Category: Leadership

  • Moving Too Fast to Notice Your Life

    Moving Too Fast to Notice Your Life

    Sandstone Canyon is easy to miss if you’re moving too fast. It branches off Fish Creek Wash without much announcement. A sign. A turn. If you weren’t already in the mood to slow down, you’d keep going.

    Once you’re inside, the walls come up quickly. Fifty, maybe seventy feet. The wash is still sand and crushed dirt, still not what anyone would call technical, but there isn’t much extra space. You notice that right away. The way the canyon quietly narrows your choices.

    We’re used to places that reward momentum. Sandstone doesn’t. It rewards paying attention. And not just in the “don’t hit anything” sense. This is a canyon that took millions of years to become a canyon. The walls hold light differently depending on the time of day. The color shifts as you move. If you’re only focused on getting through it, you miss most of what’s actually there.

    Most of the time, you’re moving slowly through it a little stunned, watching the walls change and trying to take in how improbable it all is.

    Every so often, you have to wait for someone coming the other way, or ease past a narrow section. That part isn’t difficult. It just makes it very clear that you don’t get to decide the pace.

    Most days, you do.

    In normal life, days are mostly a series of things to get through. The goal becomes finishing. Clearing. Moving on. You move from one thing to the next at a speed that feels efficient and, over time, becomes automatic.

    Nothing is wrong, exactly. You’re just always moving. And living at that speed flattens things. Even good days start to feel thin.

    Out in Sandstone, that’s harder to maintain. The canyon keeps interrupting you. The walls keep catching the light. The scale of it keeps insisting that you’re moving through something that does not care how quickly you’re trying to get to the end.

    You leave, of course. You always do. You go back to regular days and regular weeks and all the usual noise.

    But places like this change your sense of tempo, even if only briefly. They remind you what it feels like when time has texture again.

    And then, slowly, you start moving too fast.

    Until the next place makes you notice.

  • Stop Romanticizing the Grind: Why Misery Doesn’t Equal Meaning

    Stop Romanticizing the Grind: Why Misery Doesn’t Equal Meaning

    I’m done pretending that being miserable proves I’m doing something important.

    I’ve tried it. It just breaks things. Usually me.

    I ran into this quote on Instagram and it put words to something I’ve been feeling for a while now…

    “My competitive advantage is I’m having more fucking fun than you. Not because I don’t care. Because I care so deeply that I refuse to make it fucking miserable… I stopped romanticizing my suffering like I was some kind of war hero, and started romanticizing the kind of work I go to bed excited to wake up and continue.”

    That line about romanticizing suffering like a war hero?

    It stung.

    I care about the work. A lot. Learning… leadership… building things that actually help people. That part hasn’t changed. But my tolerance for the idea that being exhausted, overwhelmed, and quietly fried is proof of commitment?

    Gone.

    It’s not commitment. It’s just… unsustainable.

    Think about it like being out on the trail. You don’t need to know Land Rovers to get this… but if you’re off-roading and you hit unfamiliar terrain, you don’t floor it. You don’t try to smash through obstacles just to prove your vehicle is tough.

    You slow down. You pick a line. You let the suspension work.

    White-knuckling the steering wheel feels like you’re doing something… feels intense. Productive. But it isn’t. It just means you’re tense, you’re missing the view, and you’re probably going to break an axle.

    Somewhere along the way, we decided work had to hurt to count. That joy meant you weren’t serious. That if you weren’t struggling, you weren’t trying hard enough. I’ve had bosses that equated pain to dedication, to success.

    I bought that story. For a long time.

    But I’m not interested in being a war hero for a meeting agenda or a quarterly report.

    I want to build things I actually want to come back to. Momentum. Curiosity. Room to breathe. Not “easy” work… just work that doesn’t require self-betrayal to get through the day.

    This isn’t about doing less. It’s about not burning the engine out before I get to the destination. Or even worse, not even see the view along the way.

    I used to think the misery was the point. But Jude’s right… “enjoying your life makes it much easier to keep showing up.”

    And I want to keep showing up.

    So, you can grind until you hate the work.

    “I’m gonna enjoy the work until I win.”

    That’s the plan for 2026.

  • Adoption Isn’t Impact: The Quiet Failure of Learning Innovation

    Adoption Isn’t Impact: The Quiet Failure of Learning Innovation

    I keep seeing the same pattern across schools, organizations, and learning platforms.

    The tools keep getting better.
    The outcomes… not so much.

    AI is more capable. XR is more immersive. Platforms are more polished than ever. And still, leaders feel it. That quiet, nagging sense that learning isn’t actually working the way it was promised.

    Engagement spikes. Pilots multiply. Dashboards fill up.
    Clarity about impact stays frustratingly out of reach.

    This isn’t a technology problem.
    It’s a design problem.

    Most learning systems were never built to absorb this level of change. New tools get layered onto old structures. Innovation gets bolted onto workflows designed for stability, not adaptability.

    The result is fragmentation.
    Good intentions. Scattered execution.

    I hear versions of this all the time:
    “We’ve adopted the platform.”
    “We’ve rolled out the tool.”

    What’s missing is the harder question:
    What is this actually changing about how people learn, think, and make decisions?

    Adoption is visible.
    Impact is not.

    Impact only shows up when there’s alignment. Between learning strategy, leadership expectations, culture, and the realities of day-to-day work. Without that, even the most advanced tools struggle to matter.

    Another common miss is over-indexing on features instead of purpose.

    Yes, AI can personalize learning paths.
    Yes, XR can simulate environments.
    Yes, analytics can surface patterns.

    None of that answers the real questions:
    What capabilities are we trying to build?
    What skills matter here?
    What should change when the tool is no longer new?

    When those questions go unanswered, technology defaults to efficiency, not meaning.

    I also see responsibility for learning outcomes get diffused. Innovation teams experiment. IT enables. Designers design. Leaders cheer from a distance.

    No one owns coherence.
    No one is accountable for the system as a system.

    Learning doesn’t break down because people aren’t trying.
    It breaks down because no one is tasked with connecting the dots.

    The organizations making real progress look different.

    They slow down before they scale.
    They clarify what learning is for before deciding what to buy.
    They treat technology as a lever, not a strategy.

    Most importantly, they treat learning as a leadership function, not a procurement decision.

    Leaders are involved early. They set priorities. They make tradeoffs. They resist the urge to pilot everything and instead commit to a few things done well.

    Learning stops being something that happens “over there.”
    It becomes part of how the organization thinks and operates.

    This shift isn’t flashy. It doesn’t generate big announcements.
    But it creates durability.

    What’s encouraging is that more leaders are starting to feel this gap. In conversations with superintendents and edtech leaders, I hear the same frustration surfaces again and again.

    Money is being spent.
    Capability isn’t always following.

    There’s a growing recognition that more tools aren’t the answer.

    The path forward isn’t about rejecting technology.
    It’s about designing systems that can actually hold it.

    That means:

    • treating learning as a connected ecosystem, not a collection of initiatives
    • aligning leadership expectations with learning goals
    • designing for judgment, adaptability, and human skill, not just completion and compliance

    When learning is designed this way, technology amplifies it.
    When it isn’t, technology just accelerates confusion.

    The future of learning won’t be decided by the next platform or algorithm.

    It will be decided by whether organizations are willing to do the harder work of design. Clarifying purpose. Creating coherence. Building systems that support how people actually learn and grow.

    The organizations that get this right aren’t chasing better tools.
    They’re designing better systems.

    Everything else follows.

  • How AI Helps Leaders Uncover Blind Spots and Build a Culture of Thinking

    How AI Helps Leaders Uncover Blind Spots and Build a Culture of Thinking

    I was working with a new leader recently who said, “I know I’m missing something, but I can’t tell what it is.”

    She wasn’t lacking skill.

    She was bumping up against the part of leadership nobody likes to admit.

    Our brain fills in missing pieces without asking permission.

    That’s a blind spot.

    Not the thing you didn’t notice, but the meaning you assigned without realizing it.

    This is exactly where Cultures of Thinking shows up in real leadership work.

    Ron Ritchhart talks about creating a culture where people examine their own thinking, question their interpretations, and stay open to multiple perspectives.

    But leaders rarely do this for themselves.

    They are too busy moving on to the next thing.

    Here’s the good news.

    You don’t need an AI note taker or a perfect transcript to start seeing your blind spots.

    You just need a way to challenge your own first read of a situation.

    Here’s what I showed her.

    After a meeting that felt heavy, instead of replaying every detail, I asked her to write a few sentences about what she thought happened.

    Not the whole moment.

    Just her interpretation.

    Then I had her ask AI:

    “What’s another possible interpretation of this situation?”

    That’s it.

    No magic.

    No pretending AI “knows” the meeting better than she does.

    AI simply widened her lens.

    It offered alternatives she hadn’t considered:

    “Maybe the questions showed engagement, not doubt.”

    “Maybe the tension was about workload, not your leadership.”

    “Maybe the silence meant processing, not disagreement.”

    She looked at the screen and said, “I didn’t even think of that.”

    And that moment is the core of a Culture of Thinking.

    Not the right answer.

    Not the perfect insight.

    Just the willingness to look at your own thinking and stretch it a little.

    Blind spots aren’t signs of weakness.

    They’re signs that our assumptions are running ahead of us.

    AI helps you pause long enough to ask,

    “What else could be true?”

    If you’ve ever walked away from a meeting feeling uneasy but unsure why, this kind of thinking might give you the clarity you didn’t realize you were missing.

  • How a Simple Thinking Routine and AI Help Leaders Get Clarity After Tough Meetings

    How a Simple Thinking Routine and AI Help Leaders Get Clarity After Tough Meetings

    I keep coming back to something I learned at Harvard’s Project Zero Summer Institute.

    Teachers use simple “thinking routines” to help students slow down and make sense of the world.

    Nothing fancy.

    Just structured steps that help your brain stop jumping all over the place.

    One of the classics is See Think Wonder.

    It asks three basic questions:

    What do you notice?

    What does it make you think?

    What are you still wondering about?

    It sounds simple, almost too simple, but it works.

    And honestly, adults need it more than kids.

    The problem is leaders rarely give themselves time to sort their thinking. Most of the time you close the laptop and instantly open the next tab in your brain. There’s no buffer. No moment to process what just happened.

    This is where AI has become a helpful partner for me.

    Not to “do the thinking,” but to slow me down long enough so the thinking can actually show up.

    Here’s what it looks like in real life.

    Let’s say I just wrapped a meeting on Zoom and something felt off. Maybe it was the tone, the reactions, or something in the chat. Instead of jumping straight into the next task, I open my AI chat and type:

    “Can you walk me through See Think Wonder on this?”

    Then I give a few sentences about what happened.

    And the conversation usually unfolds like this:

    AI: “Let’s start with what you noticed. Describe only the concrete things. No interpretations yet.”

    So I list what I literally saw or heard. The actual facts.

    AI: “Now, based on those observations, what did you think was going on?”

    This helps me separate facts from interpretations. Most leaders mix those together without even realizing it.

    AI: “What are you still unsure about?”

    And suddenly I’m naming the questions I didn’t know I had.

    Things like, “I wonder why there was hesitation,” or, “I’m not sure if the concern was about the idea or the timing.”

    That’s the routine.

    Nothing complicated.

    Just a simple structure that helps your brain stop spiraling and start thinking.

    It’s amazing how often clarity shows up once you slow down long enough to see what you actually saw.

    Leaders don’t need more noise.

    They need more structure for their own thinking.

    And AI, used in the right way, gives you that structure in the moment you need it.

    Post 3 is next. We’re going to talk about blind spots and how AI can surface the things you swear you “didn’t miss”… but absolutely did.

    If any part of this routine sounds useful, try it once and see what shows up. I’d love to hear what you notice.

  • Finding Clarity Again: How AI Helps Leaders Breathe, Pause, and Think

    Finding Clarity Again: How AI Helps Leaders Breathe, Pause, and Think

    In a directors meeting the other day, someone said something that hit everyone at once:

    “It’s a good time to come back to our values. It’s been busy. We need to get grounded again.”

    You could hear the collective sigh of agreement.

    Because when things get too busy, it shows. You feel it in the way people talk, decide, rush.

    Busy takes over, and thinking goes out the window.

    Not because leaders don’t know how to think, but because they are reacting to everything thrown at them. All day. Every day.

    Years ago, I went through a comprehensive training with Ron Ritchhart on Cultures of Thinking and later attended Harvard’s Project Zero Summer Institute. The biggest lesson I walked away with?

    Your culture isn’t what you say you believe. It’s whatever your behavior proves you believe.

    And if i’m being honest, most leaders unintentionally show that speed matters more than clarity.

    “Just get it done” becomes the vibe.

    This is where AI has actually helped me slow down.

    Not to do the work for me.

    To force a pause.

    Simple example:

    If I’m about to send a decision or a tough email, I’ll drop it into AI and ask,

    “What assumptions am I making here?”

    Ten seconds later, it shows me the exact things I would have missed because I was rushing.

    It’s not magic.

    It’s a brake pedal.

    If we want teams that think, not just react, we have to model that pause ourselves.

    This is the first post in a short series on how leaders can use AI to create cultures where thinking actually happens.

    My question to you:

    Where in your work would a simple pause actually help you right now?

    And who else would benefit from reading this? Have them subscribe to the blog!