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If my three-decade journey in the corporate world has taught me anything, its that in business, as in life, the only certainty is uncertainty. In the past 20 years, periods of upheaval, from pandemics to financial crises to AI hysteria, have restitched the fabric of how we work, travel, and communicate. While this uncertainty can generate tension and turmoil, it also forges the best leaders. Ive seen bosses and colleagues navigate all types of volatility, where the margin between success and failure can come down to a single action or inaction. So, what distinguishes leaders who can successfully shepherd teams through uncertain times from those who cant? I believe those who can share these three distinct characteristics. DOUBLE DOWN DURING DOWN TIMES Theres a tendency for companies to become ultra-cautious in times of uncertainty. While this may seem prudent, its difficult to get ahead of whats coming with your head down. The best leaders look ahead and make smart investments even when markets are down and sentiment is grim. In the wake of 9/11, I was at GE Aviation (now GE Aerospace). Overnight, the airline industry was grounded. While other manufacturers hunkered down and leaned on existing IP and products, we increased our budget on new jet engine development. Counterintuitive? Perhaps. But we were confident in one thing: People would fly again. Typically, a new engine has a combined new product introduction cycle and payback period of 15 to 20 years. With such an extended runway for ROI, manufacturers that dont make a bet to capture market share often struggle to get back into the game. Eventually, airline demand resumed, as did the need for next-gen engines, and we were one of the only companies that could deliver. ABSORB THE FEAR In Stephen Kings The Green Mile, prisoner John Coffey has a remarkable gift: He absorbs the sickness and pain of others, assuming their burdens at significant personal cost. Sci-fi? Yes, but it symbolizes a skill every leader needs. During times of change and anxiety, leaders must absorb the emotionalburdens of their employees, their fear and insecurity, and then project a path forward. The best leaders Ive seen take on their stakeholders doubt and replace it with a clear-eyed vision of the opportunity that exists amid the chaos. Listen, digest the concerns, and replace apprehension with hope. The pandemic was a period of intense uncertainty for companies, and Twilio was no exception. It was also the catalyst for equally intense growth, as circumstances and shifts in consumer behavior accelerated digital transformation. Nearly every organization needed a way to engage its customers digitally, and we were there to help build it. But by early 2024, when I became CEO, we had a lingering post-pandemic hangover. We simply werent winning as fast or frequently, and without credible points on the board, I could sense increased anxiety across our employee base. Hope is the currency that reenergizes teams and reassures external stakeholders, but empty hope is useless without a concrete path forward. I made it my mission to deliver that. For us, hope meant aligning on a clear, measurable vision for continued growth and a roadmap that everyone could get behind. This served as a compass, allowing our 5,500 employees to rebuild momentum and get us to the other side. CUT SUGARCOATING FROM YOUR CORPORATE DIET Theres an inclination for leaders to protect their people during periods of uncertainty. Withholding information, changing the message for each audience, or filtering it through rose-colored glasses insulates your stakeholders from the reality of what needs to occur. Fight those urges. Be transparent, while adjusting the altitude of information nuances required for each audience. In my first year as Twilio CEO, I was on the road meeting with stakeholders roughly 70% of the time. I sat down with customers, employees, investors, and board members to listen and communicate the companys path forward. My goal was to candidly talk about where we were as a company and where we were headed, so that everyone with skin in the game had the same playbook. Without candor and a consistent message, stakeholders cant grasp the full picture and the steps needed to fix it. You cant obfuscate the truth or change your tune depending on who youre talking to. You have a board, shareholders, hundreds or thousands of employees, and customers relying on your transparency. Whether its at a monthly town hall, an industry roundtable, or deskside conversations with investors, open and consistent communication simplifies your job as a leader. Thats the real gift of transparency: There are no skeletons to remember to hide or stories to change. Most critically, it reinforces trust, which puts points on the board. THE UNCERTAINTY IS TEMPORARY Theres no telling how any leader will respond to periods of uncertainty or hardship until theyre faced with them. No matter how impassable the road looks, the upside of uncertainty is knowing this too shall pass. After 9/11, we flew again. After the pandemic, we gathered again. And even as AI reshapes our work fundamentally, well continue to have meaningful careers. These periods of uncertainty are temporary, but when you string them together, they make up the long-term success or failure of your company. So, when the future isnt fully written, our job as leaders is to make smart investments, absorb the fear, turn it into clarity, and build trust. Do that, and in my experience, there are always better days ahead. Khozema Shipchandler is the CEO of Twilio.
Category:
E-Commerce
The narrative is familiar: Revolutionary technology arrives, promising to liberate women from domestic drudgery and professional constraints. The electric oven would free housewives from coal-burning stoves. The washing machine would eliminate laundry day. The microwave would make meal preparation effortless. Yet as historian Ruth Schwartz Cowan argued in her landmark book, More Work for Mother, these innovations didnt reduce womens workload. They simply shifted expectations, creating new standards of cleanliness and convenience that often meant more work, not less. So when we speak of AI as the solution to professional and personal burdens, skepticism is warranted. After all, technology has repeatedly promised liberation while delivering new forms of constraint. The question isnt whether AI will change professional and personal work; its whether this change will finally favor womens autonomy rather than merely reorganizing their obligations. Recent data Duckbill collected alongside Harris Poll reveals that 47% of women avoid asking for help to prevent burdening others. This hesitation reflects not just conditioning around self-sacrifice, but hard-won wisdom about technological promises that rarely materialize as advertised. SELF-LIMITATION ISNT ALL ON US The reluctance to seek assistance isnt a character flaw; its a rational behavior within systems that have historically penalized women for taking up space. When 31% of women aged 18-34 procrastinate on booking their own medical appointments, and 76% report that even in their free time it feels like there is something they should be doing, were witnessing the manifestation of decades of messaging that female needs are inherently secondary. This isnt about women doing it wrong. Its about women making calculated decisions within structures that werent designed for their success. AI PROVIDES AN ALGORITHMIC ADVANTAGE What makes AI uniquely positioned to address this dynamic is its fundamental departure from human-built social contracts. Theres no emotional labor required, no reciprocal obligation, no concern about imposing on someones bandwidth. Theres no judgment. The technology can exist to purely augment human capability, making it perhaps the first truly guilt-free form of assistance available at scale. Consider the surgeon who uses AI to optimize her schedule, allowing her to focus on life-saving procedures, rather than administrative minutiae. What if that surgeon also used AI to handle her insurance claim after a kitchen flood, researching coverage details, coordinating with adjusters, and handling repairs? Or the venture capitalist who has AI analyze market trends and simultaneously asks for it to research the best schools for her daughter, approaching both with the same fidelity and precision. These are examples of resource allocation that refuses to compartmentalize professional efficiency and personal fulfillment. Unlike previous technologies that further entrenched women in prescribed roles, AI has the potential to follow women across all domains of life. So, how do we fix this? 1. Redefine productivity as self-care When 78% of young women report they are simply trying to get through the day, were looking at a crisis of sustainable solutions. AI offers an alternative: What if getting things done could be both excellent and guilt-free? This shift requires a fundamental reframing for women. Instead of asking Am I capable of doing this myself? the question becomes Is this the highest and best use of my capabilities and time? Suddenly, outsourcing restaurant research or flight refunds isnt lazy, its strategic. And when tasks are streamlined and coordination becomes effortless, the mental bandwidth that was once consumed by logistics is freed up for vision, creativity, and genuine rest. Unlike previous technologies that created new forms of performance pressure, AIs most radical feature could be its indifference to human social hierarchies and gendered expectations. 2. Shape the algorithm to work for us For AI to truly serve womens needs rather than simply digitizing existing biases, women must be active participants in shaping these tools. Women are adopting AI at rates 25% less than their male counterparts. That adoption gap isnt just a missed opportunity for individual efficiency; its a systemic risk that AI development will continue to prioritize male perspectives and use cases. Every time a woman trains an AI assistant on her specific work, teaches it to understand her communication style, or provides feedback on its suggestions, shes contributing to a more inclusive technological future. This is not just about representationits about functionality. We cannot afford to let this technology develop without us, only to discover later that it replicates the same systems that have historically constrained us. WOMEN DESERVE SUPPORT WITHOUT LIMITS In a culture that has long demanded women take on more tasks to become more, AI represents something revolutionary: technology that encourages taking up space by alleviating pressures. Its permission to ask for what you need without apology, to optimize for you rather than survival, to treat your time and energy as genuinely valuable resources. The women who understand this arent just early adopters of technology, theyre pioneers of a new paradigm where support isnt scarce, help isnt shameful, and free time is not a luxury, but a human right. In embracing AI, theyre not just changing how shit gets done, theyre modeling what it looks like when women are able to be as big as their ambitions demand. Meghan Joyce is cofounder and CEO of Duckbill.
Category:
E-Commerce
ChatGPT can make mistakes. Check important info. How many times have you seen that message? More importantly, how many times have you actually stopped to consider what it means? No doubt youve noticed italong with millions of others who now rely on AI for everything from planning product launches and rewriting emails to turning their beloved pets into cartoons. The adoption speed has been remarkable. In just a few years, AI has gone from a buzzword to a daily fixture in countless workplaces. And for many, its already hard to remember what work looked like without it. Like anything that makes life easier, its easy to see why it caught on so quickly. Whats harder to see (and easier to forget), though, is how quickly weve tuned out can make mistakes. Thats why business leaders must be deliberate about how they integrate AI into their operations and clear about where human judgment must lead. SPEED AND THE ILLUSION OF INTELLIGENCE AIs value is undeniable. It can summarize meetings, analyze data, write copy, solve coding problems, create images, and so much more. That amounts to real progress, unlocking hours that can be focused on more creative and strategic work. But as AI becomes increasingly embedded in our lives, and its work becomes better and better, it also becomes easier to overestimate what it can do. Part of that stems from fear. If we believe it can replace us, we start to believe it can think like us. We need to be clear-eyed: AI does not actually think. Not yet, anyway. It predicts what words are likely to come next. Its a mirror into the ideas, concepts, and content that already exist in the world. When we forget that, we stop questioning. We assume that because something sounds smart, it is smart. And thats where mistakes begin. WHY HUMAN JUDGMENT WILL ALWAYS BE A DIFFERENTIATOR The more powerful AI becomes (and it will!), the more tempting it will be to pass off not just the underlying tasks, but also the reasoning behind them. If judgment were as simple as analyzing data and making a decision based solely on that, wed be in trouble. The reality, however, is that judgment requires interpretation, empathy, and lived experience. As a communications professional of nearly 20 years, its easy for me to imagine how badly AI overreliance could go wrong. Picture a company embroiled in a public controversy. Rather than consulting with someone who has years of experience navigating corporate crises, the in-house team turns to AI for a statement. Absent context or emotional intelligence, even a well-phrased message can make a bad situation worse. Not to mention those excessive em dashes in the company statement will be an obvious flag to anyone whos read copy drafted by AI. Its not just outlier events, either. Every day, business leaders must decide how to communicate sensitive changes, interpret market signals, and navigate nuanced situations, all of which require perspective. AI can tell you whats been said or done before, in whatever format you wantand what a useful tool that is alone. It can surface information, make suggestions, and help speed execution, but human oversight will always be crucial. What if the right course of action based on a lifetime of experience is to take an approach thats never been done before? If we can only look back and use that intel to inform decisions, how do we truly evolve? BUILD A TRUST, BUT VERIFY CULTURE AI is the first technological innovation that appears to possess true intelligence, which makes maintaining a healthy dose of skepticism essential. Trust, but verify isnt about second-guessing technology, its about recognizing how AI can make our lives easier and more efficient without losing what makes us unique: Our lived experience. That starts with everyday habits. Remember, AI is a starting point, not the finished product. Encourage your team to ask: Does this sound right to me? Would I stand by this if my name was attached to it? Whether verifying facts and stats, confirming sources, or reviewing tone and feel, these actions prevent speed from turning into sloppiness. As leaders, we must set the tone. By framing AI as a tool for making us more efficientnot a replacement for human judgmentwe reinforce what will always drive great work: judgment, creativity, and accountability. Grace Keith Rodriguez is CEO of Caliber Corporate Advisers.
Category:
E-Commerce
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