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AI Likes Kissing Up to You

Personal Tech columnist at The Wall Street Journal, Nicole Nguyen, wrote in Why I Told My Chatbot to Stop Kissing Up to Me, “AI is trained in part on what people like, and people prefer the brown-nosing, says Myra Cheng, a computer-science Ph.D. candidate at Stanford University and lead author of a March study on agreeable AI. Participants rated sycophantic AI responses significantly higher in quality and, after interacting with a more obsequious model, said they were more likely to return to the AI.” The study found that “AI affirmed users’ actions 49% more often than humans, even when queries involved deception, illegality, or other harms. In three preregistered experiments, even a single interaction with sycophantic AI reduced participants’ willingness to take responsibility and repair interpersonal conflicts, while increasing their conviction that they were right.” This is foreboding. If you take AI to be an authority in your life, the pressure to take responsibility and self-correct is muted. If you are always right, the incentive to take your cues from AI will drive you to return again and again at your own peril. Follow us on Instagram and X for additional leadership and personal development ideas.  ...

2026/8/23
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Mastering Uncertainty

WE all face uncertainty. The question is: how can we keep performing when faced with the disorder of uncertainty? Life will not happen according to our expectations. Peak performance at all times is not realistic. Instead, success is about optimal performance. Rich Diviney states in Masters of Uncertainty that “True success in life and business hinges instead on optimal performance, which means delivering your ‘best’ in the moment, whatever your best looks like in that moment. Sometimes your best is about persevering, moving forward step-by-step in the midst of challenges, embracing the messy, grueling, and unpolished reality.” Diviney’s Mastering Uncertainty Method comprises three steps: Move Horizons, Keep Going, and Stay Cool. Move Horizons Asking what I know now and what I can control keeps you in the here and now without overthinking and spiraling into negative thinking. Levels of uncertainty are determined by three key factors: Duration (How long will this situation last?), Pathway (What should I do next?), and Outcome (What is the goal?). “Moving Horizons is a process where you remain anchored in the present while actively shaping your own Duration, Pathway, and Outcome. Life’s unpredictability often leaves us without clear timelines, defined steps, or guaranteed outcomes for our challenges.” It’s how we best deal with uncertainty one step at a time. Through this process, “you sequentially grow the sphere of what you know and control.” Keep Going As you progress, keep setting goals that are not too big but just outside your comfort zone. A rightly...

2026/8/21
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Leading Thoughts for August 20, 2026

IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with: I. Creator of the iPod, iPhone, Tony Fadell on building a company: “I needed to learn. And the best way to do that was to surround myself with people who knew exactly how hard it was to make something great—who had the scars to prove it. And if it turned out to be the wrong move, well, making a mistake is the best way to not make that mistake again. Do, fail, learn. “The critical thing is to have a goal. To strive for something big and hard and important to you. Then every step you take toward that goal, even if it’s a stumble, moves you forward. And you can’t skip a step—you can’t just have the answers handed to you and detour around the hard stuff. Humans learn through productive struggle, by trying it themselves and screwing up and doing it differently next time.” Source: Build: An Unorthodox Guide to Making Things Worth Making II. Maynard Webb on finding inspiration: “Inspiration often starts with frustration. It begins with what seems like intractable problems—and then an unwillingness to accept that there are not any answers. I keep these intractable problems in my head and keep a lookout for answers or insights that can come from anywhere. “Even if you do not have the answers you need right now, I promise you that your solutions...

2026/8/21
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Quickpoint: The 3Cs of Self-Reflection

PROFESSOR of Management and Strategy at the Kellogg School of Management, Harry Kraemer, Jr., explains the 3Cs of self-reflection in Your Values-Based Legacy. He says we self-reflect to examine our pasts for clues about our future journeys. We are influenced by our connection, our community, and our choices. “When enhanced by self-reflection, these three Cs enable us to gain clarity about what we’re currently doing, what we’d like to do, and how all the aspects of our lives come together with a sense of purpose.” There is no right or wrong way to engage in self-reflection. The key is to find time when you can be silent and contemplate what matters most. In these quiet moments, I look back on the day and ask myself: What did I say I was going to do today, and what did I actually do? If what I did was different than what I planned, what were the reasons? What went well, and what did not? How did I treat people? Am I proud of the way I lived this day? If I had the day to live over again, what would I do differently? What did I learn today that will have an impact on howI live the next day, the next week, and going forward? Why do this? Only by being self-reflective can I truly know myself. If I don’t know myself, I cannot lead myself. If I can’t lead myself, I cannot lead other people. These statements always point me...

2026/8/19
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Does AI Lie?

WE’RE used to living with small lies. I was confronted by this fact when, recently, as I was preparing for a dinner party, I climbed onto a step-stool and reached into the liquor cabinet. One by one, I pulled down bottles that were nearly empty. Not surprisingly, at some point over the years, my young adult kids had helped themselves. As they were growing up, we navigated our share of lies. We had conversations about drinking. We had rules. And still, like all children, they lie at times. But I’m invested in them anyway. I love them, and I trust them. I understand that we won’t always tell each other the full truth. That isn’t dysfunction. It’s human. Human lies are tangled up with relationships. People stretch the truth out of fear, protection, embarrassment, ego — even kindness. When I caught my kids lying, it revealed something deeper — discomfort about independence, boundaries, identity. The lie isn’t the whole story. It’s a signal. And now we say AI “lies.” The claim in this context is misleading. Human lies involve intent — someone knows the truth and chooses to distort it. AI has no such awareness. What we call an AI “lie” is usually something subtler: an answer that sounds authoritative but turns out to be incomplete, outdated, or overly certain. That difference matters. AI does not lie in the moral sense, but it also has no loyalty to the truth. It generates confident responses without reliably signaling uncertainty and...

2026/8/18
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The Panoramic Leader: How Great Leaders See Differently

TO make the best decisions, we need to expand our view and think through a wider range of experiences and opinions. See panoramically. Increasing change and complexity require that we get more complete and diverse information and look outside of our usual suspects. We need panoramic intelligence. In The Panoramic Leader, Cornelia Choe and Marshall Goldsmith say that “panoramic intelligence is about training yourself to see through more than just your own lens. The real power is when you move beyond simply noticing others and start to see the world through their eyes, understanding the experiences and beliefs that shape their maps.” The lenses we choose to see the world determine the reality we see. The authors have identified three lenses—inner, outer, and relational—that allow us to see more fully. The inner lens helps us to gather self-awareness through self-reflection. It impacts how we see the world through our outer lens. The outer lens expands our view through our interaction with others, “taking in the systems, perspectives, and shifting conditions that define the world around us.” The relational lens creates insights between our inner and outer perspectives and transforms each with the insights gained from that enhanced perspective. We grow from the intersection of each lens. The relational lens gathers the insights we develop internally and shines that light back outward to our stakeholders through our outer lens, expressed in dialogue and leadership. This continuous refraction of insight—taking in light and returning it transformed—is what distinguishes panoramic leaders. They...

2026/8/15
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Leading Thoughts for August 13, 2026

IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with: I. Bill Burnett and Dave Evans on detachment: “A state of mind that is fully engaged but calmly detached is the best place from which to do design. When you are fully engaged in any task—really buckling down and getting the work done—you have the best chance of unlocking a great solution. However, most of us can’t shake off the fear of a bad outcome, and this tends to stifle our creativity and burden our actions. But when you can cultivate a mindset that is detached from outcomes, which are ultimately out of your control, you are the freest and most creative. When something goes as hoped for, you’re pleased. When something unexpected or negative happens, you’re bemused and happy to learn from the experience (which is why you come to think that just about everything is a prototype).” Source: How to Live a Meaningful Life: Using Design Thinking to Unlock Purpose, Joy, and Flow Every Day II. Gary Hamel on decision-making: “Paradoxically, as decisions get bigger, the ranks of those able to challenge the decision maker get smaller. Hubris, myopia, and naivete can corrupt decisions at any level, but that risk goes up when the decision maker’s power is, for practical purposes, incontestable. Give someone monarch-like authority, and sooner or later there will be a royal screw-up.” Source: What Matters Now: How to Win...

2026/8/14
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Build Your Day from the Top Down: Why Your Goals Should Shape Your Calendar

LOOK at how most people plan. They open the calendar, see the squares, and start filling them. A meeting here, a block there, a few tasks wedged into the gaps. By the end, the week looks full and feels productive. It is also completely backward. Starting with the calendar means you are organizing your time before you have decided what any of it is for. That is how founders end up busy for months and somehow no closer to anything that matters. The fix is to flip the whole thing. Build your day from the top down, not the calendar up. Borrow the Inverted Pyramid I spent years writing before I built businesses, and the most useful structure I ever learned came from journalism: the inverted pyramid. You lead with the single most important point, and everything below it exists to support that point. The further down you go, the smaller the detail. That structure became the spine of the Time Management Inverted framework, a productivity system that I've built over the past decade. At the very top sits the most important thing you have, the one I call your Grand Vision. Everything beneath it, all monthly goals, weekly tactics, and daily tasks, exists only to support that vision. Nothing earns a place on your calendar unless it props up the thing at the top. Most planning advice has you building from the bottom. You stack up tasks and hope they add up to something. The inverted pyramid does...

2026/8/12
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Be Coachable: Ten Truths of Being Coachable

SPORTS analyst Ric Bucher wondered, after rubbing shoulders with some of the greatest athletes, which traits separate the best from the rest? The common denominator was: I was coachable. In Coachable, Bucher explores ten truths of coachability through the stories of all-time great athletes. The truths are applicable to all walks of life. What is coachability? “Synthesizing your vision of who and what you want to be with someone else’s vision of who and what you can be by collaborating to realize that shared vision.” TRUTH 1: Giving In Is Not Giving Up Change is a constant in the short and long term. Sometimes what you set out to do is not what you should be doing. Giving in to a pivot may be just the best thing. It’s not giving up on your dream; it’s growing. “Being coachable is fundamentally about self-improvement. I want to get better, and I’m willing to go backward to go forward.” TRUTH 2: A Fixed Flaw Is a Fountain of Faith Humility to take correction and do something with it. Every problem is there to teach us something—to move us forward. The frustration of having to reconstruct something as fundamental as his shot led Stephen Curry to learn to have faith in the process. He told Bucher, “There’s faith that comes with going through that, working toward that intended outcome of who I want to be. But that whole process, for me, requires having trust in myself to be able to solve whatever...

2026/8/8
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Leading Thoughts for August 6, 2026

IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with: I. Jeremy Pollack on certainty: “Certainty is the nemesis of peace. Our drive toward certainty, which underlies our subconscious and conscious desires to be right, is antithetical to our capacities for flexibility, open-mindedness, and collaboration with those we perceive as sources of conflict. And the unfortunate news is that our brains are certainty-seeking machines.” Source: Wired for Peace: Using 7 Neuroscience-Based Principles to Resolve Conflicts II. Phil Le-Brun and Jana Werner on organizational slogans: “Your organization’s clarity isn’t found in your mission statement; your employees and stakeholders find it in what they experience. They find clarity in the last difficult decision a leader made and how it made sense given their understanding of the business. They find clarity in the project that got funded (and those that didn’t) and how it matches the mission as everyone understands it. They find clarity in the last person who got promoted because they operate in a way that reflects desired values. These actions are the signals that communicate ‘what matters here.’ If your stated clarity contradicts these lived realities, the slogans are worthless.” Source: The Octopus Organization: A Guide to Thriving in a World of Continuous Transformation * * * Look for these ideas every Thursday on the Leading Blog. Find more ideas on the LeadingThoughts index. * * * Follow us on Instagram and X for additional...

2026/8/6
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