as well with your work at FIT, is there’s such beautiful experiences that happen when you swim in different lanes. And what you learned from these powerful brands like Gap, Ralph Lauren, Apple, is so unique to that brand. Staying in the same brand, sometimes you miss those opportunities. And there’s more similarities among them than differences when the focus is on people.

How do you lead frontline teams so they love the work?

Missy (07:20): But think about it from a frontline experience. For me, as a leader for the frontline teams, it was important to be alongside them every day, and really identify and understand what our frontline team members are going through, and what we can do as a leadership team to help make their jobs easier, and more satisfying, and give recognition for what they do every single day. It’s hard.

Missy: In all of these companies that I worked for, they all have their vision, their mission, but ultimately as a leader it was our objective to bring the vision to life and help our teams understand what that vision is. And it was all about customer satisfaction. Everybody wants to have great customer experiences. Every team member wants to love what they do. Yes, they are passionate about the product, there is that motivating factor. But ultimately, how we lead is: how do we instill trust? How do we ensure our team members know that we have their back and we support them? I had to identify what I wanted to be known for as a leader, and that was a leader who helped get things done for our team members, and be the voice of our team members on the front line.

Ron (08:55): And you did that so beautifully, because you didn’t have the corporate roles. At Apple, you were running the store on the Upper East Side. You weren’t just observing it from afar. You knew exactly what they needed every day. And I have such admiration for that. Similarly, when I joined Apple, I joined as store director of one store, and it kind of kicked my butt for a while, because I hadn’t actually done that. And it’s hard. This was a long time ago, but it’s still hard. When you’re in there, and I was there on launch day recently for the new film, that is hard.

Missy (09:20): Yeah. And we try to make it fun, and our team members are so passionate about the product and working with each other. That’s something that’s really important for leaders to do: how do you create an effective team where people love working with each other and love coming to work every day? That was something we spent a lot of time on. What’s going to make you want to love coming here every day? We would do many things in our stores to make sure that happened. But being alongside them is so fun. You’re making me reflect back on so many of those moments, where those are the best moments of my career, when I could be next to the team member when they’re working with customers and working with each other.

How do you assess a new team when you take it over?

Ron (10:15): I love what you said around love what you do every day, come to work loving your job. And I think we actually do that better in the field than people do in corporate environments. So how do we translate that? My question is, when you’ve walked into these new environments and you’re assessing the situation, what’s your go-to strategy? What’s your playbook, if you have one, to figure out what’s actually going on, how people feel?

Missy (10:56): Yeah, I think the most important thing when you go into a new environment is get to know each person individually. Take the time to spend time with each individual and learn about them. What makes them tick? What’s their motivating factor? What are they excited about? What brought them here in the first place? And then I love to do a start, stop, continue approach. What’s working? What’s not working? What would you like to see done differently here, to make sure that everybody is excited about being there? I would then pull all that together and recognize the patterns.

Missy (11:40): And I also use that 80-20 rule. So let them speak 80% of the time, and you speak 20% of the time. Really go in with a curious mindset, asking all those questions to get to know them, and then take the time to summarize back what they’re saying. I love reflective listening. I have a mentor in my life that really taught me reflective listening, and that was a skill that shifted my leadership approach tremendously. The person you’re talking to really feels heard, and you’re clear on what they’re saying. So that 80-20 rule is really important.

Missy (12:20): And then there are times where I was given feedback by a team member. She said, well, I want to learn about you. I want to learn about who you are. So then it helps me open up more. I said, my story is not that exciting, but then I realized, she’s like, no, you’ve lived and overcome some adversity, I’m sure. And so I really had to dig deep and be vulnerable and be an authentic leader and share stories. That’s when I realized that I would connect easier with people. That’s when you really instill trust, when they believe that you’ve overcome things similar to what they’ve overcome. That’s how I found connecting later on in my career was really important. They want to hear your mistakes. They want to hear the struggles that you may have had and how you overcame them, because then they know that you’ll be able to help guide them as well.

How do you get retail staff to adopt new technology?

Ron (13:15): That’s a learned skill, that ability to build connection through vulnerability. I think that’s hard for all of us in leadership roles. What do I share? What do I not share? Do I look weak? I love your perspective, that that’s actually how you got buy-in and moved them forward faster. I want to move into this idea of adoption, because you have worked for brands that have also led in technology. Apple’s an obvious one. But Ralph Lauren at the same time has been a leader in tech adoption. So when you’re thinking about how to do this, how do you get trust built from your team to adopt? Because adoption rates on new technology in retail, in the field, can be rocky. So what’s been your strategy around tech adoption?

Missy (14:20): Throughout my career, I really saw the evolution of technology. I was there during the internet, and I’m now here during AI, and tools that our team members can use on the front lines that can help make their job easier. Working for Apple, we had some of the most innovative tools to use, but Ralph Lauren as well. I remember starting at Ralph Lauren, and I would receive books of these beautiful product knowledge books, that I think I still have, because they were stunning and beautiful. But you can’t scale that. So we knew we had to move to digital training and digital clienteling and information. We were using AI before it was called AI. Many of the companies I’ve worked for, we were using technology before it actually had a tag name. We were using augmented reality at West Elm prior to it actually becoming a thing.

Missy (15:03): So I think what’s really important is to understand the impact it will have. And when you’re helping people adopt this new technology, it is getting them to try it. It’s finding the team members that know how to use it effectively and pick up on it quick, and using those people to help everyone else adopt to this technology. Because for some people, technology is very easy to pick up. If you grew up with technology, we have team members that were born and didn’t know life without an iPhone. Those are the people that know technology and pick it up really quickly. And then there are people that had technology later on in life. So the adoption rate can shift based on people’s experience with it.

Missy (15:55): When you get people to utilize it, it can be scary. So you have to identify those people that need a little bit more time to understand how to use it, and then help them see the value of it, because technology can make our lives so much more efficient and effective if used appropriately. But it’s really taking time, investing the time in those that need a little bit more time to adopt. And then when they see the success of it, it’s the practice. For the frontline team members, they can add so many more clients to their database. They can have more effective relationships with clients using technology. They can personalize their relationships with clients through technology. So there are many ways to utilize it. It’s just getting that buy-in from the beginning, taking the time with those that may struggle with technology. And there are still people today, I’m advising different companies on using technology, where it’s sitting down with them, showing them how it can be useful, and then giving them the time to practice and recognizing the successes that they have.

Why does forcing technology on a team backfire?

Ron (17:18): And clienteling is one that I think is so tricky, because you are introducing technology to a human relationship. My clients want this, my clients want that, and this is how I communicate. I only text them on Tuesdays between five and seven. You and I have heard it all. I remember building, with our mutual mentor Matt Marcotte, clienteling solutions at Tory Burch. And this is before they were available to buy, so in the build years. I remember visiting stores and they would not use this technology. Absolutely not. My clients are in a binder, and I text them, and that’s how it is, Ron, and you need to get over it. There’s this evolution that continues to happen, but sometimes the most important part of any retail business is the human relationship. We were literally taking a binder out of someone’s hands. We were threatening to do that. I’m going to throw your binder away if you don’t use this technology. Reflecting back, I’m like, why were we so aggressive? Why were we forcing people to do that? I’m just curious if you’ve had great experiences, or things that really surprised you.

Missy (19:00): I think where I’ve seen it work is when you have the data to back up what you’re sharing. So for example, we know customers have shopping patterns. When they shop for a product and a fit, they will purchase it in multiple colors. So if you have that customer’s buying patterns, and you can show your client specialists or your team members that they will have success if they reach out in this way, and this is proven, that’s where they’ll get buy-in. We encourage them to try it. We’re alongside them. A lot of times people weren’t sure how to communicate to their customers, or what to say. Now there are some amazing tools on how to do that with AI, but our leaders can guide them on what to say, and be there with them, and coach them and give them feedback.

Missy (19:38): And then we would see the success of the customer response. When the customer responded to what they were saying, we’d celebrate that in front of everybody. So then everybody said, wait, I want to do what they’re doing. Especially with commission-based team members, they would see that their paychecks were impacted when they’re utilizing these tools and these resources. And ultimately our customers are also giving very positive feedback on these experiences. So the human factor, the human connection, comes through the personalization, and that personalization comes from the technology that we’re utilizing. It’s a balance of both.

Missy (20:30): I also learned the impact of peer-to-peer relationships at this time, because there were team members that did this extremely well, clienteling and utilizing the technology. And now you can schedule times to reach out to customers, you can even put an out of office in your texts, so you can manage your time more effectively. So our peers would share these best practices with each other, and we’d see team members respond to that. We’d have mentorship within stores, and that would help the adoption happen quickly too.

What do leaders get wrong when they roll out new tools?

Missy (21:10): And then of course there’s the resistance. I think the resistance would happen when we move too fast, when we don’t slow down. As leaders we tend to go into solve mode very quickly. Especially if we’re getting pressure about meeting numbers, meeting results, we move quickly because we’re feeling the pressure. That’s the most important time to slow down. We have to bring in key stakeholders and talk to people before we roll things out, because that’s where we make the biggest mistakes. And then also, when we make the mistake, admit to the mistake. If you move too fast, that’s okay. Pull back and say, we’re getting negative feedback on this, acknowledge it, say I’m sorry, and you will get back on track quicker. But if you avoid it, if you avoid talking about it, that’s when I’ve seen it go haywire, and there could be a lot of dissent among the team if we don’t acknowledge it.

Ron (22:30): And because there are so many new tools being developed, and the current AI growth state, this conversation about adoption in the field continues to come up, because more and more tools are being introduced, platforms are being consolidated. I’m on multiple calls a day where they say, Ron, how do we make sure the field uses this? And it’s what you just said, Missy, exactly that. You ask questions, you determine what they need, why they need it, how they will use it, when they will use it. And you provide the solution to the team that is most beneficial to their business, and to their employee and customer experience. If you’ve missed all those steps and you just say, surprise, we went to NRF and we bought this, we’re going to roll this out, and the team’s like, why, why did you, we’ve never asked for this. You will not ever get what you expect. There are basics around adoption that to you and me sound like common sense, but are not. So the more you share that story, the better. This is only going to escalate.

Missy (24:00): It’s so true. It’s moving so quickly, and it’s a huge investment for companies. So that first step of, let me pull in some team members before we get this going, and just get their input, advice, feedback, tell them you need their help in rolling this out. And they do. They work out the kinks, they help you answer some of the questions before you roll it out, so you’re not getting slammed with all the questions up front. So being a collaborative leader is really a great approach that I see.

How would you describe your leadership style?

Ron (24:30): I want to move into some time about your particular leadership, the success that you’ve had in the brands and coming from the field. How do you describe your particular leadership, and how do you teach it to others?

Missy (24:45): Yeah, it’s evolved over time. I am so grateful for the feedback that I’ve received throughout my career, and I really listened to it. There were moments where I was getting feedback and I’d say, what am I going to do? This is all I know. I don’t think that I can move forward. But because I had people that guided me and invested in me, and I have mentors in my life still today that I go to, you’re one of them. One thing that I’ve really tried to focus on is being an authentic leader. Being vulnerable, being authentic, being emotional. Humility is something that I’ve learned from my father, and that’s a whole other conversation. I have respected him and he demonstrates that so much, so I try to emulate that. I don’t know all the answers.

Missy (25:30): When team members would come to me throughout my career, we’d be open and honest with each other. I’ve had some very difficult conversations where people have shared feedback to me, and I take it to heart, because I take it that they care. I wear my heart on my sleeve. I don’t hide my emotions. People know how I feel. And I stayed in the field for so long because I love being in stores. I love being with our teams and with our customers. That’s something that really motivated me and excited me. Just being alongside them. I learned the most from them, being in the break room, informal moments. It’s one of the reasons I love being a volunteer guide at Apple, because I could do these volunteer events and be with team members in a more casual atmosphere. So those are many of the things that define me as a leader. And that’s feedback that I would receive when I was leaving my career. A lot of people would say that they saw that I was just who I was. You knew who I was. I wasn’t hiding anything.

Ron (27:00): Do you think that comes from particularly leading frontline teams? And I say that because most of us are all in this a little bit by accident. A variety of educations, no education, a variety of prior experience. It’s this kind of mashup of miscellaneous people. And that’s what I love about it. I’m going to take this group and we’re going to do great things together. And I do think it requires leadership, as you’re describing, that is more emotional, because if it’s too serious, too corporate, I don’t know that that plays very well in the field. I’m speaking for myself, who also feels like I’ve just led with honesty and authenticity, and the good, the bad and the ugly.

Missy (27:21): And every store we go to that you were leading, everybody raves about you and they love working for you. I think it’s exactly that. You are exactly that person. Authentic. You care, you show care by listening and checking in with team members. So absolutely. You don’t need a college degree to get into retail. It’s great if you have it, but you don’t need it. There are people with so many different experiences and backgrounds, and we can learn from each other, learn life lessons, personal lessons. I’ve learned so many things personally as well. So I think being that kind of leader is great.

How did Apple change the way you give and receive feedback?

Ron (28:00): And you’ve worked for organizations that were deeply rooted in feedback. Particularly Apple. It’s a core foundation of how they operate, peer feedback, up, down, every direction. As the last many years being there, did it change how you thought about feedback, and how you received it and gave it?

Missy (28:20): Yes. When I joined, I remember people saying to me, let me give you some feedback. And they would say, we don’t do it that way. And I’m like, was that really feedback? I said, I don’t know if I’m going to find my place here, because this is what I know. But feedback really is something that you take the time to seek to understand why somebody did something. That’s something I take with me professionally and personally. I want to understand why somebody did something before I give them feedback, because they may tell me something that I wasn’t even thinking about, and I don’t want to make assumptions. Reducing that bias when I’m giving somebody feedback was really important for me. People have so many different backgrounds, so many different experiences, that they may have been doing something because that’s what they knew.

Missy (29:27): And that’s what I would say when people would give me feedback about something I was doing. I’m like, this is all I know. I only know to treat customers this way, because that was my experience at my previous company. At Apple, you treat everybody the same, which is great, and that’s what makes it so special. We had VIP customers at Ralph Lauren, VIP customers at Apple, everybody gets treated the same. I also believe there’s this positive intent. 99.9% of the time, people want to do a great job, and they’re doing things because they think it’s the right thing to do. So giving people a little bit more grace prior to giving feedback, I think is really important.

Ron (30:20): And you’ve led really large teams. Being able to do that at scale, there are hundreds of people in the mansion, hundreds of people in every Apple store in New York City. How do you do that at scale? That’s great leadership.

Missy (30:35): Yeah, I think what I’ve seen work is when you empower team members to do it with each other, and focusing on those steps, because people get defensive. I’ve heard people say to me, I gave them feedback and they got a little defensive. And I’m like, well, how did you get the feedback? When you skip that step of asking questions, or making assumptions when giving feedback, that’s when somebody can get defensive. Again, personal relationships, I saw that happen. So the way to scale that is empowering the team member to give it to each other, and ensuring that everybody knows what their goals are. We’re all after the same thing. We’re not here to compete with each other. We’re here for the greater good. So ensuring that when you’re building those teams, it was really important for people to know that we’re all here for this main goal. We’re here together, and we have each other’s back.

Why is storytelling a leadership skill?

Missy (31:30): I look at any sports team, coaching, any of that, that’s where some leaders that I would love to emulate are. How do you make sure that people are in it for each other, and for the greater good? And I also just want to share, storytelling is such a critical skill too. That’s something as a leader I developed over time. I wasn’t great at it when I joined Apple, but I reflected back on the many companies that I worked for. They were founded by masterful storytellers. So I spent a lot of time studying that, watching these amazing leaders. Ralph Lauren telling stories visually, and anytime he would talk about his inspiration was great at storytelling. Steve Jobs, all about storytelling. Chuck Williams and the Fishers, all of them. So that I find is a great way to ensure that people understand the vision as well. When we’re talking about the greater good, that was through storytelling as well.

Ron (33:00): Amazing. And you’re right, those storytellers are all around us in retail. It’s the best version of retail. Up and down Madison Avenue, where you are, there are stories of new brands, female founded brands, powerful new players in this market. And I’m always hungry for those stories. Why, how, what’s your goal, what’s happening. There are many happening right now. Countless. Being community driven, client driven, sustainability, giving back.

What is Missy Poole doing now?

Ron (33:15): Last couple of questions, Missy. Tell us a little bit more about what you’re doing today, and how people can support you.

Missy (33:25): Thank you. So I am humbled to say I am on the board of FIT and the FIT Foundation, which focuses on supporting our future creative talent in fashion design, in cosmetics, in toys, and in technology. There’s so much that FIT does for this city that I had no idea about until I joined the board. By the way, we have a food pantry for students there. There are many ways to support FIT, through sponsorships, through connection, internship programs. So if brands want to get involved with FIT, I’m so happy to connect them, because I think our students can benefit from so many brands out there. That’s one major portion of what I do.

Missy (34:20): I’m also on the board at the Madison Avenue BID, our business improvement district. Our focus is to ensure that Madison Avenue continues to be the premier shopping destination, that we are driving traffic and showcasing the amazing businesses on the Avenue. I also co-chair the gala committee for City Harvest, which is our major food distribution in New York City. They provide to all the food pantries in New York City, and they do incredibly great work. So if anybody’s passionate about helping food insecurity in our city, City Harvest is a great way. And then I am doing advisory work for different companies, where I’m supporting and helping these technology companies get connected with retail brands, as we were just talking about, to help ensure that the customer experience is seamless, more effective and more efficient.

What is the single best way to roll out new technology in retail?

Ron (35:20): Thank you. We’ll make sure that your contact info is in the notes, and probably LinkedIn is going to be the best way. Any kind of volunteer work, donations, events for these incredible organizations that you’re part of, I’m certainly here to help you with FIT as much as I can now, because you and I share that passion for supporting current students and recent grads, getting them into this exciting and fun-filled adventure ahead. And last question, around advice that you would give to any company that they could do right away around adoption, rolling out new tools. There’s going to be a lot of this in 2026. What advice would you give, coming from a big brand like Apple and Ralph Lauren, to do this really well?

Missy (36:15): Yeah, I would say be a collaborative and servant leader. Identify your team members that you’ve built trust with and have influence on the team, and pull them into any rollout of any new adoption. Build the why together, and how it will benefit those that are using it. Create the story together, so everyone can be aligned on the message. And then get out there with them on day one, and bring it to life with them side by side. I loved when corporate team members would come work with me side by side in the stores. It showed that they really cared about what they were rolling out, and it also helped troubleshoot if there were any issues. But being with your team side by side on day one can be really enlightening and inspirational for so many people.

Ron (37:12): Great advice, and relatively easy to do. Go visit stores. See your people. Thank you, Missy, for your time here, and our two plus decade friendship, and the work that you’re doing that we’ve done together. I really admire everything. I’m excited for this next chapter for you, and thank you for sharing your story with us here on the show today.

Missy (37:35): Thank you for allowing me to, and thank you for always being there with me and for me, and championing me, and just being there for any advice. I really appreciate you so much.