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Twenty years ago, as the top digital and innovation executive for Citi’s credit card business, I led the team that spent months building what looked like a brilliant partnership. We’d found a startup with a disruptive payments platformone that became the forerunner of what has become a new payment type used by millions of consumers today. The deal: strategic investment in exchange for access to the startup’s codebase as a sandbox for innovation pilots. No more waiting in the legacy systems queue. Just rapid prototyping with leading-edge developers. We built the entire partnership in a silo of supporters, treating resistance as something to avoid until absolutely necessary. Then came final deal approval day. The senior executives heading risk management, compliance, legal, finance, regulatory affairs, and profit and loss (P&L) weighed in: “The regulators won’t like this.” “Have we gotten corporate approvals?” “What’s the ROI?” “We’ve never done this kind of deal.” Deal torpedoed. Within a few years, that startup was acquired for close to $1 billion. The loss wasn’t just financial. It was a failure to recognize that resistance contains intelligence about reality that plans built-in echo chambers inevitably miss. Colleagues felt blindsidedasked to bless a final deal rather than shape an evolving strategy. The resistance wasn’t about the idea. It was about being excluded from the journey. I’ve spent the two decades since distinguishing the signal from the noiseand teaching leaders how to avoid the expensive mistakes we made. Why We Keep Making the Same Mistake Leaders faced with pushback default to a familiar playbook: build innovation in a protected silo, surround yourself with enthusiasts, keep resistors at arm’s length. The logic seems soundprotect the new thing from the “antibodies” of legacy thinking. But here’s what we discovered the hard way: unfamiliarity, fear of the unknown, turf protectionthese weren’t just emotional reactions. They were signals. Risk and compliance leaders felt threatened because no one had involved them early enough to anticipate possible regulatory concerns. P&L managers pushed back because the project diverted resources from their quarterly targets. The resistance contained intelligence about implementation realities that an enthusiast-only team couldn’t see. When 70% of change initiatives fail despite massive investment, the problem isn’t that people don’t understand the plan. It’s that the plan doesn’t account for what people understand about reality. Learning to Translate Resistance Into Intelligence The shift starts with listening differently. When someone says, “We tried this before and it didn’t work,” leaders typically hear obstruction and respond: “This time is differentwe have better technology.” But what if you asked instead: “What specifically failed last time, and how does this approach account for those lessons?” Suddenly you’re mining history for intelligence about why elegant pilots don’t scale. When a stakeholder says, “Our customers won’t understand this,” the dismissive response is “Of course they willwe have market research showing they favor this concept.” The intelligence-gathering response: “That’s an important observation. Where do you see the greatest failure points that we should account for?” Or consider: “This conflicts with our other priorities.” Many leaders hear bureaucratic gatekeeping and respond by promising to “make the case” at prioritization meetings. But that’s still trying to convince. The intelligence approach: “We have a full load of urgent priorities, you’re right. Where do you see the biggest stress points this project might create?” These aren’t just nicer ways of saying the same thing. They’re diagnostic questions that surface constraints the plan hasn’t addressed. When you ask, “Where do you see the biggest stress points?” instead of selling your solution, something shifts. You’re signaling genuine understanding, not persuasion. That act of listeningwhat former hostage negotiator Chris Voss calls “tactical empathy”builds the trust that determines whether your initiative scales or stalls. Why This Matters More Now AI experimentation is amplifying every dysfunction in how organizations handle resistance. Consider a common pattern: A team builds an AI assistant for customer service reps. The tech enthusiasts love it at pilot stageimpressive accuracy, clean demo, excited exec sponsors. But they never involved actual service reps. So, they didn’t discover until scale that the assistant couldn’t handle the 20% of calls requiring human judgment, created more work documenting exceptions than it saved, and made reps feel surveilled rather than supported. Adoption stalled. The pilot became another “AI experiment that didn’t work.” The same dynamic plays out with creative teams resisting generative AI. The pattern sounds familiar: Our brand spends millions to sound like itself. The moment we start prompting a model trained on every competitor’s campaign, we’re paying to erase what makes us different. Beneath the pushback is stewardship of hard-won brand equity, not necessarily technophobia. The intelligence-gathering response: “What if we approach AI as rough-draft only? How might we develop explicit guardrails for tone and references to preserve what makes us distinctive?” From Stakeholder Management to Coalition Building Traditional stakeholder management maps who supports and who resists, then tries to convert resistors through better communication. Coalition building does something different: it engages across the spectrum from the start to build trustthe foundation that determines whether change scales. I’ve seen this work. When innovation leaders don’t own a P&L, they face scrutiny from business unit managers who question whether “the innovation people” truly care about quarterly targets. One way through: explicitly align early experiments to P&L managers’ top prioritiesnot to convince them your idea is right, but to demonstrate you’re invested in making them successful. Shared values become the bridge when you disagree on tactics. The Questions That Change the Conversation In my workshops with senior leaders across financial services and other sectors, I consistently hear the same story. As one CTO told me: “We built our gen AI strategy with only the innovation team. Now we’re stuck because compliance wasn’t engaged early.” Here’s where to start: “What do you see that we might be missing?” Assumes intelligence in the perspective, not obstruction. “What would need to be true for this to work in your world?” Surfaces constraints before they become deal-killers. “What shared outcomes mattermost to both of us?” Finds the values bridge when tactics diverge. The fundamental shift: from “How do I overcome resistance?” to “What intelligence am I missing if I don’t engage this perspective early?” Twenty years later, companies are still building partnerships, AI pilots, and transformation initiatives in silos of supportersthe same mistake my Citi team made. Still treating resistance as friction to manage rather than intelligence to integrate: The billion-dollar missed opportunities keep piling up. What changes when you treat resistance as the intelligence it actually contains? You build coalitions instead of echo chambers. You gain insights that improve your plan and trust that enables scale. And you stop repeating the expensive mistakes we learned from the hard way.
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E-Commerce
As an operative researcher for luxury retail companies, I spent my career grabbing onto one corporate contract after the next, like a tree-swinging retainer monkey. But in a tariff-distressed industry, those contract branches grew further and further apart until I was left hanging. Then a colleague experiencing a similar work gap said, Well, I guess were retired. Ive been called a lot of things in my life, but nothing prepared me for the word retired. I’m a freelancer, so no one is coming to my house with a gold watch as a reward for loyal service; I have no desire to move south; and I dont play golf. My equally self-employed friend Roland had a suggestion: Why not consider myself situationally retiredthat is, retired until the phone rings. Its funny how one word can make or break your spirit. I was crushed by retired because the concept is foreign and frightening. But adding situational made it comfortingly familiar. After all, for us freelancers every corporate contract is situational; you might even say that situational is my superpower. A friend whos spent decades in a grueling C-suite position still cant bring himself to retire, despite vested stock and a strong financial footing. Happy or not, he remains in the grip of his job, unable to let go of a role he believes defines (and so ultimately confines) him. Ive been an outside observer of corporate America long enough to understand his struggle, although it is not my own. Redirecting your energy As an independent contractor working for different companies, each with its own ecosystem, I constantly adapted my work persona to fit each unique corporate culture. Fluidity is what stabilized my career and so the loss of a fixed identity was not my retirement problem. My issue was displaced energy. Whether writing a history of plaid for a fashion CEO or helping the VP of design at a boutique hotel chain find just the right urban neighborhoods for expansion, every project required a tremendous amount of advance work. From sleuthing out relevant reference resources to searching for subject-specific experts, my research work was as fascinating as it was fun. I rarely left my desk yet built a national network of specialists and accumulated wide-ranging knowledge that often dovetailed, making every project a little easier. When the work slowedand then stoppedmy detective skills had nowhere to go. I cant remember how long I was in that uncomfortable standstill until Rolands use of the word situational got me moving. To kick off Project Retirement, I went on my usual research prowl. Every day, about 11,400 Americans turn 65the traditional retirement milestonefueling a busy and lucrative media market spanning content, publishing, and podcasts. But the most valuable operative research is not about finding the most information. It requires you to find the right informationinformation that is directional, that you can build upon, that can help steer your project to a successful conclusion. Redefining retirement For me, the initial guiding principles came from the YouTube channel Small Retired Life and Raina Vitanovs practical yet inspirational attitude. Her conversation about being rebellious enough to redefine and rebrand retirement broadened my understanding and freed me to choose my own norms and values. But the most significant contribution was her observation that in retirement, Productivity is not the conversation. Using the Roland method, I added a word and had a revelation: Transactional productivity is no longer my conversation. The time between contracts used to feel borrowed; now I own it. And all that research joie de vivre that I enjoyed over my corporate years is mine to use as I like. Sit next to me if you want to talk about the architecture of Shaker communities, art in ’80s New York, or the difference between Ivy style and preppy fashion. I also started a side gig in a small boutique where I once shopped whenever I needed to outfit myself for a rare visit into corporate America. Because Ive never had a structured straight job, I find the work to be fresh and interesting. Its also rewarding because I get to use decades of style research on real live women, many playing out their own life-shifting issues through the lens of their wardrobes. Although Im not sure I can pull off being an introvert cosplaying as an extrovert for more than my customary two workdays a week, I might give it a shot. Because now that Ive got the hang of it, situational retirement can be whatever I want it to be.
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E-Commerce
Hello and welcome to Modern CEO! Im Stephanie Mehta, CEO and chief content officer of Mansueto Ventures. Each week this newsletter explores inclusive approaches to leadership drawn from conversations with executives and entrepreneurs, and from the pages of Inc. and Fast Company. If you received this newsletter from a friend, you can sign up to get it yourself every Monday morning. The World Economic Forum Annual Meeting in Davos brings together an incongruous mix of celebrities (this year included Matt Damon, David Beckham, and Katy Perry, who was accompanying ex-Canadian Prime Minister Justin Trudeau), world leaders (President Donald Trump), and nonprofit leaders. The event also reliably assembles an unrivaled group of global CEOs who offer a window into where business is heading. Some CEOs see sunny skies ahead This year, though, I found the window very foggyand I wasnt alone. According toPwCs 29th Global CEO Survey, released at the start of the meeting, only about a third of CEOs (30%) say they are confident about revenue growth in the next 12 months, down from 38% in 2025 and 56% in 2022. Yet Paul Griggs, CEO of PwC U.S., says the American CEOs he spoke with in Davos are feeling much more optimistic than the survey would suggest. While they acknowledge that theyre dealing with high levels of uncertainty, theyre also more prepared to deal with complexity through new workflows and processes to keep them agile. I met with 10 CEOs today, and it was a day of optimism, Griggs says. Sharon Marcil, who leads Boston Consulting Group in the U.S., Canada, and Mexico, is also seeing bright spots. A new report, BCG AI Radar 2026, finds that four out of five CEOs say they are more optimistic about the returns on their AI investments than they were a year ago. I do think 2026 is going to be a growth year, she says. Whos feeling blue? Most consultants I spoke with say European and U.K. CEOs are less confident than their U.S.- and Asia-based counterparts. AIs impact beyond the hype The impact of AI on jobs was also hotly debated at Davos. While most CEOs and executives continue to insist that AI will make work better by reducing mundane tasks, a few CEOs have started to talkpublicly and privatelyabout the roles AI will eliminate and the need to prepare workers for changes. Were focused on being completely honest with our workforce, says Kate Johnson, CEO of Lumen Technologies, a digital network services provider. Johnson says the company is committed to training employees for new roles in the organization but adds, We have to reimagine what the world will look like in the future, and [employees] need to imagine a world where their current job may not exist. Conversations about AI have also shifted away from applications (think OpenAIs ChatGPT) and agents (software that can make decisions and complete tasks) to infrastructure. Throughout the week, executives shared insights on the energy and networking capacity needed as data centers built specifically to support AI crop up. The big question now has gone from the potential to operational reality, says Aamir Paul, president of North America Operations at energy technology company Schneider Electric. (Fast Company partnered with Schneider Electric on a series of videos in Davos.) How do we make it happen . . . getting data centers built, getting energy access, getting it in a way that it doesnt affect retail costs and consumers dont have to take the burden, and doing it in a way where were still meeting our sustainability goals? These are daunting challenges that will require investment and inventiveness to solve. Luckily, one of BCGs recent business surveys saw a 14% uptick in mentions of innovation versus a year ago. Perhaps thats another reason for optimism in 2026. Your views on 2026 How are you feeling about the year ahead? Do you agree with the prevailing sentiment at Davos, or are you less optimistic about whats coming? Id like to hear your thoughts and why you feel that way. Please send them to me at stephaniemehta@mansueto.com. I may use your comments in a future newsletter. Read and watch more: Fast Companys Brendan Vaughan offers his take on Davos CEO insularity threatens dialogue goal at Davos CEOs at Davos are buying the agentic AI hype
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E-Commerce
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