Category: Leadership

  • What AI Revealed About My Biggest Leadership Weak Spot

    What AI Revealed About My Biggest Leadership Weak Spot

    I saw this question reposted on a friend’s Instagram and decided to ask AI, since it knows me well:

    “If a competent CEO got to run your life in 2026, what is the first thing they would eliminate?”

    The answer wasn’t subtle. AI was quick to call out my chronic overcommitment.

    Not my ambition or creativity, just the part where I say yes to things that don’t move my life or work forward.

    A CEO would open my calendar, scan the clutter, and immediately notice the pattern that I’m a top performer doing work that doesn’t require my level of expertise… simply because I can.

    The Sneaky Part About Overcommitment

    It rarely looks like chaos. It looks like competence. Things like a quick review of a friend’s manuscript that turns into a redesign or a small favor that becomes a six-week long advisory council commitment.

    Helpful? Sure.

    Strategic? Not even a little.

    What Needs to Go

    So since I am the CEO of my life, here’s what I need to cut:

    – Automatic yeses that steal time from the work that matters.

    – Unpaid emotional labor that solves problems others could handle.

    – Tasks I absorb because someone else is moving slowly.

    – Volunteer brilliance that drains the energy needed for my long-term goals.

    Why This Matters

    Because 2026 isn’t about doing more; it’s about doing the right things.

    VR/AI curriculum.

    Leadership writing.

    Consulting.

    Growing the work that actually changes lives requires space. Space I keep giving away out of habit.

    And here’s the part that ties back to my work guiding others:

    I can’t coach people toward intentional, human-centered leadership while running my own life on overdrive. Clarity creates integrity and boundaries create authenticity.

    And if I am committed to being a leader, then modeling the hard choices gives others permission to do the same.

    So yes, my AI bestie called me out. But it was the nudge I needed.

    So in 2026, I’m firing the overwhelm. Not because I can’t handle it, but because I finally know I don’t have to.

  • When the Waiting Room Becomes an Echo Chamber

    When the Waiting Room Becomes an Echo Chamber

    This morning I find myself in a packed dealership service waiting room because apparently every single one of us had the same “brilliant” idea: get the car checked before Thanksgiving travel.

    I’m sitting in a living, breathing echo chamber.

    We all had the same plan, same timing, same logic.

    No one questioned the obvious. We all just… showed up. Ugh.

    And as I sit here watching the room fill beyond capacity, it has me thinking about work, and the fact that this happens in leadership far more often than we admit.

    We fall in love with alignment. We assume shared thinking means we’re on the right track. But when everyone is thinking the same way, no one is actually thinking. Consensus feels safe, familiar, efficient even. But more often than not, it’s a sign we’ve stopped asking the harder questions. It’s actually exhausting to sit in meetings with everyone just saying “yes” to whatever idea gets put out there.

    True leaders who move things forward aren’t the ones who blindly follow the pattern everyone else defaults to. They’re the ones who pause long enough to ask:

    “Is this actually the best move, or just the expected one?”

    Strategic divergence is underrated. It’s not rebellion for the sake of rebellion; it’s curiosity with a spine. It’s the awareness that if you only ever make the same choices as everyone else, you shouldn’t be surprised when you end up in the same waiting room at the same time, frustrated for the same reasons.

    A little intentional questioning goes a long way, in both car maintenance and in leadership.

    P.S. Safe travels to everyone hitting the road this week. And may your service appointment move faster than mine. 🤪

  • Trusting Reality: The Impact of AI-Generated Deception

    Trusting Reality: The Impact of AI-Generated Deception

    Plato never heard of a deepfake, but he understood the prison it could build for the human mind.

    I remember reading his Allegory of the Cave my first semester of community college. In the allegory, prisoners are chained to a wall, forced to watch shadows dance across the stone. They have never known anything else, so they believe the shadows are the world. To them, the flickering shapes are not illusions but fundamental truths.

    Does the darkness feel familiar? (Hint: It should…)

    In our time, we are all inhabitants of a new, digital cave. The shadows are no longer cast by firelight but by algorithms designed for engagement at any cost. New AI makes it scarily easy to create believable fakes. It can make fake videos of world leaders saying things they never said, or create totally computer-generated news anchors. It can also make videos of events that never happened, or copy the voices of your family and friends so perfectly it’s chilling.

    Our minds, wired over millennia to trust what our senses tell us, are being turned against us. For most of human history, the simple act of seeing was believing. Then, as photo manipulation became common, our collective skepticism adapted. The mindset shifted from “I’ll believe it if I see it” to a more cynical, “I’ll only believe it if there’s video.” We instinctively clung to the moving image and the human voice as a higher, more reliable bar for truth. But now, that final refuge of sensory trust has collapsed. With AI able to fabricate convincing video and clone voices with chilling precision, that instinct has become our greatest vulnerability. The puppeteers casting shadows on our walls are no longer human. They are automated, relentless, and they leave us all asking, “Now what can I possibly believe?”

    The Corrosion of “I’ll Believe It When I See It”

    When Plato’s prisoner was dragged from the cave into the sunlight, the truth was blindingly painful. For us, stepping into the light means navigating a media landscape so fractured that the very idea of certainty feels like a relic. The danger is not just being fooled by a single fake, but the slow, corrosive effect on our ability to trust anything at all.

    This is the new psychological tax of modern life: that quiet, persistent whisper of doubt. Is this real?

    • Deepfakes don’t just create lies; they breed distrust in the truth.
    • Synthetic images go viral, while the corrections are buried, leaving a permanent stain of doubt.
    • AI can replicate the voice of a trusted colleague or family member, turning our most intimate connections into potential scams.

    That hesitation, that constant, low-level cognitive friction, is the true damage. When we can no longer trust our own eyes and ears, the foundations of our reality begin to crumble.

    When Our Shared World Fractures

    This is more than a crisis of information; it’s a crisis of connection. Plato warned that people who mistake shadows for reality will fiercely defend their illusions, even against those trying to show them the light.

    Today, we see that happening in real-time. The consequences are deeply human:

    • Isolation: We stick to our own groups, where everyone shares the same opinions. This makes us feel validated, but it makes it easy to forget that the people who disagree with us are just as human as we are. We start seeing them as simple “enemies” instead of real people.
    • Erosion of Empathy: Social media sites are built to promote posts that get a big, angry reaction because that’s what gets the most clicks and attention. They don’t care about spreading calm or helpful understanding. This just makes everyone more divided and helps us forget that we’re arguing with real people, not just a username on a screen.
    • Learned Helplessness: With so many lies coming at you all at once, it’s exhausting. It feels easier to just disengage and stop paying attention, instead of doing the hard work of separating fact from fiction.

    This isn’t a distant, dystopian future. It is the world we inhabit now. And unlike Plato’s cave, there is no single, easy exit.

    What It Means to Find the Light Now

    Escaping this new cave doesn’t mean finding one ultimate “truth.” It means reclaiming the human capacity for critical thought, empathy, and discernment. It means choosing to be active participants in reality, not passive consumers of it.

    This requires a conscious, human-centered shift:

    • Question Your Emotions. The most powerful misinformation is designed to trigger an immediate, emotional response. If a post makes you angry, fearful, or self-righteous, pause. That feeling is a signal to scrutinize, not to share.
    • Invest in Human Connection. Rebuild trust in small, tangible ways. Have conversations with people you disagree with. Prioritize local, verifiable sources of information that are accountable to a real community.
    • Embrace Humility. The goal is not to be the person who knows everything, but to be the person who is willing to learn, to admit uncertainty, and to change their mind. Certainty is a trap; curiosity is a path forward.
    The Choice We All Must Make

    Plato’s story wasn’t just about shadows. It was really a warning: people often prefer a comforting lie to a hard truth. It’s easy to get lost in the “shadows,” especially when they’re designed to perfectly match our own opinions, hopes, and fears.

    But our ability to connect as human beings relies on us being brave enough to look away from the screens and toward each other. In this age of AI fakes, being able to see clearly isn’t just a skill. It’s a basic survival tool.

  • Unlocking Innovation Through Curiosity and Risk

    Unlocking Innovation Through Curiosity and Risk

    It’s been a few months, but I’m still processing the lessons I’m taking away after sitting in on the d.school book club chat with Sarah Stein Greenberg about her fantastic book, Creative Acts for Curious People.

    The entire conversation was a masterclass in leading creative teams, and it completely reshaped how I think about my own role as a leader. Here are my biggest takeaways.

    It’s Not About Being ‘Creative’—It’s About Being Curious

    The first thing that really clicked for me is that we put too much pressure on the word “creativity.” Sarah mentioned that for many, it feels exclusive. She offered a much more accessible starting point: curiosity.

    Curiosity is the “gateway,” the entry point that helps people embrace their own creative abilities.

    We got to experience this firsthand when she led us through the “Seeing Exercise. She showed us an ambiguous picture and asked, “What’s going on in this picture?” As I always do, I tried to find the “right” answer. But the real lesson came later when someone asked what was actually happening in the photo. Sarah said she has intentionally never looked it up. She likes to “sit with that feeling of not knowing” because it’s a constant reminder of what our teams feel when faced with ambiguity.

    My takeaway: My job as a leader isn’t to have all the answers. It’s to model a deep and genuine curiosity and to create situations that encourage my team to slow down, observe, and question their own assumptions.

    Psychological Safety Isn’t Magic; It’s Architecture

    We all talk about wanting our teams to feel safe enough to share wild ideas, but how do you actually build that? Sarah’s approach treats safety not as a feeling, but as a direct result of intentional design.

    She described her “My Favorite Warmup Sequence,” and it was a revelation. It’s not a random icebreaker. It’s a carefully structured process designed to “build psychological safety piece by piece.” You start with a safe one-on-one interaction. Then, that pair joins another pair to become a quartet, and the activity becomes a little more playful. It gently eases people into a state of vulnerability and connection, rather than demanding it all at once.

    My takeaway: I need to stop thinking about team-building as just “fun activities” and start thinking about it as a structured process. True psychological safety comes from designing interactions that strategically build trust over time.

    You Have to Make the Work Visible

    When a project gets really complex, it’s easy for a team to feel overwhelmed and paralyzed. I learned that a leader’s critical role here is to fight that fog by making abstract challenges tangible and visible.

    Sarah mentioned a concept called “distributed cognition,” which is about taking the ideas out of your head and putting them into a shared space so you can expand your ability to think about them. She offered two specific assignments from the book that I can use right away:

    • Map the Problem Space: At the beginning of a project, this helps a team get all their thinking out and organized, creating a shared view of the landscape.
    • The 100-Foot Journey Map: When you’re deep in a project and drowning in data, this tool helps you physically map out every step of a complex process, bringing immense clarity to the system.

    My takeaway: I can’t expect my team to navigate complexity inside their own heads. My role is to provide the structures and frameworks that allow us to get it all out on the wall, see it together, and find the key leverage points.

    The Biggest Risk Is Often Doing Nothing at All

    Perhaps the biggest mindset shift for me was how Sarah reframed risk. We often focus on the risks of trying something new, which can scare teams into inaction. But she challenged us to consider the other side of the coin.

    What is the risk of not acting? What is the risk of continuing on the current path?

    This question alone changes the entire conversation. To put it into practice, she pointed to the “Expert’s Assumptions” activity in the book. The process is simple: have the team list all the assumptions and constraints they believe are true for a project. Then, pick one, flip it, and spend just 10 minutes imagining what you could build if that constraint didn’t exist. It’s a structured, low-risk way to give people permission to be radical.

    My takeaway: My job is to reframe the conversation around risk. By helping my team challenge their assumptions and consider the cost of inaction, I can unlock a more innovative and courageous approach to problem-solving.

    Final Thoughts

    Leaving the book club, I realized the most profound shift for any leader isn’t in finding better answers, but in learning to ask better questions and build better rooms. Modern creative leadership isn’t about being the source of every great idea; it’s about being the facilitator of them. The real work is architecting the environment where your team’s collective genius can finally show up. The most powerful question we can ask ourselves isn’t, “What’s my vision?” but rather, “Have I created the conditions for theirs to emerge?”

  • Why Leaders Need Trail Markers

    Why Leaders Need Trail Markers

    When I’m off-roading, there’s a moment every adventurer knows well. You’re deep on the trail, the terrain is uneven, and suddenly, you realize you haven’t seen a trail marker in a while. That’s when doubt creeps in. Am I still on the right path, or am I about to waste daylight backtracking?

    One time, I missed the markers completely because I was chatting with a friend who had joined me. By the time I realized it, I was 20 miles further than I had planned and ended up staring at the Salton Sea. It wasn’t catastrophic. I still had gas, daylight, and options, but I lost time, energy, and focus. The trail had taken me somewhere, just not where I meant to go.

    Leadership feels like that more times than not. The obstacles are different, sure. Things like competing priorities, stretched budgets, multiple staff asking if you just “have a moment”… but the risk is the same: drifting further and further off course, only realizing later how far you’ve gone.

    That’s why Charlotte Burgess-Auburn’s book You Need a Manifesto should be required reading for all leaders. She describes a manifesto as a compass, not a map. It doesn’t spell out every twist and turn. Instead, it’s the equivalent of those markers on the side of the trail that reassure you you’re still on track, even when the terrain is unknown.

    As Chief Academic Officer with 25 years in education, I see how often schools operate without these markers. We hand teachers a vision statement or a beautiful Portrait of a Graduate poster, but it doesn’t show up in the day-to-day decisions. When leaders are unmoored, every trail looks the same, and that’s when we burn precious energy circling or overshooting instead of moving forward with intention.

    A manifesto changes that. It anchors decision-making in values you’ve actually named. It gives you language that cuts through noise and offers reassurance in complexity. On the trail, that’s the difference between pressing forward with confidence and burning miles in the wrong direction. In schools, it’s the difference between progress and burnout.

    A Challenge for Leaders

    Don’t wait until you’re lost at your own “Salton Sea moment” to wish you had trail markers. Write a manifesto that’s small enough to remember, clear enough to use, and visible enough to check when the fog rolls in.

    Because whether you’re off-roading in the desert or steering a district through turbulent times, one truth holds: the terrain will test you. The question is whether you’ll have trail markers when you need them.

  • Designing Belonging: What a Pizza Box Taught Me About Connection

    Designing Belonging: What a Pizza Box Taught Me About Connection

    I’ve written before about the time I ordered a pizza to reconnect my ex-husband to the outside world. No car. No phone. No internet. A disconnection, both literal and emotional. We used Domino’s delivery notes as our 21st-century carrier pigeon. It worked, but only because someone made the effort to reach out, to bridge the gap, to make belonging possible when the system failed.

    I was thinking about that moment when I read Design for Belonging by Susie Wise.

    “The work of belonging is to counteract [othering]. It is to open up spaces and places so that all people regardless of their backgrounds can join in and contribute.”

    I can’t stop thinking about how often we overlook the micro-moments where belonging breaks, and how many more we ignore where it could be rebuilt.

    That pizza box moment was belonging by design, even if I didn’t have a name for it then. It was messy. Unconventional. A little ridiculous. But it worked.

    And maybe that’s the real design challenge: how do we notice when belonging is fractured? And more importantly, what do we do next?

    When Wise talks about the “design levers” of rituals, roles, spaces, systems, it isn’t just a nice framework for planners and strategists. It’s a lifeline for educators, leaders, and humans trying to hold fragmented communities together. Especially when those communities are separated by distance, devices, and distraction.

    I’ve seen this in classrooms. In Zoom faculty meetings. In Twitter (“X”) threads that start with good intentions and devolve into ego matches. And I’ve felt it in the silence after someone says something unintentionally harmful, followed by… nothing.

    That’s where the work is.

    We talk a lot about invitation. How do we invite students into learning? Colleagues into collaboration? Families into school systems that weren’t built with them in mind?

    But Wise pushes us further. She explains that invitation isn’t just about showing up. It’s about showing up in a space that sees you. Hears you. Values your perspective.

    That only happens with intention.

    I think about how many times I’ve created systems that worked “in theory” but didn’t feel like belonging in practice. The school-wide email that no one read. The virtual office hours that no one joined. The peer feedback protocol that favored the loudest voices. None of those were belonging, even if they were well-designed.

    Because belonging isn’t the form. It’s the feeling.

    Wise also talks about dissent and repair—two words we don’t sit with enough in schools.

    We love our norms and expectations and “we’re all in this together” mantras. But what happens when someone pushes back? When they say, “This space doesn’t feel safe for me,” or “That comment hurt”?

    Too often, we go straight to defense. Or worse—silence.

    But real belonging means we stay. We sit in the discomfort. We acknowledge the impact even if it wasn’t our intent. We ask what repair could look like—and then we act.

    Sometimes that action is a redesign.
    Sometimes it’s an apology.
    Sometimes it’s a damn pizza box with a handwritten message to reboot the phone so messages arrive. haha

    I don’t have a neat ending here. Belonging is squiggly like that. It’s a process, not a product. But what I’m learning from Susie Wise, and remembering from my own messy, human moments, is this:

    We can design for belonging in every space we touch.
    Even the ones that feel too big, too broken, too remote.
    Even the ones held together by pizza and Post-it notes.
    Especially those.