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Mickey Drexler redefined retail by radically remaking Gap and J.Crew, and working alongside Steve Jobs to guide the creation of the Apple Store. Now Drexler assesses some of the biggest stories in the retail industry today, from the weight of crippling tariffs and U.S. manufacturing skepticism to the controversial American Eagle campaign featuring Sydney Sweeney. Feisty as ever, Drexler shares his unvarnished view on in-office work, AIs limitations, and why leaders need to follow their gut or get out of the way. This is an abridged transcript of an interview from Rapid Response, hosted by Robert Safian, former editor-in-chief of Fast Company. From the team behind the Masters of Scale podcast, Rapid Response features candid conversations with todays top business leaders navigating real-time challenges. Subscribe to Rapid Response wherever you get your podcasts to ensure you never miss an episode. In many ways you helped create the modern playbook at Gap, at J.Crew. What’s your assessment of what the state of retail is right now? Well, I’m a very tough critic since forever. I find retail now, it’s a whole different world. I think the merchant has gone out of the business a bit. A lot of people who lead the companies in my opinion are not true-born whatever merchants. It’s about numbers, it’s about earnings, but at the end of the day, the most important issue in any business is the product, the goods. And I don’t think a lot of people really pay that much attention to the goods or in fact aren’t comfortable with the goods. And with investors, in my experience, it’s all about the earnings, all about the money, mercenary in terms of money, money, money. The irony of that is your approach has always been as much about getting the style as about the mechanics of the business, and yet that has led to more profits and more money, right? Like the quest for money doesn’t necessarily lead to that money? Not at all. I think it’s true of every business. Now, I’m not an expert on all this stuff. I’m an observer of the world. And you don’t have to be an expert to be a customer or an observer of the world. I look at the cars out there. I used to love cars. I can’t tell the difference between the brands at this point. And if you don’t have the creativity, you then can’t move forward in the business because creative is inventive. You always loved walking through physical stores. I remember you taking me along. We went to a J.Crew and to a Madewell, and you were pointing out why some displays worked and what things didn’t, and how sometimes you even saw the product differently once it was out on the floor. Today, of course, so much happens online in these direct-to-consumer channels. Does that in-person experience still matter the same way? Can digital be just as effective? It’s a really good question. The store is easy. I go in, it takes a minute to know if we look good or not. Online, I find, and I always complain about a lot of things, but I find that websites are never-ending and a customer doesn’t need that many choices. What do you love? What message do you want to give? And being a merchant is as much about trusting your gut. It’s like you’re a curator, right? Beyond right. I had a big debate the other night. There were 10 of us at dinner and the subject of AI came up. One woman was on the board of AI and they were all my friends, but I get a little passionate and my wife says, “Calm down.” They said, “Well, it’s going to cost a lot of jobs. It’s going to do this, this, and that.” I said, “I’m not really concerned with AI. I don’t think AI will be able to pick colors. I don’t think AI will know how to invest in merchandise. I don’t think AI is going to know how to negotiate with a factory owner worldwide.” And then the fireworks started. And you know what I said? I gave up after a while, but I knew that none of them were creatives. And when you work with creatives like Steve Jobs, who was the best in the world, you’ve got to say to yourself, I love that idea. I love this. I love that. The instinct and gut for me drives the business. And I’ve been wrong. Who’s not wrong? You make mistakes, but that’s my feeling. My best friend is what I feel. You mentioned Steve Jobs. You worked with Steve as he grew Apple into a juggernaut. You were on the Apple Board for over a decade. Sixteen years, yeah. What do you think Steve would think of today’s AI craze? Would he be into it? I guess he’d have to be into it. Steve saw the future and he died way too young and the world misses Steve, but what he wanted to do, then his last thing and then he passed away, he wanted to do an electric car and he wanted to design it. And when he brought up the first Tesla as an example, the ugly two-seater, and I said, “Steve, that car is really ugly, he looked at me with disdain, which I loved when he got mad or whatever, disagreed. He said, “It’s not about the design of the car. Anyone could design a nice car. It’s about what’s inside the engine. He was just smart, really smart and not easy, but I don’t know of any real bosses who are easy. If they’re easy, they’re not great bosses. Demanding you have to do better and be as competitive as anyone in the world. I want to broaden out a bit to the leadership landscape right now for CEOs and others in business. CEO turnover stats are quite high, maybe higher than ever. Has the role of a CEO gotten harder and riskier in 2025? Well, I have an opinion about CEOs and boards of directors. Every oneyour best friendscan qualify as an independent director. When I was on Gap’s board, I didn’t have any vote except when I invited Steve Jobs on the board, we made a deal. I wouldn’t go on his board, I was stupid. After a year, he said to me, I’ll never forget this: “You go on my board, I’m joining the Gap board.” And I said, “We have a deal.” And he lived up to being Steve Jobs. He was irreverent, critical. The corporate world today is, I think it’s like a friends club. A CEO . . . I understand they don’t want anyone who’s going to give them a hassle. There’s a company, Outdoor Voices, I was the chairman of for a year between J.Crew and Alex Mill. I [told the board]: “This would be a Lululemon competitor. And I was saying, “You need to make a management change.” They didn’t care. Couldn’t care less. Really, someone needs to have a course on no bullshit.
Category:
E-Commerce
When the world stops making sense and everyone’s looking to you for answers, that’s when real leadership begins. I learned this in the most extreme of circumstancesfirst, as a SWAT team Tactical Commander where split-second decisions meant life or death, then as CEO of a major public company where market crises could make or break thousands of our customers’ livelihoods. The skills that kept our team alive in tactical operations are the same ones that helped steer our organization through economic downturns, industry disruptions, and unprecedented challenges. Crisis leadership isn’t about having all the answers; it’s about having the right framework to make decisive moves when the stakes are highest. The OODA Loop: Your Crisis Leadership Framework Air Force Colonel John Boyd developed the OODA Loop by studying why American F-86 fighter pilots dominated technically superior MiG fighters in the Korean War. The framework he created became the gold standard for decision-making in competitive, high-stakes environments, and remains standard methodology in tactical operations today. The loop takes you through four key steps: Observe: Rapidly gather information about the evolving situation Orient: Process observations against your experience and current reality Decide: Choose your course of action with incomplete information Act: Execute decisively while preparing for the next cycle Speeding through the cycle becomes your ultimate competitive advantage. The leader who can take these steps faster than the crisis evolves wins the game, or, in some cases, the dogfight. Observe Without Panic In SWAT operations, observation meant survival. You had to see everythingsuspect behavior, environmental hazards, team positioningwhile filtering out distractions under extreme stress. The same discipline applies in business crises. During business challenges, other industry leaders typically make reactive decisions based on incomplete observations, or worsefail to make decisions due to analysis paralysis. Instead, I apply Boyd’s observation principles: gather data systematically, look for patterns that others miss, and resist the urge to act before you truly understand what’s happening. Here’s the landmine: The moment you let emotions cloud your observation, you lose your competitive advantage. Orient Faster Than Your Competition Boyd believed orientation was the most critical phase, where you synthesize observations with experience and strategic context. In tactical operations, poor orientation gets people killed. In business, it gets companies killed. During the COVID pandemic, while I was CEO of RE/MAX, competitors were still trying to understand the paralyzed market. We had to orient to the new reality of Zoom showings, curbside closings, and overall new ways of doing business immediately. To combat this, I drew on my law enforcement experience of reading situations that didn’t match expectations. We recognized that the market continued even with different protocols, and we had to adjust how we did business. This rapid orientation gave us a significant market advantage, even in the hardest-hit areas. Companies that survive crises orient to new realities fastest and most accurately. Decide with Tactical Precision Boyd understood that having perfect information is a luxury you can’t afford. Whether breaching a door or entering a volatile market, you decide with 70% information and 100% commitment. When you have multiple options but incomplete data, apply the same process we used in high-risk operations: identify your primary objective, consider second-order effects, choose the option that advances your mission, then commit fully. The decision-making process builds confidence to take action. Waiting isn’t decision-making, and waiting for nonexistent information is a fool’s game. How would you feel if the SWAT team had no next step while you were the hostage in the building? Same thing in businessgather just enough information to lean toward a decision. In a crisis, the worst decision is usually no decision. Act While Others Hesitate Action without observation and orientation is reckless, but observation without action is worthless. Boyd’s framework only works when you complete the cycle, then immediately start the next one. During market shifts, our actions required balancing financial and operational oversight against financial challenges and legal restrictions. Crisis operation isn’t just about moving fast; it’s moving with purpose while staying flexible to changing rules that shift daily. I built what Boyd called “implicit guidance and control” into our systems. Our team knew the mission well enough to act independently when circumstances changed faster than communication could keep up. When offices and franchisees located around the globe called with questions, the decision framework was simple: “What’s right that aligns with the values of the business?” Elite performers cycle back to observation before competitors finish their first decision. Getting Inside Your Opponent’s OODA Loop Boyd’s real insight was “getting inside your opponent’s decision cycle.” By going through the OODA Loop faster than your competition, you make them react to your moves instead of executing their own strategy. At RE/MAX and other companies I oversee, we institutionalized rapid OODA cycling through what I call the 3-2-1 decision-making process. Instead of asking management questions and waiting for responses, I empower people to come up with 3 ideas to solve a problem, create 2 best options, then make 1 recommendation. This quick process gets action taken immediately. By the time our competitors made their first major move, we were already three moves ahead. Building Organizational OODA Capability You don’t develop OODA Loop mastery during the crisis; you must develop it beforehand, implementing steps like: Accelerate Observation Systems: Create information flows that give you earlier intelligence than competition, and host weekly clarity meetings for everyone aligned. Sharpen Orientation Through Training: Regularly run exercises like what-if games, so orientation becomes automatic during real disruptions. Practice Quick Decision-Making: Create safe environments for consequential decisions under pressure and build the understanding that it’s okay to make decisions. Build Rapid Execution Systems: Design processes that implement decisions faster than circumstances change. Communication Within the Loop Boyd understood the OODA Loop isn’t just individual, it’s organizational. Your team’s ability to share observations, align on orientation, coordinate decisions, and syncronize action determines collective speed. Maintain OODA coherence by applying tactical communication principles: Observe together Orient collectively Decide with clarity Act in coordination As you get used to “dancing the OODA” together, you’ll see instinctive decision-making perpetuate team success. The Ultimate Weapon Crisis leadership is more than just being fearless; it’s about being intentionally and strategically faster. Colonel Boyd’s OODA Loop that kept fighter pilots alive is the same framework that kept our businesses thriving during market downturns. Whether facing armed suspects or market volatility, the fundamentals remain the same. In competitive environments, the speed of decision-making becomes your ultimate weapon. Not reckless speed, but the disciplined speed that comes from mastering Boyd’s cycle. When your next crisis hits, the question isn’t whether you’ll face uncertainty and pressure; the question is whether you’ll cycle through your responses faster than the crisis itself can evolve. Your competition is counting on you to hesitate. Your team is counting on you to lead. Time to close the loop.
Category:
E-Commerce
Every company wants to have an AI strategy: A bold vision to do more with less. But theres a growing problemone that few executives want to say out loud. AI initiatives arent delivering the returns they were hoping for. In fact, many leaders now say they havent seen meaningful returns at all. IBM recently found that only 1 in 4 AI projects hit the expected ROI. And BCGs research goes further still: 75% of businesses have seen no tangible value from their AI investments. Stop buying tools your team doesnt know how to use The fix? Increase your investment in AI training to support your business transformation. The data tells a simple story. An Akkodis survey suggested only 55% of CTOs believe their executive teams have the AI fluency needed to grasp the risks and opportunities of the tech. Yet, it is these same executives who are trying to reengineer entire workflows, teams, and business models around tools that their people barely understand. And when performance disappoints, the knee-jerk reaction is to buy even more tech. More platforms. More licenses. More dashboards. But that only makes the problem worse. The teams that were struggling to learn one tool are now juggling five. Everyones overwhelmed. No ones effective. And adoption flatlines. Even if you have the most advanced tech in the world, if your team doesnt know how to use it effectively, its worthless. Expand your training budget But, equally, throwing money indiscriminately at AI education alone isnt going to fix the problem. The training investment must be smart. And that means implementing training programs that are truly pan-company and aligned with the business objectives. Too many businesses funnel their AI training into a tiny corner of their workforceusually just their IT, engineering, or data teams. And while these teams do need support, theyre not the ones who are going to deliver the productivity gains that you are trying to realize. That job falls to the rest of your company: the 90% working in frontline roles and business functions where the AI transformation will be felt most. Whether thats operations, strategy, product development, sales, finance, marketing, HR, legal, or customer service. These are the people who run your business. And if they dont know how to apply AI to their day-to-day work, your transformation will stall. If the goal is to modernize the business end to end, your training needs to reach end to end. Teach Data and AI literacy before you teach tools At the same time, surface-level AI training that focuses only on toolssuch as how to write a prompt, where to click, and how to navigate an interfacewill also fall short. Effective AI training needs to build capability and not breed dependency. The best results come when your people understand whats happening under the hood. Dont get me wrong, your team members dont all need a PhD in computer science. But they do need solid data literacy. They need to know how to interrogate, interpret, and act on data. The real value of data comes from understanding what it can actually doseeing its potential and seizing it with both hands. Without even the most basic data skills, AI will create beautiful spreadsheets that cant be acted on. And thats not the revolution anyone had in mind. Train your managers just as muchif not more Equally, when it comes to AI training, theres a myth I sometimes hear: Managers dont need AI training because they’re not doing the work. Their job is to manage the team or set the vision, not run the tools. But that logic falls apart quickly. Firstly, I can think of countless ways that AI can make managers more effective: being able to synthesise and extract lessons from performance data, providing their team with hands-on guidance on how to use AI, and spotting opportunities to reengineer workflows. But, more importantly, it is the bad message that not training your managers sends to your wider team. It runs the risk of your wider company writing off your transformation as “hot air” and “warm words” rather than concrete, in-the-trenches implementation. Wide-scale transformation needs managers who can lead by example. If you train the team but skip the managers, dont be surprised when nothing changes. Build a culture that lets people use what they learn Finally, even the best training program will fall flat if your workplace punishes people for using it. In many businesses, employees are quietly, and perhaps unconsciously, discouraged from using AI. Theres a genuine fear that if theyre seen to be using AI, they will be criticised for cutting corners or cheating. The result? Team members keep their heads down and go back to old habits. In other companies, colleagues are afraid to give AI a go in the first place. Theyre hamstrung by a fear that theyll make a mistake or get something wrong. In both cases, your training budget goes to waste. So, if you want this to work, you need to create a culture of experimentation and entrepreneurship, where trying something new is actively encouragedand not seen as a riskand where teams share learnings, trade prompts, and build real know-how together. Too many companies are pinning their hopes on the next big AI tool. But no tool, no matter how powerful, will move the needle if your people dont know how to use it. The smart move right now isnt just buying more software. Its training your people to work smarter with the tech you already have. Thats how you make AI worth the investment. Thats how you turn strategy into results. And thats what will, ultimately, stop your AI vision from dying on paper.
Category:
E-Commerce
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